{PROLOGUE} 🐛

In my life, there are roughly two important milestones that have molded me into the quirky 27 year old writing to you today. 

The first was reactively choosing an unconventional path in the beginning of my 20s. I leapfrogged to East Africa for four months in a time where people around me were fast-tracking into glitzy career paths of their young unadulterated dreams. I had no idea that a 4-month stint in Tanzania would cascade into shaping my worldview: a deeply invested interest in observing worldly cultures and philosophies, prioritizing lived experience above all. It was the first time I realized I could be whoever I wanted. A kind of social liberation. On the fringes of safaris and savannas, I’d quickly learn to appreciate concepts like beauty, pleasure, and privilege and form opinions on each.

The second milestone was proactively shedding all of the limiting beliefs and heavy masks that plagued my sense of self-concept. Being glued to Toronto for all of 2020 was probably a divine blessing, because it forced me to sit down and interiorize all the mischief in my head — the perfectionist part, the relentless romantic, the contrarian clown. The gulf between who I ought to be and who I could be increasingly widened, twisting and transforming into unrecognizable territory. But I could feel myself unravelling the cocoon in favour of new fluttering mindsets: a maturing man who expresses, a curious mind who experiments, and a spontaneous soul who entertains.

A frame I’m crystallizing: A life lived intuitively is a highly nutritious one.

With the help of writers and creatives who are much more eloquent than I am, I’ve also been juggling a few profound questions around this nebulous idea of maturity:

1. What is living your “best life” supposed to look like?  

2. How does the way you care for yourself and others change with increasing freedom and maturity? 

3. How do you know that you’ve reached your calling, and when do you commit? 

Then comes the torrents of ~Big Questions~ rushing intensely at my psyche: how happy am I with myself right now? How do I feel about growing up so quickly?

Okay, before we get caught in the spidery struggle of over-philosophizing life in the late 20s, I want to mark this piece as the last chapter of my formative years. I've always been a fan of building miniature time capsules for Future Sam to dig up, and it's fitting that I line up this winding trail with my final days in South America.

So here’s my scrapbook of memories that mark my transition into completely new planes of life: views from an unexpected nomadic life, chronicles on cultivating interpersonal relationships, and future-looking commitments to ease into the reality of a full-time artist. I'll do my best to tackle those head-scratching questions above, but I'm much more excited to reveal a series of “scrapshots” that have most vividly coloured this era of growing up. Yalla, habibi!

{ACT I: INDEPENDENCE} 🪲

If I were ever reincarnated in another life like the Buddhists and Hindus preach, I'd want to be a grasshopper. One with well-built hind legs, ready to take flight at a moment's notice. One with antennas sensitive to the sounds and sensations of the outside. One with a pair of sensory membranes tucked under its airy abdomen, adept at relating and responding to the shouts and songs from its fellow insects. One with a mind programmed to just take the leap whenever a delicious opportunity arises. 

While this extended metaphor has a bit of hyperbole, I did fully embody the spirit of a grasshopper without ever realizing. This might be a shocker to some, but I never intended to take up a cross-country conquest when I boarded the one-way flight to Istanbul in 2021. The snap decision to uproot myself again, after only four brief months in New York, was driven by an important jump into the scorching land of technology startups. If I were a young adult novel protagonist, this is probably how my narrator’s reel would read:

POV, August 2021: A starry-eyed Sam gazed wistfully out the window of the afternoon Q train to the imposing Manhattan skyline in its sunny glory, promising the very promised land that he'd be right back.

Naked and exposed to the unfamiliar environment of the Middle East, I set out to absorb as many formative experiences as I could. Within months of being on the road, I reoriented focus to my emerging intuition, and this eventually grew to ways I could actively listen to my physical body. From hours of slow strolls beside the Bosphorus Strait around Arnavutköy, I learned that there's a thin line between independence and isolation, but that in moderate doses, both are inherently healthy for you.

Life on the road is not always glamorous, but at least it guarantees space. Leaning into introversion, introspecting with strangers, engaging with art — severely underrated skills in the moment, but very invaluable for developing my independence. I tell myself: I’m not abandoning my home castle to go corral a suite of nameless kingdoms. I’m playing a game of collection and curation. This is my victory lap: the one last chance I can explore without consequence, to step away from the regular routines for a short while. 

My eventual willingness to bounce beyond the borders of Turkey started to warp the texture of the remote journey: from mindless meandering to intentional investigating. I wanted to open up the heartbeats of the cities and cultures I traversed. This was like a style of rapid prototyping: I'd immerse in a given place for at least a month and then observe the micro-level changes to my emotions. In what ways had I changed? Had the immersion made me better? Do I see a potential home here?

Seasoned writers often romanticize, criticize, or otherwise de-stigmatize their personal connection to cities, and I think it's a charming angle to help make sense of how you view a “good lifestyle” when it comes to choosing a home (by extension, this is a choice of independence). After five months of desert life, Sasha Chapin describes the mood of attaching to cities as a matter of maximizing:

“You go to cities for commerce, optionality, stimulation, sex, culture, bright lights, and the feeling of being relevant. Cities tell you that, whatever human life is about, you are right on top of it. New York instructs you, through a million signals, subtle and otherwise, that you are part of the heart of all that matters. To own that city is to be assured that you’re the royalty of the world, to be sure that you’re getting the maximum juice out of your short lifespan.”

If the point about "owning" a city to maximize the zest of life were true, then aren't I making a massive sacrifice by grasshoppering around so much? My endless curiosity pulls me one way, while potential stability pushes me to another. 

After almost two years of living like a wandering camel nomad, I try to convince myself that this is normal. The ordeal of settling, grounding, pausing — it's like a birthing and decaying process, full of organs and shedding and blood. But then I am reborn, whether in the form of a beady-eyed grasshopper or not, and I adjust. I assert my scrappiness onto a replicating array of blank canvases, trusting that the mid-20's period is all about abstract trial-and-error. Trying to uncover what home means, testing out configurations in crazy wilderness. And part of this testing process is flirting with a city's heartbeat to uncover what best fits your maturing needs.

On gloomier days on the road, I boomerang back to Venkatesh Rao’s1 takes on being nomadic and illegible:

“Nomadism has almost nothing to do with the rooted-living behavior it nominally resembles, travel. When voluntarily chosen, nomadism is not a profession, lifestyle, or restless spiritual quest. It is a stable and restful state of mind where constant movement is simply a default chosen behavior that frames everything else. True nomads decide they like stable movement better than rootedness, and then decide to fill their lives with activities that go well with movement

If I have romanticized nomadism it is because nomadism is a fundamentally romantic state of being. If you can sustain it, it is somehow fulfilling without any further need for achievement or accomplishment. The pursuit of success is, for the rooted, the price they must pay for immobilizing themselves geographically.”

Then, this is my version of storybook romance. I want to carry the aesthetic edginess of Paris, bluntly striving for perfection but savouring the creative process to the fullest. I want to capture the mesmerizing flavours of Bangkok, beckoning with its embrace of tradition-laced modernity. I want to bottle the contrast of Rio de Janeiro, where nature scenescapes coalesce with a cosmopolitan cocktail, along with its shade of grime. I want to sponge up the cultural cores and controlled chaos of Istanbul, completely boundless in its beauty. I want to catalogue the intrinsic inspirations of Brooklyn, so that I can return to revitalize my soul, again and again. 

But it’s selfish to want to have it all, at least all at once. As my all-time favourite business buddha says, strategy is about choosing what not to do. I think what I'm converging on is a prism of patterns collected from my time spent in vastly different cultures. By flipping through these mosaics, I feel confident that I'll be re-integrating into a life in New York with new luggage, transporting thoughtful trinkets in the form of vivid memories and spoils of a war waged against my old identities.

I've learned that being totally receptive to these labyrinthine pathways and infinite choices offer so much richness to your whole being, as a makeshift acid test to your perceived identities and ideals. But I have to be clear that this channel of leveling up is not isolated to untamed travel, and does not mean you should surrender yourself to roam freely. I think the more practical principle is one of opening. Open every ounce of yourself to the goodness and unexpectedness that blows your way — opening your eyes, your heart, your mind, your hands. Combine that with an action-first mentality, and you’ll be catching unbelievable experiences like they’re rare fluorescent butterflies in no time.

I have endless gratitude for every local, villager, foreigner, expat, nomad, host, guide, and street cat I’ve met on the way. It’s impossible to sum up how much each interaction, each conversation, and each collaboration has influenced my growth in a million microscopic ways. Instead, here’s a heartwarming compilation of the best moments, in scrapbook form: 

It seems to me like the starry-eyed 20’s ideal of living your best life takes on wildly different shapes, where the nomadic story is more than pithy promises of happiness-filled freedom.   

With the end of my independence arc and nomadic isolation, I'm ready to leap into an intimately interdependent lifestyle. My new motto: Catch feelings, not flights!

{ACT II: INTERDEPENDENCE} 🐝

One of my favourite journal entries is titled friendship philosophy, from late 2021. I look back fondly on this piece because it has since sprouted so many meaningful dialogues with random strangers and has fueled many inner monologues that I obsess over. One excerpt from the essay: 

“But as we mature more into the dizzying, unforgiving environment of ~The Wild West of Mid-20s Responsibility~, friendships gradually shift underneath our feet like tectonic plates. A heightening volcano of external pressures and relentless interactions can be equal parts exhilarating and distracting. You realize there's an important tension: the human desire to meet and interact with new people vs. sticking to meaningful connections that already exist.”

(1) I’ve been slowly marinating thoughts about adult friendships, especially on how much they mutate over time. I like the weight that “mutation” implies here because you can never predict the trajectory of 20’s-friendships: they can blossom remarkably through reignited passions or opportune reunions, or they can fracture and fade by a lack of intentionality. The 20’s also adds another sticky wrench to the mix. People enter continuous loops of transition and integration, donning updated costumes as they attempt to reinvent meaningful aspects of their lives. The transitions that have the biggest impact on personal identity — location, community, career — often exert the most significant friction on friendship, but are practically inevitable as our identities morph with maturity. 

The silver lining is that it's never too late to resurrect buried friendships, just as much as it’s never too late to welcome new friends into the fold. After all, a steady stream of characters will keep emerging like a never-ending carnival game of whack-a-mole. It’s useful to remember that the Late 20’s is a period characterized by fluidity and priority. The “optimal” next step is to decide where to place your care and attention so your battery for social connection doesn’t get sucked dry. Only then can you harmonize your personal progress with the paths of the people around you, and invest in those you truly give a shit about.   

That last part sounds painfully obvious, but it extends to a larger cloud of physics-inspired philosophies that I call friendship velocity and friendship density. My theory is that the long-tail of meaningful connections we make follow a barbell model: brand-new friendships can be quickly cultivated through short bursts of contained intensity and intimacy2, while age-old friendships can be nurtured through the same intensity of being deeply invested in each other’s lives.

These are dense relationships with diamond-like durability, because even if the first side is filled with fleeting encounters (as most of my scrapshots illustrate), the impact on your emotional self can be surprisingly enduring. Meanwhile, the pals at the tail-end who have helped you check off juicy milestones also flourish because of the built-up momentum from years of shared commitment, so long as you keep the flywheel flowing.  

I might be over-complicating something simple, but it helps to reflect on the role that all the various characters play in my life. There are existing friends that you pour into, ones you don’t see too often but charged with fiery enthusiasm right at “what’s up”, a hunger to unpack everything substantial that has happened since last meeting. Then there are those that you trickle into, punctuated with more frequency, proximity, and lightness; you get to witness their gradual evolution over smaller speed bumps. I feel comforted to know that my only job is to figure out whether I'm still happy in these friendships or not.   

More than shared interests or associated activities, I think shared struggle is the best leading indicator for the relationship’s long-term survival rate (or more poetically, thrival rate). When you confide in someone at critical times — life pivots, existential crises, grand resets — and vice versa, a deeper undertone of camaraderie emerges. The mutual suffering normalizes the reality of being fallible humans, and it warms us to each other’s sensibilities through the feeling of being seen. It transcends the problem of proximity because a significant piece of you is embedded within them, seeding trust and weaving the web of mutual commitment. 

This principle is exactly why mates like Genn and Aaron (Scrapshot 13) continue to inspire me from halfway around the world, even though I might see them ~once every quarter. The density developed over years of varied involvement in each other’s lives, observing shared struggles and lending firsthand support, is hard to understate. On the flip side, the quality of newer, nascent friendships can still be driven by velocity. I lean on recent relationships formed in South America that also hold so much weight despite their immaturity: from camping four nights in the Amazon Rainforest with a pack of Dutch women, to inconspicuous meet-cute encounters in Argentina and Peru that started as trivial courtesies, but quickly morphed into substantial connections about lifestyle trade-offs and value systems.

Talking about intention, the priority for my late 20’s is to keep both sides of the garden tended: the beautiful buds who have grown up with the old Scrappy Sam and supported my chaotic twists and turns, and the sprouting seeds of new creative conspirators who will enter the stage as my new artistic identities bloom.  

(2) When I talk about interdependence, friendships are the natural vector of connection because all it takes is just one other person. But I think the holy grail of late 20’s fulfillment is tackling the need for belonging, the conscious choice to be part of something larger than yourself. The desire to find social-market fit becomes urgent as your interests and curiosities follow a new rhythm. This is a time where singular personalities upgrade into collective associations, satiating the urge to connect deeply and co-create meaning with others.  In this quest of searching for “my people”, I want my strengthened sense of independence to act as a compass, reorienting my mental bearings and putting out a bat signal to the people who energize me the most.

Since it pays to be proactive, I’ve been thinking a lot about the role and design of third spaces as a fruitful breeding ground for organic community. One of the core tribulations of adulthood is learning where to find and form new relationships that best fit your evolving needs. What does an ideal third space look and feel like?

A quintessentially “good” coffee shop means much more to me than just the quality of their Colombian roasts and Ethiopian pourovers, and extends beyond the feel-good ambience used for work hubs or first dates. Rather, the shop becomes a playground that will activate my full sensory range. The second-hand taste of warm pastry, the subtle smell of ceremonial matcha, the reassuring touch of mahogany decor, the tender white noise of a dozen criss-crossing conversations, and the complete panoramic view of each small speck in the space, softly working in concert to create a unique universe that can only be lived just this once, before hard-resetting itself. 

Even more importantly, the space acts as fertile soil for serendipity, ushering in ebbs and flows of different humans for any degree of potential contact. As someone wise once said, all it takes is for some random stranger to appear once to change your life completely. Corny, but I love the optimistic jingle that an everyday choice can bring. And while the coffee shop is the most obvious example, I’ve been finding success by hanging around specialized scenes that facilitate the same energy. In recent months, I’ve joined a few collectives that embody this vision for connectedness:

I’m fascinated by the trajectory of these intentional, hyper-localized communities because their sole purpose is to provide structure to the search, while leaving just enough serendipity to retain the organic nature of the connections. There’s also an important element of self-selection and identity alignment that helps preserve the integrity of these spaces — birds of a colourful feather will flock together. Take for example the parallels drawn by The Neighborhood NYC, a new initiative to create a contained block of interconnectedness in East Williamsburg, Brooklyn: 

“Combines the serendipity of a college campus, the co-creation of Burning Man, the agency  of Silicon Valley, the vigor of a Midwestern high school track coach, and the culture of NYC.”

“The vision of a co-owned multi-family building with a solarpunk school and coworking space (think Montessori x MIT Media Lab x Aristotle x Chobani).”

I admit, the branding sounds both grandiose and goofy, probably appealing to a hyper-specific niche of humans. I’d take a leaf out of The Commons’ playbook, because their ethos of home outside of home resonates louder, one where “play, curiosity, and creativity define the culture”. Music to my ears! But to knock the efforts of grassroots community builders is to dismiss the sheer difficulty of wrangling people purely around the joys of camaraderie and companionship.

I reference these live-time budding communities because these are exactly the groups I want to surround myself with for the rest of my 20s. To me, this is peak interdependence: when you’re able to find a tribe of people who just get you, who shares in your struggles, who strives to push you, challenge you, and encourage you. That’s what I want to come home to.

When I place these building blocks side-by-side and spin these different shapes in my head — a thorny game of friendship tetris and community geometry — I’m left with the ultimate takeaway that acts as a guiding North Star for my late 20’s motivation:

“Don’t surround yourself with “smarter” people. The trick is to surround yourself with people who are free in ways you’re not.”3

My independence tour de force has shaped my worldview on what being free looks and feels like. With a more mindful outlook on the virtues of being a full-fledged adult, I’ve refined my taste palette of people I want to be around, charging the circuit for interdependence. The dream of freedom to pursue my versions of creative expression sets the stage for the last piece of my scrapbook, in which I commit to a big bold intention that my 20-year old self would’ve never imagined in a million years. Here’s the pièce de résistance to come full circle: intention.

{ACT III: INTENTION} 🐌

I’ve since done away with intense goal setting exercises and frothy new year’s resolutions, but if I had to distill ONE intention that is calling me in 2023, it is: 

But like, what does this even mean? Like the Herculean feat of scaling a 5000 meter high glacier-filled mountain, this phrase oozes with dramatic effect — from nomadic tech bro to full-time artist?! Let me try to extract the madness from each word:

To “make it” gives off the impression that there has to be a supreme success formula, like scaling my artwork to a grand exhibition hall or deriving ~80% of my income from my creative work. But setting these arbitrary milestones would be spitting in the face of early 20’s Sam, who by all accounts had mastered the value of doing something for its own sake, a lover of process over outcome.

To me, the hallmark of “making it” expands to the mindset of being free — if I feel the aliveness of every single day through the act of living and creating, then that’s all that matters to me. This is a sentiment that is hard to measure and quantify as a traditional goal, that I've consciously designed to be "unoptimizable".

“Full-time” is next in the hot seat, and the logical inference might be that I will transition my life into a newly evolved 9-5. One important note about my current 9-5 is that I'm on track to make a massive career bet that will shape my next professional decade: a charged entry into the urgent universe of climate tech4. On paper, splitting focus for both the technical & artistic sounds like a classic recipe for disaster: how can you go full-time on two things?

I want to emphasize that I do not want to completely uproot my built-up routines and rituals. As long as I find dedicated time in both my day job and night hustle to create, I'm hoping the "yin-yang, work-play, etc etc" duality absolves the need to drop my path as a technologist completely. I visualize a synergy similar to that of bumblebees and flowers: where my vocation cross-pollinates and inspires blooms of artistic action. In this way, the label of “full-time” serves as an orientation to life — seeing, thinking, and feeling artistically — rather than a blocking constraint.

The most nebulous part of the intention is the word artist, which happens to be where I spent the most time ruminating on how to neatly define. So I traced moments of my past to summon the times where I felt the most creative, and the associated activities that I can use as stepping stones. By looking backwards, three foundations emerge: my quirky personas developed in the thick of the performing arts, my emotional sides formed from a rolodex of memoir pieces and flash poems, and my well-mannered attempts at constructing visual art once in a blue moon. Phew, it looks like I’m not totally empty-handed when thinking about how to articulate my artistic identity.  

By crafting this personal pyramid of artistry — performance, language, visual — I head into the unmarked creative terrain with a bit more confidence, because at least I know where to place my time, energy, and attention. Here’s more flavour into how I’ve applied the pyramid model in practice:

The base of the pyramid embraces the performer's mindset, where the tenets of improv have penetrated every aspect of my life5. I view stage improv as the rawest, most generative form of art that I'm most confident in. From the early days of playing as Riff in Westside Story at age 15 to gaining the amateur-level chops at The Second City at age 21, performance has become such a cornerstone of my once-hidden artistic affinity. These days it’s less about actually getting on stage (a possible resurgence one day), and more about metamorphosing the skillsets as practical improv — showing the ultimate party tricks, hosting workshops for startup founders, yes and-ing the conversational volley in spontaneous dates, and finessing my way through new cities.

The middle of the pyramid is all about words. One of my future stretch goals is to write a fiction novel, steeped in magical realism and inspired by my favorite authors — Murakami, Kafka, Borges, Ozeki. But the process sounds harrowing. I’ll probably be traversing wildly varied forms of language in the meantime, particularly memoir and poetry. I think of crafting poetry akin to collecting drywood in a damp rainforest. Just as camping in the Amazon jungle taught me, you need to observe deeply to find the best materials. It can be a very frustrating procedure to sift through the wilted branches and unusable timber, but it’s a practice with massive payoff at the end.

I find the life of a poet fascinating because they seem to work in the extremes: alone, attempting to stitch together a world out of nothing; and connected, bridging their emotional interiority with human-to-human authenticity. You can read guides, tutorials, books, join communities, attend open mics, build writing groups, and cover yourself in literary inspiration. But in this realm the only way to get better is to do the work (aka keep publishing garbage and WIP drafts) and live a life worth living.

The third element around visual art is what I’m most intrigued to test because it literally allows me to get my hands dirty, to transfigure my wacky ideas into creatures of unique form and fashion. Despite what the cheesy smile in Scrapshot 19 suggests, I’ll be the first to say that me and pottery don’t really mix that well — my way with the clay is quite lacking and doesn’t feel like a natural extension of my creative juices. We’ll just have to dabble with other mediums — if I can teach myself software engineering, surely I can pick up a practice like acrylic painting, right? 

My biggest concern with embedding the artist’s way into every fabric of my lifestyle is facing an amplified version of imposter syndrome. I may have shed all doubts about my abilities as a product builder by hacking my way to technical prowess, but the unfortunate difference here: I have no existing background in the creative scene. I didn’t take any formal arts education, I have no works to showcase in a portfolio, I lack the established network to find my co-conspirators for cool projects. But I remind myself that the illustrious Murakami didn’t start writing fiction until he was 29. There’s the kicker: I have the will to start, but that doesn’t mean I’m not still scared.      

I have no doubt it’ll be difficult to combat my fearful mind, who will plunge into the recesses of my chronicled childhood and claim that art never is, and never will be, my calling in life. Despite these mental whirlwinds, I head into this next phase ready to embrace every second of discomfort. The dominant common thread that neatly wraps these three art forms is my love for storytelling, which both anchors my self-expression and drives momentum. I’m grateful for all the lived experiences and tender communities that consistently function as my renewable energy source. After all, I am always looking for the most extreme version of an experience.

I started to sketch how I could make this new identity a reality, in a format I like to call dream drafts. The premise of this exercise is super simple. First, you dream. You assemble your fragmented aspirations and inspirations that are lodged inside your heart. You spawn a list of these seemingly crazy possibilities, and let each simmer in your brain. Then, you must dare to do. Start small and execute one action that will make one of those dreams a little more legible, a little more believable. I’m hoping that if I run with this approach long enough, I won’t even recognize myself by the time I hit 30. 

Scrapshot 21 represents the live trial after a fortnight of dream drafts and a blazing set of mental gymnastics. Is my poetry even good enough? What will the seasoned lyricists in the room think? But this is why I’m here: the purpose of expressing truths that I only I can express, and the desire to dance with the same type creatives that charge me up.

I read my flash poem clairvoyant voyager, which applied the motif of outer space to illustrate the early stages of romantic love. In my terms, it's a cocktail of melancholy, sensuality, and lyricality. Shoutout to my favorite Mongolian momma Bolor, who encouraged me to craft something at the previous event and kept me accountable to share just a morsel, even if it felt like morse code to me.

When this idea of seriously pursuing art popped into my head on a cold November night, I wanted to laugh it off as another one of my silly schemes to chase a new type of novelty. I confronted a sincere question of why I care so much about being artistic and creative in the first place, especially if it signals such a massive departure to where I’ve taken my life up to this point.

My current answer boils down to two words: purpose and people. I realized that art is the only medium that allows me to be me. Meaning: any idea I want to explore, any modicum of meaning I want to express, any connection I want to pursue… the MVP (maximally-viable pathway) is art. Simply, the people I want to surround myself with have a similar intensity of spirit: one that relishes in the chaotic messiness of creation, one that appreciates the flavour of aesthetics in everyday things, one that prioritizes wonder and imagination over concreteness, one with performative playfulness.

The breadcrumbs from my personal blog reassure me that I was planting all the right seeds even a year ago, while I pranced around the museums in Madrid. A glimpse into the germination from my old piece titled art forms: 

“Art forms are simultaneously a window, a mirror, and a microphone. Art is giving your voice tangibility — something is artistic because it has soul, heart, and essence that only you can imbue. Art forms are a container that enables the delivery of a fundamental human craving: connection.”

{EPILOGUE} 🦋

These days I ask myself whether this new direction in life will make me happy in the long-run, because of all the struggles and sacrifices that will follow me into the unforgiving void. But then I counter: is happiness really the end game to all of this? 

This apt quote from Michelle Jia's “Self Care is an Illusion” opened new flood gates on defining feelings of happiness vs. investing deeply in life: 

"I’m not that happy, I began, but. Given this time in my life, I think I have something that’s more important to me than happiness. I struggled to put this thing into words. Embeddedness, maybe? Or, rather… I feel very interested in my life. I find my life very interesting. I feel like an animal in the forest, with all of her feet on the ground. I have many things to grip onto, and I have things I want to do. I feel deeply involved in my life. I am invested in it. I do not want my life to end."

