Finding Ikigai

I quit my job this week!

I've been extremely lucky so far in life. My locally optimal decisions have generally turned out to be globally optimal. It would be nice to attribute this to intelligence or taste, but for most of my life I've acted without a sense of purpose, and just winged it.

Luck in this context could also be viewed as optimal starting conditions, where it's impossible to get stuck in local maxima until you've reached a global maxima. I've been lucky my dad taught me how to code as a kid, instilling wonder and quixotism. I've been lucky to find myself in interesting and challenging jobs, and to have worked with good people (including meeting my wife!). I've been lucky to have had the time and resources to pursue my interests, leading to a virtuous cycle of creativity.

A few things have happened to me so far in my 30s. The most fun right now has been getting randomly into basketball and golf. But more poignantly, I've had the opportunity to zoom out and think about what I want to get out of the next 30 (or 30 after that). And it's not clear to me that I've been on the right path.

I've been thinking about the Japanese concept of 生きがい, which has slightly more essence than the French raison d'être. It's a Venn diagram of four circles: what you love, what you're good at, what the world needs, and what you can be paid for. The intersection of these four circles is your Ikigai.

For the last 10 years, I've been surfing the intersection of what I'm good at and what I can be paid for. I've been missing the sense of purpose that comes from building something the world needs, and I've been missing the sense of joy that comes from working on something that I love. Side projects help, where I can learn new technology, but the feeling is fleeting if I don't have time to maintain them.

I've been at a startup managing two teams of engineers for the past couple of years, and have found great joy in helping engineers grow by teaching them best practices and hard-fought lessons. The people at Vanilla are kind, ambitious, and talented! I loved building with my teams, but I found management to be intellectually uninteresting. Zoom meetings and quarterly planning drain the joy from shipping code.

Entrepreneurship seems to solves this for me. Despite the stress and chaos, I've felt most alive while pursuing my own businesses. I've been lucky to have had the opportunity to do this a few times, including selling a business with my friend Chris after we were turned down from YC.

I spent the next year contracting and looking for my next project. I tried for YC again the next year after building a no-code app builder. Rejected again, I had to find work to pay the mortgage. I gave up on another project.

YC's criticism had consistently been around the growth of the products, which was frustrating to hear at the time but in retrospect was spot on. It's difficult to grow a business when you have to work on it part-time.

Fortunately, I won't have that restraint this time - I'm going full time on Grok! I also won't have to search for funding - I'm going to bootstrap. The bridge of a pirate ship is an exciting and terrifying place to sit.

It feels like everything is aligning for me to take this leap. We have savings and our expenses are low. My wife has a stable job and has encouraged me to take this risk. With exercise and sobriety, I'm in the right place mentally and emotionally and have the energy to hustle.

I'm excited to build a business helping people improve their lives by teaching them how to code.

Time to ship! 🚢🏴‍☠️