In this territory, we've had many conversations about depth vs breadth in career path. Kevin Kelly is non-binary in this regard - he tends to go deep enough and on many things. His interviewer is the same, serially accomplished, with so many medium-sized achievements they can't be worn like a crown even if they deserve one.
I started to take pride in this ‘cool girl’ approach to work. I joked about having never been promoted, but could feel my scope, impact, and relationships with colleagues growing. I remember rejecting a (well-meaning) manager’s suggestion to build out a five-year career plan. I scoffed at people who cared about titles, did things for money, and had professional headshots on their LinkedIn.
And then, I’m not sure when the switch flipped, but I started to have a sinking feeling that I had it all wrong the whole time. I looked around and felt I was being outpaced by my colleagues—specifically by the MBAs and the people who chased titles, promotions, money, and building teams. And it wasn’t just a vanity thing. They genuinely seemed to be focused on bigger, more interesting problems. And they were having more impact. They were mentoring young talent, influencing top lines and bottom lines, and had their fingerprints on all kinds of cool industry-recognized work.
I think most of the conflict stems from simple, singular achievements being easier to recognize than complex, nuanced ones. Easier for yourself to recognize too. Being very valuable yet unrecognizably so is hard to make peace with.
Kevin Kelly would say it’s good to have an “illegible” career path—it means you’re onto interesting stuff.
“I don’t really pursue a destination,” he said. “I pursue a direction.”
Kelly’s version of doing his life’s work seems so joyful, so buoyant. So much less … angsty. There’s no suffering or ego. It’s not about finding a hole in the market or a path to global domination. The yard stick isn’t based on net worth or shareholder value or number of users or employees. It’s based on an internal satisfaction meter, but not in a self-indulgent way. He certainly seeks resonance and wants to make an impact, but more in the way of a teacher. He breathes life into products or ideas, not out of a desire to win, but out of a desire to advance our collective thinking or action. His work and its impact unfold slowly, rather than by sheer force of will. Ideas or projects seem to tug at him, rather than reveal themselves on the other end of an internal cattle prod. His range is wide, but all his work somehow rhymes.
Kevin Kelly has made peace with it. And maybe that's the thing he'll be recognized most for.
I thought I was here to go deep on working Hollywood style, but as I sat there with Kelly in a room of what are best described as his toys, I realized that the most interesting thing about him is that he seems happy. At ease in the world and in his skin. I wasn’t there with Kelly for permission to work Hollywood style. I was there for permission to work with both ambition and joy.