I‘ve also been finding it hard to describe my current state of being as this nebulous quality of ~happy~. The pangs of wistfulness and loneliness still ring true, as I stare back into the vibrant vortex of Brooklyn, a world temporarily left behind.

But with so many recent moments of pleasure and excitement in South America, doesn't that dissonance feel a bit strange? Should it? Perhaps satisfied fits better as a more diluted emotion. No, that isn't quite right either — I'm definitely more than satisfied with my current direction in life. After all, my second round of country-hopping mixes together familiarity and freshness in a way that oscillates between intensity and intentionality, with just the Goldilocks warmth I'm looking for. I may have lost a bit of momentum from the collectives and communities I joined over the past year, but the beauty of these groups is that there’s always room on the boat if I decide to set sail with them again.  

On another corner of the internet, Ava’s “patterns and progress” expresses a state of being so deeply woven in my current lifestyle — the fact that I’m too good at jumping:

“When I started this blog I was scared I was someone who could never stick with anything. I’m too good at leaving, too good at packing. Meaning: too good at jumping into a new life. But now I know that I’m also capable of persistence over time. I’ve proven that to myself. My need for exploration is tempered by my need to put down roots. I will always be the same, but… I am constantly shapeshifting, adapting, and evolving.”

Both Michelle and Ava point to choosing a high quality of life. Being so immersed in something, or many things, pushes you to prowl like an animal, fully alert and attentive to the world created underneath your footprints. To search for the social gravity enhanced by the energy of other souls on similar journeys. To care about something so much that you are completely absorbed by it and in it. To transition from freeform exploration to anchored adventurousness, in the name of true rootedness.

Living on the road with a backpack for the past two years has served one ultimate purpose: to make me entirely comfortable in my own skin, no matter what the occasion or context or environment. This mindset queues up as the backbone for my late 20’s, because the artist’s way is a road paved with spikes and tar and potholes and dynamite. If I’m not careful, I might trigger an explosion, or worse yet, an implosion of my maturing self.

But maybe that’s okay. Maybe that’s entirely the point. Maybe the process of becoming someone who I can’t recognize is designed to be severely treacherous. Maybe towing the line between utter self-accepting weirdo and complete charismatic world builder is more than a nice thought, and becomes a constant source of pride. 

I feel a strange sense of nostalgic novelty6 as I close another important chapter of my life. I’m collecting fragments of stability, hoping to clean up my scrambled jigsaw. Some pieces will inevitably click together as I find the fit, but some don’t fit at all. Again, that’s totally fine! See, you can’t please everyone, so you’ve got to please yourself. I say, play your own way! Don’t dance the way the public wants you to, like some circus monkey stripped of its free will. What’s wrong with feeling good?

This is what the rest of 2023 is going to be all about: acting on those impulses, curating an assembly of artsy muses, and breathing life into unformed emotions. As an homage to the late Joan Didion, the end of this scrapbook marks the beginning of the year(s) of magical making. I’m willing to start over as many times as necessary, to make sure the next installment of my narrative is filled with kaleidoscopic streams of my creations — no matter how misshapen their forms may be.

A note to my future struggling self: When you're chasing your dreams, your job isn't to figure out how things are going to work out. Not knowing keeps all the possibilities open, it keeps all the worlds alive. Just keep showing up :) 

Sending off the mid-20s to the scrapyard,

A Pre-27, Savoury Sam 🙆‍♂️

Hey, y’all! It’s been a while since I’ve popped anything in this newsletter. Every time August rolls around, I get random bursts of creativity and inspiration that stem from the anticipation of turning older. While birthdays continue to lose their luster, my fascination with the world consistently expands. Since 2021, a lot has transpired after I went fully nomadic and started wandering the Middle East. The unifying thread that I tell myself: A constant search: for culture, for conversation, for connection.

If solo backpacking has taught me any valuable lesson, it’s that constant change never goes away. Another year of earned wisdom tells me that the most important thing is to pay close attention to your levels of curiosity, comfort, and contentment so that you’re living the way you want to. If not, you can always reset and re-calibrate.

Last year I published a thorough “life-in-review” and conjured 10+ different custom frameworks to highlight the most formative experiences in my first quarter of life. Slightly self-aggrandizing, but playfully introspective. Today’s piece trades the typical technicality for more subtle sentiments about different approaches to live life fully.

I want to distill three major life elements to help illuminate the winding labyrinth called the “Late-20s”. In classic sam’s sandbox fashion, I’ve crafted a three-part model that serves as our guiding compass to navigate what it means to run life experiments, what it means to build taste, and what it means to enter scenes. We love feedback loops around here, so let me introduce you to the Fluxus Flywheel:

PS. Today I’m eschewing my love for spontaneity and taking myself on a planned date for my 26th. If you’re curious about how I structured my itinerary, take a peek here!

1) “Yes And, Sam”: On Experimentation 🔬

Shaping spontaneity: an experimental life is an exciting one!

Recently I’ve been obsessed with an avant-garde artistic movement in the early 1960s called Fluxus. Let’s just linger on this word for a moment — saying it out loud slowly produces a certain kind of strength in your speech, doesn’t it? The root definition of flux implies “continuous flow or change”, which really mirrors the emergence and evolution of events in our own lives.

Birthed by Lithuanian-American artist George Maciunas, Fluxus was an artistic revolution where a fluid international group of artists, poets, and musicians came together with a shared impulse to integrate art and life. An illustrious bunch, notable contributors included Nam June Paik, Yoko Ono, and Alison Knowles. The nucleus of the movement thrived in New York, but cities like Berlin and Tokyo quickly adopted this quirky style. Fluxus resists categorization and embraces absurdist humour, involving spontaneous physical expression and democratizing creativity in a DIY fashion. This form is special precisely because it is atypical. Maciunas on flux:

“When asked to define Fluxus, Maciunas would often respond by playing recordings of barking dogs and honking geese, perhaps confounding his questioner but also demonstrating the experimentation and embrace of absurdity at its core.

Fluxus’s signature insight was that the best things in life are simple and often free. Fluxus was both a movement as well as a rebellion against the rigors of movements.”

I surface this fragment of art history because if you dissolve my current lifestyle into a boiling pot of water and extract the two most essential ingredients, the result is a strong affinity for experiences and experiments. This coincides with the core tenets of Fluxus and is why the movement resonates so strongly. The philosophy of “anti-art” is to collapse the boundaries between art and life by encouraging experimental thinking.

It’s no surprise that my favourite comedians of this generation — Nathan Fielder, Sacha Baron Cohen, and Bo Burnham — have developed the most profound art forms through intentional experimentation. They’ve directly tested bold big bets that range from unorthodox consulting services (Nathan For You, The Rehearsal) to fictional foreign journalism (Borat) to technology-induced existentialism (Bo Burnham: Inside).

To me, that’s best-in-class performance art: making people laugh, think, and feel deeply, while also shining a critical light on the most intriguing and insidious parts of human behaviour. Embodied parody, cringe comedy, method acting, mask work — you can brand the art form in dozens of different ways, but the takeaway is the same. Each of these comedians cracked the code on their own personal style and taste after thousands of thought experiments and field experiments.

“Okay, this is all great and nice and we can appreciate the idea of Fluxus, but how does this lead us to discover and develop taste?”

Let’s add shape to the spontaneity. It’s not too useful going through life just by trying random activities or hobbies once and calling it a day. This is generally okay, but we’ll have to be a bit more intentional if we want to develop taste. Of course, people try new things on a regular basis using the same language: I’m testing a new 5-step skincare routine OR I’m experimenting with hot saunas and ice baths. What usually tends to happen is that there’s a lack of accountability and integration with these tests — not only because of a lack of interest or momentum but a lack of guardrails and processes for learning.

As a Growth PM, I run product experiments for a living. I’m laser-focused on iterating and learning, when I tinker with the observed user experience or when I conduct large-scale statistical tests on our core features. We can adapt the same experimentation framework to expand our field of personal possibilities. The Yes, And principle comes back into play, where we superimpose our initial curiosity (“What do we want to try next?”) into actionable progress (“AND How does this help me develop my taste?”)

2) “Delicious, Nutritious”: On Taste 🍵

Cultivating identity: a taste-filled life is a richer one!

Taste is an interesting segue from experimentation because unlike the latter, it’s such a hard concept to pin down. Taste is usually tied to the philosophy branch of aesthetics. When someone has “good taste”, it means they appreciate the beauty and complexity of something “tasteful”. People typically conflate taste with any of its close cousins: interest, preference, and passion. These are related, but they’re passive: they don’t articulate the nuances in interpretation, expression, and action of tastefulness.

To me, taste is an important part of cultivating a multivariate identity detached from just work life or a basic set of interests. It takes a lot of consumption and curation to refine our tastes. Taste is also inherently mimetic at first: we sponge up the massive pools of likes and dislikes floating around in our immediate circles. Important life decisions are made with our inner taste programming that runs in the background — where we chose to live, what we keep in our homes, how we nourish our bodies, and what we choose in a life partner.

An important callout is that both appreciation and creation are forms of taste, but we don’t necessarily need both. I explored this idea last year in Appreciating Art for Non-Artists, where I argue that anyone has the capacity to engage meaningfully and introspectively with all kinds of art.

In Susan Sontag’s breakout essay Notes on Camp (1964), she details how taste typically comes in lanes, as a commitment to deep attention:

“There is taste in people, visual taste, taste in emotion — and there is taste in acts, taste in morality. Intelligence, as well, is really a kind of taste: taste in ideas. One of the facts to be reckoned with is that taste tends to develop very unevenly. It's rare that the same person has good visual taste and good taste in people or in ideas.”

I suddenly found myself in a mini meltdown mode. Do I even have taste in anything? I decided to run a quick & nerdy thought experiment: what if I plot different dimensions of taste on a bubble chart to evaluate where I stack up? The visualization:

The x-axis represents how developed my taste is in each category, while the y-axis illustrates the extent to which the category impacts my everyday life and others. While we can dissect every single quadrant in this graph, I’ll pick out the biggest bubbles to discuss, where relative size = relative importance. As I dive into creative communities, you’ll see categories like Art, Music, Comedy, and Literature shift more to the right. Recreation is a bit of a weird bucket of things because it refers to having a keen eye for experiences and events, and I’d like to think my novelty radar steadily strengthens as I get exposed to more. I’ll accept my defeat in areas like sport and fashion though!

Technology is a funny-sounding category (how can you have good taste in tech?), but its pervasiveness in today’s society is exactly what separates a casual user from a plugged-in proponent who appreciates the software intricacies of something seemingly simple like a chat app. Dichotomies exist: someone might prefer Apple Notes over Notion or Telegram over Whatsapp. But as we’ve acknowledged, it’s not about comparing raw preferences but instead having empathy for the merits of everything in the genre.

This note about appreciation is also important when we zoom into a more notorious category: art. People have polarizing opinions, and the danger is falling into the trap of turning snobbish over taste. Take this abstract art piece I saw at Art Paris in April:

Many people might be immediately put off by such a non-sensical painting, dismissing it as a random hodgepodge of scribbles and shapes. But a subjective interpretation shouldn’t be mixed up with a value judgment. In other words, different individuals might tag a given piece as “good” and “bad” (like my writing), but those within a threshold of taste can both disagree and still respect the artist’s creative process.

The journey of cultivating taste draws further parallels to the writing and editing process, via George Saunders:

“The way I revise is: I read my own text and imagine a little meter in my head, with “P” on one side (“Positive”) and “N”on the other (“Negative”). This involves making thousands of what I’ve come to think of as “micro-decisions.” These are intuitive, instantaneous — I just prefer this to that — I just have a feeling and react to that feeling, in the form of a cut phrase, or an added word, or an urge to move this whole section, and so on. And then I do that over and over, for months, sometimes years, until that needle stays up in the “P” zone for the whole length of the text…”

To get to this level of mastery and intuition, it takes thousands of reps and iterations where the majority of output ends up as failures. It’s like we’re waging a relentless war with ourselves to keep testing, keep refining. There’s a cautionary tale here around the risk of passive consumption: all the time we spend reading Twitter and scrolling Instagram and browsing bookstores and watching Netflix modifies us in a thousand little ways. Only when we allocate enough attention and dedication to something specific that we can slowly coax taste out of its cocoon. It’s the same with people: spend enough time with someone and they’ll bleed into us. At the extreme, we can reframe taste as a quality: having well-formed and well-informed opinions held loosely (openness to experiment) and tightly (firmness of articulation). Delicious nutritious, indeed!

3) “Man’s Search for Belonging”: On Scenes 🎩

Creativity from unity: a scene-based life is a fulfilling one!

In improv, the atomic unit of creation is a scene. Within the span of minutes, characters enter and exit, environments are architected and annihilated, and premises contort and coalesce in a crescendo of creative choices. A scene is by definition, in flux, and cannot survive without the collective creativity of players who are in complete synchronization. There’s that famous Shakespeare quote of “All the world’s a stage”, but I actually suggest a slight remix: “All of life's a scene”. A scene is not a place, but a living shapeshifting organism that evokes movement and multiplication.

Our job in life is to create the best damn scene in the way we want to with the people who get us. This is a direct callback to our Fluxus Flywheel: start with an experiment, develop the unique taste, and aggregate other outliers into a coalition.

After our nth experiment and the struggle of refining taste, the question morphs into: Where do we play? We know there must be others like us out there; we seek scenius.

. . .

Scenius = Scene + Genius

The father of ambient music, Brian Eno, coined the term as a product of Fluxus-style thinking. The communal form of genius: when buoyed by scenius, we act like genius. Eno observed that:

“What really happened was that there was sometimes very fertile scenes involving lots and lots of people – some of them artists, some of them collectors, some of them curators, thinkers, theorists, people who were fashionable and knew what the hip things were – all sorts of people who created a kind of ecology of talent.”

In last year’s birthday essay, I gushed about the huge value of the digital communities I joined over the pandemic. One year later, and I’m no longer active in any of them. This isn’t to say that I didn’t get immense value from being part of these amazing groups — aside from educational and professional opportunities, the number one benefit was the top-tier people I connected intimately with. My favourite type of personal network effect is when you see the cross-pollination of old friends into new spaces, providing a continuity to reinvest in established relationships.

As Joey DeBruin describes in the context of crypto communities, “humans are always balancing the need for inclusion and the need for differentiation”. The updated way to view communities isn’t as siloed buckets, but as a constellation of overlapping clouds:

Yet communities are porous — both barriers to entry and exit costs are minimal, and lack of participation doesn’t result in punishment or banishment. Despite efforts to onboard community evangelists and deploy engagement strategies, traditional community health is still tied to outcomes to achieve tangible goals rather than the process to express creativity (i.e. taste!)

Scenes are technically an extension of a full-fledged community, but a more precise definition would be: communities whose influence extends beyond the group itself and becomes foundational for a new way of thinking, doing, or creating.

Austin Kleon, the author of Steal Like An Artist (a very solid read!) on scenes:

“What I love about the idea of scenius is that it makes room in the story of creativity for the rest of us: the people who don’t consider ourselves geniuses. Being a valuable part of a scenius is not necessarily about how smart or talented you are, but about what you have to contribute—the ideas you share, the quality of the connections you make, and the conversations you start.”

So while we typically reference revolutionary movements like Fluxus, Silicon Valley, The Renaissance, and Les Années Folles as grade-A case studies, there’s something so empowering about the dreams of grassroots collectives that start from ground zero yet embody the DNA of scenius — mutual appreciation, rapid exchange, inspiring chaos.

In many ways, living in New York City is kind of like immersing in a microcosm of a 21st-century creative scene. Fluxus started in New York, and my modern rendition of the movement is also taking root in this monolithic metropolis. New York flows by default: city where you can both lose yourself and find yourself in the same blush. It's a type of immersion within a wildly diverse population, not unlike a forest canopy lined with critters, crawlers, and creatures that all contribute to the rich ecosystem. Swirling and swishing, that's what makes the New York energy so undeniably enticing.

We’ll see if my feelings last, but either way I’m going to be keeping a keen eye out for budding scenes on the horizon. I think one tangible way to explore this (outside from joining early-stage creative communities) is by harvesting the intrinsic power of physical places and gathering grounds. Well-designed third spaces can act as a core conduit for scene formation. Repeat players foster a deep loyalty and want to keep playing for the sake of play, rather than striving for a nebulous quantifiable objective.

One emerging scene that soft launched less than a week ago is The Commons, classified as a “space for inner-outer curiosity, co-created play & collective flourishing in SF”. I’m already emanoured by the range of experiences that members have shared: group meditations, music method classes, Bob Ross paint nights, French salons, and weekend hackathons. If this doesn’t scream scenius, then just listen to how they think about their concept:

“We may be a physical space yes, but what we really are is a container for humans w/ shared values of playful curiosity, kindness, and earnestness towards exploring their inner-outer worlds”

What tethers me to New York currently is not some fluffy optimism or some abstract desire for a fabricated American dream. It’s about mapping the truths, seeking the zeitgeists, searching for subcultures, and aiming for immersion; all these activities work in concert for discovery. Frankl’s Man’s Search for Meaning often gets touted as a masterclass for its take on inner freedom and happiness, but I see this as a distant stepping stone in my personal pantheon of pursuits. This is my story and it’s called Sam’s Search for Belonging — not in the friendship sense, but in the hunt for scenius.

Star Gazing: A Telescopic Outlook of the Late 20s 🌌

Quoting from one of my favourite authors, Ruth Ozeki in The Book of Form and Emptiness:

“What makes a person want so much? What gives things the power to enchant, and is there a limit to the desire for more?”

I think this is such a powerful set of questions that I keep coming back to because it always seems like I’m on the neverending quest for more. Every time the fated birthday fades into the next ordinary day, there’s a leftover hunger to want and do more. It’s time to build! Let’s plunge face-first into a scene! I want to dig within myself, and then keep digging past the cliches, the bad first drafts, the failed ideas, the shelved projects. To keep myself constantly off-kilter, to expand the search space, to want to know. Life is a two-part excavation: of the undiscovered outer world, and the unexamined within.

It’s the experiments, tastes, and scenes that help bridge the gap and provide colour and depth to a neverending excavation. But it’s also soothing to realize we can just chill out from time to time — no rush, let’s pause & play!

To cap off the end of my 25th in a more whimsical manner, I asked DALL·E 2 to construct what its 12-billion parameter GPT-3 brain believes as “living a fun and fresh lifestyle in your late 20s”. This is what the AI spits out for me:

So I guess the real next step is that I’ll be adding in more moments of jumping into my days. Up and down, high and low, from toe to toe.

Still in flux,
Sam

Subscribe now

This week features a collaborative piece that my friend Serinda and I crafted. We wanted to run a simple experiment: to test how deep we could stretch an author’s work to unlock new means of intentional reflection. Our premise goes beyond book reviews and book clubs that often only scratch the surface of mindful introspection.

We’re super happy to publish our responses to Between Two Kingdoms, a powerful memoir that touches on themes like illness, loss, uncertainty, presence, and renewal.

🌱 The Revival of a Soul

Two kingdoms, three messages

by Serinda Kong

Suleika Jaouad: diagnosed with leukemia at 22, fought for her life the next 4 years, and embarked on a 100-day, 150,000-mile road trip shortly after remission. Her journey leaves you in sympathy with how her cards were dealt. When you juxtapose my “normal” life as a healthy, 25-year old on the brink of a quarter-life crisis, the points of connection are far from limited.

While I enjoyed watching Suleika’s entire journey unfold in Between Two Kingdoms, there are three quotes that especially resonate and draw parallels to my own life.

“Ultimately the events of the last few years have been a terrible lesson in being present, and not just being present in my own life, but being present in the lives of the people I love.”

Death, or near-death experiences, shakes us up and reminds us to relish in all that we have. It puts a pause on the ruminating thoughts of past missteps and plans of the future. I am guilty of spending the majority of my time in the world of possibilities — from minute tasks such as what will I cook for dinner to what will my passions be at 50? For Suleika, cancer was the trigger to be present. For me, it was covid. Pre-pandemic, I would say I spent 20% of my time in the past, 10% in the present, and 70% in the future. That distribution shifted as the pandemic forced me to slow down and pause. I had to stop planning for the future, given the restrictions and uncertainty. I had to stay put.

In the past three years, I honed into being present with myself and others. Being present with myself began through a formal meditation process, but has transitioned to mindful living. Initially, I wasn’t able to sit in silence and observe myself — I felt like my mind was moving so quickly and I couldn’t hold up a stop sign. However, through time, I was able to slow down the busyness and unlock my third eye. Since developing this ability, I’ve been much more in-tune with myself — I notice when I get anxious and learn to follow my intuition. As much as I’d like to be present at all hours of the day, I often fall back into auto-pilot and go about life unconsciously. Though it takes some time to notice, all it takes is a mindful moment — of truly seeing my surroundings, listening to the sounds around me, feeling the floor beneath me, smelling the natural scents, and tasting my meal for its entirety to ground myself in the present again.

The pandemic restrictions prevented friends and family from seeing one another or made it limited to outdoor spaces or a specific number of people. This made me truly cherish the time I saw people in person. To be present with others meant physically putting my devices out of sight and mentally silencing the thoughts of what I was going to do after or what I should’ve done prior. Being present has allowed me to really listen, observe, and understand others. Although I am now a 15/35/50 split for past/present/future, there is still room for improvement. Though the pandemic predominantly triggers a negative sentiment, gaining more presence was a silver lining for me.

“What scared me more than death itself, was the thought of being remembered as someone else’s sad story of unmet potential.”

Suleika couldn’t have said my deepest fear more clearly. When you are raised in an immigrant family, there is an invisible weight of privilege on your shoulders. For I have not had to see my siblings get into relationships they didn’t want to be in, for the sake of the family’s future. For I have not had to flee my well-paying and respectable job in my home country for the possibility of a better life. For I have not had to survive in a place where I don’t speak the language and find my way alone. For my parents, and many like them, passion wasn’t part of their vocabulary. You were in a profession because it generated money and all pursuits led back to the objective of survival and just having “enough.”

Though my parents had not pressured me towards making a name for myself (they actually persuaded me not to pursue medicine), I will always know that no struggle I experience today will be comparable to what my parents and other immigrants have endured. To know that I’ve had access to higher education, healthy food, and community, put me at a better starting point to make the most of my life. For my parents, dreams were just dreams.  For me, dreams have the potential to be turned into reality. That’s the scariest part.

For Suleika, her fear of unmet potential came out during the process of battling cancer. My fear comes from reaching the age of 25. I very much identify with the quarter-life crisis and the invisible weight of privilege makes my fear of unmet potential even greater. This is especially when I’ve been constantly told that I have great potential in the contexts of career progression, learning a new skill, and in reference to “life.” Potential sounds great, but potential doesn’t bring in money, fame, or pride. In fact, potential is an empty promise unless it is fulfilled. With that said, I’m always left questioning what this potential is, whether this potential will be reached, and ultimately, whose definition of potential I’m working towards. Is it society’s or my own? Society may measure potential by money, fame, or pride, but to me, it’s a measure of how true I am to myself and if I feel like I’m living life to my fullest.

I’ve been in crisis-mode for the past 4 months, in between coasting at the baseline to living up to my potential. Baseline is life on auto-pilot — the activities of the day are routine and repetitive in nature and I feel bored, stagnant, and weary. Living up to my potential is having a beginner mindset, full of curiosity, and learning and growing each day. I feel driven, full of energy, and motivated. 

I want to live a life with presence and adventure, with new experiences, activities, and ideas to help me develop into the best version of myself. With this definition, there is no end to potential, as my life will constantly evolve, pushing the finish line further and further away. This fear of unmet potential is then somewhat irrational and impossible to achieve — I just need to remind myself of that.

“I can’t keep waiting until I’m ‘well-enough’ to start living again.”

Prior to her diagnosis, Suleika lived a life of adventure. As she began to heal, the spark of spontaneity reentered, in the form of a cross-country road trip to visit the strangers who wrote letters to her. Though people around her were hesitant about her adventure, she knew she couldn’t wait until she was “well-enough” to begin living.

Though covid has definitely had an influence on taming my daring nature, I’ve found myself delaying my next adventure of moving abroad. I’ve had a desire to live in a foreign place for some time as I crave the discomfort of new environments, love connecting with others from different cultures, and am eager to see my growth through navigating the unknown. A few years ago, I had been so set on moving — actively applying and interviewing for jobs, networking, and researching visas. Now, I’ve been hesitant, wanting to wait until the world has calmed down, for my career to be stable, for my brother to graduate high school, and for many other reasons my anxious mind fabricates. It feels ironic to think I want to control as much as I can in a world with so much uncertainty.

