#1: the purpose deficit
Why the pursuit of achievement feels empty and how meaning replaces it
I will never forget the day I told my parents I was dropping out. I remember the blank stares as I walked through my reasoning. What they didn’t say I could see written all over their faces: “The grades, money, time… what was it all for? Why are you doing this?”
I told them university wasn’t for me. That I could get to where I wanted to go faster (and with far less debt) by opting out of school. Aside from saving money, this was the last thing they wanted to hear. After all, my parents were refugees of the Vietnam War. This was what they sacrificed everything for and I was throwing it all away for something uncertain. They understood credentials and achievements. Dropping out was outside of their realm of understanding entirely.
Growing up, I barely questioned “why?”. Whether it was the cultural inheritance of respect for your elders that had been so ingrained in me, or the fact that I had not yet developed the confidence to trust my own instincts, the muscle of asking myself why wasn’t something I flexed.
But as I achieved and progressed through life, this question surfaced more and more. Not just at major turning points but naturally as I built up my identity. It became especially evident when I moved out. There I was—fully independent. Living on my own, figuring out life skills, moving countries, needing to make decisions on my own. I was in the driver’s seat and nobody else could do this but me.
When I started to ask myself why and prioritized meaning more personally defined, it led me to make some of the best decisions of my life: changing majors halfway through freshman year, quitting a job and taking a risk to be employee #1, leaving a VC partner track, starting a company, and recently exiting to do it all over again.
At first, these were just experiments. Over time, each transition felt more genuine not only to the identity I had been building, but also to 8-year-old Karel who did things for intrinsic enjoyment.
After exiting, I found space away from the relentless pace of working. To refresh and build. To exchange ideas with brilliant people as I consider where I want to redirect my ambition next. And to think about where purpose really comes from.
This essay is a letter to my past self. And if you’re working on building identity and finding meaning, it’s for you too.
inheritance of sacrifice
My parents were some of the Vietnamese boat people who fled the Communist regime, and their story first begins with my dad. At 16, he claims to have been a “playboy.” He was a bit rambunctious. He loved popping wheelies on his motorcycle, street racing, and inviting girls to ride with him. With Vietnam becoming increasingly unstable, my grandma worried his loudness would lead to his early grave. So she sent him and his cousin out to flee the country by boat as the rest of the family waited it out. My dad was on one of the first boats out, his cousin on the second. This would be the last time anyone would ever hear from his cousin again.
Bound for Singapore, the boat was small and overcrowded, with 49 people huddled closely together. Just one day after departing, their motor died and the boat started leaking. From day to night, the passengers desperately scooped out buckets of water to prevent the boat from sinking. Adrift at sea, my dad and others from his group made a makeshift sail out of their ragged clothes. This put them entirely at the whim of the elements, which made it difficult to evade some of the dangers at sea—chief among them were pirates. Some were just emboldened fishermen taking advantage of refugees who left their homes with their most prized possessions, others were the real thing. The fishermen would at least give them food and water in exchange for jewelry and other valuables. The pirates were merciless and didn’t care about their livelihood. My dad recalled a pirate holding him down with a machete at his neck. In another instance, three wives were taken away from their husbands, never to be seen again. People came, took what they wanted, and left them as they continued to drift. On day ten of the voyage, my dad’s boat encountered its first thunderstorm. The open seas brought tumultuous waves that pushed their limits further in efforts to keep the boat afloat. It was only then that my dad thought he was going to die. Miraculously, the storm calmed and they finally made landfall. In the end, 46 survived and they were later moved to the famous Sikiew refugee camp in the Korat Province in Thailand.
Sikiew was originally a prison and detention camp built to detain Vietnamese civilians who immigrated to Thailand before World War II. When my dad arrived in 1981, he had just missed the window for international acceptance of refugees and was forced to stay put. It was at that point that Sikiew started to house Vietnamese refugees fleeing the war. Some arrived by boat like my dad, others by foot. At first, there were only 70 people. Little did he know that two years later, my dad would be living among nearly 30,000 other Vietnamese refugees.
