What Was I Wrong About?

The most educational conversations I have had about building things have not been about what went right. They have been about what went wrong — specifically, about the beliefs that were confidently held, acted upon, and then definitively refuted by what happened.

The problem with this kind of learning is that it requires acknowledging the original error clearly enough to learn from it. Most people do not do this. They acknowledge the outcome — yes, that did not work — without acknowledging the belief that produced it. The surface admission happens; the belief itself goes unupdated.

Here is an honest attempt at the version that requires more.

I was wrong about what makes clients stay

For a long time I believed that client retention was primarily a function of outcomes. Deliver results, keep the client. This is not wrong, but it is incomplete in a way that cost me at least one important relationship.

What actually keeps clients — I understand this more clearly now — is the experience of being genuinely understood. Not just receiving good work, but feeling that the person delivering the work sees their specific situation clearly, is thinking about their specific constraints, and is invested in their particular outcome rather than producing a generically good product.

The client who left was receiving good work. They were not receiving the experience of being seen. Those are different things, and I had conflated them. The update is not just to deliver better work — it is to deliver work that is demonstrably calibrated to the specific person receiving it, in ways they can feel.

I was wrong about how quickly people change

I used to believe, somewhat romantically, that people could change rapidly when the right insight or intervention arrived. That a single conversation, or a well-timed piece of feedback, or a significant enough setback could produce real, lasting behavioral change.

The evidence of a decade disagrees. People change slowly, and mostly through accumulated experience rather than singular moments. The insight that lands powerfully in one conversation has to be reinforced by many subsequent experiences before it actually shifts behavior. The feedback that is heard and genuinely agreed with in the moment may take years to fully integrate into how someone acts.

This has changed how I approach development conversations — less expectation of quick change, more patience for the slow accumulation, more investment in repeated small signals rather than singular large ones. The single impactful conversation still matters. It is just not the whole intervention.

I was wrong about what I needed to keep going

In the early phase of building, I believed that what kept me going was the conviction that the outcome would be good. The faith that the effort would compound into something real. The belief that the work would matter.

What I have found, over time, is that the conviction fluctuates. There are months when the evidence for the direction is strong, and months when it is genuinely unclear. The conviction is not a stable resource.

What actually kept me going, in the periods when conviction was low, was not belief in the outcome. It was attachment to the process — genuine interest in the specific problems I was working on, enjoyment of the craft of doing the work well, the relationships with clients and colleagues that made the day-to-day meaningful independent of the larger trajectory.

I had underestimated the process and overestimated the vision. The vision gets you started. The process keeps you in.

What I am still probably wrong about

The honest version of this essay requires acknowledging that the errors above are the ones I can see — which means they are probably the ones that have already been corrected.

The errors I have not corrected yet are the ones I cannot see. They are currently manifesting as things that feel true and are in fact wrong. Some of them are probably beliefs that will be on a future version of this list.

What I can do is create the conditions for catching them faster: stay curious about my own assumptions, stay in contact with people who will tell me when something does not make sense, and keep the question "what am I wrong about?" active rather than treating it as an exercise done once a year.

The answer is always something. The value is in finding it before the evidence does.