The last time I felt truly audacious was in 2019, when I made the decision to quit my first full-time job, only after 2 months of employment. I was in a specialized graduate program, on a paved track to accelerate my career, and with young and fun colleagues — what more could a 22-year old business graduate want? Apparently a lot more.

This was an important milestone for me, as during this period, I had an awakening. An awakening of who I was, what I valued, and what I wanted. I became aware that my core values of learning, connection, health and wellness, were not met. This trigger of misalignment between my profession and my values is what led me to leave my role, with the uncertainty of what I would do next. Following that mental release and liberation — recognizing my values, leaving my job, and deciding to move cities in a few weeks — I was seeking serenity, with a hint of adventure. Nature was calling.

I’ve always been fond of being among trees, water, and mountains as they bring a calming energy and often allow me to slow down. Algonquin Provincial Park was always on my list of places to visit, so I took this as an opportunity to go. The twist? Going solo, by means of hitchhiking.  

The trip kicked off with a nervous energy. Ahead of me was a whole lot of discomfort — discomfort in having to talk to new people, discomfort in possibly running out of food, and the discomfort of having to hitch a ride. That all dissipated as I watched the city fade into the distance and became engulfed on both sides by endless trees. After being dropped off at my hostel just on the outskirts of the park, I could hear the streams of running water, feel the dirt roads beneath my feet, smell the fresh air, and see the single winding road that would connect me to all the trails in Algonquin. I just needed a way to get there.

This trip had endless possibilities. I could’ve ended up meeting someone who would kidnap me (which is what my mom thought), meeting someone whose idea of adventure would be to rock climb down mountains (which I wouldn’t be entirely opposed to), or running out of food and having to fast (again, not the worst thing ever!) But none of those possibilities panned out. Instead, I met a few special people during that trip — a passionate emergency medic from Germany, who became my hiking and portage buddy, a values-driven learning & leadership partner at my current place of employment (talk about full circle), and a honeymooning couple, who left at sunrise and returned at sundown with freshly caught fish, each day. To date, I still admire my boldness in going on that adventure. 

There’s no doubt that traveling and adventures that push me outside my comfort zone, make me feel alive. These types of experiences challenge and re-energize me in ways that sleep or good food don’t, and are what I’ve been missing the past few years. 

Suleika has reminded me that I don’t need to be waiting until I’m ready and for everything to be in its place before making the leap. That means acknowledging my inner critic, but not allowing the objections or concerns to dictate how I live. Time is progressing, whether I like it or not, and things may never be fully “ready” for me to feel completely prepared. 2022 is the year to break out of my familiar, pandemic life and to seek discomfort and uncertainty, through the means of competing in my first jiu-jitsu competition, publicizing my writing (thank you Sam), and ultimately uprooting my life to somewhere new. Suleika said it best — “I decide to trust what feels unknown and frightening will soon feel familiar and safe.”

I don’t need to lose my loved ones or to have a near-death experience to be present with myself and others, to understand my own definition of potential and the impossible nature of achieving it, or to release the need for control to live freely. Suleika’s story has sparked reflection and inspiration that all in all, life is short, and it’s time to let my soul fly. 

So to all of you reading this, here’s my commitment to live more presently, to continue to grow into my best self, and to free the adventurous soul — the soul that solo backpacks Spain, that skydives over Byron Bay, and hitchhikes into provincial parks.

With gratitude,

Serinda

Leave a comment

🔮 The Kingdoms of Reality & Fantasy

Floating between two internal worlds, trying to find myself in the mix

by Sam Wong

I’ll admit, with great privilege, that sickness has not played a big role in the life of me and my family. It’s definitely true that I haven’t felt the extent of grief, loss, pain, and uncertainty that cancer brings. But where I resonate especially with Suleika Jaouad’s memoir is found in the title itself: being trapped between two proverbial kingdoms. For me, these two kingdoms are what actually happens (reality) and what I want to happen (fantasy). 

As Suleika speaks to the musicless nature of hospital hell, I can’t help but draw parallels to another type of liminal space — being alone with your thoughts, in all their idealistic, illogical, intense forms. Instead of the incessant beeping of medical equipment and muted chatter from hospital-goers, I find myself getting lost in IV drips of my own thoughts. This self-talk sways and beckons me in an almost infinite number of directions: “You could do this, you should feel this way, you would do better if you consider this 300th possibility, and you must keep asking yourself the question: what’s next?” 

Now, you might argue that this type of neuroticism isn’t necessarily a bad thing. Many people would kill to have acute self-awareness and the ability to process a lot of ideas at once. Yes, I do owe a lot of my personal development to a few “future-forward” guiding principles, which have formed a strong foundation for my early adult life. Among them: chasing novel experiences, harvesting my curiosities, and making large-scale changes. And yes, I do pride myself in being a possibilities thinker, striving to envision all sorts of possible futures and relishing in the beauty of asking “what if?”

To me, fantasizing is the ultimate form of intoxication. It’s easy to fall into daydream mode: imaginary career pivots, imaginary creative projects, imaginary encounters. I mean, why not let yourself dream a bit? The promise of what ‘could be’ acts as a temporary emotional lubricant, romanticizing the charm of The “New” instead of finding meaning in The “Now”. Mindfulness interventions like meditation provide the first line of defence, but wearing this armour can feel heavy at first as distractions continue to assault you. In other words, the practice of being present feels urgent, but competes on attention with an idealistic future.

What I tell myself: If reality is punishing, then fantasy is promising. 

(1) The Now vs. The New

The problem is if you’re like me and you spend a bit too much time in the fiction-verse, you tend to ignore the fact that you’re writing your own history in real-time. It’s the classic double-bind: both the movements of reality are not in your control and the events of fantasy are likely not going to play out in every desirable way. Escapism is certainly healthy in controlled doses, but only if you’re able to pull back and anchor your sentiments to the present. Suleika describes the same eagerness to look ahead but highlights how the looming threat of cancer strips away the joy of fantasizing: 

“My twelve-year-old self had different types of conversations from the ones I had at sixteen, or at twenty. But they all shared something in common: They were looking ahead. With mortality in the balance, one of life’s most delicious activities when you’re young—imagining your future—had become a frightening, despair-inducing exercise.”

Suleika’s cancer-induced situation shook her life philosophies to the very core, creating a sort of forcing function that prevented her from planning more than a few steps ahead. Survival was paramount. In my own situation, I can appreciate that it’s not just disease that can turn futuristic thinking into an infinite loop of despair. Even the most microscopic interruptions — an undesirable work project, an unexpected friendship break, an uninspiring conversation — can change the way we view our basket of prospects. 

I think it’s only fitting that we drive through memory lane before deciding how to best balance the competing pressures of reality vs. fantasy. I’ll share three substantial life moments, which intentionally mirrors Suleika’s own growth across her 20’s: romantic love, personal identity, and solo travel. I’ve linked to longer personal essays that cover each of these themes in-depth if you were curious: 

In February 2019, I attended a one-week business competition in Copenhagen and got bit by the love bug along the way. This wasn’t an uncommon sight at these events, as you’d be surrounded by highly motivated attractive people who were all in an emotionally-heightened state. My fatal error was visualizing all potential scenarios with this person, forecasting a non-existent relationship without taking the time to seriously consider what I wanted and needed in the present.  

In February 2020, only 6 months into my first corporate job, I found my mind already wandering to new spaces: what skills should I learn next, what new themes and topics would be most interesting to discover, and what would make me into the budding genius polymath? At work, most of my starting class would not be thinking about these grandiose thoughts, and I realized I was grappling with a few difficult questions: Why was I already charting out my corporate escape plan? Who should I become? What is my real potential?   

In February 2021, all I could think about was escaping the winter wasteland of Toronto at the height of almost draconian pandemic measures. I started designing a digital moodboard of my top destination draft picks: New York City, Los Angeles, London, Singapore, Sydney, Hong Kong, Tokyo, Paris, Istanbul... I noticed that I had defaulted to travel as an escape valve. As much as I try to convince myself that it would be super fulfilling to adopt a digital nomad lifestyle and immerse myself fully, the dominant reason for wanting to leave was my fear of stagnation. The funny thing is my default reaction is to leap forward, rather than to pause or reset. 

You could say I get stuck in a vortex of fantasy in the month of February: Futuristic February as I call it. I mean, can you blame me? We’re in the thick of the darkest point of the year: the sky hibernates in bated anticipation for brighter spring energy. With darkness comes a hunger, a stronger desire to seek light and illuminate a path forward. What my three chosen experiences had in common was the unfortunate habit of abandoning the pleasures of the real, and being controlled by the flattering attractions of the unreal. 

You ask: is there a remedy to stop us from going into fantasy freefall? What’s the point of all this preamble? The answer shouldn’t be surprising: being present and sharing presence make up the two-shot elixir. Yet I also want to offer some practical gifts to better illustrate this point, taken from both my life adventures and inspirations from Suleika. 

(2) The Present Time

I’m not intending this piece to be a pessimistic cautionary tale that claims future thinking is a terrible thing. After all, by sheer willpower and a willingness to reinvent herself after her chemotherapy chaos, Suleika carved out an unimaginable new future. This desire created a new design space in her life, where previous liabilities coalesced with new liberties. In her quest of leaving the familiar, she crafted new routines and rituals that hypercharged her post-cancer rebirth: from immersing in creative work like the Hundred-Day project to seeking silent refuge during forest cabin excursions. 

One ritual that comes to mind is appreciating the rites of passage we cross in life. Building on this spiritual take, I consider rites of passage as formative experiences that unshackle us from the phantoms of the past and ground us back in the present. In recent memory, this looks like: quitting jobs, moving cities, and making connections. 

These rites of passage allow us to migrate from one phase of our lives to another; they keep us from getting lost in transit. They show us a way to honor the space between no longer and not yet”

For Suleika, new love injected more passion and texture back into her life — we see that with her re-entry into the dating market. For Suleika, writing represented a flexible method for recounting experiences, sharing gratitude, and processing emotions — we see that when she actively engages with her letter pen pals. For Suleika, travel hurtled her out of old ways of being and created conditions for new ones to emerge — we see that from her trek to India, and later with her US road trip. 

Even though my present path feels drastically different than the author’s, the act of walking and crossing through these passages is what remains universal. 

For me, I’m still single, but happily accepting the current trade-offs of my nomadic lifestyle and understanding that “love” extends beyond just romantic contexts. For me, my personal identity is no longer tied to flashy titles — product manager, startup operator, technologist — but is framed as a kaleidoscopic career where “writer” and “comedian” are just as part of the equation. For me, solo travel is about extending the channels of connection: living, laughing, and learning with others from completely different worlds and on my own terms. In their own strange ways, I think all of these elements teach me how to be present, how to be a better human, and how to live. 

The “how to live” is the trickiest to untangle. Just like a seasoned chef’s refined recipe, figuring out the optimal flavour is a deeply personal endeavour. Though tastes change over time, I think a life worth living mixes foundational with aspirational elements. Not too bland where you feel stagnant, not too spicy where you feel numb without stimulus. This begs the question: what is the universal idea that anyone can tap into, as an antidote to living life with presence? My answer: connection.   

I love Suleika’s mentality of sending personal letters as a creative gateway to connection:

“The idea was that if you wanted to connect with someone out in the world, someone far removed from your own life, someone who maybe even seemed unknowable, you didn’t let the distance stop you—you said what the hell, and you wrote.”

Connection with others might just be the greatest equalizer, because it’s almost an unspoken requirement to be present in the presence of someone you care about. I think I want to take this specific ritual even further: giving thanks to people who I often don’t give enough credit to or take for granted, including my favourite online newsletter writers, old teachers and professors, and friends sprinkled across the globe. Integrating this type of routine into your daily affairs can be life-changing, especially with the level of serendipity that it boasts.    

I’ll summon a classic gardening analogy to tie it all together: routines and rituals become nutrient-rich soil that germinates all of our seeds of opportunity into the present. As long as you direct your attention to nurture this little corner of energy, you truly reap what you sow. That’s precisely what my goal-seeking for 2022 is all about: a year of focus, prioritizing attention to what really matters to me. Some practical tactics that I’m experimenting with: balance the number of “yeses” I say with firm “nos”, start with the one small thing, choose health first, go deep instead of wide, and share my gratitude with people who have significantly influenced me. 

(3) The Two Kingdoms, Remastered

I want to leave this response to Suleika’s memoir as a memo of hope and freedom to everyone who finds themselves stuck in an inescapable bubble, between two kingdoms.  

This is especially directed at the high-achiever crews I often find myself floating around — it seems second nature for the structured management consultants and ambitious tech founders to get clouded by future judgments. Funnily enough, these two groups use the same vocabulary: “x years and then exit”. For my increasing base of creative friends, I empathize with your lofty ambitions that may compete against enjoying the process for what it is: the desire to be published, the desire to be prolific, the desire to be perceived as someone of worth.

I’m not bashing any particular career decision. On the contrary, I wholeheartedly think where we choose to spend our time and energy, whether initially by choice or not, is the root of a self-confident & self-resilient identity. The important distinction here is resisting the tendency to flatten your self-worth into titles or outcomes. The golden rule: don’t let your identity be taken hostage by people or processes misaligned with your truth! 

There might come a point where something unexpected happens to challenge your identity to the core, to topple the foundation that made you whole. Sometimes this amorphous thing is a life-shattering event — for Suleika, it was cancer. Other times, the collapse takes the form of an emergent species, evolving with the changing environment — for me, it was the constant chase of novelty, through blind love, professional success, or faraway worlds. 

I’ve been meditating deeply with what it means to let go of the relentless pursuit of novelty; to put up the windshield wipers and swat away the allure of another new, shiny thing. There’s a human nature element at play: we flock to what we think we need and ignore what is often right in front of us. But there’s also subtle conditioning that happens constantly in our lives, where dozens of custom narratives are being constructed and flaunted around us. If we aren’t self-aware and present enough to notice, we get swept up in the wave of someone else’s kingdom. We lean into easily accessible defaults and activate autopilot on impulse. Time trickles by, and it de-weaponizes pain. Suffering gets bottled up until it becomes volcanic, exploding at the cusp of a destabilizing life event. Can we really be present when this whirlwind of chaos threatens to choke out our very essence of being?    

As my existential psychotherapist frequently reminds me, there will always be a subtle sense of suffering that lurks in the shadows. And that’s okay because you can’t have a happy utopian life in the present without confronting its complementary opposite: setback. 

To overcome possible setbacks in our mission to be present, we need to open ourselves to moments of intimacy, tenderness, and honesty. We need to invite dialogues with both people that seem to just “get us”, as well as people outside of our natural orbit. We need to accept that not everything is in our control, that shit just happens. We can either brush it off and keep moving or let it destroy us from the inside out. 

Pulling from one of my favourite sci-fi authors, Ted Chiang describes: “Past and future are the same and we can’t change either, only know them more fully.” I think that’s also key — knowing we have full agency over our own present helps shape the reality we want. 

In a beautiful excerpt at the end of her memoir, Suleika expresses similar observations in a wonderfully eloquent manner: 

“LIFE is not a controlled experiment. You can’t time-stamp when one thing turns into another, can’t quantify who impacts you in what way, can’t isolate which combination of factors alchemize into healing. There is no atlas charting that lonely, moonless stretch of highway between where you start and who you become.”

I know there’s no easy atlas to bring me back from fantasy into reality. Reading Between Two Kingdoms and crafting this response has been truly cathartic, breathing life into a dizzying array of emotions that I previously had no language for. I just need to remember that the map is not the territory; that even with all the unexpected and unwanted situations threatening to attack my essence at every angle, I’m still me and everything will be okay.

I wish you more presence,

Sam

Six months ago I was toiling away at a WeWork in West Village, Manhattan. At the cusp of my 25th birthday, I sat in dim light stringing together disparate thoughts to craft my “life in review”. I distinctly remember staring out into the boundless big city void, the evening streets buzzing with dreamy summer energy. My inner voice told me that even with all the change that had already occurred, my personal lifestyle curve would continue to explode exponentially towards another local maximum. It was right.

This past year was coloured with tones of discovery, creativity, and a predominant feeling of just “figuring things out”. I built a pipeline of online-to-offline friendships. I jumped from a beloved coffee giant into an early-stage technology startup. I grabbed a one-way ticket and moved to the Middle East. I dedicated intentional time to creative pursuits: hacking, designing, writing, storytelling, performing. Words like spontaneity and serendipity dominated my vocabulary. The common thread is that I didn’t really plan for things — I mean how could you really with the global insanity? — but trusting an unknown and unnamed process also brought a fair share of fears, doubts, and pains.

As I carry over this chaotically-curious mindset into the new year, I’m pausing to sit with an important truth: I’ve been in “divergent mode” the entire time. During this divergent period, I strived to broaden my inputs, ideas, and insights. Less was not more, and saying yes became an existential mantra. I invited in travel, career, love, identities, hobbies, communities, and all. Imagine me at a discount casino buffet, loading my plate to the brim and gorging on the supposedly satisfying nourishment.

But as my appetite for novelty and variety starts waning, I want to shift this design model towards convergence. To me, converging is about condensing the number of to-dos and ruthlessly deleting distractions. Converging is about making choices instead of glorifying optionality. Converging is about shifting from conventional success measures to an individual sense of deeper fulfillment. Convergence is focus.

If 2020 was a year of widening possibility and 2021 was a year of welcoming change, then 2022 is the third instalment about witnessing my focus in action.

This piece is a snapshot summary of my new goal system for 2022: The Flywheel of Focus. The flywheel framework is a reference to the early combustion engine, invented to transfer energy into the target vehicle as efficiently as possible. The more force you apply to the flywheel, the faster it spins, and the more energy it multiplies. The same principle is often applied in technology to stoke viral user growth, but my preferred application is around personal growth. We can think about decisions and actions that are self-reinforcing; those that generate momentum for our lifestyles.

Disguised as a new years resolution post, this is my fresh take on directing attention to what really matters to me. As the inimitable internet icon Visa expresses:

I want to see more unconventional applications of technical thinking. I want to see the birth of more purposeful creative projects. I want to see meaningful connections sprout organically, cultivated through a shared love of craft in all shapes and forms. Technically creative, deeply connected. Let’s focus on how I’ve packaged these goals!

A. Information system

My goal-setting process has largely evolved over the years: from a scientific, top-down brainstorm into a more introspective, bottom-up approach. While putting a rigid bullseye on a suite of quantifiable metrics can be effective for accountability, I wanted a better way to capture disconnected ideas and thoughts over the year. The objective: to create a robust time capsule for 2022 planning. With some technical duct-taped Frankensteining, I assembled a latticework of tools that would theoretically help me:

At first glance, this diagram definitely looks cool. In practice, this system sucked. You can probably guess the main design flaw: too many tools. It turned out to be a grossly inefficient, and honestly broken, version of Zettelkasten (a popularized tool for atomic note-taking). The capture was sporadic, while the retrieval was manually taxing. If the whole point of something like Obsidian is to see a robust knowledge graph of your archived content, the important caveat is that you need a high volume of tagged data points and backlinks for this to work. I think there’s a risk of info hazard: over-engineering these poor note systems to a point of breakage. We forget analogue solutions exist and function well: shoutout to pen & paper for always being there.

A note-to-self recommendation: pick one, run with it, and automate wherever possible. I’m probably migrating all my notes into Mem given its blistering speed and charming aesthetic. Can’t wait to play with the SMS and Zapier integrations as well!

Geeking aside, I combed through treasure troves of screenshots, notes, links, quotes, essays, & photos to prime the next step: visualizing key highlights in a mood board.

B. Moodboard design

You might be asking: Sam, who even uses mood boards nowadays? Isn’t Pinterest a dead app? I think inspiration and curation go hand-in-hand — you can only earn the right to play when you have all the puzzle pieces properly laid out. I realized platforms like Pinterest were more about reaching outwards for ideation, but I needed to connect what I already captured and focus inwards. To me, a well-constructed mood board is more than just a decorated collection of beautified stock images. It becomes a composable canvas to uncover patterns and add a multimedia layer to classic goal-setting. As the influencers would say, a mood board can be a mental lookbook of sorts.

Since I already spend a good chunk of my professional life in Figma, it naturally became my playground of choice. I arbitrarily landed on a four-quadrant orientation, which by coincidence morphed the style into something surprisingly structured (i.e. an internal-external split; textual-pictorial spectrum):

Organization is the key tenet here, channeling my inner Marie Kondo on the copious amounts of information & insights distributed across my various digital gardens. Going through this content carousel allowed me to revisit forgotten moments and bite-sized memories, transforming fleeting ideas into fresh perspectives. It’s always interesting to see what captured my attention at certain points of the year; these media are high-signal beacons of imagination that I act on or store for future use.

The verdict for 2021: my attention was scattered with no sense of linearity. But I suppose that’s the way my brain has worked since… forever. This year will be the first time that I deliberately disrupt this flurry of entropy towards a single source of truth. It’s time to hold space for a routine of paying attention to what I pay attention to.

With the mood boards in place, I was ready to extract my focus areas for 2022 (first-order) and distill a series of goals that matched the theme and timing (second-order).

C. Focus framework

I asked a handful of close friends how they would define “focus”, and the majority responded with: choosing one thing that you deem to be most important. Merriam-Webster provides another point-of-view: “directed attention”. In other ways, focus prioritizes the destruction of distraction, choking out the oxygen of things that don’t matter before they poison our mental & emotional spaces. Is there a right answer?

I think there’s merit in all these interpretations, but my framework intentionally prioritizes breadth. Just like how Netflix greases its subscriber-producer flywheel with personalized data, content library, and optimized distribution, I’m also keen to adopt a multi-layer approach, while retaining the principle of focus as tightly as possible.

Two of my favourite online writers in a distant orbit immediately come to mind as inspirations: Patricia Mou and Linus Lee. I love how both of them have a strong sense of who they are and what they care about, and how they maintain depth of thinking despite the breadth in their interests and aspirations. In a subtle way, these thoughtful thinkers influence my nascent mental architecture through a kind of idea osmosis. Here’s the first iteration of my flywheel, framing each theme with various “F words”.

Fitness refers to taking care of myself on all levels as the first line of offence; a health-first peak performance. Fortune describes the engineering of luck and prosperity; being both experientially and financially “rich”. Friendship covers both investing heavily in close connections and tapping into communities that make my soul sing. Freedom anchors the system by directing focus to the personal and professional vision I have for myself. The focus scale slides from foundational to aspirational elements and then loops back again to reinforce itself. Each quadrant reflects a quarterly sequence, adding a time dimension to maintain focus over the year.

Overarching objective: It’s not a perfect model, and I might be sacrificing clarity for lyricality with all of the wacky alliterations. Critically though, this is capital-F ‘Focus’ on my own terms. I’m here to create a virtuous cycle of raising my health capital, financial capital, social capital, and spiritual capital to new heights. The other productive way I perceive my flywheel is an enabling function for what I want to see more of in the world. If there’s one all-encompassing philosophy that remains after the dust settles, stripping away all formal pretence, it has to be this:

“I want to build cool shit with cool people.”

Perhaps I’m positioning this as the ultimate gatekeeper of everything I choose and do. Features, feedback, functions, formulas, fears, futures, feelings, failures. All necessary ingredients to translate this somewhat vague mental model into something that feels more real, more alive — goals that can be communicated and shared across the pond.

D. Goal map 🧭

2,000+ words later and four frameworks later, here are my 2022 goals. As many of you know, I’m a fan of seasonal planning and quarterly OKRs as a health checkup. But I’m adding another twist this year in the form of a pirate’s treasure map. Plotting goals on a map helps gamify the system to an even larger extent. Overall, the most important trick I can implement as a hedge against overcommitment is purposefully saying “no”. Thus, the map is not the territory, but the map is the directional guidepost for focus.

Q1. Fitness:

1. [Mental] I want to build and launch 2 major technical side projects. “Mental fitness” is my goal of staying sharp. Whether I give birth to these children through conventional code or not, this is my route to shipping projects that push me to learn something new while producing something valuable to others. 

2. [Emotional] I want to publish at least 1 weekly writing piece. “Emotional fitness” is my goal of expressing openly. I’m already doing well here by focusing on my personal blog, so if there’s any stretch target here, it would be putting aside fears and sharing my work more widely, as tools for deeper conversations.

3. [Spiritual] I want to commit to 3 hours of meditative activity each week. “Spiritual fitness” is my goal of striving for internal calm, peace, and love. Meditative activity can be anything from sitting in silence and guided practices to digital detoxes and seaside walks (thank you for your easy access, Bosphorus!).

In both fitness and technology, one concept is pervasive: feedback loops. While these goals form the cornerstone of Q1 and are more aligned to fundamental habit-forming (i.e. building, writing, meditating), they are also meant to be composable lego blocks for 1) my overall approach to life and 2) a supportive bedrock for the balance of 2022.