A few days in, my dad orchestrated an escape from Sikiew. He and seven others couldn’t bear the thought of being trapped within the prison walls. Unfortunately, their escape was thwarted and the group was detained by the soldiers. My dad was put in thumbcuffs with his hands suspended above his head. Any weight he put down led to painful pressure on the bones and nerves of his thumbs, making sleep impossible. Today, thumbcuffs have been condemned as a violation of human rights and many groups are calling for their prohibition.
By the time he was out, Sikiew became the central hub in the region for Vietnamese refugees and they began to merge other smaller refugee camps together. This left the camp desperately in need of manpower to distribute food and water, clean, and guard. My dad, despite his earlier escape attempt, was identified as an enterprising individual and was assigned to water duty. And it was here that he first met my mom.
Every family at Sikiew was allotted one bucket of water a day. They’d need to ration it to drink, cook, and wash. After meeting my mom, he snuck her and her family additional buckets whenever he could. And through that, a romance blossomed. In 1983, after all of the harrowing hardships they had been through both at sea and on land, they finally received sponsorship and made it to Canada. Safe at last.
Survival had been their sole purpose throughout this ordeal. Then stability as they rebuilt their lives. My dad working odd jobs picking strawberries and in Chinatown grocers, my mom going back to school to become a mechanical engineer. After having kids, purpose shifted to ensuring we found success as proof they didn’t just survive, but had also found a way to thrive. And if you’re an Asian immigrant, you might relate to how this often manifests: study hard and go become a doctor, lawyer, or engineer.
the achievement contract
Credentialed achievement isn’t just the goal of immigrant families. It forms the basis of the achievement contract that everyone enters into today. And it finds its roots in an education system that has long promoted metrics and credentials as a proxy of success (high GPA, test scores, college admissions). Later, the goals shift to collecting names of prestigious companies and promotions.
It was a game I played well. I was what most would consider a high achieving person, but still I felt something missing.
I had great options heading into college, deciding between software engineering at Waterloo, health/life science at McMaster and the University of Toronto. Some of the toughest programs to get into in Canada.
I loved to build things growing up. Initially with the mismatched Legos my family managed to scrounge together from garage sales. When we got our first computer and dial-up internet, my world grew infinitely. A constantly flowing tap of new knowledge and access to new virtual worlds through games. I started creating MySpace and Neopets sites, initally for myself and then for others as a digital lemonade stand of sorts. I became obsessed with StarCraft, a legendary real-time strategy (RTS) game that kicked off the esports movement. I played constantly and loved building custom maps in UMS (Use Map Settings). I was enamored with the process. Deconstructing how others made things, stitching together logic, and seeing it all come together by playing what I made with my friends. Come high school, I was making websites for small businesses and the City of Toronto. Building was in my blood.
Despite all of that though, I opted to become a doctor anyway. My parents never explicitly said that I had to, but it was obvious that was what they wanted. The way they lit up when we talked about the profession. And the marks I had in biology/chemistry reinforced the seemingly clear path. In high school, my (now late) mom had been diagnosed with an autoimmune disease called scleroderma. It was relentless and it put her and our family through a lot. This served as another nudge towards becoming a doctor.
The common thread across all of this? It was mainly defined by external forces. And I over-indexed on it.
For immigrants, we have another layer to the achievement contract. Achievement becomes moral currency for parental sacrifice. Each grade and each promotion delivers dopamine hits that feel like purpose. Not achieving made me feel guilty. Thinking about dropping out and stepping away from the path to get my degree made me feel worse, even though I knew it was the right thing for me. This binding through duty is why my sense of borrowed purpose felt real and like it was mine. Until it suddenly wasn’t.
The default outcome of achievement-as-purpose is purpose that isn’t your own. It’s shallow and lacks meaning. And it can only be overcome when you stop optimizing for external metrics and start building it up from your own identity and values.
