I’ve been trying to connect with a journalist who reached out a few days ago. He’s working on a story from way back in my career – the early days of Wired, circa 1995. It’s taken a few attempts to find a time. Despite the fact I’m no longer running a company full time, my days are still packed with meetings and obligations and new priorities. It probably doesn’t help that I keep my phone silenced, so I miss serendipitous calls, a favorite tactic of good journalists. But between various board meetings, community work, time blocked for writing, client and advisory work, investment reviews, exercise, and friends and family, squeezing in a 15-minute call feels just as hard now as it did when I had an EA, a Chief of Staff, and two full-time jobs*.
Is it strange that while I’m not “working” nearly as much as I used to, I still feel just as busy? Is that a good thing, or a problem?
I’m thinking out loud about this because lately I’ve been feeling a bit at sea. For most of my life, I had a ready answer whenever anyone asked “so, what do you do?” I was always the guy running a new media or tech startup. When I moved to New York eight years ago, I told myself I was done with running startups. But then some pals convinced me to launch The Recount. When we sold it in 2023, I tried out a new term designed to explain the state of my career: “Unretired.” Not surprisingly, it didn’t stick.
For one thing, I ended up running something new yet again: DOC. For the next two years, I was once again in charge of something. Now that DOC has a new CEO, I once again face that existential question: What the hell am I doing with this one wild and precious life?
There’s a lyric in the Grateful Dead’s seminal “He’s Gone” that’s always stuck with me: “Nine mile skid on a ten mile ride.” I’ve never been certain what Robert Hunter meant when he wrote that line, but I’ve referenced it several times over the years, usually to reflect on how hard it is to change a long-held habit. Every time I think about hitting the brakes on something, I wonder about that tenth mile. Did the train start skidding at mile one, and come to rest at mile ten? Or did the engineer hit the brake too late, with catastrophe the inevitable result?
I’ve been trying to hit the brake on having one big project define my life for what feels like a “nine-mile skid.” First when I moved to New York, then after The Recount’s sale, and now again after hiring my replacement at DOC. I’m pretty sure I’m near the end of the line, at least when it comes to being the chief bottle-washer at a newly created company. But that big question – what now? – remains uncertain. I’ve been working on a new book project, focused on many of the issues I write about here. But I’ve had trouble convincing myself I have the ability to pull it off. On any given day, I’m either eager to throw myself into it entirely, or I’m certain I’ve already missed the story and shouldn’t even try.
With books, there are no investors, employees, or customers demanding that I perform. It’s just me vs. me, and that’s a bit terrifying. Plus, I’ve got plenty of distractions: I advise at least a dozen companies and non-profits. I’ve accumulated a pastiche of investments over the years, and each of those deserves more attention. I’m on a working committee focused on economic development in my hometown, and I teach every Spring. I write here at least twice a week. And I’m still active at DOC, running the program and generally trying to be a good co-founder.
But now that I am no longer running a venture-backed startup, things are definitely starting to slow down. My tenure on LiveRamp’s board is coming to a close (pending formal approvals, the company will be sold to Publicis at the end of the year). Signal, an events and media platform I ran for P&G with my long-time partner Stacey Foreman, ended a wonderful 14-year run in 2025. I’ve prioritized time with family and friends. Exercise, always central to my life, feels less like a chore and more like a celebration. I’m even sleeping more. Thanks to a lot of luck and hard work in collaboration with many others, I’m at a place in life where I can afford to not work, should I chose that path.
And yet…and yet I continue to feel like I need One Grand Project that creates purpose in my life and offers a tidy answer to that damnable question of “What do you do?” Is that because I can’t imagine life without it? Or because I’m terrified of that damned book? Perhaps it’s my own inability, as Mary Oliver wrote, “to be idle and blessed?” Does it just come down to facing the final chapters of my life, uncertain of the best way to spend them?
I think perhaps the answer to all those questions is yes. And I sense I’m not alone, at least, not amongst friends and colleagues of a certain age. So I’m putting this post out into the world, hoping that it might resonate with a few of you. If it does, reach out. I’d love to compare notes.
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*Yep, I’ve had multiple full time jobs at least three times in my career. WTF?!