I didn’t intentionally neglect the physical fitness aspect, but I’ve previously found it hard to manage goals like “run 5 km per day” without biohacking the shit out of my life. I had a similar feeling to building things: I felt stuck more often than not. I think the culprit was falling into a negative feedback loop, mistaking the work required to be really good at building valuable projects for the work required to get started at all.

Q2. Fortune:

1. [Experiential] I want to engage in at least 5 unique experiences each month. This goal is tied to a desire to expand my luck surface area. I’ve kept it a bit vague on purpose to account for different flavours of experiences. My lifestyle structure is set up to account for these possibilities: I’ll be spending a month in Portugal in March, a month in France in April, and a mystery mélange of cities in May.

2. [Financial] I want to generate 2 new sources of passive income that will add more financial stability. This builds on Q1’s mental fitness, where I stumble on a lucrative sweet spot through content creation, monetizable software, or other ventures. I already invest in crypto, but being proactive in web3 could be a win.

The focus of the Q2 phase is to refine my relationship with “being rich”, and find a way to create more stability when it comes to my livelihood. This means conjuring more luck in a focused manner, whether that means a chance encounter with a star local in Lisbon or Paris or an inconspicuous interaction with an online pen pal.

I’ll admit that “Fortune” is a rather strange word to choose here, but I didn’t want to make this quarter solely finance-focused (partly because my costs will still likely break even with my inflows during my travels). My mood board exercises made me realize that I’ve never made life decisions with financials as the prime motivator. This isn’t to say that I’ve been irresponsible with my earnings and savings — I’m supposed to be a mature adult, after all — but money just hasn’t been a core driver or detractor. On the flip side, I do acknowledge how important having capital reserves is to live fruitfully.

Q3. Friendship:

1. [Social] I want to hold >5 meaningful conversations each week. “Meaningful” can be subjective, but is typically associated with nontrivial conversation topics or dedicated spaces for connection. Originally this goal was about interacting with 10 new individuals per week, but I felt I would be falling into a trap of over-indexing for volume & variety rather than focusing on quality.

2. [Communal] I want to join a community I’m proud of. I took the complete opposite approach last year, where I dipped my toes into 10+ fellowships / DAOs / programs at any given point, with huge variance in my participation. This will hopefully build on the scaffolding of Q1 emotional & Q2 experiential, nurturing new friendships in artistic spaces like comedy and creative writing.

At first glance, these goals don’t look too difficult to meet consistently. I’ve taken the liberty of adopting a Goldilocks approach —not as stringent as my line-by-line #GOALSEEK 2020 spreadsheet, not as fluffy as my high-level Strategic Pillars in 2021. The crucial component about friendships is that they require lots of emotional energy and directed attention to nurture. That sounds obvious, but for someone who has been solo traveling and seeking stimulus, this goal holds an important weight and urgency.

When it comes to communities, I like that there’s both a culture of creation and an attitude of accountability if I decide to focus on only one or two. Instead of splitting my time and care into a spider web of groups, where efforts become arms-length and half-assed, I want to consciously give and share with people I’m invested in. This means subscribing to an age-old adage: “leave something better than when you found it”.

Q4. Freedom:

1. [Personal] I want to end the year with one capstone creative project, something that will become an essential part of my “life’s work-in-progress”. This extends the narrative of “Sam is building and shipping these neat weekend hustles” to “Sam is working hard towards this one thing with pure conviction”. This goal is part of a longer pathway to unlock true creative independence and strengthen my voice.

2. [Professional] I want to align on one clear direction for my career in the short term. This goal is in direct reference to the number of equally shiny, equally enticing paths glowing brighter in the distance. Do I want to jump ship to another high-growth startup? Do I give up my soul for the life of a founder? Do I apply to Big Tech for the option to spend more time on creative projects?

3. [Existential] I want to articulate a one-line vision statement for my life in a clear and truthful way. While I’m an expert at elongating and overcomplicating things to the max, things that are concise and punchy are just as attractive to me. This goal could take shape as part one of my 2022 reflections as well, along with a baked-in reminder to schedule time with my wonderful psychotherapist.

While I’m not in the business of choosing favourites, there’s a soft spot in my heart for the potential that Q4 holds. On closer examination, you’ll see the duality that the Q1 and Q4 goals form, just like a pristine mirror. Specifically, the focus on creative work and spiritual health resurfaces. This is where I want to settle back into a more spiritual vibe, to contemplate how I traversed the outer and inner worlds that I’m privileged to call my homes. Processing the thoughts and emotions, one at a time.

The goals in this part of the flywheel are loftier and overarching, but by no means less measurable. On the contrary, they can be viewed as a cumulative checkpoint that is tied to what happens in the first 9 months of the year. That’s the magic of the focus flywheel: even as the goals reach their curtain call for the quarter, they persist in the background as the cycle spins with more fervour, more vibrancy. From the wise words of the iconic Ferris Bueller: Life moves pretty fast.

Postscript: from wishes to wheels, a sam story ☄️

If you told me a year ago that I'd have pivoted into technology with no prior experience in just a few months, I'd have laughed. If you told me a year ago that I'd be promoting and publishing my own projects & pieces across different channels, I'd be chortling. If you told me a year ago that I would move across the world to live in Turkey, I'd have rolled on the floor. But with my constantly nonlinear life path, I'd have stood back up and seriously considered each scenario. To remind me again:

If 2020 was a year of widening possibility and 2021 was a year of welcoming change, then 2022 is the third instalment about witnessing my focus in action.

Far from being a post-mortem, this piece is yet another widget on the reflective time machine that I've slowly started building for myself. Writing in public has been a powerful practice — it has activated me intellectually and supercharged me emotionally. For that, I'm so grateful for the creative tailwinds carried from 2021.

If you're somehow STILL reading this word vomit, I appreciate you more than you'll ever know. We're all gonna make it. Here's to new saucy shenanigans in 2022.

I wish you focus,

Sam

Lately, I've been tapping more into the creative part of my identity, even venturing outside the comfortable ambiguity of the improv stage. Instead, I wanted to expand my toolkit with sketch comedy, which places a heavier emphasis on storyboarding and smart humour injected intentionally. In many ways, sketch is even more of a hairy beast than improv. You’re making a bet on one core concept and fleshing out a story arc entirely. You can’t iterate on the live environment with your quick-witted scene partners, and it’s hard to tease out games and plotlines with no immediate reactions. Every stroke of genius that gives birth to a Borat-level character comes with hundreds of half-baked duds and dead script skeletons. My instructor’s response to most of my sketches: “Decent setup and wordplay, go further with each beat, not enough jokes.”

What inspires me the most to explore comedy as an art form is how it combines multiple sources of media together — dramatic screenplays, stage performance, video production, and written speech — to convey unique points of view. It helps me realize that language is truly the most decentralized technology we have. A timeless tool for transformative thought that is both universal, yet nuanced for any individual. By cleverly applying aspects of language and speech, you're free to explore complex concepts and thoughtful themes about anything, in a lighthearted playful manner.

I think this kind of narrative structure is so freeing and raw. Taking from both the world and from within. Knowing that the simplest way to “get laughs” is to just stay absolutely authentic and true to your own way of worldbuilding. That’s the ultimate goal for me: to draw from every single aspect of my reality to become a multimedia comedian. If I manage to keep up this enthusiasm, this might be the start of a super ambitious goal: to aim for the SNL staff writer role one day. A true creative aspiration!

The following sketch is a 3-hour brainchild, where I challenged myself to craft a parody in the style of SNL's Weekend Update. The format takes the traditional news broadcast and organizes skits & jokes based on topical current events. Here's the result of combining my fascination with the technology world with a nod to the iconic Wizard of Oz. Presenting my inorganically organic work, “Wicked Witch of the Web”:

Subscribe now

I'll be peppering in brief commentary throughout this script about my creative choices and moments of inspiration drawn from personal experiences. The premise of using the web as a window into the world gave me lots of flexibility and variables to play with, especially with my goal of creating a more mischievous tone. The first beat builds the backdrop and develops the universe: Who is this witch? What does she really care about? How does she view the world and the web?

Wicked Witch Weekend Update Sam Wong Vf

24.2KB ∙ PDF file

Download

Download

At the outset, I needed to make this witch character just as malevolent as her counterpart in Wizard of Oz. This meant pulling from the witch's motivations, quirks, patterns, and symbols — all in the context of this new digitally-informed landscape. That’s the main catch with writing monologues instead of the multi-character skit format. Breadth is replaced with depth. The main subject has to feel fully fleshed out. The line “Double, double, toil and trouble. Emails burn & notifications bubble” is actually taken from the witches in Macbeth, but I weighed giving her an almost poetic voice as more important than strictly staying in the narrative bounds of Oz. The audience learns about her devious goals and holier-than-thou attitude, as she harshly dismisses vanilla white hat hackers as just “sweaty programming peasants”. Sorry, developers!

To replicate the SNL personality, I dedicated the second beat to incorporate more physical comedy into the scene. The classic stirring-of-the-cauldron motion harks back to a witch's core means of creation: magic potions. Blending the visceral imagery with cooking metaphors expands the scope of horror and hilarity. This choice also accentuates the witch's crazed craving for causing turmoil on the web. At this phase of the script, I embrace the creative direction by exposing hints of the bigger picture and taking jabs at current events. For example, the monolithic entity of “Big Tech” often gets a lot of flak for designing addictive user experiences to convert attention into monetization (e.g. TikTok’s secret). This results in an extractive race to the bottom mindset. The witch is fully aware of this. “Digital destruction” is her goal, after all. In a sobering twist of fate, the institutional power now resides in the hands of a slick sorcerer who casually controls the levers of online virality and toxicity.

This third beat is where the sketch escalates further by layering in a subtle societal sub-commentary on sensitive tech topics: cybersecurity and continuous consumption. While we're desensitized to algorithm-centric products like TikTok and Twitter — masking as essential tools through their ubiquity and utility — we’re actually more conscious of things that explicitly affect our quality of life. Everything from technical bugs that limit our communication to the charm of magic money that is mysteriously programmable, capitalizing on our interest and ignorance. Importantly, this sketch centers around the idea of pinning a single source of blame (the Wicked Witch of the Web) to all the problems of being too plugged in. Imagine a world where we could re-direct all our frustrations to a single named body and re-allocate our priorities to dismantle these broken systems in place. Note: I also go crazy with the tech puns, associating ghoulish & Google and giving Slack and Zoom some quick cameos too!

You also can’t escape the presence of crypto while surfing the web nowadays. The promise of an ownerless, borderless, decentralized internet is in the name of pure prosocial value, but this sentiment is often corrupted by the focus on financialization. In other words, the mass market shilling of so-called “shitcoins” promises riches beyond anyone’s imagination. Again, we see the strength of skating across real truths of our current reality through comedy. It’s not a surprise that I make the witch take full advantage of such manic energy, which sets up for the ultimate curtain call:

A Meta Commentary 🧬

Unlike most SNL Weekend Updates that present their climax as a buildup of previous jokes, my ending conjures a different twist. Just when you think the witch is done with her technological tirade, she shows her final hand and transforms the host into an internet troll. When I first thought of this idea, I almost laughed my way out of this framing. Way too silly, not enough substance, right? Then I remembered what all my improv & sketch teachers had drilled into my mind: be absurd only if you can be specific and believable. Since the callback is derived from the witch's supposed spell-based superpowers, the troll joke doesn't betray her character’s philosophy. Rather, it adds a splash of depth into the mix! It also gives me the liberty to call out the not-so-pleasant parts of internet sub-forum culture on open hivemind platforms like Reddit.

There were also many other technical concepts I could have sprinkled into the story: antique web relics (paywalls, targeted ads, malware), explicit callouts with witchcraft wordplay (Apple & poison apples, Facebook & spellbooks), and deeper extensions of the witch's universe (dark web, blockchains). In my view though, the cherry of this script is giving space for the witch to inhabit her own mysterious cryptic vibe through lyrical dialogue. The best thing about crafting a monologue with a well-known muse is that the tried-and-true tropes already exist as scaffolding. So instead of stressing about custom character backstories, the decisions become simpler: how do we apply these pre-vetted LEGO pieces to the funny social commentary we want to propel?

At the end of the day, writing sketch comedy requires difficult trade-offs, and there's no way of telling how audiences will react to jokes until the moment they're executed. If I’m honest with myself, I don’t think my work is conventionally funny — my brain doesn’t default to cheeky one-liners like sensational standup artists. There is a silver lining though. As long as I stay true to the characters and the environment, there are “no wrong choices”; only different pathways that hopefully coalesce into a sound story. Only then will the laughs naturally come!

There’s one quote that has always stuck with me since the improv training days:

“The times we're living in just defy all logic. So we find and make truth in comedy by doubling down on absurdity and commenting on human nature authentically”

And to me, personal authenticity is the most beautiful part of the comedic creative process :)

Share sam's sandbox

In September I spent a whole weekend floating through every little nanny and crook of Mexico City, eagerly taking in its rich culture, flavourful cuisine, and authentic chatter livening up the streets. The most striking thing to me was the mixture of art and architecture that branded the city with a particular aesthetic. The contours of winding neighbourhoods created a web of welcoming sights & sounds, laced with symmetric cobblestone bricks in one corner and unpaved freeform roads in another. The antique history blended with a modern-day gloss. The freeform vines hugged and wrapped around sprawling buildings in a sea of city greenery — a true urban jungle.

After some reflection, I realized we don’t pay nearly enough attention to the artistry surrounding us on a regular basis. Periodically visiting museums and pop-up exhibits satisfies some of that deficiency, but implies you can only find these elements in specialized showrooms or glorified galleries. Then there’s the consequence of how being groomed in a traditional business bubble stifles our sense of creative wonder. We get bogged down in the megacity ivory towers and forget to enjoy the scenery. We neglect the sensations swirling around us. A reminder that presence is so crucial.

While in Mexico, I picked up a book of a non-profit art project birthed in Brussels, called Rectangle. It was a true spur-of-the-moment decision. I originally thought, “I don’t really have any formal qualifications to conduct an art critique”, but knew I wanted to better understand how to interpret art as a self-proclaimed non-artist. I know there’s probably a camp that is completely averse to overthinking art, arguing the whole point is to subjectively just “feel it”. But my counterpoint is that making meaning and collecting inspiration is only possible if we intentionally apply art as a magnifying glass to search for nuggets of truth — both about us and about the world.

As I think about how to build a better world as a new technologist, core principles hold weight: Intentional design matters. Understanding the human condition matters. Excavating for more beauty, more elegance, and more tenderness matters! While this piece is anchored by first exploring the art style of Rectangle’s project, I also want to extend these timeless observations to the technology-enabled world we live in. So I propose practicing “artistic audits” as a way to seek truth through all art forms. With this desire, I pose several follow-up questions: What are the merits of transience vs. permanence in artistic contexts? To what extent is art embedded into the DNA of modern technology stacks? Is today’s digital art wave through NFTs just part of the boom-bust culture cycle, or is a massive paradigm shift in the air? Let’s find out.

I. Physical Art: Interacting With Intention 🧩

Rectangle aimed to challenge processes of image-making: how can everyday objects be applied creatively? The main artistic medium is unconventional: configuring creativity into custom out-of-home billboards. Every two months, the group would blow up a different image showcasing ideas from the invited artist and unveiling their solo exhibition in the studio space below the board. The consortium refers to these creator-led environments as “off-spaces”, contributing to a sense of silent activism:

“We have developed a particular interest in advertising and its apparatus. Our purpose is to challenge both its visual language and its proliferation in public and private space.”

I think the intersection between art and outdoor advertising is fascinating because the form function expands beyond visual appeal and takes on a psychological angle. Your senses get attacked several times: once by the imagery, twice by the instigation to act. Notably, the call to action is typically making some kind of purchase, but the most successful out-of-home campaigns are those that allow some kind of feeling to linger. We normally overlook the artistic value of billboards, as we associate them with large-scale corporate campaigns looking solely to harvest customer eyeballs and share-of-mind. Historically, the use case of billboards supported that narrative, productizing the viewing experience and reflecting the rent-seeking ideals of mass globalization. Artistically, billboards offer an intimate double-sided invitation: an invitation for artists to play with open canvas, an invitation for citizens to pause, consider, interact.

The most interesting part of Rectangle is its focus on accessibility. I empathize with the premise that you don’t have to go to a fancy art gallery to appreciate the creativity of localized creativity in your own backyard. The ability to decide the destiny of a space empowers emerging artists to challenge norms. The rotation of exhibitions adds impermanence and imbues the project with ephemeral beauty. In other words, billboards play the role of fleeting artistic ghosts. They are as much a container as a canvas, a conduit to support the emotional exorcisms that happen in two parallel experiences: the artist’s creative process & the visitor’s interpretive process.

To support my own interpretive process, I crafted a quick three-step framework to analyze four of my favourite works in the Rectangle catalogue. Since our main goal is to open up the conversations about art as non-artists, a systematic structure works!

1. Here Comes Your Neighbourhood (2013) - Peter Scott

• Investigation: Four regular individuals are playing with and photographing each other and the surrounding High Line in Manhattan. They’re all standing elevated on a pipe, each capturing different moments of being and living.

• Interpretation: I perceive this piece as a literal “living billboard”, offering the visitor & viewer the chance to experience themselves as both seeing and being seen. Urban research and observation is an underrated channel for thought.

• Introspection: I like this one because it shows simple interactions with outdoor environments is one the easiest ways to connect with a space. It makes me appreciate the value of taking breaks and the value of noticing the obscure.

2. Redemption (2012) - Jérémie Boyard

• Investigation: A mixed media installation that makes use of lighting, shadow, and objects to build a vertical structure. Below, a ring of large jugs filled with bright yellow fluid forms the base, tethering the wire branches to a bulky base.

• Interpretation: I admit this one is more abstract, but the multiple sources of light are worth discussing. The yellow jugs remind me of gasoline, proverbially speaking to energy sources that power our latticework of ideas and inspiration.

• Introspection: The exhibit’s triple layers “light” up my soul here: the top, shone by the external environment; the bottom, supercharged by our internal tanks; and the middle, the culmination of both worlds that spark my brightest ideas.

3. Canoë (2012) - Philippe Durand

• Investigation: A monochrome landscape with a curtain of greenery is the focal point, flanked by a tall red banner and a shorter stand, illustrating one premise: “it’s time for MIKO ice cream!” The river flows gently; a tender, idyllic break.

• Interpretation: I think even the most picturesque public places in the world are subject to rapid modernization. I like the contrast: aggressive advertising by travel agencies transforms serene spaces into a performative playground.

• Introspection: Durand’s subtle creative choice helps me consider what it really means to “unplug” from the world, away from sweet stimulants and impulses as simple as ice cream. I value the ability to go into a forest and just sit and see.

4. Family Affairs (2013) - Melanie Bonajo

• Investigation: A geometric structure is formed with an eccentric arrangement of props, including common household items, colourful crafts, distinct shapes. In the corner, an isolated and exposed woman faces away from these objects.

• Interpretation: Through clever physical design, Bonajo illustrates concepts of the domestic situation and the literal clutter in our lives fed by object-driven pleasure. The alienation is palpable, as the woman is reduced to mere object.

• Introspection: This speaks to me at multiple levels, as a series of cautionary tales: to not lose myself in the deluge of commoditization & commercialization, to embrace the non-linearity and non-symmetry of life, to respect raw solitude.

There is one common thread that ties all four chosen exhibits together: a conscious choice of physical materials and symbols that pave the way for deeper dialogues. Conducting a three-step artistic audit — investigation > interpretation > introspection — is cathartic, an exercise of both the heart and mind to organize net new emotions.

Tom Viaene speaks to the ethos of Rectangle, paving the way for a potential epilogue:

“It was not only by way of externalizing, and making more visible, the codes of contemporary art, that it played into changing institutional mores: through their opening up of spaces for dialogue and participation, the billboards were also there to counteract the aloofness of a lot of visual art contexts.”

II. Digital Art: Embedding New Meaning 🪄

The beauty of the Rectangle project is derived from its impermanence — one day the artwork is there, and the next day it could be gone. This transient nature leads to inherent novelty and beauty through its built-in scarcity. As viewers, we can extend the exhibit’s life cycle by snapping a picture with our phones to capture the aesthetic, writing to bottle up our thoughts, and chatting with friends to recount the memories. However, this impermanence places a limiting constraint on the long-term growth and motivation of the artist. Just having a static billboard in one setting restricts their ability to gain recognition, relevance, and remuneration. The pain of “starving artists” is positively correlated with the public accessibility of their work and their air time.

We must extend our search to the digital realm to understand how permanence is the main path forward to preserve more beauty. In recent history, the art scene has seen a complete revival, a digitally-enabled creative Renaissance of sorts. The web now acts as a force multiplier for artists: they are empowered to grow audiences & communities through high-impact, financially-viable projects. Let’s welcome a special guest: NFTs.

NFT Effect: Generative, Interpretive, Speculative Art ⚡️

Artistic expressions in the technology of today come in several forms. One especially attractive trend is the rise of non-fungible tokens (NFTs). Modern artists immortalize their digital creations on the blockchain, allowing tribes of collectors, curators, and communities to congregate. NFTs also pave the way for new modes of ownership. The thing with crypto-skeptics is that they will always give the argument that digital art is nothing but overinflated JPEGs, GIFs, and media collectibles with no true value or meaning. But what they’re missing is a crucial point about artistic endeavours that we’ve unpacked so far: new forms of art can help us imagine new futures and inspire new possibilities for progress, and open up more access points to intrinsic beauty.

Interestingly, if we play back the billboard advertising analogy, there are crossovers with NFT projects: the latter scales awareness through symbols and status. NFTs represent a new digital billboard, compartmentalized into a personal and portable format. Importantly, the scarcity component is also retained: “non-fungibility” means the unique art is not interchangeable. And unlike the contained concept of the Rectangle project, there are almost boundless permutations when it comes to NFTs.

To see these creative combinations in action, let’s examine a curation of NFT projects I’ve invested in, with three distinct lenses and twists: music, gaming, and ecology.

Generative Art & Music: Tunes

Music. Tunes is a NFT project geared towards musical artists, giving owners the right to a randomly-generated song title. Audio, cover art, artist name, and functionalities are intentionally omitted for others to interpret and create. Some of my favourite titles include: “Half-Baked Enlightenment”, “Toucan-Toed Juice”, “Bed Bath & Beyonce”, “Molecule Men” — holders can find both meme value and musical value with Tunes.

Generative art is a burgeoning field that is based on the concept of “creative coding”. The artist initializes their first set of design components, then runs their machine learning algorithm to multiply the artwork automatically. Tunes hits two beats of this: first with the original song titles, and the second with custom cover art that can only be minted by the Tune holder. I think these types of synthetic media represent a key turning point for the art of the future, introducing randomness and abstraction to the creative process. We can appreciate the fact that the first forms of generative art have a rich history dating back to the 1960s, and the rise of neural nets and blockchains only serves to amplify this medium. This is largely positive: we can configure new methods for art & engineering to coexist, pushing the boundaries of our imaginations.

Interpretive Art & Games: Loot

Gaming. Loot is one of the most fascinating case studies in NFT art. The premise of the original launch was providing Loot Bags, which were simply text files with 8 phrases overlaid on a black background, with each phrase representing gear akin to those found in Dungeon & Dragons or World of Warcraft. The drop was so popular that it spawned the addition of More Loot (mLoot) to incentivize more participation.

Interpretive art is not an official term, yet is a useful one to help frame why Loot is so compelling. One of the quintessential terms you hear a lot in web3 is composability, the drag-and-drop building block quality of open-source software. You might already see the artistic appeal of this: the owner of the Loot NFT has complete freedom of what they do with it, similar to Tunes. At the simplest level, you decorate your own custom avatar as seen above. But if this concept is taken to the extreme, then we can appreciate the immense world-building potential. Unlike conventional top-down exhibits that are dictated by just the creators, Loot follows an inverted bottom-up approach. While yes, the idea originated with a single source, the artist makes a conscious choice of outsourcing further developments and iterations on top of their artistic scaffolding. In Loot’s case, this includes everything from new play-to-earn games, item rarity trackers, community guilds, developer tools, and more.

Speculative Art & Ecology: Ecodao

Ecology. In collaboration with a new decentralized autonomous organization ecodao, artist Wendi Yan merges aspects of science fiction, synthetic biology, and raw nature to craft Primordial Vision — a visceral and liminal narrative, “seeing before language”. Yan’s brilliance is summed up by her artistic process:

“The way I created Primordial Vision: 02021 was very much like a combination of alchemy and 3D printing. In the software, I layered images, gave them varied heights and roughness, mixed their colors and opacities, stacked them in specific orders, and added weathering or other natural effects. The result is these orbs, floating in a slightly tinted void that even I, the ‘creator’, don’t completely understand”

Speculative art is the best way to describe the almost dreamlike combination that results from unique ways of making — in this case, alchemy and 3D printing are called upon. Extending from the popular genre of speculative fiction, this type of art forces us to ask: how can we use our vivid imaginations productively in order to hold space for other voices and other stories, with care and compassion? These imaginary spaces are crucial. They keep us grounded and afloat together at a time when it’s still easy to feel shaky and uncertain about our future selves. Meanwhile, ecodao aims to be the frontrunner in developing a novel universal basic income (UBI) scheme for artists, as well as the 1st member-owned museum. This bold vision makes me immediately think back to our earlier exploration: what if the community-crowdsourced model were applied to Rectangle? Would such an isolated project benefit from more contributors and artists, each having a vested interest in experimenting with different formats and feelings? My heart says yes: imagine a concerted effort by an artist collective to wrestle back corporate control of billboards across the world, showcasing localized talents of passionate creators. Breathtaking!