Dropping out was my way of course correcting. After changing majors, going through my computer science program, and working at internships, I still felt like something was missing. Your mileage will vary but I felt that I was learning a heck of a lot more when I was outside of university and in SF or Waterloo. But being three years in to getting my degree, I grappled with the feeling of being so close, yet so far. I felt every ounce of opportunity cost. It was at this inflection point of self-actualization that the equilibrium had finally swung. Away from externally defined goals and expectations to meaning that was entirely self-directed.
the inflection point
The first inflection hit when I realized achievement-as-purpose had failed me. I had achieved everything I set out to achieve, but still felt nothing.
It was the realization that the goals and the path I set out on were no longer for me. Sometimes the goals weren’t even mine to start, and other times they were but I had long outgrown them. The realization manifested in a few different ways.
proxies become the goal
Credentials and metrics started out as signals but later had become the target. I stopped asking “does this matter?” and started asking “does this advance the metric?”. Goodhart’s Law became a reality. It became obvious to me even early on but I interpreted it as a means to an end. And they were and still are for the most part. Great grades unlock great schools, which unlock great careers. But without deeper intentionality for those goals, you start to wade through experiences feeling aimless.
A high GPA became the target, not evidence that I had learned something or that it was even something I cared about. Landing a prestigious company became the goal, not a proxy that showed me I had grown or was making an impact. As I achieved, I started to feel like I was on autopilot. Like somebody else was laying the tracks and I was just doing all of the right things necessary to keep chugging ahead, ensuring I excelled at it. I couldn’t fully figure out why, and I just accepted that it was how things were supposed to be and that was silly for me to even question it in the first place. So I worked hard, kept busy, and achieved. Somehow, I had gotten caught up optimizing for the metrics because measuring them was far easier than deep evaluation.
defensibility trap
It turns out I had been opting for a path that was easy to justify to others. First to my parents and family, but also friends and strangers. It wasn’t because I really intrinsically wanted to be a doctor or to remain in school. The safe, default thing takes the form of landing recognizable schools and prestigious jobs—all well-understood trajectories that people praise.
When I started to consider dropping out, my immediate instinct was to worry about what my parents would think of me. What would others think? That I had terrible marks and failed out? It couldn’t have been further from the truth. This was at a time when dropping out was far more non-conformist than it is today. Now, dropout culture and becoming a founder is a bit more mainstream and increasingly celebrated. I didn’t know it at the time but I had fallen into the trap of outsourcing judgment to consensus so I didn’t need to defend unconventional choices. The reality is that defensibility and authenticity rarely align so neatly, and I didn’t figure this out until later on.
achievement plateau
As I progressed, I felt like I had been checking off boxes (great college, company, title) but each win accrued less meaning than the last. The gap between “I did the thing” and “I feel different” started to widen until it was undeniable. For me, these feelings of diminishing returns on achievement have always been the most potent. It stirred feelings of burnout or boredom. Burnout when I was working constantly (9/9/6) on things that didn’t mean much to me. Boredom when I started to get comfortable, able to excel at everything but knew I wasn’t learning or growing in the process.
I’m someone who’s wired to explore limits, both in myself and in all of the things I was doing. I am inherently competitive and excited by meaningful challenge. Like in college, I set out to reach the rank of 1v1 master league in StarCraft II. I put in the work, played a ton, and learned as much as I could about the game and all of the strategies I could employ. After making it, I set my eyes on hitting grandmaster (top 200 in North America). It took a ton of time and effort but eventually I did it, and it felt incredible! Especially because it was a goal I had personally instantiated. Achievement and purpose are rolling—goal posts that are perpetually changing and in motion. There’s always a plateau to be hit, and it hits even harder when achievement is externally defined.
These different symptoms don’t often coalesce as a single inflection point that changes everything for you. You don’t just become a changed person who, after that point, has everything figured out.
I found myself experiencing combinations of these at various times of my life. But someone might experience them individually, or they could be layered atop one another all and happen at the same time.
This used to materialize as a midlife crisis in your 30s or 40s after decades of achievement. These moments were once deferred.
