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Let's talk a little more about the complicated business of figuring out what to work on. The main reason it's hard is that you can't tell what most kinds of work are like except by doing them. Which means the four steps overlap: you may have to work at something for years before you know how much you like it or how good you are at it. And in the meantime you're not doing, and thus not learning about, most other kinds of work. So in the worst case you choose late based on very incomplete information. ^[4]

The nature of ambition exacerbates this problem. Ambition comes in two forms, one that precedes interest in the subject and one that grows out of it. Most people who do great work have a mix, and the more you have of the former, the harder it will be to decide what to do.

The educational systems in most countries pretend it's easy. They expect you to commit to a field long before you could know what it's really like. And as a result an ambitious person on an optimal trajectory will often read to the system as an instance of breakage.

It would be better if they at least admitted it — if they admitted that the system not only can't do much to help you figure out what to work on, but is designed on the assumption that you'll somehow magically guess as a teenager. They don't tell you, but I will: when it comes to figuring out what to work on, you're on your own. Some people get lucky and do guess correctly, but the rest will find themselves scrambling diagonally across tracks laid down on the assumption that everyone does.

What should you do if you're young and ambitious but don't know what to work on? What you should not do is drift along passively, assuming the problem will solve itself. You need to take action. But there is no systematic procedure you can follow. When you read biographies of people who've done great work, it's remarkable how much luck is involved. They discover what to work on as a result of a chance meeting, or by reading a book they happen to pick up. So you need to make yourself a big target for luck, and the way to do that is to be curious. Try lots of things, meet lots of people, read lots of books, ask lots of questions. ^[5]

When in doubt, optimize for interestingness. Fields change as you learn more about them. What mathematicians do, for example, is very different from what you do in high school math classes. So you need to give different types of work a chance to show you what they're like. But a field should become increasingly interesting as you learn more about it. If it doesn't, it's probably not for you.

Don't worry if you find you're interested in different things than other people. The stranger your tastes in interestingness, the better. Strange tastes are often strong ones, and a strong taste for work means you'll be productive. And you're more likely to find new things if you're looking where few have looked before.

One sign that you're suited for some kind of work is when you like even the parts that other people find tedious or frightening.

But fields aren't people; you don't owe them any loyalty. If in the course of working on one thing you discover another that's more exciting, don't be afraid to switch.

If you're making something for people, make sure it's something they actually want. The best way to do this is to make something you yourself want. Write the story you want to read; build the tool you want to use. Since your friends probably have similar interests, this will also get you your initial audience.

This should follow from the excitingness rule. Obviously the most exciting story to write will be the one you want to read. The reason I mention this case explicitly is that so many people get it wrong. Instead of making what they want, they try to make what some imaginary, more sophisticated audience wants. And once you go down that route, you're lost. ^[6]

There are a lot of forces that will lead you astray when you're trying to figure out what to work on. Pretentiousness, fashion, fear, money, politics, other people's wishes, eminent frauds. But if you stick to what you find genuinely interesting, you'll be proof against all of them. If you're interested, you're not astray.

Following your interests may sound like a rather passive strategy, but in practice it usually means following them past all sorts of obstacles. You usually have to risk rejection and failure. So it does take a good deal of boldness.

But while you need boldness, you don't usually need much planning. In most cases the recipe for doing great work is simply: work hard on excitingly ambitious projects, and something good will come of it. Instead of making a plan and then executing it, you just try to preserve certain invariants.

The trouble with planning is that it only works for achievements you can describe in advance. You can win a gold medal or get rich by deciding to as a child and then tenaciously pursuing that goal, but you can't discover natural selection that way.

I think for most people who want to do great work, the right strategy is not to plan too much. At each stage do whatever seems most interesting and gives you the best options for the future. I call this approach "staying upwind." This is how most people who've done great work seem to have done it.