Sentimental Sam: Big shoutout to everyone who’s been part of the first 25 years so far! From elementary pals to high school homies to case competition friends to global travel encounters - whether you’re a subscriber or a stranger, I’d love to hear from you :)
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
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:
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”
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!
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.
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.
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.
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.
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:
Creating positive impact for others ['authenticity', 'charity'] = impact
Honing my creative expression ['learning', 'curiosity'] = skills
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 :)