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

and I didn’t get very long into my interview preparations to realize that I wasn’t only writing about a personal hero

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.”

His range is wide, but all his work somehow rhymes.

It was so much fun connecting with Kelly over these random little objects—I felt I was learning something about him I couldn’t through his books and blog posts

“I don’t really pursue a destination,” he said. “I pursue a direction.”

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 off by asking him whether there is a unifying theme to his seemingly diffuse life’s work, which has included old-school magazines and books, bleeding-edge technology, conservationism, photographing Asia, and teaching. “Following my interests,” he said simply.