After the Grind — 3 of 6
There’s a voice in me that has been saying the same thing my whole life. You should have known better. You should have done better. You should have seen it coming. It’s not a cruel voice exactly. It wants me to be good, to be right, to hold the standard. But it operates on a belief that took me four decades to recognize as false, and the belief is this: that being wrong is a kind of failure, and that a person who was actually competent would have avoided it.
I believed that for most of my life, and it cost me more than almost anything else I can name. Not because it made me reckless. The opposite. It made me careful in the worst way, the way that mistakes thoroughness for safety. If being wrong is failure, then the move is to never be wrong, and the way to never be wrong is to analyze a thing to death before you touch it, build the whole foundation before you’ll take a step, and treat every bad outcome as evidence of a flaw in you rather than as information about the world. I got very good at the front half of that. The back half quietly tore at me, because no amount of foundation-building stops you from being wrong sometimes, and every time it happened the voice was right there to file it as proof.
What I eventually understood is that I am not actually built to avoid being wrong. I’m built to learn by being wrong. Those are opposite operating instructions, and I’d been running the first one over the top of a person designed for the second one, which is about the most reliable recipe for self-friction I can imagine.
The way I actually figure things out, the way I always have, is by trying them. By making contact with the real thing, finding its edge, and keeping what holds while discarding what doesn’t. Most of what I know that’s worth anything, I learned by walking into something, getting it partly wrong, and reading the wrongness for what it was telling me. The deals that didn’t close, the bonds that broke, the ventures that ended early. Every one of those, the should-voice logged as a failure. But they weren’t failures. They were the curriculum. They were me learning the only way I’m wired to learn, which is by experiment, in contact, at the edge.
The clearest time I ever trusted that, before I had any language for it, was a deal I walked away from at the closing table.
In 2023 I ran a full acquisition of a second-generation moving-and-storage business in the Front Range of Colorado. I mean a full process. Broker agreement in the spring, signed letter of intent at midyear, a summer of purchase agreements and ancillary documents, motor-carrier registration with the federal regulators in the fall. By late October I was at the table, and the deal was real, and it was mine to close. Roughly a million and a half dollars in total consideration, a chunk of it a seller note I’d be personally on the hook for. A two-hour round-trip commute to an industry I’d never worked in a day of my life. And I walked.
I walked because somewhere in the final stretch I saw the thing the whole analysis had been built to avoid seeing. I wasn’t buying an asset. I was buying a job. The business ran on its owner. Take him out and put me in, and the company didn’t become mine, I became him, with a personally guaranteed note and a commute and no path back out. Everything I told myself I wanted from independence, the deal would have quietly taken. I’d have woken up inside a structure that depended entirely on my presence, which is the exact trap I’d left a corporate life to escape.
Here’s why it belongs in an essay about being wrong. By the standard of the voice in my head, walking was a catastrophe. Months of work, real money in legal fees, a registered carrier authority I’d have to file out of existence, and nothing to show for it. You should have seen this earlier. You should never have gotten to the table. A competent person wouldn’t have spent six months on a deal he’d abandon. That’s what the should-voice said, and it said it loudly for a while.
But that’s the voice grading the wrong exam. The walk wasn’t the failure. The walk was the single most correct move I made in that entire year, and I could only make it because I’d let the process run far enough to teach me what it needed to teach me. I didn’t know in April what I knew in October. I couldn’t have. The knowing came from being in it, from making contact with the real shape of the thing, from getting close enough to the edge to feel where it dropped off. The six months weren’t wasted. The six months were how I learned. And the lesson, the one that became the spine of everything I do now, came directly out of a deal that by every conventional measure I “failed” to complete.
If I’d been running the avoid-being-wrong program cleanly, I’d have closed. That’s the irony I sit with. The careful, never-be-wrong version of me would have done the analysis, gotten the numbers to pencil, and signed, because signing is what you do when you’ve come that far and don’t want the discomfort of having been wrong about pursuing it. It’s the experiment-and-read-the-edge version of me that walked. The part the should-voice was always trying to override is the part that saved me from buying a job at the cost of my family’s balance sheet.
What I’ve been doing since is learning to let that part do its job without the other part pre-judging every move. It’s not that the standard-holding voice is wrong to exist. It keeps me honest. But it makes a terrible navigator, because it reads every experiment as a verdict and every wrong turn as a character flaw, and a person who’s built to learn by trial cannot afford a navigator like that. The reframe I keep practicing is plain enough to write on a card: a wrong turn is information, not a referendum on whether I’m good enough. The bond that didn’t hold, the deal that didn’t close, the thing I tried that didn’t work. That’s not the record of my failures. That’s the data I needed, arriving the only way it ever arrives, which is after you’ve moved.
I’m slower to call things failures now. When something doesn’t work, my first question is no longer what’s wrong with me that I didn’t see it coming. It’s closer to: alright, what did that just teach me that I had no way of knowing before I tried it? That question has a completely different feeling in the body than the old one. The old one contracts. This one opens. And it turns out the open one is not just kinder. It’s more accurate, because it describes how I actually learn, which the contracted one never did.