III. Practical Applications: Embracing Art as Technologists 🖍

At this point, astute readers might point out the most logical intersection between art and technology: Design. Product design, UX design, UI design… that’s what it means to practically embrace art in tech, right? Well, not quite. If our coverage of NFT art projects has taught us anything, it’s the emergence of new art forms that are critical. The interplay goes way deeper than just a blanket classification, and extends into our final consideration about building artistic systems in a technically-advanced world.

To unpack what artistic systems might mean in practice, we can draw inspiration from the sensational May-Li Khoe, former VP Design at Khan Academy and ex-Design at Apple. She builds the case for an imaginative way of thinking through a process called subverting the status quo. Ways to do this include starting small, building on history, experimenting with format, creating spaces of change, and minding symbolism in life.

“People tend to have a very vivid imagination when they work in design: you actually, literally, have the tools and you're constantly drawing possible futures. When you are iterating, you are literally drawing multiple possible futures. So, if you take a second and think about something that you want to change, and you look around you… this is really an invitation to you to make some friends and start some shit and joyfully subvert the status quo!”

I find the idea of drawing multiple possible futures very appealing. Because that’s really what any artist strives to do, creating alternate versions of reality through their work. Status quo doesn’t exist in an artist’s world. The number of blank canvases accessible to them is the biggest clue: from paper to wood, from crafts to colours, from billboards to NFTs. The skeleton gets filled in with layers of text, texture, code, colour, sounds, styles, swishes. Art then, is a process of experimentation.

Essayist Yuk Hui’s Art and Cosmotechnics (2020) has a powerful quote on experiments:

“Art is the experimental mode of thinking between philosophy and engineering… Scientific thinking wants to improve the capacity of the senses, while philosophical thinking wants to develop other senses. It is in art that both can be united.”

This sentiment takes us full circle and connects all the disparate points raised in this piece, respecting the artistic standards of both physical resiliency and digital non-fungibility. Artistic systems connect all the different modes of feeling and thinking in a truly sensory fashion. Creating systems — spaces — lowers the costs of creativity. An experimental approach means a full commitment to trial-and-error, to thinking out loud, to intentional reflection; perspectives that are easily overlooked when you start commoditizing your work and playing for productivity. This is a love letter as much as it is a wake-up call, especially to techies who feel compelled to take on a new passion project every other week. Let’s make room for honest artistic exploration.

Rectangle taught us that collectively owning shared space is powerful: an invitation to use the exhibited artwork as an instrument to philosophically dissect the problems of how to live and coordinate. NFT projects reinforce the same message, where connection & coordination give rise to unique creative combinations. These phenomena about expanding space and coordinating ideas are poised to reach the masses as we shift to newer altered realities. To create long-lasting beauty, we need to put our brains and hearts together. To create long-lasting lessons for life, we need to embrace our differences and deficiencies as humans. To create good art, we need to meet people where they are.

What kind of aesthetic do you want your possible futures to look like?

Keep imagining and keep creating,

Leave a comment

For a while, I’ve been telling people that 2020 was probably the best year of my life. As I turn 25 today, I’m laughing at how the world works because the real kicker is that 2021 has already eclipsed 2020’s showing. I’ve never felt happier, more fulfilled, and free than I do now in these closing chapters of the early 20s. Society often labels these as the best years of young adult life, but I wonder if that’s just settling for the local maximum instead of chasing more exciting moments?

The “25 things I’ve learned in 25 years” structure has long been overdone and usually devolves into laundry lists of motivational musings. To flip the script, I’ll be mapping out my winding pathways and quirky decisions that have largely characterized my journey. If this piece inspires a few people to think differently about their mid-20s existence, that would be a win in my book. More than anything, I want this article to be branded as an inconspicuous time capsule item for a pleasant late 20’s surprise.

While I’m not discounting the difficulties and anxieties that are closely tied to growing up, it’s reassuring to know that there are really no rules in the game of early adulthood. I’m bullish on the idea of a quarter-life catalyst, as a direct counterpoint to the conventional quarter-life crisis. I love the gardening analogy here: to sow the seeds of growth involves finding your own truth and making commitments on what matters. To dive into the exact catalysts that have supercharged my entry into 25, we’ll start with the most tangible (professional) and work our way to the intangible (personal).

A portfolio of personal bets

Graduating with a degree in Finance means little for my current career trajectory, but bubbles up through the way I logic through problems. I argue that modern portfolio theory fits well as a mirror for managing ourselves as value-generating assets. Instead, this portfolio reflects how the aggregate of our intentional choices can drive sizable quality of life changes. Inspired by the inimitable Erik Torenberg, we can think of significant life choices — our quarter-life catalysts — in terms of big bets:

📈 Asymmetric bets (2020-2021)

1. Spending 1000+ hours and ~$10,000 on 10 different cohort-based courses, online fellowships, and upskilling programs. In my mind, the ROI is latent and the downside is capped as I’m indexing for both learning and networking.

2. Switching out of food innovation in a corporate powerhouse into a high-growth early-stage edtech startup. The leap here is drastic and follows the same tune of my willingness to carve out an unconventional career narrative.

3. Shifting into new hobbies and geographies from my comfortable business bubble in Canada to the artistic melting pot of New York. The reignition of old creative passions ensures that my identity capital stays well-nourished.

💯 Annualized returns (2020-2021)

1. Language expansion: Startup land has propelled gains in my vocabulary. Bat signal, building in public, bias to action, engineered serendipity, hypergeneralist, generative, signal-to-noise, T-shaped, the list goes on! Bantering with new witty metaphors calls back to my literature chops and offers compounding benefits.

2. Passion extension: A sea of side projects and hacky initiatives later, I’ve developed expertise in UX design, no-code, and technical storytelling along with domain interests within the future of wellness, education, creators, and crypto. Having a growing set of fascinations eliminates any concept of boredom.

3. Mindset evolution: Being surrounded by so many high-potential, high-integrity, and high-velocity people has shaped the way I view the world. Seeing in systems, seeing in patterns, and seeing what others see: there’s comfort knowing that my empathy muscle is constantly being stretched in these new environments.

Many people ask me how I have the time and motivation to take constant action and achieve all of this. It’s a bit tricky to untangle, though evidence suggests that the recipe contains a healthy dose of creativity, a sprinkle of discipline, and a few splashes of eager beaver enthusiasm 🦫

Above all though, my secret sauce has long been tied to energy levels. Taking some wisdom from my all-time favourite internet writer, Ava builds the case for harnessing energy from a brief tweet and her hallmark essay on permitting intensity:

bookbear express: “It’s okay to need and want intensity—we praise moderation and balance but it’s pretty evident that some people crave a high level of intensity throughout their lives, and that intensity feeds their creativity and productivity.”

It’s a neverending interest in the peculiarities of life and the pursuit of knowledge that continues breathing oxygen into my impulses. The thing about energy is it’s not just about the absolute volume, but how far you can accelerate the area of effect. In other words, constantly recycling your energy tank by drawing from similar energetic environments. Aside from this unquantifiable reservoir of energy & enthusiasm, there must’ve been a concrete set of actions I took, right? Yup — here’s the inside scoop:

Optimizing for curiosity and maximizing learning. Obsessing over personal development. Being the scientist of my own life. Playing an infinite positive-sum game with others. These philosophical principles have been made the foundation of my early-20’s mission —practically what that means is I will always invest in myself.

What made the difference

Goal systems

Weirdly enough I was never too organized with goals during my formative years. There was always some vague “North Star” metric we business kids often raved about, but I would restrict the granular thinking in favour of more fun things. In fact, I’m still a huge proponent of productivity anti-advice. I don’t really time block. I multitask incessantly. I frequently do small unimportant tasks and dive into random rabbit holes, fully knowing there’s a big delicious nutritious fish outside that won’t cook itself.

At some point I realized the truth in an ancient Chinese proverb: the best time to dig a well is before you get thirsty. Even with my unstructured-structured approach, I’m also aware there are wasteful inefficiencies of leaving too much chaos in the cauldron.

So for the first time in my life on January 1st 2020, I kickstarted an intentional New Years Resolution regime with a few pals. The inception of this idea came after I had so much excess energy from romantic endeavours that fell flat — the perfect time to be extra productive. My simple desire was to prioritize creativity, community, and clarity. Operation #GOALSEEK 2020 was born, the cheeky name deriving from the Excel function that enables sensitivity analysis. If you’re curious about the goals, see here.

This spreadsheet approach taught me that there’s power in seasonal planning. Not so rigid to a point of forcing inconvenient daily habits, but not too loose or far enough out where you lose the vision. Whether you literally map out seasons and tell yourself…

Winter is for connecting & resting, spring is for nourishing & growing, summer is for adventuring & playing, and fall is for releasing & restarting

…or adopt the tried-and-true tech model and set quarterly OKRs for yourself, the main point is that goal systems do work if there’s sufficient follow-through. As pandemic-fueled fate would have it, I was able to accomplish these goals at a breakneck pace consistently during the bulk of 2020. Work begets work, momentum feeds itself.

While I could have sustained this system into 2021, I wanted to run a different experiment. Coincidentally I started embracing more first-principles and systems thinking in my day-to-day grind. So instead of setting every single goal by category, rationale, accountability, and progress — clearly an unsustainable strategy — I raised five pillars that act as broad guiding principles revisited on a monthly and quarterly basis:

Proactive wellness

Robust health routines have always been a fluctuating force in my life. My closest friends know that sleep is the first sacrificial lamb I give up to more deeply pursue shiny opportunities. The trade-offs hit hard, which is why a big focus area for the back-half of 2021 is practicing essentialism and re-balancing routines. A brief aside: with some recent success in hacking on Lucid, the Yelp for personalized sleep solutions, it might be time to finally give sleep tech a real shot!

Similar to the goal systems, I wanted to validate whether there was a way to connect all aspects of health together in a personal one-stop shop: physical, mental, emotional, and perhaps most intriguing to me, spiritual health. After a year of A/B testing and tinkering, I’m happy to say that my wellness suite consists of three core elements:

• Existential therapy. For the past year and a half, my fantastic existential psychotherapist Will has taken me to the edge in considering limiting beliefs and on-demand mindfulness interventions. Through tailored cognitive-behavioural therapy techniques, Will taught me that self-reflection is a massive superpower in dealing with the swamp of ambiguities and paradoxes:

“Over our time together, my main intention is to armour you with the systems and frameworks of CBT thinking and unpack your subconscious limiting beliefs. We’ll take this to an extreme boiling point where you unlock the art of self-therapy.”

• Mindful meditation. As a method to test meditation consistency, I wrote about my favourable experiences with short-form meditation, catching the attention of Calm’s leadership team. I actually attribute unguided meditations to create the zones where I find the most equanimity, partly inspired by Naval’s practice:

“Meditation isn’t hard. All you have to do is sit there and do nothing. Just sit down. Close your eyes and say, ‘I’m just going to give myself a break for an hour. This is my hour off from life. This is the hour I’m not going to do anything.’ ”

• Sensory running. I’m a big fan of experiences that make full use of our five senses. Running has been an amazing find in that regard. Since moving to New York, I've recently cut out any distractions from my evening sunset runs, including music and podcasts. This helps me blend physical fitness with spiritual awareness more easily. In this vein, I always think back to Haruki Murakami’s legendary “What I Talk About When I Talk About Running”. An excerpt that summarizes the meditative duality experienced with full-sensory running:

“To deal with something unhealthy, a person needs to be as healthy as possible - in other words, an unhealthy soul needs a healthy body, and the unhealthy and healthy complement each other”

Digital communities

It would probably be a gross understatement to say that joining On Deck has been an absolute game-changer to the trajectory of my life. The ultimate momentum came from connecting with world-class superstars and feeling an intimate sense of belonging. There’s not really anywhere else that could’ve inflated my professional network and personal passions by ~10x. You can read more about my new On Deck feature here, where I equate the career journey to an abstract extended metaphor about animals supporting each other in a large forest.

The simple truth with joining digital communities is that you get back a significant multiplier of what you put in. Committing acts of generosity goes a long way in scaling yourself and stretching your purpose. Coupled with the blistering movements in the metaverse and Web3 technology adoption, finding tribes that you resonate with will be increasingly important to stay authentic in a complex digital landscape.

There is an array of other communities I owe a lot of my personal hypergrowth to: Endeavour Consulting, Co.Lab (You Belong in Tech), Develop For Good, Skillful. I’d recommend any of these for folks looking for practical upskilling and an on-ramp towards career pivots in tech. In the meantime, I’m going to continue exploring evergreen pastures on the horizon. To name a few: Makerpad’s no-code community, Kernel’s crypto collective, and Reboot’s techno-optimism dream.

Constructing a core values canvas

Every year during my business undergrad, we were told to complete a values-driven exercise — StrengthsQuest, Emotional Capital Report, Personal Values Assessment. When I look back it seemed like I had a good grasp on what mine were, but I never chose to internalize them and form healthy, sturdy life principles. I justified them away as a scary undertaking, as there was a risk of opening up the emotional flood gates.

Closely tied to values is the idea of identity: Who am I? Why do I like what I like? What has changed about my perception of values over the years? Digging deeper into these ontological prompts has proven to be a good buffer against what I call The 3 D’s of Despair: doubting yourself, discounting yourself, and disqualifying yourself. In some ways, they are the shadow triggers of quarter-life crises.

So what’s our first line of defence to avoid the deadly 3 D’s? I believe inspecting your personal code base is quality assurance for your soul, debugging any inhibitions and insecurities in the process. In the spirit of being proactive, this thorough reflection gives rise to another personal framework, as well as a captivating party trick whenever someone asks me: “so what do you do?” Well, I say I’m a…

Builder, writer, improviser. I think striving to be a multivariate human being makes life more interesting. When our identities are tied to a single entity, institution, or concept, we expose ourselves to a feedback loop of negative self-talk when the very thing that tethers us is disrupted. Maybe the biggest draw to a multivariate viewpoint is that life is just more fun when you enjoy a lot of different things. I never want to give that childlike curiosity up. We explore these three dynamic descriptors herein:

• Outside of my core circle of startup tech, being a “builder” is not a common character trait — understandably so if the output is PowerPoint decks or Excel models. But even so, the builder mindset extends beyond tech products and into other creative avenues like dramatic theatre, urban research, and digital art.

• I think writing helps me achieve three things: figure out what I’m thinking, leave breadcrumbs to trace these thoughts, and scale these crumbs into compounding learnings. On a meta level, writing is about making observations and identifying patterns, which has applicability across everything we do.

• Lastly, improv comedy is a topic I’ve written extensively about and a practice that never fails to bring joy in between the grind. Being a better listener makes people more interested in you. Saying “yes and” builds an openness to experience and invites new stimulus — a true generative activity.

We’ve taken a detour and skirted around the primary topic of values, so let’s take an in-depth look into my canvas mapping exercise, which I’ve segmented into methods, machines, and magnets. We’ll also revisit a childhood classic: math.

The methods 🖍

Global boy. Sweet & spicy. ENTP, Enneagram 7w8. Witty, wacky, wonderer, wanderer... All sorts of adjectives have been used to describe me, but I figured this question was much more complex than what a few words or personality quizzes can express. For the longest time, it was difficult to verbalize what my core values were without making them too corny or trite. In all honesty, as much as I liked to believe in the past ~5 years that I was a “self-aware” person or that I was “self-assured” in my own skin, the dots didn't truly connect until the giant wave of 2020 goal setting.

The simple solution to unlock these insights: I just wrote them out! With cognitive-behavioural therapy, I developed confidence and certainty in my values system after a few introspective exercises. One example was transporting back to my childhood to see what I enjoyed and what I obsessed over. This type of internal time travel unlocks a new sense of adulthood, as we come back with a basket of resurrected trinkets from the past. Meet the Lego blocks that make up my values machine:

The machines 🏮

I consider each of these components to be cogs in the greater machine that provides the renewable energy for my soul. The nicest part is that they all reinforce each other!

1. Authenticity: Displaying my truest self in all situations and contexts and embracing my key strengths, opportunities, and differences. Making a mark my own way, no matter how unconventional or unorthodox.

2. Charity: Giving back to others in any way and supporting communities (friends, family, other) through mentorship, meaningful conversation, capacity building, and more. Give, give, give, give, give, and then ask.

3. Curiosity: Asking consistent questions and exploring novel topics at a deeper level, whether intellectually, emotionally, or spiritually. Finding beauty in the most mundane things, and getting constantly excited about everything.

4. Continuous learning: Advocating for the pursuit of new knowledge, skills, and abilities and enjoying the process of learning as a whole. Understanding that there are many sources. The day I stop learning is the day I proverbially die.

5. Optimism: Viewing and reframing events, moments, and other aspects of everyday life with a positive, hopeful lens. Being optimistic in today’s world can feel stifling with reasons for skepticism, but can also be an empowering act.

It’s become so important to remind myself of these operating principles that make up the “Sam Manifesto” on an ongoing basis. This structure also has the added benefit of acting as a playbook for career growth. By stacking the Lego blocks with different permutations, we arrive at my definition of purpose:

1. Creating positive impact for others ['authenticity', 'charity'] = impact

2. Honing my creative expression ['learning', 'curiosity'] = skills

3. Sustaining a happiness & fulfillment loop ['optimism'] = impact + skills

What this all sums to is a common thread of consistent curiosity, a contemporary competitive advantage. I consider myself a huge possibilities thinker, where every idea is possible by default (improv!) and I practice ambition by consulting my database of limitless actions. That’s how we normalize discomfort and spin our flywheels.

The magnets 🧲

These values are important for me to understand how I can draw people in with my innate electromagnetic field. On the flip side, it’s also fascinating to understand what external magnetic forces pull me towards others. My heuristic in a lot of cases is looking for people who are: good at being granular, good at being highly specific in how they think, and arrive at elegant conclusions. What I find especially compelling in other people and what I tend to romanticize:

• How people talk about themselves: This blends both the expression of thoughts and feelings. I get drawn to those who are emotionally-literate and can channel their self-expression and self-identity as a way to enhance self-awareness. Also, confident and crisp communicators who can express complex thoughts simply.

• How people engage with literature: This integrates a person's aptitude to read, write, and communicate about a range of topics in critical ways. To me, this is a leading indicator of a person's intellectual horsepower and willingness to engage in more than surface-level topics, which naturally aligns with my values.

• How people apply their skills in unique contexts: I've met many high-calibre people who have the innate ability to build, create, and design compelling works of “art”. It always energizes me to not only open routes of dialogue with these individuals, but also watching them just take action and iterate ruthlessly.

• How people approach growth and self-development: This one is pretty self-explanatory, but from my observations not everyone has reached a point where they have the mind space and emotional energy to think about these topics in an almost obsessive way. A lot of people want to be but they don’t want to do.

In tandem, I play my own values as a harmonizing instrument in the grander orchestra of life. I’ll keep doing me and continue to see who best fits with my sound.

The… math? 🧮

While I’ve consistently dabbled in many domains such as philosophy, anthropology, chemistry, ecology, economics, and engineering, there’s one discipline that always shows up in delightful ways: math.

You might think that all the years of algebra, geometry, and calculus would be so irrelevant after graduation. I thought so too. But there’s a surprising amount of math that follows us throughout adulthood that when applied, masquerades as useful metaphors for life. Exponential functions model compounding impacts, logarithmic functions showcase diminishing effects, and step functions suggest the link between waiting, then jumping. Perfection is an asymptote.

Non-linearity is the most important point. This applies directly to career pursuits as the key is to follow your own intuition and carve out your own path. “Run your own race”. Power law distributions take this concept even further. From the cheeky Philosophy In Hell newsletter:

“There are profound asymmetries and power laws at play in the pursuit of meaning – a split second decision might be the most important one you make; years of lounging around in cafes and on beaches might pay off more than years of hard work, if it results in one extremely good idea.”

Connecting back to goals and communities, we observe the power law of serendipity: each year you meet a fair number of people who you could become very good friends with, but the long-tail of people mostly end up as acquaintances. And that’s okay, because the potential of harvesting lifelong relationships with a select few is all it takes to skyrocket our happiness and quality of life. The lesson here: never stop putting yourself out there and be a beacon of kindness wherever you go.

For the small but mighty fraction of readers that want to dig deeper into applied math, the two books that have greatly shaped my perspectives are Infinite Powers: Calculus & Algorithms to Live By. If math just isn’t your thing, I’d still highly recommend playing with behavioural economics, game theory, and decision theory to nurture your mind!

C. Next moves

It’s hard to describe the feeling that 25 brings. Quarter-life catalyst does have a nice ring to it though. One thing became clear after I took a step back this weekend to refresh. You don’t really need that much to be happy day-to-day. Buddhists, essentialists, stoics all point to a similar conclusion. As it relates to our professional identities, a career is just a very long theatrical play, with you as the main character controlling the performance and viewing each job as a uniquely experimental outfit.

There is no fear “wasting 1-2 years of your prime adult” life on a bad choice. Because there is no bad choice. So I’ll just keep choosing and I’ll keep being. Being fully present is the direct gateway to fulfillment and joy, and it’s important to preserve a possibilities mindset. Here’s a brief snapshot of what I’m thinking about next:

🌝 On the current menu

• Hacking: Scaling my side projects to a place where I can generate passive income and optimize for both curiosity & compensation.

• Writing: Practicing different sides of writing and cultivating my preferred voice. Adventurous on Twitter, analytical on Slack, and authentic on Substack.

• Performing: Doubling down on improv as a creative outlet and being in tune with what actually makes a good story and a good joke.

🌚 On the bucket list

• Local artistic explorations: Satisfying my creative itches by curating intriguing pop-up events, science fiction-focused book clubs, and unassuming exhibits and places around the city. Reserving “Blue-Sky Sundays” to be present.

• Elevated outdoorsy immersions: Booking an off-grid weekend in a remote yet picturesque setting. I’ve been especially interested in booking treehouses to facilitate a solo self-care retreat playfully filled with literature and nature.

• Global travel excursions: Checking off South America and Antarctica in the next five years and complete a personal vanity metric of 50 countries before I hit 30. A key reminder here: emphasize shades of cultural appreciation.

To me, having made matters more than being noticed. And so I’ll keep making. Here’s to 25 more big ones :)

Sam

Leave a comment

Last week I experienced probably one of the greatest exhibits in my adult life. Titled “Liminality”, the NYC-based Musem of Future Experiences (MoFE) puts a dreamlike spin to immersive entertainment. It was almost like a 70-minute meditation, guided by sensory storytelling and supercharged sound systems.

Unfailingly, August always seems to be a month of marination and reflection for me. Attending Liminality was likely the last puzzle piece I needed before fully embracing new unknowns and fresh ambiguities. A forcing function for change. This is probably best visualized through a custom framework inspired by Geoffrey Moore’s hit classic:

Taking an evolutionary biology lens, crossing the mid-20s chasm multiplies the number of open pathways and realities available to catalyze our growth. In my case, reality expands into aspects of changing geographies (from Vancouver to New York), pivoting careers (from food innovation to education tech), and updating philosophies (from fixating on perfectionist quality to taking permissionless initiative).

Naturally, this philosophical piece is about exploring the realm of the liminal. The timing is super fitting since I’ll be leveling up from 24 to 25 in just a mere week. It’s quite an interesting milestone — both an insignificant integer yet a significant step in my life’s narrative. The retrospective & reflections will be saved for next week’s issue.

I’m especially interested in the role of technology in helping shape our realities, both in the fleeting present and in sustained perpetuity. During our exploration, we’ll also grapple with the implications of digitally-enabled reality and explore what emotions, thoughts, and spaces are enabled through these contemporary channels.

But first, more on liminal spaces…

Liminality is an anthropology concept that refers to states of transition, i.e. a great “in-between” where the regular order of reality is suspended. Liminal spaces are usually compared to rites of passage, where an individual is at the threshold between two different states of being. Throughout life, we’re constantly plunged into uncharted limbo territory. Some liminal spaces are more significant in terms of the quality of changes that occur right after. Others are just plain scarier.

One application of liminality that is near and dear to this newsletter: adolescence, the intermission between childhood and adulthood. The period where the sandbox is substituted for more established structures and stimulants. While these times often feel slippery, unfixed, and confusing, we can take comfort in knowing that core parts of ourselves — i.e. personalities, values, beliefs — typically persist through the gap. This phase yields new realities and allows new defaults to bloom.

