Coming back to school


Me painting the sky

After a year and a half of traveling, and founding two startups that raised over $1.5M, I've decided to come back to school. This draft has been a long time in the making. To me, this has been somewhat of an existential dilemma, so I'm writing this mostly to organize my thoughts, and document my takeaways for future reference.


I took a leave from school because I was okay about coming back to school if it turned out to be what I wanted in the end. It was such a fruitful, eye-opening experience, as I traveled, learned, built, and opened my perspectives in ways I've never imagined. As the deadline to drop out approached, my deliberations rose to a full-blown existential crisis, and finally I decided to leave startups and come back to Waterloo.

Why I'm choosing school

There are a lot of stories about people dropping out of college to do startups. The opposite pathway seems quite a bit less common, partly because they don't make good stories. Me coming back to school isn't a meticulously planned manifestation. Rather, it's a reckoning with what I really value in life. I want to come back for two reasons:

  1. Learning: A year in industry made me realize that the focus is almost always on practicality. When I'm building, I can naturally pick up on skills and experience, but unless I intentionally focus on learning and intellectual growth, I might end up spending years making random saas webapps that I don't care about, without getting none the wiser. I still want to learn the fundamentals out of genuine curiosity - even if it isn't immediately applicable. College offers drop-in lectures, research opportunities, and easily accessible professors; the perfect place learn far and deep.

  2. Friendships: I've been lucky to achieve a level of success I would never have dreamed of, yet I feel lonelier and emptier than ever. Since high school I have always prioritized work over relationships, but now I've come to a realization that my all-in approach to work comes at a great cost, and that cost is the intimate, lifelong relationships that give so much warmth and meaning to life. After college, it's hard to come by real friends who genuinely like you as a person instead of for convenience or benefit, and the activation energy to meet people is much higher. I'd like to use the opportunity to learn how to be compassionate and build relationships.

  3. Living: Running a startup takes up every second of my waking day. In the frenzy of building quickly, doing market research, hiring, and raising money, there is little room to rest, both mentally and spiritually. Looking back, all I remember is a haze of stress and sleep deprivation. In heads down hustle mode, I had no time to grow on an intellectual and personal front. Why the rush? As I figure things out, it might be good to also slow down and smell the flowers.

Why now

Q: Why don't I just keep at my startup and come to college after I sell the company? A: I am clay. I am still young and impressionable. I worry that if I spend these years surrounded by an environment and value system that focuses on big money, returns, and quick results, that my thinking will be further coerced against what I truly value. Disclaimer - I'm generalizing a lot about VCs and startups here, the industry isn't all like this but the overwhelming theme of it dominated my experience in SF. Also, conforming effects occur in every group and industry - spiritual independence is probably the answer to this problem but until I develop it I might need to first find a safer space to do it.

Bullet train inertia

It is really hard to change course when you are going fast and have traveled far in one direction. During the past 8 months, I was able to learn the ropes, build connections, and get some decent traction on the companies I worked on. It feels foolish, nay stupid, to leave such opportunity behind. I had gotten used to one way of thinking, and it had subconsciously become part of my identity and image. At this point, leaving startups felt hard because it almost feels like the equivalent going back to square one.

A world with no people

When I was trapped in confusion and self doubt, one thought helped me so so much. I'd ask myself - What would I choose if I were the only person left in the world? In other words - if external judgement, validation and interaction did not matter - if society at large was a non-factor, what would I choose, as an untethered individual seeking to live my best life? The answer to this would be a resounding DO WHAT YOU REALLY WANT sort of answer.

What I really want is to do is to just be. To play with the absurdity of the world, learn about its intricacies, to create beauty and function, and to share love with other souls. Don't we all? In my inexplicable, infinitesimal and brief flash of existence, the best I can hope for is to consistently pursue what I genuinely care about. In the grand scheme of things, what else matters?

Writhing this feels like formally concluding a chapter of my life. I'm grateful for my journey that brought me around the world and back. With new perspective, I'm looking forward to an awesome time at school and beyond.