I had a follow-up thought to my most recent post... Last week I said:
I should mention that I tend to consider a fairly wide array of activities through the lens of “Projects.”
I also tend to consider a fairly wide array of activities through the lens of “Experiments.”
To me, experiments are noncommittal. They’re low pressure data collection, which reduces the stakes to merely learning what works and what doesn’t—something that seems useful on life’s long road.
Experimentation means trying things. I took a month off my extremely conventional job to see what it felt like working an extremely unconventional job. I’ve done a host of therapies. AA, NA, and meditation too. And some habits and hobbies that I was fairly certain I didn’t care for. I’ve always tried (tried) to give these trials a fair shake, figuring my data collection approach is only as good as the data I collect.
I don’t mind dropping a thing, but I know I’ll feel better about it if I push through the initial discomfort to feel more confident in whatever conclusion I arrive at.
Our land was, and is, an experiment. A relatively pricey one, sure, but it cost a tiny fraction of what we might have spent on a house. And when we bought it, part of our “This is an experiment” calculus was the knowledge that California real estate—if it loses value at all—is likely to depreciate only so much.
I share a small boat with my friend Rob. I proposed this co-parenting the first day we met, and he was very into it.
We looked for the right boat for a couple months but pretty quickly landed on the idea that time was of the essence—the theoretical value of the theoretically perfect boat, and the many more months spent hunting for it, was outweighed by the value of the time spent on the water, learning by doing, and experiencing first-hand what worked and what didn’t. It was an outlook that emboldened us to pull the trigger sooner than later.
Maybe the boat isn’t forever. But it’s been a formative experiment in learning the local seafaring culture, exploring the waters, and experiencing a collaboration—and an occasionally challenging one—with a friend.
There too the entire investment is unlikely to vanish—though boats do sink in a way that land does not—but, even still, amortize that cost over the years of ownership and the fees paid for the experiences and the lessons learned can feel pretty reasonable.
After our property burned in 2020 I was really missing having tools and a place to tinker. I suggested to my friend Joey that we go in on some cheap shop space. We stumbled across a small and affordable spot in an… um, rustic neighborhood. So small and so affordable it beckoned a “Why not?” experiment. The use of it has waxed and waned and the size restricts tool and project ambitions. I’m sure we’d do it a little different today. But the intimate knowledge of what it’s like to have a shared workspace and how our approach might evolve could only be gained from experience.
In my Tools book I advocate for buying the absolute cheapest version of a tool to experiment with whether or not it is useful. Use it. Break it. If it has a place in your life, you’re now armed with the knowledge to buy the better-suited and improved model.
That $30 power tool from Harbor Freight or the Temu special is a great answer to “What’s my cheapest entry to this?” and little different than my shop space or the land Molly and I bought—both were budget versions and about all we could afford. When I made the plea for Just Start, on Anything I was championing the idea that folks looking to DIY projects are in need of a hands-on learning win, so they should take aim at the most affordable inroad, rather than getting bogged down under the daunting weight of the impossibly aspirational. Experiment… at a small scale.
This newsletter is a lab for me to experiment. It’s an every-two-weeks system of accountability that encourages me to exercise my writing muscle. I get to play with thoughts, flesh out ideas, and explore topics that might make their way into future work, or a book, or whatever.
It’s a place to try things, and some of those things just might not be great. (Or might veer weirdly meta.)1

Sure, some decisions are more consequential than others. Having a child seems like a big one. Voluntary amputations, of course. Those are the two main ones most folks face. And certainly finances can be a fixed anchor. But even still, I’ve found that I—and others—tend to overestimate the financial risk (especially when there’s an asset that can be sold), or the potential fallout or permanence, of a pivot. The list of life and limb concerns probably isn’t quite as long as it so often feels.
The reality is you can absolutely stop reading a book, or sell a piece of gear, or re-home a pet iguana. You can move back to the city you left, sink your boat for the insurance money, or sell your plot of dirt. New ventures are just new data. That’s what I tell myself, anyway. The only way to learn if a thing is the right fit—or what else might be a better fit—is to probably just do it.2
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Or veering a little advice-y, which gives me some pause. I need be cautious about getting up on soapboxes. And in fact I’m probably legally barred from owning soapboxes, given a hefty back-catalog of poor decisions and missteps.
Thank you to Nike for sponsoring this post.
Love it.
Similar to people wanting to get into a sport. Take cycling for example; my friends would ask me what bike to buy and I just tell them to get something cheap and simple. Then get out and ride! Some you’ll figure out what kind of riding you like, what trails or roads are around you and what people you want to be around. Then you can fall into the pit of buying a stable of 5 bikes. Haha!
Really appreciate this perspective & the framing of it. We’ve lived on our sailboat for many of the last years, and the number of people who have asked if we’ll do it “forever” always entertains me.
Nothing is forever!
…But for as long as it’s fun & traveling in a slow, mildly uncomfortable, oft-broken way makes some sense, it’ll continue to be our freedom-hack of choice! 🤣
(Ok I guess kids & voluntary amputations are forever but you clearly get my drift!).
Would love to hear more about the shared shop space — it’s an idea my husband and I have tossed around as a support to his growing boat-repair business 👀