One related question that I’ve been pondering lately: if “realities” are so fluid and continuously oscillating, how do we best cultivate comfort and confidence to navigate moments of liminal transition?

The liminality-reality interface is a mental model I hacked together to build greater clarity and insight around the unnerving, fleeting sensation. Drawing on a software engineering analogy, I view the idea of liminal space like an API for life transitions:

In this case, moving from living in tradition to transformation requires a jump through the liminal layer. Instead of acting as a messenger that connects two technology platforms, the API calls signify conversations and interactions between the ‘traditional’ you and the ‘transformed’ you to help cement the change.

This might sound borderline bonkers, but the truth is that we’re completely alone with ourselves in these liminal moments. Philosophically speaking, we are both the sole actor and the sole audience waiting for that fated curtain call.

Drawing slanted rectangles on top of each other is a quirky way of showcasing the relationship, but begs a more practical question: what other types of systems can plug into this new type of API?

With our basic understanding of liminality, we can now integrate other versions of “reality” to appreciate how each component strengthens the overall stack. The following three sections will cover trends and developments in virtual reality, extended reality, and even the most underrated source of liminality… real reality.

My thesis: by intentionally immersing ourselves in the metaverse, we unlock enhanced sensory experiences that are additive to our personal growth. However, this condition only holds true if we reach a sort of stable equilibrium with an equally important force in our actual universe: real reality. Let’s explore these domains within our three acts:

🤖 Act I - VR: The Relevance of Virtual Reality

Sharply branded on the MoFE website, VR is a conduit for enabling present-altering experiences:

“We believe the phantasmagorical nature of VR has a particular power to open our minds to new perspectives and broaden our notion of consciousness. We seek out VR works that play with perception, explore new ideas, and expand our imaginations.”

Hearing a descriptor like phantasmagorical immediately nudges the brain to prep for a virtual drug-induced journey. I applaud the creators’ intentional balancing act of completely activating your senses with intense visual theatrics in one portion and then submerging you in a soothing meditative sound bath in the next. I think the most interesting historical driver of VR’s emergence is the connection to psychedelics, circa 1999. Advancements in virtual therapeutics (“cyberdelics”) are starting to peek out through mainstream outlets, but more on this trend for another essay.

The main point is that both a VR storyline and a psychedelic trip represent analogous disruptions to the natural sensory experience. And if the environment is optimized for this armchair travel, we get sucked into the vortex of lucid states and liminal spaces.

Immersive exhibits like Liminality are not trailblazing inventions by today’s tech standards and have fallen off the mainstream media’s radar. Regardless, I think these types of experiences change the value equation for future leisure opportunities. What starts with high-fidelity enhanced entertainment could seed further discovery of consumer solutions that directly improve our quality of life. I personally daydream about VR-enabled artistic simulations, adventure quests, and wellness interventions.

Before we get too carried away with such a theoretical product roadmap, it’s important to understand how VR stacks up in the current market landscape. One approach is to map out life cycle maturity in different industries and pinpoint where VR is being deployed. But since we’re exploring the broader implications around reality and liminality, we should think through what VR helps enable instead. A study from Deloitte Digital published in 2019 helps provide the backbone research here:

Simply put, the significance of VR is around elevating the ordinary. Learning, connecting, exploring, knowing, and thinking are all fundamental actions as part of the human experience — VR serves to enhance and escalate the current reality into a version with bountiful possibilities. Historical literature sources colloquially refer to VR as “the empathy machine”, with analysts and architects fascinated about the practice of soft skills development through uniquely assembled roleplay scenarios.

However, viewing each element in isolation discounts the richness of the underlying technological artform. After all, how can we describe a full-sensory performance such as Liminality with just one of these tags? To my delight, there is one use case missing from the ranks that is arguably the most important of all: play.

The playbook of playfulness comes back in full force, as play is positioned as the masternode that guides us into full immersion. It acts as the nectar that activates our inner child or inner science fiction geek, gradually driving adoption throughout the virtual excursion. Imagine a world where you could willingly tap into a diverse array of creative, immersive, and collaborative experiences, with just a flick of a switch.

But the relative scarcity of artistic VR exhibits coupled with production cost constraints limits potential advocates looking to explore new realities. Industry analytics validate that less than 20% of Americans have tried any type of virtual reality, with enthusiasm levels stagnating. We can likely point to socio-cultural hesitance and perceptual barriers as key pain points to solve before appetite for experiential VR takes flight (let alone mass consumer clamour for “seeking the liminal”).

👽 Act II - XR: The Vision of Extended Reality

As much as I adore optimistic frontier-tech fiction from the likes of Ted Chiang’s Exhalation, our S-curve analysis suggests we might be a ways away from the ultimate sci-fi vision. But if we view VR as the first level of crafting out-of-body experiences, there must be innovation happening at other corners of this digitized maze.

Enter XR. More formally, extended reality is the umbrella term that describes the merging of virtual and physical worlds — virtual reality, augmented reality, and mixed reality are all subsets. Because this piece is not meant to be a technical primer on these topics, we will instead abstract out the central concept: our relationship to spaces.

The popular crypto publication 1729 recently resurfaced an article about spatial interfaces. They argue how preserving higher dimensionality (i.e. 3D) is essential for more simple and intuitive digital user experiences:

“Humans are spatial creatures. We experience most of life in relation to space… We sense ourselves in space in relation to all of the other objects in our environment And this is powerful knowledge that we've left out of lots of software.”

The author considers a slew of commonplace applications to build the business case for spatially-informed design: everything from floor plan Outlook calendars, circular-oriented Zoom calls, breadcrumb Chrome browsing, and VR-simulated conferences.

I think critically assessing spacial interventions in our digital solutions is interesting because we often take broken UX for granted and consider it as a feature, not a bug. As for physical spaces, it’s typically a combination of defaults, signals, affordances, and constraints that dictate our core behaviour. In some ways, liminal space is the extreme case of being stuck in-between, where the concept of “space” is completely warped and we seemingly lose access to all these heuristics.

But wait, how does space relate back to extended reality? From a virtual worldbuilding perspective, fully empathizing with spatial thinking provides technologists with the highest degree of confidence to replicate an environment where UI renderings match their real-world counterparts. In essence, “extending” reality through a digital twin equipped with knowledge on human-centered design principles.

Pushing XR all the way to the boundaries of its nascent existence, we converge to one phenomenon that has recently exploded with public market interest — from big tech CEOs (Zuck, Nadella) to Packy McCormick’s comprehensive coverage — yup, the Metaverse.

The metaverse summarizes our entire discussion so far because it effectively illustrates Zuckerberg’s pitch of an embodied internet where, instead of just viewing content, you are in it. One builder who has neatly packaged metaverse insights into a few digestible articles (market map, value chain, experiential) is Jon Radoff. I’ll let his well-labeled visualization provide the tee up:

Much of this visual references back to both our anchor exhibit and the consumer VR use cases. If executed perfectly, the virtual world should come packaged with features that mirror real reality very closely. As eloquently summarized by Radoff:

“Building on much of the technology that enabled virtual worlds in games, the metaverse will give us the ability to socialize through activities rather than simply socializing through sharing photos and news links.”

Activities, stories, creations, immersions, collaborations… all these values form the cornerstones of a collective vocabulary shareable across platforms and people (so-called “interoperability”). As someone who subscribes to the techno-optimist lens of scaling high-quality socialization and creativity online, the potential for an enduring Third Place especially appeals to me.

Of course, we can’t just ignore the inherent limitations plaguing XR evolution. Right now, I can't easily transfer my custom-generated content from one platform to another. For example, if I bought a snazzy NFT avatar from OpenSea, this wouldn’t be portable to characters that exist on a Unity or Roblox server, since assets are locked up in owned corporate systems.

The antidote is a familiar rehashed story from crypto land: a push for blockchain-powered decentralization to put safety guardrails around transactions, identities, and connections created in the Third Place environment.

How about liminality? Does the infrastructure of XR make these transitory states more or less accessible as an internet citizen getting exposed for the first time?

As it turns out, the connection to liminality may be relatively straightforward. Carla Calandra explains the role of liminal spaces as gateways for “entering the metarealm”.

Communities in the Metaverse are constructing a new world where participants are straddling physical and virtual realities. From political campaigns to real estate and entertainment, the evolving metasociety forces consumers and brands to rethink our conception of spaces and places.

🍁 Act III - RR: The Joy of Real Reality

The frame of “real reality” might sound a bit unusual and unconventional, but it offers a sobering reminder that the natural world can delight, excite, and surprise us with comparable energy to the virtual stratosphere. A crowdsourced quote from Technopedia sheds a pragmatic light on the progression of “realities”:

“The term is also part of the philosophical debates that foresee a time when human beings will be overwhelmed by and spend most of their time in virtual reality. For example, the evolution and popularity of online social networks could reduce the amount of time people physically spend together, leading to a sort of virtual friendship that, arguably, does not exist in real reality.”

To address the looming concern of the metaverse consuming our fabric of human interaction, we can look to real reality as the reprieve. Specifically, let’s link back to our favourite fleeting friend: liminality. Threads in the subreddit r/LiminalSpace predominantly feature simple photographs and captions of the elicited moods and emotions. Often, liminality boasts a sense of eeriness and even supernatural connotations, a direct consequence of their architecturally baren makeup.

What comes out of this surreal browsing exercise is a series of personal experiments that try to provoke the question and allow on-demand access to liminality. Actionable methods to synthetically engineer this feeling into daily life include:

• Visiting empty (standard) locations: This will involve going to a typically inconspicuous place — library, mall, school, airport, construction site, etc. — but at a time where no one is around.

• Seeking abandoned (non-standard) locations: This will involve going off the beaten track, and finding conventionally “haunted” environments to trigger the liminal mindset.

• Wandering around unfamiliar neighbourhoods: This will involve embodying a sense of wanderlust and wonder that may lead to uncovered pathways and an induced meditative state, just through the act of walking with intention.

While definitely not as flashy as virtual experimentation or metaverse immersion, a creative outlook on relishing in the real helps ground us into specific states of consciousness. Consider it a splash of familiar flavour in the sea of digital inundation.

✨ A liminal contemplation

Dramatizing my experience at Liminality a bit, I felt I’d returned from a completely distinct dimension after taking off that VR headset and completing the final seated meditation. On a more intergalactic level, I can’t help but wonder what degree of liminality Bezos and Co. felt during their space exhibition a couple of weeks ago. Did the feeling differ throughout the various touchpoints, i.e. right before the Blue Origin rocket lifted off, as they were cradled into space, and right before the graceful landing back to Earth? Isn’t outer space the ripest setting for these special sentiments?

In any case, it’s clear that VR and XR will have an increasingly substantial role to play in bridging the openness of a decentralized web with the tenderness of a real-life presence. However, it’s also no secret that the current state of metaverse functionality struggles to replace the sense of empathy and intimacy provided by physical spaces and community gatherings.

While avatarized personalities, tokenized communities, and virtualized landscapes hold massive game-changing potential for the future of the web, these inventions are still antithetical to how physical and digital realms are currently segregrated. The containerization of real sensory experiences into code packets (games, chatrooms, simulations) still doesn’t capture the beauty in its entirety, leading to a type of real-life packet loss.

But if it’s any recourse, I think it pays in a metaverse universe to dream well and dream big.

See you next week in the liminal space between 24 and 25,

Sam

Last time I wrote a piece about formalizing the practice of play — how playfulness mixes with mindfulness to form a modern-day cocktail of wellness practices. To my pleasant surprise, a whimsical white paper on a new crypto concept dropped in early June titled “LAMP”. Naturally, my brain saw this as a sign to fall face-first into the deep depths of crypto.

But since there are more than enough commentaries that highlight the technical utility of common coins, I want to deploy a comedy-first lens as an unusual, yet viable way to navigate this murky environment.

In this makeshift teardown, I’ll be dissecting the anatomy of LAMP in graphic detail. That is, filling this evaluation with playful puns and photos of high-quality lamps and shining a light on the idea’s underlying significance. We’ll also discuss the domain of Dogecoin and a fresh framework I constructed called the meme marketing funnel.

• The main point: technical white papers are often dry and lengthy, but this one flips the cryptographic script in a very engaging way.

• The post-mortem: my thesis extends beyond the existence of LAMP itself and into broader applications of technological absurdism.

On the whole, I think that satirical comedy and shareable memes will continue feeding the living organism that is the contemporary cryptocurrency space for years to come. Hopefully, this playful viewpoint will be an atypical adventure for crypto connoisseurs, comedy aficionados, and non-technical pundits alike.

I imagine this piece will be the most chaotic one I will ever attempt to write in my life, but like the sensational standup superstar Steve Martin asserts:

“Chaos in the midst of chaos isn’t funny, but chaos in the midst of order is.”

Let’s start cracking this comedic code!

Subscribe now

I. The Tokenized Theatrics of $LAMP

“Things like lamps have come to be seen as a dated, inefficient use of electricity in the face of the promising world of digital currency, and we stand on the precipice of another dark age” - LAMP Developers

As we might already expect, the LAMP white paper is structured in a very comical and unconventional way. The first seven pages comprise long excerpts of the history of fire, electricity, and computers, all extracted directly from Wikipedia. The developers took an evolutionary angle to set the scene for LAMP. In short, the cheeky chain of logic posits that:

• Steve Jobs created lamps in 1976,

• Pixar ramped up digital lamp production in the early 2000s,

• Rapid progress in lamp technology hypercharged the growth in Silicon Valley, as lamp switches require Silicon

Sprinkles of subliminal lamp imagery within eras of massive technological change force us to consider the potential genius beyond the gag. If my improv training has taught me one thing about memorable performances, it’s that the gradual build-up in a scene is crucial. Any classic comedy routine is composed in “chunks”, feeding audience members seemingly disconnected bits and gags before ramping up to the hard-hitting punchlines. That’s what helps generate large-scale buy-in.

As seen above, the LAMP paper conquers this first act in spades, doubling down on its own peculiarity to keep the reader intrigued. Of course, comedy for the sake of pure shock value is not a substitute for substance. One important question that we must ask now to maximize our understanding: What are the atomic units that create LAMP, and what makes this concept so intriguing? I’ve organized my commentary through the exploration of three core principles: technology, symbolism, and linguistics.

🔆 Core Component #1: Technology

“Lamp is the kernel: the program in the system that allocates the machine's resources to other programs you run. The kernel is an essential part of an operating system, but useless by itself; it can only function in the context of a complete operating system”

In the interest of keeping this post technically light but maintaining a minimum viable level of correctness, we’ll need to chat through the cast of cryptographic components. Thankfully, LAMP is framed in a way that emphasizes simplicity despite the underlying complexity. The Ethereum environment refers to the inimitable community-run operating system, the blockchain that powers its cryptocurrency (ETH). Reimagining LAMP using a classic nature metaphor, it is another tree that stems from the giant nutrient-rich forest named Ethereum.

The premise of the white paper is that the construct of LAMP is widespread, yet hidden. In other words, people just don’t realize that LAMP exists. To pull back the veil, here’s the equation describing the bilateral relationship between these variables:

Lamp = ETH + Lamp (aka “ETH/Lamp”)

Both need to coexist in a symbiotic way for the math equation to hold. Lamp: Too shady to understand, too blinding to see, too timely to scold.

—

On paper, the digital aspects of LAMP still seem shrouded in mystery. This is partly due to the need to dive into the source code of each block to gain deeper insights. But I think the most intriguing part about LAMP isn’t the underlying blockchain engine that powers it, but rather the choice and positioning of the object itself. A simple yet salient technology. A commonplace house appliance that we all take for granted. An antique relic that is arguably more aesthetic in style than dynamic in function.

We’ll return to this thought later, as there are potential philosophical questions around the latent value of withered technology — and how we can use this frame as a blueprint for creative reconstruction and in the simplification of abstract concepts.

🔑 Core Component #2: Symbolism

“Our platform is built upon the fundamental concept that memes will be the currency of the future… This cryptocurrency will change the landscape of the Blockchain in the same way Albert Einstein changed the landscape of lighting in homes through lamps.”

The phrase “putting lamps on the blockchain” reads as both amusing hyperbole and an unexpected aphorism about the new dominance of the distributed ledger. In dramatized speak: Everything on the blockchain, the Web3 world order. Such technical intricacy is native to these applications, so the push for the lowest common denominator of understanding is essential for mass acceptance and mass adoption.

Memes take on symbolic significance as they become the simplest currency to buy a ticket to the world of improved comprehension. Memes lower the entry barriers into sophisticated conversations. To me, the hallmark of a sustainable symbolic meme is replicable relevance: first comes laughter, then comes longevity.

Fascinatingly, the LAMP authors take the symbolism to the next level and craft a masterful metastory in the backend. Typically, the Appendix section of any literary or scientific work contains supporting evidence and secondary sources. Unsurprisingly, LAMP counters this cliché. Applying a stream of consciousness narrative, Blockchains are personified as their own living species. A series of LAMP memes are then layered throughout, building a sense of self-awareness and self-deprecation that, oddly enough, enhances the stickiness of the white paper.

Because the storytelling quality is quite indescribable, here’s a piece from one of my favourite fiction novels, Ducks, Newburyport depicting similar energy:

📣 Core Component #3: Linguistics

The denouement of the white paper is summed up by just three words:

“few understand this”

Punchy language coalesces with a cryptic undertone to produce something that virally stretches beyond LAMP itself. The use of polarizing phrases segments the population into in-groups and out-groups differentiated by level of understanding. This helps build a sub-culture where meme-fuelled tribes develop their own methods of description and communication.

Technical jargon exists in every domain, but I think crypto is one of the rare cases that encourages open participation on multiple fronts. After all, not everyone speaks in bits and bytes, but everyone can speak in memes.

Something so brain-scrambling shouldn’t elicit such enduring and memorable reactions, right? The punchline is that the added comedy layer and analogy-laced language bridges complexity with simplicity. In an increasingly information-rich world, the meme-based symbolism represented by LAMP and similar creations is the connective tissue that helps shape reality.

🔥 The Second Switch: My Extended Metaphor of Lamp

It wouldn’t be a performative piece unless I attempt to remix the beauty of LAMP into my own cybernetic Frankensteinian creation. For this exploration, we’ll need to venture in with a suspension of disbelief as we metaphorize the lamp to the max. We can structure our discussion by decomposing the elements of an everyday lamp into its literal building blocks — imagine that each part of the lamp corresponds to each layer within a blockchain.

Slapstick comedy on one hand, but sharper clarity on the other front.

• Layer 0: The Base ≈ Ethereum: The backbone of the decentralized internet and the settlement layer for Web3. Taking the perspective of the actual appliance, Ethereum parallels the sturdy nickel-plated brass that acts as supporting infrastructure for the lamp’s light-giving ability.

• Layer 1: The Stem ≈ Protocols: The set of rules that define how products and applications are built. These can take the form of open-source, permissionless developer platforms. Comparatively, the stem holds the lamp’s filament, as the conducting wire between the supporting base and the light generator.

• Layer 2: The Socket ≈ DAOs: The member-owned, code-based communities that enable safe ways to collaborate and commit funds to a specific cause. Meanwhile, the socket provides the collective light source that radiates out into the air, distributing the power of lamp into many hands of a proverbial digital family.

• Layer 3: The Shade ≈ DApps: The use of smart contracts combined with a classic frontend interface produces high-fidelity outputs like decentralized marketplaces (OpenSea) and exchanges (Uniswap). These are completely visible and tangible to the public, as is the main “interface” of the lampshade.

If we extend this metaphor to the extreme, consider the projects and applications that could launch out of a “LAMP DAO”. I’m imagining a group of tokenholders that collaborate globally to maintain the electrical grid in a fully distributed fashion. We can escalate further by tying the whimsical name to a broader cause. How about broader renewable energy projects that could make a massive difference in emerging markets, where lamps are still the primary source of power?

Forking LAMP in creative ways may be the ultimate hedge against such concepts falling out of favour into humourous obscurity.

II. The Longevity of Crypto Memeification

LAMP feels like a light dash of sugar in an evolving medley of flavours. While it signals a lighthearted addition to the fragmented crypto crusade, this form of memeification is not new news. We’re living in a world where the means of creation converge to memes of creation.

To me, the sheer unpredictability of meme-fuelled movements and a concerted refusal to conform are the most fascinating areas to probe deeper. We can assess the impact of memeification by zooming out and exploring the meme market’s underlying time series: past, present, and future.

🐶 Historical: The Domain of Doge

We can point to the birth of Dogecoin in 2013 as one key inflection point. Notorious altcoins like Doge draw their staying power from the hype cycle, including initial investor mania and a sustained cult-like fan following. Interestingly, Dogecoin’s intrinsic “value” represents a departure from the logical store of value or long-term speculation purposes, and takes its shape primarily as an online tipping mechanism for content creators. Dogecoin: a disarming look, but with some underlying bark.

The reality is that volatility reigns supreme here, making swings in public equities seem laughable. For example, it’s not uncommon to see the indexes coloured with a sea of red before completely flipping to fields of green the next day. As new waves of crypto culture are reconfigured and reimagined, the meme market morphs accordingly. Catalysts in this space no longer trace earnings reports and company announcements, but are instead characterized by content-fueled blasts. The more portable and relatable, the better.

The age-old sticky situation here is separating signal from lots of noise. For shrewd contributors who believe in the Web3 ecosystem, the million-dollar question becomes: how might we mitigate the rampant pump-and-dump mentality in this landscape and discourage bad actor behaviour? One optimal outcome would be positioning comedy as a conduit towards motivated development instead of humourous distraction.

Of course, Dogecoin is not the first meme-worthy case study and not the last. We could sit for hours to draw out all the standout memeable moments throughout the past six months and their comedic, cultural, and cryptographic impacts. For LAMP’s sake, its nuanced narrative could ladder up to a possible competitive advantage, but only if developers stay engaged to discover use cases and push protocol updates.

💡 Topical: The Meme Marketing Funnel

If we buy into the thesis that crypto is a Gen Z game, marketing magic becomes essential for capturing share-of-heart and converting bystanders into believers. Beautified branding and values-aligned storytelling rise as core components in this design space. Expressed in a recent New Yorker post about the social media stock market, Caroline Lester argues:

“Starting a cryptocurrency is a bit like starting a religion. Without large-scale buy-in, the system looks like a cult”

This motivates a broader discussion about the role of memes in driving adoption gains in the crypto space. Which channels are most useful to foster buy-in at each stage of the meme-filled journey? From a psychological perspective, what actions and emotions are elicited by clever social engineering? Let’s bring in a mental model:

The meme marketing funnel takes the tried-and-true growth framework and maps out the relevancy of different distribution channels. New coin concepts are pushed through the viral vectors of YouTube, Twitter, and TikTok. This trigger initiates the process that I’ve coined meme mitosis, which is seen tangibly through the leading indicators of clips, posts, retweets, and articles. As the multiplication continues down the consideration phase, the super-spreader memes entice a subset of audiences to stake real money into these concepts. A smaller subset of folks become enamored with the technology and onboard themselves into the many high-activity, high product velocity Discord channels. The battle for share-of-mind, share-of-wallet, and share-of-voice intensifies until the ideal outcome is achieved: full emotional resonance.

Through this lens, memes are the gateway drug into greater involvement in the crypto community at large. From a classical business standpoint, the marketing promotion hooks us but the product makes us stay. Stretching the comedy analogy, we cheer for the live performance but continue following the life of the performer.

🔮 Hypothetical: The Memeification Crystal Ball

As alluded to earlier, the biggest existential risk to meme-oriented coins is being banished by the fickle fans that boosted them in the first place. An abandonment of engineering efforts would also be another nail in the coffin.

Just as a comedy venue needs bodies and laughs as the lifeblood of the show, crypto spaces need a steady stream of miners, developers, and influencers to continuously steer the narrative.

That isn’t to say that memes are only reserved for accelerating top-of-funnel engagement. CoinDesk reporters Daniel Kuhn and Benjamin Powers presented a commentary where they linked several examples to support the extensive value hypothesis for memes. As argued:

“So memes not only play a role in making things like dogecoin more popular, but also serve as shorthand communications mechanisms for traders who need to signal something quickly… there are people with familiarity in marketing that see memes as a potent way to ‘brand' crypto.”

In our funnel framework, the true success metric is maximizing the probability of full conversion from a skeptic to a seeker. Memes inherently have a strong community-building function packed into their pixels. This helps tackle shiny toy syndrome and retention risks of products that bombard our newsfeeds frequently.

My prediction is that we’re going to ride the early stages of the crypto comedy S-curve for the foreseeable future, marked by increasing meme mutation and tokenholder empowerment.

III. The Lessons Learned from $LAMP

Looking at LAMP itself, the point stands that the developers took an everyday object and breathed newfound life into it. As the lengthy descriptions of fire and electricity in the white paper allude to, the architecture of the traditional lamp is ancient and archaic.

