I want more role models like Kevin Kelly. People that proudly whistle while they work. Who have boundless energy and healthy gums. Whose enthusiasm is contagious. Who are well-adjusted and emotionally regulated. Who have solid relationships and happy families. Who are hungry and impactful and care deeply, without being jerks. And I want more people... See more

I learned that Kelly doesn’t think in outputs. For him, doing is part of learning. “I don’t really pursue a destination,” he said. “I pursue a direction.”

I asked Kelly about the tradeoffs of focusing on a single thing if you want to be great (which is what I had been getting at before). “Greatness is overrated,” he said, and I perked up. “It’s a form of extremism, and it comes with extreme vices that I have no interest in. Steve Jobs was a jerk. Bob Dylan is a jerk.”

In my free time, I coached a JV high school soccer team, volunteered at Dandelion Chocolate (all that working on software made me want to make something with my hands), and finished writing a novel.

I started to reflect on my own trajectory with fear that it didn’t mirror my ambition, work ethic, or deep care about the role of work in a life. Had I pointed my ambition in the wrong direction? What did I have to show for all my effort? Had I made some irreversible, unforced error with my career? How much money had I left on the table? Would the ... See more