I don’t often write about personal things here, but the two most-read posts of this past year were Mastering The Rudiments, about my journey with learning the drums, and Unretirement, a personal reflection on my career.
I wrote both of those back in May — a shoulder month between seasons. In May, the year hasn’t hardened into disappointment or routine, there’s still time to change course. Now that the year has passed, I’ve found myself wanting to Think Out Loud a bit, in particular about a goal I set for myself this year. In “Unretirement” I explained that after seven companies, I had decided to get off the startup train for good: “As any founder can tell you, being in charge of millions of dollars of invested capital and scores of trusting employees is exhausting.” What I didn’t mention was that I promised myself I’d not commit to anything full time — no new startup, to be sure, but also, no project of any kind that would dominate my time and warp reality in its wake. My goal was to simply…be.
Twelve months in, I find myself wondering: How’d that go? And, what, if anything, has changed?
I’ve been doing basically one thing for 35 years — starting companies. And even as I did that, I was manically spackling in projects like writing books, joining boards, investing in other startups, teaching, and running conferences. For most of the past few decades I was so damn busy that the world narrowed into an overburdened to-do list. The high priority items on that list — “Raise the B round” or “Close General Motors” — seemed so damn important that a lot of “life” got pushed to the periphery. Over time the non-work portion of life, even if dutifully minded and enjoined, well, it gets relegated. Yes, I have to go to the gym. Yes, I will call or possibly even visit my mother, who aged from a young 55 to a spry 90 over the course of my career. Yes, I will be at the soccer game, the birthday party, the parent-teacher meeting. But was I really there? I honestly can’t remember. In fact, one of the most remarkable things I’ve come to realize about the past few decades is how little of it I can actually recall. What the fuck is that about?
Oddly, the things I remember best are the parties. The time spent with family and friends where I…