Yet there may be a broader human truth here about going "back-to-basics" to uncover hidden secrets — calling back to the idea of leveraging withered technology.

As Packy McCormick eloquently expresses in The Great Online Game, “crypto is just more fun”. I’m especially enchanted by the argument that novel crypto applications have the powerful potential to integrate values of play into the fabric of Web 3.0 and beyond. Memes provide the basic backdrop, allowing the most technical minds of the new generation to also embrace a largely upbeat, optimistic attitude while they build.

However, we still need to solve a core UX optimization problem. How can LAMP and other comedic concepts transport themselves out of abstract territory, and encourage use cases that enhance our daily lives or make digital experiences more whimsical?

Whether LAMP survives the war for consistent attention, given the daily downpour of newer protocols and projects, is a mystery. Regardless, all of this discovery work has exposed a nuclear insight: the philosophy of comedy in crypto is pervasive, anti-fragile, and perhaps most importantly, unfailingly entertaining.

From the burrows of the internet rabbit holes,

Sam

Share sam's sandbox

From the clickety-clack of a Lego tower snapping perfectly into place, to the fresh evergreen scent of scaling Vancouver cedar trees, play has been a formative part of my personality and self-concept. Through my days of random frolicking in sandboxes and seesaws, I’ve realized that adopting play into all aspects of life is a happiness hack. Even today, my commitment to the art of improv comedy grounds me in feelings of openness, spontaneity, and joy against a busy backdrop of business life.

While my own lived experiences are not exclusive, the concept of play falls out of fashion as we mature into a world of responsibilities. The transition from childhood to adulthood often erodes our sense of curiosity and wonder in favour of productivity and momentum. The shift from playfulness to mindfulness naturally takes shape as life stressors take over, leading us to crave mental stability over free-flowing fantasy. 

As mainstream mindfulness boasts substantial benefits through routines that help us reset and relax, recent literature suggests they are not a one-stop-shop to optimizing wellness. Modern methods like meditation and reflections have been commodified and are treated as a magical panacea for life’s ailments, perhaps to a fever pitch. 

Revisiting and reframing play as a wellness mechanism may be an authentic antidote to our mental and emotional health. This claim gives rise to a key question: How might we incorporate ‘play’ in practical ways to build towards a mindful and happy life? 

To address this pressing prompt, I’ve developed a framework around a new concept I have coined: whimsical wellness. This model combines scientific theory and personal experiments to achieve one simple outcome: inviting moments of play to enhance your mental and emotional health. I’ll also examine the impact of contemporary “fun-first” digital solutions that embrace a layer of whimsicality in their UX. Let’s start playing! 

🧠 I. The Philosophy of Practical Play

To prime our deep dive into the whimsical wellness framework, we need to first understand how the premise of play has evolved over the years. Superficial coverage of this topic has been prevalent in mass media outlets, so I wanted to take a scholarly spin and unearth as many peculiarities from the datasets as possible. 

Understanding the Progression of Play

In recent years, other non-profit organizations such as the National Institute for Play (NIFP) and the US Play Coalition have attempted to codify and democratize the values of play for all. While these initiatives provided the groundwork for credible conversations, they lacked the staying power to scale the messaging to play-deprived masses in corporate America. The problem is compounded when we benchmark against the research-heavy mindfulness movement, which tends to do a better job persuading and enticing skeptics through a wide distribution of data points.

I think the root issue driving the rejection of play is a lack of accessible and tangible methods to even get started. This is particularly problematic when we consider that very few are raving about play in our social circles. The founder of Ness Labs’, a virtual gym for the mind, presents the playfulness as a practice (PaaP) system. She argues there are two broad channels to kickstart this process:

• Direct play: Specific activities such as live-action games and stimulating exercises to provoke exploration, discovery, and creativity. 

• Indirect play: Playful reframing of situations such as through imagination, improvisation, and pleasure in learning and knowledge-seeking. 

With this bimodal lens, it becomes easier to appreciate how having options helps alleviate the pressure of “force-fitting” play into our lives. We often talk about mapping and measuring life at both a personal and professional level, but I argue that a choose-your-own-adventure approach at a playful level helps us stay more present.

The fact that a simple reframe of unassuming everyday events can help stoke our child-like curiosity is already a significant babystep in cultivating a healthy mind.

Considering Gamification

At the mass market level, data-driven gamification has been tested at great lengths throughout the years to simulate playful energy in consumer applications. In this case, we embed the touch and feel of games directly into our workflows, indirectly bringing us one step closer to a free-form playful nirvana.

Unfortunately, the main limitation of traditional gamification is that its primary goal is not to encourage play for the sake of the act itself. By design, to “gamify” is to imbue an experience, task, or activity with just enough of a playful element to drive broader goal-oriented outcomes. For example, Robinhood’s animated, socially-oriented user interface breaks the barriers of public market investing. Calm’s daily short-form meditations and sleep stories pull in game-like repetition to make mindfulness more accessible. And TikTok’s content creation engine feeds on attractive pop culture trends, as users embrace song, dance, and play as forms of social proof. All of these high-growth products have compelling value propositions, but the jury is still out whether they help foster a sustainable practice of play for the long-term.

While gamification provides a fractionalized version of play, proactive and consistent efforts to embody a whimsical mood are key to improve wellness.

Applying the Scientific Method

To my surprise, further discovery suggests that there have been decades of in-depth systematic studies on how play interfaces with prescriptive wellness and happiness outcomes. Laura Richardson, an industry design leader, developed “The Periodic Table of Play” to characterize all the unique channels that birth opportunities to play:

While the model was initially applied primarily to children, we can extract these building blocks and extrapolate them to fit our circumstances in adulthood. Taking the model persona of an ambitious, early-career, time-starved tech professional, we see glimpses where these elements organically (albeit erratically) enter the equation - hacking together side projects with no-code tools, experimenting with productivity hacks, or joining an online fellowship. Through our persona, the underlying disconnect we uncover is viewing these activities solely for advancement and ambition, forgetting the exhilaration and enjoyment of the activity itself. 

It’s funny how the widely-used tech vernacular holds so many close parallels to the vocabulary of play. Just as chemical elements are commonplace in both the DNA of humans and nature, it’s really reassuring to me that the periodic table of play is equally as pervasive. Creativity is our source of oxygen. Imagination becomes the equivalent of hydrogen, while improvisation acts as the carbon link to constantly generate more nourishing byproducts — playful ideas. Aside from the geeky chemistry comparisons, I think the most important takeaway from the science of play is just one simple truth:

Play still exists in many different forms as adults, even if we don’t recognize it.

🧪 II. The Elements of Whimsical Wellness 

Bernie DeKoven, the author of A Playful Path, suggests that while defining “play” can be a nebulous task, there is one concept that is closely associated: rules. He drafts out four potential drivers that blend play and rules together: rule-seeking, rule-breaking, rule-making, and rule-changing. 

I think this view of reconfiguring rules creates a pipeline of emergent perspectives, cognitive tools, and wellness enhancements as we adopt the classic tech mentality of moving fast and breaking things. My revised philosophy of play seeks to overwrite the rigid rulebook that binds us too tightly to the reality of recurring routines. By doing so, we replace painful drudgery with a greater probability for high-impact discovery.   

In order to convert the theoretical literature into more tangible, actionable wellness practices, I have constructed a custom mental model that leverages Richardson’s periodic table elements with DeKoven’s rule-based principles to alchemize into a personal “Playful Playbook”:

My business school teachers would be proud to see me blend and graph all the atomic components together using the ubiquitous 2x2 matrix. I saw a way to integrate greater flexibility into this model by accommodating different personalities, with a bias for action measure on the y-axis and a risk tolerance scale on the x-axis. The outcome is that each quadrant represents a distinct orientation of a play strategy:

• Rule-Seeking: For those who like to stick to the essentials, this strategy has the lowest barrier-to-entry and minimal friction to our standard schedules. The most important consideration is to explicitly carve out space for these pastimes, so they can be rebranded as true moments of pleasure over productivity.

• Rule-Changing: For those who have a higher risk tolerance and want to tinker with new passion projects, constructing personal quests or challenges can be a super useful way to morph and stretch ideas. I make this approach meaningful through writing, exploring environments in-depth, and capturing life moments.

• Rule-Breaking: For those who seek opportunities for creative destruction, rule-breaking is an exciting method to actively go against the grain. For business and tech types, I find that sprinkling in artistic activities helps activate the less-exercised parts of our brain. Painting, acting, and sculpting are all fun favourites.

• Rule-Making: For those who enjoy pushing the boundaries and characterize themselves as creators or entrepreneurs, the rule-making quadrant is likely the most fulfilling. As we grow older and develop a greater awareness of what energizes us, becoming a builder inherently incorporates play into the mix.

To experiment with my own framework, I initiated a week-long regimen. To make the exercise more formal yet retain a high degree of fun I branded each of these principles as “playfulness interventions”. These were positioned as evening rituals to incentivize greater consistency and to not majorly interfere with my daily work rhythm. You could even think of these tactics as soothing self-therapy techniques!

Digging a bit deeper into my process, there are three patterns of activity that emerged from my documentation process, representing a surprising yet refreshing outcome:

• Reflecting on playful things that happened that day with the associated people and feelings    

• Recording how playfulness was used in new ways throughout the day

• Recalling how many times something “playful” occurred during the day

By placing play at the forefront, I re-gained the comfort and confidence of a curious child. How could I tell? Maybe an ephemeral sensation, but I felt at ease, at peace, fully whimsical despite all the external chaos within the week. The silver lining to tapping into the Playful Playbook is that actions taken do not have to be any less productive than activities we normally associate as value-adding or growth-oriented. Knowing this, I can distill down this new framework into three core tenets:

1. Whimsical wellness is a worldview engineered to empower and inspire.

2. Whimsical wellness is unintrusive in structure and unlimited in possibility. 

3. Whimsical wellness is a new sort of mental insulation against the suffocating heat of day-to-day anxieties and agitations.

📱 III. Whimsicality in the Wild 

While our framework shows being whimsical is largely accessible within our immediate surroundings, many new ventures are also piloting unique solutions that incorporate elements of play. I’m confident that these inventive products can shift gamification from a gimmick to a viable tool for both pleasure and personal care.    

🧩 Childlike Concepts - “Experiment In Public”

Play typically involves tactile and interactive elements, introduced when children gain the motor skills to touch and feel things. By extending this to broader tech use cases, the following products reimagine conventional wisdom in clever, differentiated ways:

• Monet: This platform refreshes the long-lasting dating app concept through the construction and sharing of drawings to find romantic love and platonic friendships.

• The Landing: This social design platform expands the Pinterest feel of shareable moodboards and encourages users to digitize their home furnishing decisions.

• Playne: This virtual game environment aims to build meditation habits through a world-building premise — the more you meditate, the more the landscape expands. 

🌳 Digital Immersions - “Find Your Flow”

When we play, we interact with an environment. As play sessions derive their value through being exploratory and experiential, the following web applications transport the user to a completely separate universe filled with open possibilities and heightened sensations. I find myself gravitating towards these platforms as a way to combat my autopilot internet browsing mode and reinstate a sense of flow!

• Tree.fm: This soothing app centers around nature escapism, providing a spontaneous soundscape that helps us appreciate our physical world and offers a wellness refresh. My favourite way to traverse nature in a digital setting.

• A Soft Murmur: This web experience leverages the toggling of ambient sounds to transport the user into any nature-based terrain. Custom realities are realized and remixed to tackle mental stress in life and facilitate flow state in work.

• Weavesilk: This simple interface situates the user on a dark screen and equips them with freeform silk threads - an “interactive generative art” activity. One of the most unique wellness boosters and creativity enhancers that I’ve seen!

👥 World Builders - “Connect With Others” 

Play often involves the participation of several hearts and souls, facilitating the ability to connect with ourselves, others, and our community. With the advent of digital gathering grounds that supersede static Zoom rooms, these solutions manifest the feeling of peer intimacy. Try these platforms in your next cross-functional group event!

• Gather.town: With a recent $26M Series A from Sequoia Capital, Gather represents the new-age approach to hosting group occasions (weddings, conventions, office hours) and providing serendipitous spaces for lighthearted social interactions. 

• Mozilla Hubs: Unlike Gather, the Hubs platform avatarizes the experience through 3D models, private virtual meeting rooms, and natural media sharing extensions, all through a playful level-editor called Spoke. 

• Topia: Similar to Gather, this solution builds on the spatial audio and video capabilities to simulate the characteristics of real-time in-person connection. With pure customization and an artistic focus, the app incentivizes having fun.

The common thread that links all of these applications together is the willingness of the creators to orchestrate experiences that place child-like whimsicality at the core. By truly prioritizing design and development efforts around a central playful mission, there is minimal separation away from the pure leisure and imagination these tools aim to maximize.

💡 Epilogue: The Powerful Potential of Playfulness

Mixing elements of whimsical, wonder, and wander into the DNA of budding tech products and our everyday decision calculus can result in countless benefits. By resisting the temptation to apply conventional mindfulness as a plug for all mental health issues, we unlock a timeless technique that transcends age and experience. Summarized in a quick mantra that I just made up but which probably exists on some deep motivational quote moodboard: To play is to live, to live is to play.

Reflecting on the connection to new-age technology, I love how digital user experience stalwart Marek Pawlowski frames the idea of whimsical product outcomes: 

There is a rare moment where people’s relationship with a product or service evolves to take on new meaning. The orbit of their behaviour becomes eccentric, no longer solely derived from the purpose of the original creation, but rather possessing gravitational force of their own.

If we view our adult lives as one long infinite game where winning is not the core intent, then the most important principle is to keep showing up and playing. Beyond maintaining our well-being at tip-top shape, I believe play is the ultimate driver for churning continued creativity — a one-way ticket to developing a kaleidoscope mind. 

It turns out being “childish” as an adult is cool after all. 😎

Till our next playdate,

Sam

Subscribe now

I often get asked about my improv background during icebreakers, one-on-ones, and interviews. It’s not a common hobby among business and tech folks in my immediate environment — I tend to gloss over the details to avoid unleashing an unsolicited technical comedy meta-analysis. If I sense continued curiosity, I point to my favourite metaphors curated from my past instructors and domain experts:

Improv is group mindfulness. Improv is yoga for your social skills. Improv is practice in being a better human being.

A continuous stream of high-fidelity conversations sparked my willingness to bring these airy-fairy claims to life. At the tail-end of March, I ran my last workshop of a three-part improv comedy series for On Deck’s (OD50-1) world-class operators and tech superstars. My ultimate goal was to create a lasting impression and appreciation for the broader discipline of improv.

I decided to integrate a systems thinking approach to my teaching, connecting the disparate themes learned through years of training at The Second City and exposing these models into the air. If I could strike the sweet spot of presenting lighthearted, yet stimulating exercises, the real gratification would come from pooling everyone’s collective energy and releasing it.

For me, the biggest dragon to slay in this creative process was: How could I coordinate improv to contain the chaos, while retaining the primary goal of just saying yes to play?

Inspired by Lenny Rachitsky’s inventive piece on “What Buddhism Taught Me About Product Management”, I’ve reflected on my workshop content and the transferable elements of my improv training that have explicitly enhanced my life. This piece is organized by a theatrical classic: the three-act structure that dives into the anatomy of a scene, stretches these first principles into product building blocks, and reveals how to live mindfully through an improviser’s vantage point. Let's start our performance!

I. The Operating System of an Improv Scene

The general flow of an improv performance follows a simple pattern: the performers ask the audience for a suggestion (a word, prompt, topic, theme) and the troupe constructs a series of scenes over the next ~60 minutes. What ensues is a fast-moving conveyor belt that converts dynamic inputs from the actors — anything from lines of dialogue, body language shifts, character behaviours — to outputs dressed up as coherent live-action stories. You might even be treated to song or dance! This form of comedy encourages suspension of disbelief with a healthy dose of relatable realism, as the improvisers strive to provide a mirror reflecting everyday human interactions.

Countering Comedy Clichés

Improv is not about making people laugh. Improv is not just for loud, extroverted personalities. Improv is indeed spontaneous, but not at the expense of its systematic nature. In many ways, you don’t even need to think quickly to become a truly skilled improviser. As eloquently expressed by blockbuster comedian Keegan-Michael Key:

People think that improvisation is moving forward. What improvisation really is, it’s walking backwards. It’s backing up that gives you discovery. People always go: “I can’t think that fast!” No no no — don’t think that fast. Just listen to the last thing they said.

Key flips the conventional thinking of improv comedy on its head and carves out an opportunity for the average layperson to pick up the ball and just play. There’s a sense of immediate intimacy that you feel by being part of this ecosystem. The feeling that everyone has the potential to be a world-class listener. To improvise is to listen. These observations suggest that improv is nuanced: an intricate web of well-documented, on-stage rituals hidden underneath the clutter of slapstick bits and artificial plot twists.

Systematizing Improv

Making sense of this wacky world involves recognizing the breadth of technical tools available to the seasoned comedy practitioner. Before we can boldly assert that these skillsets are highly applicable to our personal and professional lives, we need to understand the foundational building blocks that underlie improv comedy at its core. To give you a taste of the on-stage magic, I’ve outlined six of the most salient features:

At a basic level, the concept feels obvious but the practice seems dubious. Improv is fleeting, messy, chaotic. How might we systematize such a thorny transient activity? My scientific scholar mindset yearned to create order from the chaos, resulting in the above improv mental models. These frameworks provide the interactive infrastructure and constraints to anchor this artform.

Embracing “Yes, And”

The principle of ‘Yes And’ is considered by many as the ethos of the improv manifesto. The root: I accept your offer, and here’s how I’m adding to your thought or idea. The elegance is literally baked into its powerful simplicity — I consider this model as the lifeblood that flows into and adds strength to the other five mental models.

We develop a platform of a scene through repeated application of Yes And. We reinvest into each other’s choices, creating a virtuous cycle of ideas. We discover the unique patterns and games to play by using these two words, often not said outwardly. Yes And provokes the exploration of human behaviour and shows the subtext of the characters’ motivations from each back-and-forth conversation.

The comedic construct of Yes And stretches beyond the performance stage and seeps into our everyday interactions and relationships. In typical systems fashion, I argue that this pervasive phenomenon can be visualized through a theoretical 2x2 matrix:

Getting caught in the minutiae and mundane within our busy worklives muddles the immediate benefits of adopting the Yes And mentality. In my view, we tend to oscillate between being a passenger and a driver in the long-tail of our decisions. Worse yet, moments of pressure often strain us to become a blocker unconsciously. To work out our builder muscles, we can consider actively embedding generative practices into our daily flow, which can consist of writing, debating, pitching, or meditating.

Advancing the Story

If Yes And represents the units of comedy creation at an atomic level, then the sum of the parts naturally flow into a full-fledged story. The last step in our analysis is mapping the chronology of a scene and sequencing each mental model as appropriate.

We can think of improv platforms as a diving board that submerges us into different swimlanes comprised of three fundamental questions: what, who, and where. While the conventional mode of thinking stresses spontaneity and randomness, establishing a robust platform helps contain the scene with constraints. In other words, while there seems to be boundless possibilities of ideas at the outset, improvisers can only build based on all available information accumulated at the current moment.

If you have a background in data science, you’ll recognize this concept: this is a decision tree. Each subsequent node represents a singular unit of information presented as a gift to the other person. But just like statistical decision trees, there is a risk of “overfitting” an improv scene. Imagine one improviser compromising the character discovery with a misaligned reaction, or attacking the integrity of an established relationship by aiming too tightly or boldly at an over-the-top gag.

Structure is king, and the most memorable stories in life always bring us along for the ride — making us feel something. This is an improviser’s ultimate superpower.

The main takeaway about this operating system is that top-level improv encourages open-ended storytelling between scene partners in the frontend, while facilitated by microscopic observations, choices, and connections running in the backend.

II. The Scenework Principles for Products

By pushing improv to its logical extreme and the highest level of abstraction, we can start to appreciate its value when applied to disciplines like product management and start-up strategy. According to Bob Kulhan, a business professor at Duke University:

Improvisation is being super-pliable. Entrepreneurs and product leaders need to get out of their own way and adopt a fail early, fail often mentality.

Almost counterintuitively, improv teaches us to impose limits on our innovations as we wade through the neverending downpour of pending tasks and unbuilt features. It acts as a forcing function for creativity and serendipity. For product leaders, the improv mind can be applied to mimic customer experiences and pain points to better empathize with how the end-product will be touched, felt, and perceived in the wild.

One question that both budding entrepreneurs and technologists commonly face in developing cutting-edge solutions today: How do we build a creativity engine that enables consistent imagination and invention? I’ve explored this space in specific contexts of three builders: product designers, user researchers, and software engineers.

Design thinking

Design thinking is an ideation approach that emphasizes human-centered, creative problem-solving through making connected choices. The illustrious Creativity and Innovation Management journal published a model in 2018 called design improv, a methodology for operationalizing improv principles in early product development:

The emergence of an innovative product design can be compared to the telling of a funny joke: both combine seemingly unconnected ideas in a way that is both surprising and satisfying.

Humour is directly integrated at the heart of this unorthodox process, formalized through a set of workshops. Researchers and designers apply comedic devices to the initial discovery phase, such as stitching together visual comic strips for product use cases and playing short-form improv games as fuel for inventive stimulus.

The most important callout is the heightening step, my all-time favourite tactic to apply. The premise is elegantly simple. Once you’ve noticed what stands out as being unusual (an atypical customer pain, a reconfigured feature, a branding preference), candidly ask yourself: “if this is true, then what else is true?” This prompt pushes us to be possibility thinkers and inflate what is already absurd to drive out-of-the-box outcomes. It’s this exact transition between expansion of thought and recursion of technique that grants us the liberty to build even bigger and bolder.

Further literature also validates these parallels between performative improv and product management, specifically cultivating active listening to empathize with human needs. Cedric Chin contends in this blog post that Amazon’s Working Backwards method quickly allows the company to rapidly bet on and validate new products. The technique tells team members to visualize the ideal customer experience by fleshing out a future-facing press release and drafting a mock FAQs page.

User testing

As we learned earlier from Keegan-Michael Key’s analogy, improv is all about walking backwards to drive discovery. We willingly flip the script and reverse engineer from the aspirational end state. In this case, product management is not approached with the classical blue-sky, blank-canvas, feature-driven approach. Instead, user obsession takes precedence and every decision is laced with feedback and hyper-observation.

By a former Intercom ex-product manager and fellow improviser:

Don’t just listen and act quick. Try and digest the motivations behind what you’re hearing - the pain behind a customer’s feature request, the rationale behind UX changes a designer is sharing, or the new technology that inspired a feature suggestion from engineering.

This layers the improv models of discovery and subtext into the fundamental activity of user testing. By diving into human motivations beyond what is stated, you can create a new sense of clarity and convert constraining conversations (“No it’s not possible - the tech stack doesn’t support it!”) into value-enhancing dialogues (“Great point - how might we prioritize these pain points and requests in our issues backlog?”)

Even with these proactive principles in mind, product managers should not say yes to every single idea, feature request, or piece of user feedback. Capacity, cost, and culture still constrict what is actionable. Similarly in improv, agreement is not the same as acceptance — we don’t have to blindly say “yes” to candidly accept a point-of-view. As banal as it sounds, the most important highlight is to never let go of an empathetic and experimental mindset when building products to delight and excite eager customers.

Extreme programming

The last unconventional connection we can bridge is the overlap between improv and software engineering. In any common-day tech hub, you’ll hear the words agile development being thrown around, whereby moving fast and shipping small reign supreme. Extreme programming (XP) is a variation that emphasizes responsive rapid releases to customer needs, governed by several stage-gated feedback loops.

Just like a performance starts vague and high-level, XP works down from a macro monthly release plan down to micro hourly testing. One software principle that perfectly fits the improv system is pair programming, where two engineers work jointly on the same code. While the first developer focuses on building the code base, the other reviews it, suggests improvements, and debugs mistakes throughout.

The spirit of continuous integration and continuous delivery from two developers constantly committing code is akin to the dynamic nature of two on-stage actors developing deeper dialogues.

If we really wanted to get programmatically-philosophical, we can argue that improv choices are a series of algorithms. We imagine an infinite game of constant learning, where scene partners work together to gradually figure out the branching logic of characters and environments. For those intrigued about this extra technical territory, the application of Markov chains in probability theory deserves specific attention.

III. The Improviser’s Lens to Living Life

As a huge proponent of finding unconventional ways to live mindfully, improv principles fit snugly into various applications. Within three core themes of wellness, empathy, and play, I’ve curated a list of resources that echo the various use cases:

🔑 For you: Improv as a wellness modality

• A form of therapy: By creating a space free of judgment and free of failure, the stage can offer a collaborative catharsis for people struggling with anxiety.

• A form of uncertainty management: By assembling a scaffold of workflow adaptations and personal practices, improv principles act as reassurance.

