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LM: #346: In defense of over your head

December 15 2025 – 09:00am

We jump into projects because we think they’ll go well. They seem to always be more difficult, less fun, and take longer than we had expected.

This is one reason we get stuck in a cycle of starting, abandoning, starting, abandoning, without ever finishing.

But I’m beginning to think this is as much a feature as it is a bug.

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One of the things I appreciate about ChatGPT is it gives me the confidence to take on projects, thinking it will do most of the work. They still end up being difficult, but I wouldn’t have bothered otherwise.

And as I reflect on my own career, I realize there is nothing I’ve created I’m proud of to which the meme doesn’t apply: We do this not because it’s easy, but because we thought it would be easy.

So I do what I can to avoid drowning: Make and review predictions, ask myself what I might not be thinking of, and conducting little experiments to test my theories.

But there’s ultimately something motivating about getting in a bit over your head. It forces you to learn to swim.

Aphorism: “Who is it that, seeing the havoc of these civil wars of ours, does not cry out, that the machine of the world is near dissolution, and that the day of judgment is at hand; without considering, that many worse things have been seen, and that in the meantime, people are very merry in a thousand other parts of the earth for all this?” —Montaigne (1575)

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