Don’t run your life aimlessly.

“So I saw that there is nothing better for people than to be happy in their work. That is why we are here! No one will bring us back from death to enjoy life after we die.” - Ecclesiastes

In college, I fell into a dangerously competitive trap. I started my college experience entering in programming contests, trying to find the most challenging technical problems in order to improve myself. I was obsessed with working with the smartest people while having little regard for what I was actually building. Thinking I’d find smarter colleagues to work with, I decided to go to graduate school at a prestigious university, only to be disillusioned by the apparent lack of breadth in curricula and peers alike. (For example, one colleague had extreme depth in machine learning, but all he used his specialty for was to optimize Kellogg’s cereal profits.) Despite being fully funded and finishing all the required courses strong, I dropped out because I felt like time was worth more than the opportunity cost of finishing a thesis at a place I was unhappy and uninspired at.

Believing that industry would be better, I decided to work with the guy who invented real-time facial recognition at a Microsoft research group. He was brilliant but the way we applied machine learning at Bing was not. (It was too mechanical, in my opinion.) After a few short months, I left the research group to join an advertising startup with the allure of working directly with “veterans” who were previously executives at publicly-traded companies. The opportunity was great, but I still wasn’t really happy or excited about what I was doing. (In retrospect, I think it was because the work wasn’t challenging nor did it have much impact on the world outside of advertising.) A year later, I left to help a friend co-found a profitable performance marketing/tech company that produced multiple millions in revenue in just a year. We kept growing, we had a fantastic team, and yet, I was still not that enthusiastic about the opportunity, because it wasn’t exciting to me to just make money without purpose or passion. I ended up leaving a few years later, giving up a majority of my ownership to just stop and think.

All this time, I had been running aimlessly without reason, reaching for a better tomorrow…only to realize that I could live that idealized tomorrow — today. I quit my profitable startup, I proposed to and married the love of my life, and we traveled to 20+ cities around the world in four months for less than our costs of living in San Francisco.

During all those airplane ride reflections, I’ve come to realize that doing meaningless work will never make you happy, no matter the financial reward or external validation. We must find our own passions and interests and pursue them boldly, ignoring what other people think is important. My wife and I are now working on a health-tech startup trying to create a better database of cures for diseases — and we love it.

p.s. Here’s another great illustration.

Addendum: I spent about 8 months away from work figuring out what was really important to me. Regarding work, we ended up raising funding for the health-tech idea and moved to Seattle since it was far more affordable than San Francisco. Work is similar to relationships — you’ll know love once you see it.