• A form of addiction treatment: By actively fostering unrehearsed interactions, improv exercises boost self-awareness and addiction recovery rates.

💛 For others: Improv as an empathy catalyst

• Empathy within interpersonal relationships: Whether in the workplace or in romantic endeavours, improv finds a place in positive psychology relating to expanded empathy, immersive mindfulness, and constructive responding.

• Empathy in the age of virtual meetings: Social organizational psychologists at the Kellogg School of Management explore the hurdles of cross-talk and low empathy on Zoom calls with six improv devices.

• Empathy for essential service occupations: Particularly in the medicine realm, there has been extensive research into improv’s role in augmenting soft skills like empathy for doctors and medical practitioners.

👶 For all: Improv as a formal license to play

• On laughter and learning: “The key is using humour to enhance otherwise dull statistical methodology by tapping into students’ multiple intelligences…”

• On permissionless living: “Play gives us permission to be other than who we are in ‘real life’. It allows us to imagine ourselves as being, feeling, and doing different...”

• On playfulness: “It’s time we stop seeing play as subordinate, and start getting serious about living a playful life. Playing opens up a new time and space…”

If you’ve stuck around to the end, I really appreciate you letting me gush about improv! Feel free to shoot me a message if you ever want to talk performing arts or products :)

To end with a comforting philosophy from a budding improviser to all of you: “I got your back!”

“Psychotherapy is built on a promise: you bring your suffering to this private place and I will work with you to keep you safe and help you heal” - Todd Essig, PhD

Keeping you safe and helping you heal. This quote calls out an important tenet of traditional therapy: bottle up your suffering and release it in a detached universe away from the pains of regular reality. Although there is increasing acceptance and adoption of psychotherapy solutions, many remain skeptical. After all, why invest in a cost- and time-intensive service where the output is largely driven by yourself?

To make matters more complex, the paradigm shift to digital-by-default presents both possibilities and fears for psychotherapists and patients alike. Long gone are the days of sitting on a satin sofa and recounting emotionally charged stories to a trained practitioner nodding and scribbling away. Shared stressors for Zoom-fatigued individuals add tension to intimate connection, especially with the absence of attention, empathy, and physicality from the usual expectation.

The sobering truth is that therapy has departed drastically from its traditional form.

As accessible as therapy has become, you could argue that the telehealth trend undermines the key benefit of an enclosed haven that historically promoted feelings of safety, privacy, and reliability for patients.

But what if this digital health revolution has enabled more creative options for both patients and providers, while maintaining efficacy of traditional therapy?

To test this hypothesis, I committed in early 2020 to plunge headfirst into a new therapy-enabled growth journey. This is a tale about how a year-long exploration of cognitive-behavioural therapy (CBT) completely transformed both my internal perception and external worldview, eventually equipping me with a toolkit to perform on-demand “self-psychotherapy”. This piece will also include a deep dive into designing best-in-class wellness experiences and imagining what a future state therapy landscape could look like. Let’s start our scheduled check-in!

I. Undisturbing Yourself: CBT Tricks of the Trade

Journalist Rosie Spinks suggests in this article that literally everyone can benefit from therapy by framing it as a proactive mechanism to help model correct behaviour and replace missing support.

I was intrigued by her arguments and eager to find the path of least resistance of sourcing a proper therapist, knowing that the vetting process was much like the trial-and-error troubles of online dating. Here were my key considerations:

• Objective: Why do you want to invest time, energy, and money into therapy? I was looking to engage in rigorous exercises in self-development and self-discovery.

• Modality: What type of therapy would make the most sense with my current situation? Literature in CBT describes the method as a collaborative, first-line defence tool, which was compelling and aligned well with my generalized goals.

• Quality: How do you differentiate between therapist quality? The therapist I landed on positioned his offering as “existentially-minded CBT”, which caught my eye in a sea of comparable credentials and indistinguishable hourly rates.

I embraced a feeling of open curiosity going into the first session. I outlined three guiding goals for myself: optimizing for work, relationships, and life purpose. Upon minutes of meeting my therapist, he dropped a mesmerizing line that fully flipped my mindset from cautiously curious to enthusiastically eager for this experience.

“Over our time together, my main intention is to armour you with the systems and frameworks of CBT thinking and unpack your subconscious limiting beliefs. We’ll take this to an extreme boiling point where you ideally unlock the art of self-therapy.”

The core framework that grounded each of my therapy sessions was the “CBT Triangle”: the interplay between thoughts, emotions, and behaviours. The essence of CBT is applying proactive data-driven techniques to disrupt your mind and body in real-time, whenever there is a disturbance within any of the three elements.

This model manifests around feedback loops: negative thoughts spiral into negative emotions, which drive negative behaviours. This cycle starts morphing into a self-feeding living organism over time. Soul-nourishing in the best case, and harmfully parasitic if left unchecked. I call this the mental wellness flywheel:

Sidebar: This visual is the key reason why people are stuck in a vicious vortex of their own self-defeating patterns. The flywheel feeds on your subconscious and overrides your body’s regular programming during stressful periods. These outcomes compound over time and potentially "crowd out" activities normally considered pleasant or enjoyable. Quite a problem especially if you find ways to rationalize these thoughts!

My therapist then introduced the concept of cognitive distortions as my first homework assignment. This was critical to helping diagnose the irrational biases and decision heuristics carried over from our formative years as starry-eyed children. From catastrophizing events, adopting black-and-white thinking, or just overusing the words "Should" and “Must”, these cognitive principles laid the groundwork for deep exploration. The premise: make your inner thoughts visible by targeting the invisible.

At this point you might be saying: “Okay learning these concepts is fantastic, but how do I actually take control of my own flywheel?” This model can be stacked with the House of Cards metaphor — each card represents a different limiting belief distorted in your mind. The exercise here is to observe each layer of the card structure and toss out the ones that are not serving your wellness needs.

One of my constraining philosophies was a tendency to obsess over future-proofing my life and over-valuing potential options and outcomes that don’t even exist yet, instead of fully immersing myself in the present.

On paper, the corporate world typically sees this mentality as being ambitious, having keen foresight, and embracing a bias for action. Productivity hacking reigns supreme. Optionality is the end-game. So on and so forth. You can see how easy it is to justify the merits of any belief, especially when combined with societal norms. Some common violators include: acting solely for outward affirmations or self-absorbing over the final product instead of learning from the end-to-end process.

Reshuffling your inner house of cards and starting with a new refreshed hand can be viewed as the ultimate goal of the CBT game, as there are direct impacts on how you perceive yourself and the world (self-talk + automatic thoughts). We can make this metaphor more practical by viewing it as a bottom-up pyramid of reflective actions:

Structuring the practice in a four-part sequence allows for a common dialogue both in-session and between sessions as part of an overall mental fitness workout routine. If “Old Sam” were too fixated with the future and this belief was driving unhealthy thoughts, behaviours, or feelings, here is the systematic CBT flow in action:

1. Limiting beliefs (Identify): Stretch the analysis of deeply-rooted beliefs to its extreme end. Think: the distortions at play are polarized thinking and should-ing/must-ing. I value external stimulus through achieving. I am afraid of falling behind. I am not enough as I am.

2. Double-sided evidence (Challenge): Dig deeper into your subconscious by assessing the costs and benefits of keeping this belief. Ask: if this belief is true, what does it say about me? In this case, my internal prosecution team posits that prioritizing the future is a never-ending unhealthy cycle, while my inner defence sides with the long-term utility of always optimizing for new opportunities.

3. Mindset shift (Update): Remove the distortions and inject nuance back into the belief for a balanced view. Frame: “Even when [x would be preferred], evidence suggests that [y still occurs or z is still true]”. Even when it would be preferable that I’m set up well for future success, evidence suggests that living the present is also equally fulfilling, nutritious, and enjoyable, and can also lead to serendipity.

4. Recurring practice (Rewire): Remind yourself constantly of the new updates to ingrain them into your subconscious and displace the old. This can be achieved through a codified mantra, mindfulness meditation, or scheduled check-ins.

Despite only showing you the abridged version of my one-year therapy experience, I hope this provides greater clarity into the value of CBT. By merely having a mindful collaborator listen to the substance and delivery of my stories, I uprooted several unkempt weeds in my mental forest of beliefs. A self-driven mindfulness masterclass!

II. Designing CBT Experiences: A WellTech MVP

These CBT frameworks look powerful in practice, but we’ve made one simplifying assumption that these outcomes are representative of any inbound patient’s journey. We also have not addressed people who are seeking direct remedies for stress, anxiety, depression, or burnout, and those suffering from more chronic conditions.

The affinity, availability, and affordability of classic therapy solutions do not align with characteristics of a broader population, especially underrepresented groups.

With a vested interest to tackle this wicked problem after 6 months of CBT exposure, I kickstarted the development of a makeshift wellness web application. My goal was to apply therapy principles and address a core pain point relevant to my own immediate surroundings: burnout risk for early-career professionals. Success would manifest as a greater self-service capability for the less mentally savvy, with the platform acting as a complement to traditional CBT through tailored DIY wellness routines.

Oranga was then birthed as my self-therapy brainchild, collaborating with a full-stack developer passionate about holistic health and a product designer leading the charge at a mental health startup. The name derives from the Māori word for [health, wellbeing, and life], which definitely resonated with me during my time spent in New Zealand.

See below for a quick 2-minute pitch of the concept, and I’ve also included product design prototypes and V0 deployed web app of the initial user onboarding process.

Perhaps this solution is not as “revolutionary” as I tried to pitch (just a glorified online survey?!), but the four-week sprint was geared more towards validating and learning rather than shipping a full-fledged platform. From my POV as the product manager, I gained three takeaways for building best-in-class WellTech experiences:

• Setting a bold product vision can be clouded by intricacies in the wellness space. While the therapy industry is definitely ripe for disruption, it is easy to get caught up in trying to reinvent the therapeutic wheel instead of remixing on top of existing market alternatives. My initial customer discovery efforts revealed that each target user’s self-care routines and perceptions of therapy varied wildly, but also strengthened the case of focusing on early-stage career burnout.

• Accounting for conflicting user feedback can influence the design-dev handoff. The added complexity of individual wellness preferences pushed me to prioritize usability testing, starting with low-fidelity designs. As a result, running a typical agile process with stage-gated sprints had limited effectiveness given so many variables. Giving piecemeal insights to your software engineer constrains the ability to commit to code, especially with differing opinions on critical features!

• Spreading awareness to a small group of power users can still have a profound impact. Even with a light backdrop of 15 alpha users, the anecdotal follow-up conversations revealed a surprising, clear-cut interest in seeing further iterations of the prototype. There is inherent value in hosting lengthier “show-and-click” sessions if merely to spark collaborative consultations on an underserved topic.

  ---

III. Overcoming Barriers: The Future of Therapy

My attempt at driving an app-based approach shows the difficulty of triaging the pains of burnout with therapy modalities. This last section aims to greatly expand our discussion past the traditional and into future-forward trends. I created a positioning matrix to differentiate and plot high-growth companies in the market, based on stakeholder focus (patient vs. practitioner) and service mode (proactive vs. reactive):

While the following trends present attractive opportunities to reach patients at scale, my final caveat is that productizing therapy may never fully replicate and replace the quality of a human-centered intervention. But there is also cause to be optimistic!

Trend 1: Increasing therapy-related complements and substitutes

The broad theme around these companies is integrating the community aspect to create cohort-driven options that either work with or work around classic therapy.

• Octave’s added combination of well-being coaching and support groups: In addition to their standard therapy matching platform, Octave addresses a wide range of pain points through their breadth of support services.

• Pace’s facilitator-led wellness groups around shared interests: Pace’s model reduces the formality from therapists and replaces it with facilitators who lead personalized, handpicked small groups based on any topic or comfort level.

• Marigold Health’s community behavioural health mechanism: Peer support forms the crux of Marigold’s model, providing a closed circle of on-demand individualized support. Marigold also integrates with existing health providers.

Trend 2: Democratizing therapy modalities for everyday access

These solutions unbundle the components of therapy and repackage them into new channels of consumption with a focus on reactive diagnosis.

• Talkspace’s free 10-day healing curriculum: While an established player, Talkspace continues to innovate by curating clinically-backed lessons and practices geared towards self-restoration. Full therapist sign-off included.

• Quilt’s distributed model of talk therapy: While not branded as a direct therapy product, Quilt builds on a Clubhouse-esque audio approach to normalize authentic conversations around self-care. A natural extension: mini therapy pods!

• Woebot’s AI-powered CBT chatbot: Going one level of abstraction higher than the popular text messaging approach, Woebot leverages natural language processing (NLP) to build meaningful bonds with users asynchronously.

Trend 3: Building proactive routines for mental and emotional wellness

This group of early-stage ventures can be considered as “wellbeing-as-a-service”, touching on other important elements to proactively optimize your mental health.

• Coa’s emotional fitness gym concept: With a unique model of group-based classes, Coa is pioneering a movement to shift the narrative around therapy - from being a tool only when you’re unwell to a core building block of wellness.

• Chorus’ social layer to meditation: Injecting fun and liveliness into a conventionally low-energy, high-barrier to entry practice, Chorus is creating a group meditation experience to promote proactive inclusion into daily life.

• Intellect’s app-driven psychological training regimen: Being one of the prime CBT-oriented apps to raise seed capital, Intellect’s value proposition focuses on self-guided exercises to improve personal behaviours, relationships, and habits.

  ---

As a parting reflection, I recognize that this essay only scratches the surface when it comes to exploring and understanding the broad-based, multivariate nature of therapy. The silver lining is that incentivizing consistent coverage and empathizing ruthlessly with therapy-goers are lightweight methods to help move the needle on a crucial topic.

I envision a world where conversations about mental health are completely normalized and people are empowered to develop the skill of self-therapy.

After all, the best work of your life is the work you do on yourself.

As the public health crisis rages on with lockdown loops and mutating virus strains causing a standstill, few are talking about a potentially more wicked problem at hand: an echo pandemic quietly terrorizing our mental health. We’re presented with a balancing act of maintaining both our physical and mental wellness — a true herculean feat for many. What solutions exist that will help us achieve this equilibrium and stay holistically healthy?

This memoir aims to instill a sense of hope to tackle this pressing question. I will map my early experience with Calm’s wellness offerings, develop mindful mental models, and crystallize my learnings in the form of product recommendations.

An intentional check-in

The ugly truth: A recent study published by the Mental Health Association of Canada reported that rates of anxiety and depression have quadrupled, from 5% to 20%, with the onset of the pandemic. Unemployment rates have been highly volatile and data suggests a 1:1 positive correlation between unemployment and suicide rates. There is a compounding effect that places huge strain on our mental states, driven directly and indirectly as a result of this unique double-sided pandemic.

Whoa, don’t we already have enough proverbial pandemics as it stands? An existential risk to climate. An existential risk to democracy. Now, an existential risk to our personal wellness. There’s truly been a paradigm shift in how we view the definition of “healthy”.

The silver lining: At first blush, the debut of 2021 and the objective facts just presented don’t revive those long-lost memories of a goal-oriented, dopamine-infused January. Fortunately, 2020 has hyper-charged the birth and growth of impactful wellness solutions:

By the tail-end of Q4 2020, the world saw an explosion of high-profile financings in the wellness technology space: Lyra Health’s $175M Series E, Headspace’s $48M Series C extension, and one more notable candidate…

Calm. Calm, often touted as the world’s first mental health unicorn and our collective beacon of mindfulness, raised a $75M Series C. Before diving into how well this big $2B elephant in the room fits into this self-care puzzle, I want to share how Calm intertwines with my personal mental health journey.

A beginner’s mind

I am an innately curious person and crave discovery. This has manifested throughout my life — from searching for patterns in nature as a child, to constantly experimenting with how to optimize my life in adulthood. Taking this deep-seated philosophy to a new expansive “wellness playground”, I’ve captured a rolling snapshot of my week-long experience battle-testing Calm and its suite of premium offerings. Combining this with select user interviews, I’ve generated a collection of mindful frameworks and a roadmap for potential product enhancements.

In a cheeky attempt to inject creative flair, I structured each section to reflect the key steps in my own meditation practice. Let’s take our first breath!

Step I. Inhaling Deeply: My Calm Exploration

Meditation and I have a rocky relationship — I’ve tried several times in the past, but there hasn’t been the spark or accountability needed to inspire me to form a lasting wellness habit.

The basis for my experiment was a commitment to a full week actively using Calm premium, where I would try at least 5 distinct functionalities to develop my routines from the ground-up and layer on components as I gained comfort and confidence.

By visually graphing out my 7-day Calm experience, there are a few themes that emerge. With a goal of starting small, I focused my efforts on Calm’s cornerstones — following quick meditations (Daily Calm) and cultivating sound sleep (Sleep Stories). I’ve segmented my Yelp review of Calm’s feature set below.

Plus 💚: I pinpointed the programs I wanted to revisit over the 7 days, classifying these as programs with ‘replay value’. Sleep Stories, Daily Calm, and Daily Trip were among the best because they had distinct use cases based on time of day and offered a combination of surprise, delight, and engagement. This created a virtuous cycle of actively opening the app just to see what the proverbial “catch of the day” was. Lastly, while the benefits of meditation are usually intangible, I realized that I’ve already started to make key lifestyle shifts thanks to the app’s utility and structure provided.

Minus ❌: While features like Mood Tracker, Walking Meditations, and Deep Concentration were compelling at the outset, they lacked sufficient variety and didn’t have staying power past 1–2 days. However, I believe that each of these features address real pain points, suggesting potential enhancements in the future.

Neutral ⚠️: Extending my personal wellness playground analogy from earlier, Calm boasts a massive breadth of options for the casual user, which in my opinion is both an advantage and possible disadvantage for those less mindfully-savvy. Part of the reason I didn’t play around with every feature (e.g. Deep Breath, Mental Fitness, Sparks, etc.) is a lack of time to allocate, especially considering the priority spent on my preferred programs.

The Calming Verdict ✨: Possibly the biggest win that came out of this one-week sprint is the sheer discipline I’ve gained with sticking to habits and routines. Of course, I can’t ignore the extrinsic motivation in trying to provide you lovely folks with solid content, but even just seeing the building blocks of what is quickly becoming my new mental model for mindfulness is a surreal moment.

As for the big reveal: I’ve now fully converted to being a happy and healthy paid Calm subscriber! While I may have missed a few days of dedicated meditation since the official week of exploration, this process has taught me that it’s perfectly okay to “let it be” and move on without the angst of not following the regimen. It’s reassuring to know that the product can support more occasions and opportunities for mindfulness as I advance my mental wellness game.

Step II. Observing the Breath: Others’ Wellness Needs

It would be naive to assume that everyone thinks about and uses Calm the same way I do. Just like the plethora of breathing techniques available, each individual has their own preferences and tastes when it comes to mental wellness, which brings up a crucial question. How well does Calm’s formula hold up when presented with so many hidden, situational variables?

I was inspired by a piece from Justin De Graaf, Google’s Head of Research and Insights, who spoke to the power of understanding “need states” to drive intent.

A need state is a product benefit or attribute desired by a user in a particular occasion. Google’s search engine product is positioned in a way that meets consumers in several occasions anchored by specific emotions, i.e. thrill me, impress me, educate me, reassure me, help me, and surprise me. The benefits of a hyper-focused needs-driven approach can be distilled down to the simplest level, with just four words:

“Needs spark consumer journeys”

On that note, with such a broad buffet of functionalities in the app, it can be hard to distinguish what kinds of journeys Calm users can experience. Is it a one-stop shop for all-things mindfulness? Or do users naturally gravitate towards one key feature they have the strongest affinity to?

In order to answer these questions and better understand the implicit need states, I benchmarked my own experience vs. other avid Calm users. I had the opportunity to interview superstars from my network to compare how their experiences stacked up to mine — a management consultant, an architect-turned-designer, and a practicing psychotherapist.

It was fascinating to see the divergence in opinions, thoughts, and applications of Calm from several vantage points, which might have been expected from such a diverse group of interviewees. Interesting tidbits from these in-depth conversations included:

“Since my work hours are nothing short of crazy and my mind always runs at 10,000 miles per hour, the voice of soothing celebrities really helps me sleep well” — The Consultant

“Honestly, I’ve just really been into the concept of “biopsychology” which has helped balance some of my anxiety and feel well” — The Architect

“Some of my clients are starting to experiment, and so I’ve also found the 10-minute sessions to be a refreshing new way to keep my mind constantly growing” — The Therapist

With these quotes in mind, I was inspired to construct a custom framework that attempts to neatly connect the dots together and address this spectrum of needs that Calm aims to fill:

Structuring needs in this systematic stack acknowledges that personal wellness situations are unique, but can be synthesized in a framework that allows Calm to build experiences catered to a user’s initial need states. This opens a door to cross-convert them to other services over time. The actual journeys become more tangible — they may start with Sleep or only try Reflections, but there are endless possibilities to weave a web of wellness for consistently engaged users.

With both the frontend personal exploration and the backend user analysis completed, we are now set up well to introduce Act III — final reflections & recommendations.

Step III. Exhaling Gradually: Reflections & Recommendations

”If meditation was Act I, and sleep stories in Act II sent engagement up threefold and dramatically increased retention, I’m very excited for Act III.”

Nicole Quinn — Lightspeed Venture Partners, Calm board member

What could this fabled Act III be? I put on my product manager hat to create a potential product roadmap for Calm as it continues to push the boundaries toward achieving its audacious vision of becoming the “Nike of the Mind”. I have summarized my roadmap by including three simple buttons and tying design principles to each, while respecting Calm’s positioning of a serene, non-disruptive user interface:

1. In-app optimizations (near-term, core value): To keep users motivated and accountable, practical enhancements can be made to existing features like streak tracking & visualization to improve visibility, varied push notifications to drive different user actions, and expansion of the content library to address the specific need states described earlier. With Calm’s previous expertise using analytical tools like Amplitude to run high-impact scientific experiments, these initiatives can be quickly hacked together by Ops & Product teams to iterate and provide continuous insights for active users.

Reflect well: In-app optimizations will facilitate more intentional and insightful usage.

2. Out-of-app experiences (medium-term, adjacencies): On the overall wellness front, Calm has the opportunity to literally move outside and integrate components of the physical world into the full mindful journey of a Calm user. While features such as 5-minute Mindful Walking and Daily Calm Reflection exist, these only scratch the surface of acquiring a right to play in the entire wellness landscape. Holistic wellness routines are often characterized by additional physical modalities used in maintaining mental health — going on walks, reflective journaling, taking digital detoxes, etc.

Out-of-app can also involve connecting people together, recognizing the modern human truth that self-care has increasingly become about “joint care”. Introducing sentiments of “Mindful Messages” and “Moments that Matter” along with the existing “Share Your Stats” button to enable stronger connections, can be stepping stones to foster a long-lasting wellness tribe.

Feel well: Out-of-app experiences will fine-tune your practice by connecting with nature and others.

3. Personalization engine (long-term, game changers): While only as effective as the pool of data provided by the usage patterns of highly-engaged active users, Calm will eventually hit the inflection point of having enough insights to offer more predictive and prescriptive content. At the outset, this could involve greater education and insights about a user’s personal wellness journey, and potentially building up to therapy capabilities and science-backed medical practices. The grand theme that ties the thread together is turning Calm into a fully proactive solution — layering on top of the existing onboarding infrastructure, in-app tracking, and Apple Health API integration to truly meet the user at every step.

Grow well: A well-groomed personalization engine will foster continuous growth in all aspects of wellness.

Meditative memoir post mortem

With the looming echo pandemic in full force, there’s never been a clearer moment to just take a breath and be intentional with our energy and effort. Going through this week-long Calm retreat has surprisingly taught me a lot about general wellness principles and has completely reorganized both my schedule and thinking around what health really means. I want to share three of my key learnings that you can also apply in your personal practice:

1. Make a conscious choice to show up every day for <10 minutes to boost your personal wellbeing and happiness

2. Habitualize just-in-time reflections and quick meditations as a healthy, enjoyable part of your day-to-day (vs. a nice afterthought)

3. Understand it is totally okay to let your mind run incessantly during sessions, as meditation is truly the art of doing nothing

Just as Sleep Stories provide us with a platform to become dreamers and believers, I’ll be putting my faith into Calm to make the world happier and healthier!

The sandbox has a special place in my heart for being a place of great learning, wonder, and most importantly, fun. As I mature into the forest of adulthood, I find myself increasingly enamoured by the idea of empowering my past childhood persona. Whether related to product strategy, mental models, or life philosophies, I aim to ground any of my custom creations with three key parts of the “Sandbox Manifesto”:

1. Messy is good.

2. Imagination is the greatest asset.

3. Play is the work.

People may come and go, toys might be dropped and forgotten, and the world will move and evolve, but one constant remains true: I love play.

Thanks for reading and I hope you’ll have as much fun here as I will.

Sam