How regret minimization changed my life

Last year, I made the difficult decision to take a leave of absence from my PhD program to start a company. So far, I am really happy with my decision, and I wanted to share my thought process.

I’ve always known that I wanted to start something. I didn’t know what form it would take – business, nonprofit, community organization. In college, I was always brainstorming ways to improve the world as I knew it – usually through education and technology outreach, because at the time, those had been the largest positive influences in my life trajectory.

A few years ago, when I was a Fulbright Scholar in Cambodia, I had the opportunity to think more deeply about what makes a sustainable system as I met with many with many non-profits and startup educational institutions, making their mark on Cambodian communities with varying levels of success. Clearly, making a sustainable system takes far more than passion and follow-through. Managing to really understand a problem and then procure the skills, strategy, and network to make a change is incredibly difficult, and getting the buy-in of your community is exponentially harder when you do not know it intimately. I left my Fulbright convinced that the way to change the world is through for-profit businesses, because without a sustainable way of making money, it seemed that 90% of my time would go to fundraising and 10% of my time doing something very important (probably inefficiently because I wouldn’t have the funds necessary to hire people with the most relevant experience).

When I got back, I joined a San Francisco based startup as a Software Engineer, where I had the opportunity to observe a whole new set of ways things can go wrong: managing people is hard. A good manager should understand both the company’s goals and their employee’s goals and then find a way to align those. I moved on from that job motivated to one day build a team that people enjoyed working in.

In the meantime, I had been offered the opportunity to start a PhD in machine learning in a fantastic research group at Harvard University. I had really enjoyed the machine learning research I had done during my M.Eng, so I was excited to work on projects and do great research with some of the brightest and well-trained people internationally. I felt like I had pretty much won the PhD lottery. I was awarded support from an NSF Fellowship, an NDSEG Fellowship, and an industry fellowship. My advisor was bright, accomplished, and a great communicator, who I genuinely cared about my success and happiness.

One side-effect of undertaking something as unstructured as a PhD is that it provides some time for reflection, and with reflection, I realized something: opportunities do not last forever. Our lives provide these sort of sliding windows of opportunities. As people live, their desires and priorities change, meaning that if you want to work on a certain project or with certain people, they’re only available for a limited time.

And that was the start of several weeks of existential angst as I contemplated leaving my PhD program to start a company. Fortunately for me, I brought my considerations up to a friend who gave me some very wise advice:

Walking home after that conversation, I realized that I could estimate how much I would regret not getting my PhD in the next few years vs. how much I would regret not trying to start a company. If I got my PhD, I would find a project that I was excited about, graduate in 2-3 years, get a job at a top AI research group, and then get paid hundreds of thousands of dollars to continue doing basically what I had done for the last 5+ years. And as I kept get better jobs and higher pay, it would just get harder and harder for me to try something new. In 10 years, I’d be wondering “What if” but my window of opportunity would have already closed.

There was no contest between the two quantities of regret. I needed to take this opportunity now. I decided to move to San Francisco to start a company, and I’ll be sharing more details about what I’ve been up to soon.