The Evolution of My Thinking

The version of me at 22 was confident in ways the current version finds embarrassing and instructive in roughly equal measure.

Not wrong about everything. But confident in the wrong ways — certain about things that deserved more uncertainty, and uncertain about things that could have been resolved with more careful thinking. The ratio has improved. The underlying tendency to hold views with more confidence than the evidence warrants has not disappeared; it has just shifted to different topics.

The views I have held most rigidly have usually been the ones that changed most

There is a pattern I have noticed in my own thinking over time: the beliefs I argued for most aggressively were often the ones that contained the most unexamined assumption. The rigidity was a symptom of not having really interrogated the thing.

When I was younger, I believed that talent was primarily individual — that outcomes reflected what people were capable of, and that capability was largely independent of circumstance. This belief justified a particular way of seeing the world: success as evidence of quality, failure as evidence of the opposite.

Experience broke this progressively. Working with people across very different backgrounds, watching identical capability produce radically different outcomes depending on access and timing and circumstance — this made the original belief impossible to hold in its original form. Talent is real. Circumstance shapes what it produces. The relationship between the two is not the simple one I originally assumed.

I hold a more complicated view now. I hold it less rigidly. This is an improvement.

What changes thinking, in practice

Thinking changes through exposure more than through argument.

Argument can update a position at the margins — clarify a term, strengthen or weaken a specific claim, provide evidence for a point that was being held without it. But the deep structure of how someone sees the world, the underlying assumptions that generate the positions — those change through experience. Through living inside contexts that your existing framework cannot explain. Through repeated contact with evidence that your current beliefs cannot accommodate.

The implication is that the fastest way to improve your thinking is to change your circumstances in ways that put you in contact with things your current mental models cannot handle. Not to seek disconfirming arguments, but to seek experiences that disconfirm. The arguments will follow.

What I am more uncertain about than I was

The list of things I am more uncertain about than I was five or ten years ago is longer than the list of things I am more certain about.

I am less certain that I understand motivation — why people do what they do, what actually drives the decisions that shape their lives. The further I get from simple economic models of behavior, the more complicated the picture gets, and the less confident I am in any single explanation.

I am less certain that the right frameworks for thinking about opportunity and development — the ones I would have deployed confidently at 25 — are as robust as they appeared. The world is more path-dependent and more contingent than those frameworks suggest. Small things that seem trivial in the moment turn out to matter enormously. Large interventions that seem significant produce surprisingly little change.

I am less certain about what I know from experience versus what I have been told repeatedly until it feels like experience. This is a harder problem than it sounds. The things we know from direct observation are actually quite limited. Most of what we believe comes from accumulated testimony — other people's accounts, filtered through media and culture and the communities we inhabit. Distinguishing between these two categories, and holding the testimony-based beliefs more loosely than the observation-based ones, is a discipline I am still developing.

What has not changed

Some things have gotten more stable, not less, with time.

The belief that most people have more capacity than their circumstances have allowed them to demonstrate. The belief that the gap between talent and opportunity is the most important structural problem in human organization. The belief that directness, delivered with genuine care for the person you are being direct with, is almost always the right choice over comfortable evasion.

These have survived contact with a lot of evidence that would have been disconfirming if they were wrong. They have not been disconfirmed. I hold them with more confidence than I used to, not because I stopped questioning them, but because I kept questioning them and they kept holding.

That is a different kind of confidence than the one I had at 22. It is earned rather than assumed, provisional rather than defensive, and it sits more quietly.