There's a whole genre of TV where people buy a house somewhere with better weather than wherever they came from, and I was on the couch watching one of those when a couple from New Jersey explained how they'd ended up in St. Thomas. They told it the way you'd tell somebody you switched dentists. We thought about it, we did it, here we are. I sat there running through how, what, when, but, and a couple of words I won't type here. Then one of them said, "we're good at taking risks," like it was a skill they'd picked up somewhere along the way, and I thought, yeah, I want that.
Then I had the week I had.
I tried a barber instead of the stylist I usually see in the US. I went to a different salon for my nails instead of the one I've been going to for years. I bought a bottle of wine I'd never had before and opened it that night.
None of it worked out. It's not quite moving from Phoenix to Corsica, but I still felt like I'd failed my risk experiment.
The haircut was brutally short, which stung more because I'd had real success in a Parisian barbershop a few weeks earlier. It was bad enough that I considered a hat, which I have never once done in my life. I texted all my friends, and the reason they're my friends is that one of them wrote back, "It's not horrible, but it's not your best cut; it will grow fast."
The nails took four hours and came out looking nothing like the design I'd shown them, and by that point my butt was asleep, and I was over it.
The wine was a white pinot noir that made it about one sip before it went down the kitchen sink.
Risk and no reward
When the third one missed, what I felt wasn't disappointment. It was closer to a file closing. I actually thought, and I remember this clearly, "this is exactly why I don't do this. Risk."
It would be easy to write that up as a piece about being risk-averse and call it self-awareness. But look at the count. Three new things in one week. Whoever that person is, she isn't afraid of trying stuff.
So I went looking for what the three actually had in common, and it wasn't the stakes. Hair grows out, nails get redone in a couple of weeks, and wine costs what a bottle of wine costs.
What they shared is that in all three, I handed the result over to somebody whose judgment I had no reason to trust yet, and I paid before I found out. A barber who'd never seen my head, a tech who didn't know my hands, somebody in a vineyard I'll never visit deciding what I was going to taste that night.
Which means I don't have a control problem in the sense of needing to do everything myself. Mine is narrower, and honestly stupider. I want to know how something turns out before I commit to it, which is not a thing that exists anywhere.
Same shape, different room
Then there's AI.
I spent an entire day building an agent only to find out it doesn't have access to the filter that makes the whole thing possible. A system problem, not a me problem, and I still carried it like a loss.
I spent another two days having Claude Code build me a landing page directly in HubSpot. In the end, the result was blank. Blank. I had to start over.
Real hours, nothing I could use at the end of it. And my read on those hours was that I'd wasted them. Not that I'd found out where the edges are. Wasted.
What I want, and I hear how this sounds, is for it to be right the first time. I want to describe the thing and receive the thing. The middle part, where I slowly figure out how to ask better, registers to me as an expense instead of as the actual work.
Why this lands harder on operators
I think this hits people in my seat differently, and it took me a hot minute to understand why.
What I'm paid for is turning mess into finished work without waste. That's the product. Somebody hands me something half-formed, and I hand it back done, on time, no drama. So when I spend two hours or two days producing nothing usable, it doesn't read to me as learning. It reads as failing at the one thing I'm supposed to be awesome at.
Which is a lousy trade, because it means the person in the company best positioned to build new operating muscle is the one who experiences practice as incompetence. If you're the one everybody counts on to make things come out clean, every messy first attempt costs you something that the rest of the team doesn't pay.
What I know now that I didn't Monday
The haircut will grow out, and by about week one I had managed the cut into something cute. The wine's gone.
I've stopped calling those three things risks. They were tests; they came back with answers, and the answers were no. Getting a no is what a test is for.
The part I need to work on isn't the trying. It's what I let a single no mean about whether I should bother with the next one.
So if you're the operator on your team, the one who's supposed to make it all come out clean, here's what I'd ask you. The last time something you tried came back blank, what did you decide about the next one?
If this sounds like your week, I write about this kind of thing in String by String. Come find me on LinkedIn and tell me what your version of the haircut was.
