More Than a Rest Stop
Stumbling through a two-year sabbatical toward something new.
I never got so many job offers as when I posted on LinkedIn about starting a two-year sabbatical. Turning down work felt odd, after having spent the previous seven years hungrily snapping up whatever work I could find. I got good at it, built a company around it, and then sold it. Then I left. Even as the company grew, I struggled to shake the feeling that I was always looking for work, and it was never looking for me. But all that changed after I posted I was out of the game. All of a sudden everyone wanted to have a coffee, jump on a Zoom, or catch up over email to talk about jobs. C’est la vie.
I took a handful of calls. I told myself it would be good to see what was out there, or keep relationships warm, or a million other things. But really, my mind was just grasping for any excuse to avoid being stuck sitting in slow silence for two years. I knew I needed it, but man I sure didn’t want it. Despite the misgivings, I stuck to my plan of not working for a while to see what would happen.
I am Become Sleep, Restorer of Will
The first thing that happened was I slept. That hadn’t been the goal — it snuck right up on me. I thought I’d immediately start cookin’ on the next big thing. While I waited for it to appear, I’d often lie down to read on our big couch next to the bookshelves only to find myself startled awake minutes later as the book I was holding fell square onto my nose.
I had chosen to revisit an 8-book historical military sci-fi series about a regiment of Union soldiers that fall into a portal and land on an alien world where nomadic eight-foot-tall aliens raid settlements from humans like cattle to feed their endless march. Look, they weren’t great, but they were interesting. They had action on every page! Point is, it wasn’t their fault I spent weeks falling asleep on that couch in the glow of the afternoon sun.
After a while, I decided to be honest with myself and just lie down without the book. Jennie just let me sleep. Then she’d wake me around dinner time. I’d eat a few sleepy bites, mumble my apologies to the family, and stagger upstairs to sleep some more.
That’s burnout for you.
It’s important to point out that even though I’d been near-religious about sleeping 8 hours a night for years, it made no difference. There’s a different kind of tiredness that builds up which regular nighttime rest or even a two-week yearly vacation can’t cure. That exhaustion is only addressable once you lose access to your buzzing inbox and calendar forever. When the incessant hum in the back of your head is gone. It’s when the mind finally shuts up that the body can catch up, and the healing begins.
All that sleep felt like a huge setback to someone who was sure I’d be whipping up a new company in no time flat. It went on so long I started to wonder if I’d ever be restored to my former energy.
What if I was washed up?
What if the well was dry?
There was nothing to do but sit with it. I had to learn to be ok with the rest, practice patience, sit with the fear the mojo might never return, and be curious about it all.
That was work enough for a quite a while.
Better Questions, Fewer Answers
Throughout this time, I woke each morning with a fresh idea coupled with a surge of near-manic energy to build whatever it was. It was bullshit, of course. A hairbrained plot conjured to escape the long recovery. I pursued a few, but the energy never lasted long. Those “ideas” were nothing more than the bored throes of an overactive mind used to driving forward at all costs, unhappy to find itself relegated to the backseat, disconnected from a body that simply couldn’t go.
Between naps, I began taking long walks on the trail behind our home and, as the seasons passed, I began to feel better. Of course, better is hard to describe. But the shortest way to explain it is that I felt more embodied and days gained their own rhythm outside my own. I could feel my feet and I’m not sure I ever had before, or at least not as long as I could remember. I could sense feelings rising, and instead of being driven by them I was better able to decide myself whether or not they were true.
Summer came and went, the leaves fell, the weather turned, and my long walks turned to slow skis along the same trail. Just as those skis began to give way back to spring walks and summer runs, I noticed the ideas (which never stopped coming) had transformed in one crucial way: Instead of arriving as answers, they came as questions.
It’s easy to get excited about some thesis or hunch — a new widget, a different business model, a novel approach — but certainty is fragile. Our thinking is notoriously fuzzy and often these ideas don’t survive even the barest scrutiny. Questions, on the other hand, are scrutiny and so make much more fertile ground to explore.
Why are things the way they are?
What’s holding back change?
What prevents new futures from emerging?
I asked these questions about a handful of technologies I had interest in, and that led to analysis and yet more questions. I had conversations with experts across academia, industry, national labs, and - as the questions matured - potential end users. The key always was to hold any growing convictions loosely and let the curiosity drive. Lots of assumptions withered, many more grew in their place, until, almost without realizing it, a thesis and an opportunity emerged from where these questions intersected.
I never would have found it if I’d approached from a place of perceived answers and insane speed. Each of the technologies I had with at the outset ended up abandoned, but leading a level deeper, to questions about what would take to enable them. Being able to handle the many false passes and dead ends gracefully, instead of trying to force through them is a gift.
More Than a Rest Stop
Earlier this year, a buddy of mine had me out to his hangar where he’s working on bringing an old airplane back to life, manufacturing them for families traversing the Alaskan bush. It’s really cool work. After touring the facility, I told him about my new company. He was excited, but I could also see some disappointment in his face.
“So, it never goes away, huh?” he asked.
He’d been following this Substack (hi!) and was hoping that after building and selling a company, I was done. That the itch was scratched, that I was somehow cured. I admitted that for a long time, I thought I was done. And if at the end of this sabbatical all that I had was a new company and the same old way of doing things, I’d not be nearly as excited. Instead, I’m just done with the old way of doing things.
Time off should be more than a rest stop. Rather than a pullout from the interstate of life where we gas up, stretch, pee, buy a Big Gulp, and hit the same old road again it is a chance to go an entirely new way. As excited as I am about the new work, I am most curious about how it might be done differently.
Can a startup be built while remaining in balance?
Rather than pursuing work as an end (selling companies, boosting ego) can it be a Way?
How might our work inform the larger Work of our lives?
I have much more to say on this, and suspect it’ll become a deeper exploration over time.
As my friend
reminded me this week (courtesy of the Dao), “newness is born from stillness.” Not just new companies, but new perspectives and new ways of being, if we’re willing to invest the time. To see something from a unique angle takes space and patience. That is the true value of a sabbatical. A chance to recharge, sure, but to let life catchup and to see ourselves as we are rather than how we were. Not to hop onto the same old interstate, but pick a more interesting path. To let old stories pass away and new ones to be born and to sit, if we have the patience and courage, in the stillness and let come what may.