Playing a Career Game You Actually Want to Win

What would you be doing if no one else knew about it?

March 6, 2023

After a half-decade of working in tech marketing, I grew disillusioned by the corporate presentations and ad campaigns. I wanted to be a real writer. So I decided to pursue a degree to legitimize my intention.

Unlike law or medicine, a formal journalism degree is not a prerequisite for joining the field, but going to grad school was just something people in my family did, so I applied to Columbia, Berkeley, and Stanford, some of the most prestigious journalism programs in the country.

Submitting the applications felt like making progress toward what I thought was my goal. There were boxes to check and essays to write. I was good at this game; I had spent my life jumping through academic hoops. But it wasn’t until after I was admitted that I had to wrestle with whether I actually wanted to go.

I sought the advice of a mentor, the author Robin Sloan. We met for coffee on a drizzly morning at a café under an Oakland freeway overpass. After listening to me ramble on about the pros/cons list I had sketched in my head, Robin asked me a question that cut through the noise: “If you could go, but you couldn’t tell anyone that you went, would you still do it?”

That question helped me consider my intrinsic motivation. Was I actually interested in learning, or just in being someone with a graduate degree? Did I want to play the game, or did I only want to win?

I decided to go back to school, and I’m glad that I did. Robin helped me recognize that I was interested in taking classes and working on my craft, not just having a credential. But if it weren’t for him, I may have never taken the time to ask myself what mattered to me, irrespective of others’ perceptions.

Fast-forward five years, and I’m about to publish a book about work culture in America. I interviewed over 100 workers—from kayak guides in Alaska to Wall Street bankers in Manhattan—and met several people who achieved nearly every goal set out for them, only to realize they were winning a game they didn’t enjoy playing.