It was a quarterly business review in a rented meeting room. The acquisition pipeline came up on the projector, and I understood that the bridge we had been building had nowhere to go.

We had spent two years on this pivot. The product had been a high-end, boutique tool for sophisticated customers, and the market was telling us it wasn’t going to grow that way. So we rebuilt. New infrastructure for multi-tenancy. New product categories to widen the entry point. Documentation reworked so a customer could come on by themselves without an expensive onboarding project. I was on the platform side. We had estimated three to six months. At the two-year mark, we were still in it.

The MVPs had landed. By any internal measure, the technical march was supposed to be over. I should have been feeling relief. Instead I was looking at the customer pipeline projected on the wall and registering that the volume we had built for was not going to materialize. The VC winter was squeezing our customer base. The shift from boutique to mass-market had been built on assumptions the market had already moved past. The bridge was done. The road on the other side had been closed without anyone telling us.

I was too tired to be angry. Years of skipped vacations had crowded out most of the appropriate emotions and left a single dull register underneath everything. Around the table, people went through the motions of the meeting — taking it seriously, asking the right questions, advancing the right agenda items — while what was on the screen sat there contradicting all of it. They sleepwalked through it. I sleepwalked through it. It was just there, quiet and unavoidable. Simple validating questions, asked at the right moments, could have saved a lot of this. I had stopped looking up.

The bad numbers weren’t what hit me. The two years were. They had gone by while my head was down, and I had not noticed.

There is a particular kind of work that wraps around the work. The meetings. The tooling. The operational things that go wrong on a Tuesday morning and require a fix by Tuesday afternoon. Most of what gets done in any given week is this kind of work, and most of it is necessary. The other kind — the work of asking whether what you are building is still the right thing — happens in the slack between the urgent things, when there is room for the question to surface. Under crunch, there is no slack. The wrapping work takes everything. The strategic question gets displaced by definition: asking it requires looking past what is in front of you, and you have stopped looking past anything. Elsewhere I have written about this as accidental complexity crowding out the essential — the same dynamic, seen from inside the work rather than from above it.

The two years of platform work had been almost entirely the wrapping kind. The infrastructure was real and necessary. It also presupposed a question — is the market for the volume we are building for still there? — that no one had the slack to ask, including me. The question was structurally invisible from inside the work.

Crunch doesn’t only exhaust you. It takes away the question. You stop being someone who looks up, and then it is two years later and someone is projecting a chart that tells you what you should have been asking all along.

Crunch doesn’t only exhaust you. It takes away the question.

My career has been a series of pivots — corporate, NGO, infrastructure, Silicon Valley, consulting, startup — each one mostly accidental, mostly downstream of saying yes to something unfamiliar. It looks coherent in retrospect. From inside it was a series of things that fell out of the sky or fell apart underneath me, and I kept walking forward because there was nowhere else to go. N=1, and the bias is named: I am the one writing the essay about it. What I can say is that the trait that kept me walking forward was curiosity — the willingness to find the next thing interesting enough to enter.

Some people pick up the unfamiliar thing without being talked into it. Others have to be persuaded into anything new. I have always been in the first group, which is luck rather than achievement. That is temperament, not a virtue I earned. But temperament is only the ceiling. The practice — making deliberate time for the unfamiliar, especially when the calendar is screaming that there is no time — is what builds the muscle within the ceiling. The blog you are reading is my version of the practice. I am writing it during a period when I should objectively be doing other things: debugging the platform, building out a product line, working through how AI-augmented on-call might function for our customers. Instead I am here. Most of what I write here will not move my startup forward. That is the point. The space exists because I made it exist, against the gravity of the grind.

There is a shadow. Curiosity has cost me an identity I can pin down cleanly. I have been too many things. Sometimes I wonder what would have happened if I had stayed on the Silicon Valley track, pursued a Green Card more actively, ridden the late tech boom from a stable platform instead of pivoting again. I will never know. The counterfactual is unavailable, and the version of me that pursued it would be subject to its own uncertainties: squeezed by the layoffs of the last few years, or stuck somewhere I did not want to be by an immigration status that had stopped fitting. You are damned if you do and damned if you don’t, except you only ever get to live one side of it.

When you are tired enough, curiosity goes first. The QBR moment is the one I keep coming back to because it was the failure of the trait, not its success. I had been deep enough in the wrapping work for long enough that I had stopped asking the question underneath it. The naive optimism a founder needs to keep going under bad odds also functions, when it tips too far, as a defense against the evidence of those odds. I had been defending. I had not been looking. The discipline of making space exists because I know what the inside of the failure looks like, not because I have always practiced it well.

What I come back to, in the worst of the trenches, is a small dark-humor sentence that sits underneath everything else. The startup isn’t working. A customer churned. The runway has compressed by another month. The thing you built doesn’t fit the market that has appeared while you were building it. And then, almost involuntarily, the head tilts toward whatever is going to happen next. I wonder what happens now.

What that tilt restores, briefly, is the thing crunch had taken from me long before it took the two years: attention. Robert Pirsig, in Zen and the Art of Motorcycle Maintenance, called this Quality — not a property of the object, not a state of the subject, but the relationship between them when the attention is real. Quality is what shows up when you care about the thing in front of you for its own sake, before any judgment about whether it is serving your purposes. Pirsig’s diagnosis was that goal-oriented striving, taken far enough, severs you from the thing you are striving with. The person who has worn out their capacity to want outcomes can still attend to what is actually there. That is the thing the worn-out part hasn’t worn out.

The pipeline on the wall in that meeting room had been visible the whole time. No one in the room was in relationship with it, including me. We were in relationship with the agenda, which required updates and next steps; the pipeline required something the agenda did not, which was asking whether any of this was still the right thing. The first request was answerable from inside the work. The second was not, and so it did not get made.

That is what curiosity becomes when you have been beaten up enough. Not the trait that opens doors in the good times, but the stance that lets you keep paying attention when the moment, on the available evidence, is not going to be good. The two arguments are the same argument from different sides. In one direction, curiosity captures the upside that randomness throws at you. In the other, it keeps you in relationship with what is actually in front of you instead of with the failure of what you had wanted to be in front of you. Both depend on the same small involuntary tilt of the head. No stance guarantees outcomes. Curiosity at least keeps the doors visible — and when you cannot tell whether any door leads anywhere good, visibility is the thing.

I am not out of the trench. I do not know what is going to happen next. I am still looking up.