On Overthinking

There’s a grown man shuffling through downtown San Francisco in disposable hotel slippers, and I’m the one walking next to him: properly laced, thoroughly researched, and about to get humbled.

To explain the slippers, I have to explain the tickets. Earlier this year I fell hard for an artist named Nimino. It was the kind of falling where the algorithm quietly gives up suggesting anything else because you’ve played the same songs on repeat for a month straight. He wasn’t coming to Seattle. So I did something genuinely out of character: I bought two tickets to his San Francisco show before I knew who the second ticket was for, before I knew whether anyone could come at all, before I had thought it through in any way my normal brain would recognize.

I invited a few people. The yes came from Greg.

Greg was one of my closest friends in middle school. We were on the swim team together, and we spent countless hours playing video games and having adventures. Then life did what life does, and by this year I hadn’t seen him in, what, several years? More? He lives near Carmel now. He drove up. And within about an hour of him arriving I remembered the thing I had forgotten about Greg, which is that he is down for absolutely anything.

The morning after the show, we went for a swim in the hotel pool, because some habits from the swim-team years never fully die. Then I suggested a run. Greg was in immediately, and then realized he hadn’t packed running shoes.

Here is where he and I reveal ourselves to be different species.

I run in the Altra Escalante 4. I can tell you exactly why. I arrived at that shoe the way a government arrives at policy: months of reading, strong opinions about zero-drop and ground feel, multiple pairs ordered and tested on real runs and returned because the feel was a few percent off. I am also, and I need you to appreciate the irony here, the barefoot guy. Luna sandals all summer. Lifting without shoes. Cold plunges, minimal gear, noticing small things. My entire aesthetic is “strip it down to what matters.” I over-researched my way into minimalism.

Greg’s process: “I need new running shoes anyway.”

He didn’t want to spend the day carrying the shoes he’d packed just to buy their replacements. So he put on the free hotel slippers (the disposable, paper-thin kind you’re supposed to forget in the room) and we walked through the center of San Francisco to the Nike store, past Macy’s and the morning commuters, Greg whisper-scuffing down the sidewalk like a man who’d wandered off from a spa. At the store, he looked at the wall, picked the pair he thought looked coolest, put one on, bounced twice, and bought them. The slippers went straight into the trash on the way out. They were transportation, and they were done. Total decision time: about the length of one Nimino song.

Then we went running.

Greg smoked me.

Not narrowly. His cardio was operating in a different area code from mine. The man in the ten-minute shoes ran away from the man with the spreadsheet, and he did it easily, chatting, taking in the city, while I concentrated on not dying in my perfectly researched, correctly fitting, biomechanically optimal footwear.

I’d love to tell you the lesson landed instantly. It didn’t. My first instinct (I’m confessing this because it’s the whole point) was to wonder which shoes Greg had bought and whether they were actually right for his gait. That is the disease talking. The runner is not fast because of the shoe. The runner is fast because he runs.

So now, when I feel a decision starting to spiral, I try to ask one question: could Greg make this call in ten minutes wearing hotel slippers, with roughly the same outcome? Because if he could, then whatever I’m doing isn’t diligence. It’s stalling with extra steps.

An enormous amount of my life fails that question. Gear, obviously; the shoe saga was not an isolated incident, and there is a version of this story about backpacks that I am not emotionally ready to tell. But it goes past buying things. Side projects, where I’ll deliberate over the “right” framework long after the choice stops mattering, when what the project needs is one evening of me actually building it. Career questions, where I can model scenarios indefinitely instead of having the single conversation that would produce real information. Weeknight plans. Restaurants. I have compared restaurants until the kitchens closed.

The hours are the cheap part. Hours you can pay. The real bill is presence: every unit of attention spent optimizing a decision is a unit not spent inside the experience the decision was for. If reading reviews built aerobic capacity, I’d be pacing the Olympic marathon trials; they don’t, and the man who skipped them ran off ahead of me, enjoying San Francisco.

The show itself was perfect. Nimino live was everything the month on repeat promised, and standing next to me was a friend I’d recovered after years of drift, a friend who is back in my life precisely because I made one fast, unresearched, out-of-character decision to buy two tickets with no plan attached. The best decision in this whole story is the one I made like Greg. I try to remember that.

I won’t pretend I’m cured. I still catch myself six tabs deep into something that doesn’t deserve one tab. Sometimes I close them. Sometimes the kitchens close first. Overthinking isn’t a thing I solved; it’s a thing I’m actively fighting, with a friend’s shoe purchase as the training montage.

Because underneath all of it there’s a lesson I keep having to relearn, and I want to say it plainly: there is power in doing the thing. You can think about the run, plan the run, research the shoes for the run, and none of it makes you faster. Running makes you faster. Most of what I flatter myself by calling preparation is a sophisticated way of not starting.

So I keep score differently now. The wins aren’t perfect choices anymore. They’re fast ones: the run taken in the wrong shoes, the ticket bought before the plan exists, the project started with the boring framework. Doing over choosing. Presence over optimization.

My Escalantes have a few hundred miles left in them, and when they wear out, I’d like to buy the next pair the way Greg bought his: one song, one bounce, done. Somewhere near Carmel there’s a man who already lives this way, running easy in shoes he picked because they looked cool, not thinking about any of it at all.