What Am I Learning?

The question I find most useful to ask myself, periodically, is not "what am I doing?" or "what am I building?" It is "what am I learning?" The first two questions are about output. The last one is about whether the output is making me better equipped to produce better output next time.

Most people, when they ask this question, give themselves credit for things they are consuming rather than things they are actually internalizing. Reading a book about strategy is not the same as having changed how you make strategic decisions. Attending a conference about building is not the same as having built differently.

The learning that actually matters is harder to see and slower to accumulate.

What I am learning right now

I am learning, slowly and with some resistance, that systems matter more than effort at a certain scale.

My default orientation is toward effort — toward working harder as the response to most problems. This served me well for a long time, in the phase when the constraints were primarily about what I was willing to do. As the work has grown, I keep running into the limits of that orientation. The problem is not, in most cases, that I am not working hard enough. The problem is that the work is not organized in a way that compounds.

A system is something that produces results consistently, regardless of who is running it on a given day. Effort is what fills the gap when the system does not exist yet. I spent too long thinking of effort as the goal rather than as the bridge to the goal. The systems I am building now — in hiring, in client communication, in how I process information — are the product of realizing this, later than I should have.

I am also learning that my instinct about people is better than I give it credit for, and my instinct about ideas is worse.

When I form an impression of a person in an early interaction — about their judgment, their character, their capacity — it is usually accurate. Not perfectly, but reliably enough that I should trust it more. I have a pattern of overriding this instinct in favor of credentials or external signals, and the overrides have an unusually high failure rate.

On ideas, the pattern is reversed. I am too quick to find an idea compelling, to see how it could work without adequately stress-testing the ways it might not. The ideas I have been most enthusiastic about have not, on average, been the most useful ones. The ideas I have been skeptical of have turned out to be more robust than I initially gave them credit for. I am trying to slow down the enthusiasm curve and lengthen the period of questioning.

What I am learning from the work itself

Every sustained piece of work teaches you something about how you work, independent of the subject matter.

I am learning that I do my best thinking in the morning, and that the meetings and communications I schedule in that time are an expensive trade. I have been gradually protecting the morning more deliberately, which produces better work and also — counterintuitively — makes me more present in the interactions that do happen, because I am not coming to them depleted.

I am learning that feedback is available more abundantly than I have been using it. Clients will tell you what they actually need if you ask directly enough. Colleagues will tell you where the work falls short if the environment is honest enough. The gap between the feedback that is available and the feedback I have been collecting is larger than it should be, and it is a gap I created — through questions that were too soft, environments that were not safe enough, or a reluctance to hear things I suspected but did not want confirmed.

The meta-question

The most important thing I am learning is how to learn better.

Not in an abstract, educational-theory sense. In the practical sense of: how do I build the conditions in which I am most likely to update my beliefs when the evidence requires it, rather than defending what I already think?

The conditions that seem to help are specific: conversations with people who will be honest rather than supportive, time set aside for actual reflection rather than just activity, and the discipline of writing — which forces the kind of precision that identifies where the thinking is still vague. Without these conditions, I learn from experience the way most people do: slowly, partially, and with a strong bias toward confirming what I already believe.

With them, the learning is faster, more honest, and more useful. I am getting better at creating those conditions. I am not yet good enough at it to stop paying attention to it.