AI collapsed that timeline. Technical skills that once took years to develop now have been commoditized overnight. The achievement ladder that used to take 20 years to climb now takes 2. New grads can ship products used by millions. Teenagers can grow huge audiences and distribute at scale. When everyone can now be “good enough” at design, video, or code, credentials that once signaled capability lose meaning.
Compounding this, new grad unemployment hit 5.8% in early 2025. Students studying computer science were once told that it was a track to a guaranteed job and to make $200k+, only to find themselves now struggling to land a job coming out the other side.
Society at large and individuals have been forced to answer an uncomfortable, existential question. “If AI can do X and everyone can do Y well enough, what’s left for me?”
I would have expected most young people to be paralyzed by this, feeling helpless and lacking direction. And perhaps most are, but a subset has been responding differently. Caroline Ciaramitaro spoke to True Ventures fellows, students with early access to AI and the time to experiment with it, to see how they’re processing the disruption. Instead of being debilitated, they’ve recognized that self-expression, intrinsic curiosity, and problem identification should be prized over all else.
This isn’t just available to the privileged—AI has democratized the tools. You no longer need an Ivy League degree or venture funding to build or reach people anymore. What separates those who act from those who don’t is agency. But agency without direction doesn’t solve the purpose deficit.
rewriting purpose
We shouldn’t stop caring about achievement altogether. Rather, we should start thinking about achievement much more intentionally on an individual and societal basis. And we should be building the infrastructure in our lives to do this much sooner.
Achievement culture optimizes for legibility. Choices that look good on paper, that parents can easily explain to relatives, that require no defense. The alternative is optimizing for real personal fit. What grips and holds your attention without extrinsic success indicators. What builds capabilities you’d want, even without external validation. What you’d pursue if status didn’t exist.
This is much harder. External metrics like GPA, promotion, or company brand are clear. Internal calibration requires distinguishing ‘I want to want this’ from ‘I actually want this.’ Unlike credentials, it doesn’t require institutional access or permission. It requires attention to your own behavior and the willingness to test personal biases and assumptions.
The mechanisms below aren’t steps. They’re suggestions for how you build that distinction.
own what holds your attention
Work-life balance as a concept had always felt wrong for me because I’ve always wanted the same intensity in both domains, not separation. It was something I had struggled with in my 20s as I was so focused on work, and had been in relationships with some people who couldn’t relate. When I first met my now wife, Sam Vuong, the dynamic shifted. While so much of this is surely partner dependent and this isn’t meant to be an essay on relationships, I stopped being so apologetic about my relationship to work and tried to integrate it. In my last company, we worked together for three years to great success, and found a rhythm that worked which doesn’t often happen for most married couples. So much so that when we talked about starting a family and what mattered to us, it was obvious that we’d build our next company together. It wasn’t a compromise. Being able to do work and life interchangeably was the only structure that made sense.
What holds attention when unconstrained is a signal that most people gloss over. What you research unprompted and what problems you obsess over. The unfortunate reality is that intensity isn’t socially rewarded. Cultural pressure creates apologism (don’t care too much, don’t appear try-hard, moderate your preferences). So people tend to hide what actually matters or force themselves to care about what they think they’re supposed to want. Passion often concentrates in weird places. People shouldn’t need to apologize for the shape theirs takes.
run early experiments before your identity calcifies
I knew that dropping out was reversible. I could re-enroll anytime and pick up where I left off to finish my degree. I’d already switched majors, so changing course again had a near zero reputational cost. I knew that if I didn’t choose to do this now, there would be far more inertia later on as I built up more of life’s infrastructure and accumulated more student debt. My experiments after dropping out drove me to explore different domains of work through my role and industry. From software engineering to design, product, and venture. Within ecommerce, B2B SaaS, fintech, crypto. This expanded my world view and generated more questions that I could seek out the answers to on my own terms. It helped me figure out what I was good at and where I wanted to spend my time.
Early experiments are cheap because you’re risking reputation you haven’t built yet and testing preferences before they harden into identity. You can drop out, switch fields, join an unproven startup, move cities. The cost of doing all of this is near zero when you’re young. Later experiments are expensive. You’re trading against momentum, dependents, and the person you’ve publicly committed to being. The cost isn’t just financial or social. It’s psychological. Unwinding a decision means admitting that you had been optimizing for the wrong thing. Once you have infrastructure built around an identity (title, team counting on you, lifestyle requirements) experiments require dismantling all of that.
test your way to purpose, don’t think your way there
Sam and I didn’t decide on our focus for our next company through a single conversation. We discovered it through countless conversations between ourselves and with others that uncovered consistent patterns. Sam was a Montessori kid, product of school choice, and teacher in a past life. I dropped out and my mom taught me advanced math and calculus in middle school outside the system. None of these strands appeared to be connected until we talked about starting a family and what mattered to the two of us post-exit. Our priorities (caring about alternative paths, observing a trend of cognitive offloading to AI, heightened apathy and the decline of credentialism, believing the best learning happens outside institutions) only became clear after months of testing whether they aligned with how we actually wanted to spend time.
Hypotheses can be generated through reflection, but you need to stress-test them through action and dialogue. Most people treat their first intuition as gospel and skip or breeze past the testing phase. Startups fail this way too when they don’t ship. Purpose works the same—it emerges from iteration, not revelation.
prioritize people and proximity over prestige
I hit a plateau a month after the startup I was working at at the time raised a Series C. I was starting to feel too comfortable and like I had stopped learning. I tried to address this by working on side projects and doing more within the Waterloo community, starting one of the first local Product Hunt chapters. But it wasn’t enough. Then an opportunity came knocking. The year before, I had been in SF and had first met Vladimir Novakovski (ex-Addepar and Quora; Cognition founding advisor). He introduced me to Paul Desmarais III who was starting up Diagram with Francois Lafortune, a new venture fund and venture builder/studio. I ended up joining them as employee #1 to raise $80M across two funds and build Dialogue and Collage, which IPO’ed and exited within three years of launching. Not long after, I moved to Portage, one of Canada’s largest fintech VCs, and Sagard, an asset manager, as one of their earliest members to do practically everything under the sun. I was learning on hyperdrive.
Being within the orbit of the Desmarais family gave me proximity to successful operators (CEOs, McKinsey partners, formidable execs). I observed how they thought about ambition, cultivated relationships, and made decisions. Their standards raised both my ceiling and floor. What I thought was possible expanded, and my baseline for work output rose. Some ex-Waterloo students had gone on to become founders in Silicon Valley or early Thiel Fellows, but proximity gave me another view of similar mechanics up close. How non-obvious introductions happened, how they made non-consensus bets and validated things. Most importantly, they left the door open for me to walk through and go do.
Prestige is a lagging indicator optimized by consensus. When you’re around people doing non-obvious work at high standards, your sense of what’s achievable recalibrates. Proximity updates your possibility space faster than theory ever will.
I didn’t find the right language for all of this until more recently.
I’m a late bloomer when it comes to philosophy. It was only through Sam and Michael Strong, and through content from people like Johnathan Bi, that I’ve become more exposed to a new language of patterns I’d already experienced.
The Greek concept of eudaimonia stuck with me. It refers to a state of flourishing made possible by developing one’s character, living in alignment with one’s values, and striving for excellence. It reframed what I’d been doing through messy trial and error. Philosophy hasn’t given me the complete answer but it’s equipped me with a lens to apply to my life.
Rewriting purpose doesn’t mean abandoning ambition. It’s more about redirecting it toward what actually matters to you. Problems you care about solving, capabilities you want to develop, people and contexts that raise your ceiling for what’s possible. This compounds across timeframes and domains—the work you do, the relationships that matter, your lifestyle.
I know past Karel would have loved if somebody had sat him down to tell him all of this a lot sooner.
Love this!
I'm also a dropout and one thing I'd like to know more about from your experience is how did you navigate the job market, linkedIn, making a resume, portfolio, landing an interview all of which is so stacked against dropouts
So basically in summary how did you become legible and visible in the system that auto rejects folks without shiny logos on their resume