How much are you supposed to like what you do? Unless you know that, you don’t know when to stop searching. And if, like most people, you underestimate it, you’ll tend to stop searching too early. You’ll end up doing something chosen for you by your parents, or the desire to make money, or prestige—or sheer inertia.

Here’s an upper bound: Do what you love doesn’t mean, do what you would like to do most this second. Even Einstein probably had moments when he wanted to have a cup of coffee, but told himself he ought to finish what he was working on first.

It used to perplex me when I read about people who liked what they did so much that there was nothing they’d rather do. There didn’t seem to be any sort of work I liked that much. If I had a choice of (a) spending the next hour working on something or (b) be teleported to Rome and spend the next hour wandering about, was there any sort of work I’d prefer? Honestly, no.

But the fact is, almost anyone would rather, at any given moment, float about in the Carribbean, or have sex, or eat some delicious food, than work on hard problems. The rule about doing what you love assumes a certain length of time. It doesn’t mean, do what will make you happiest this second, but what will make you happiest over some longer period, like a week or a month.
Unproductive pleasures pall eventually. After a while you get tired of lying on the beach. If you want to stay happy, you have to do something.

As a lower bound, you have to like your work more than any unproductive pleasure. You have to like what you do enough that the concept of “spare time” seems mistaken. Which is not to say you have to spend all your time working. You can only work so much before you get tired and start to screw up. Then you want to do something else—even something mindless. But you don’t regard this time as the prize and the time you spend working as the pain you endure to earn it.

I put the lower bound there for practical reasons. If your work is not your favorite thing to do, you’ll have terrible problems with procrastination. You’ll have to force yourself to work, and when you resort to that the results are distinctly inferior.

To be happy I think you have to be doing something you not only enjoy, but admire. You have to be able to say, at the end, wow, that’s pretty cool. This doesn’t mean you have to make something. If you learn how to hang glide, or to speak a foreign language fluently, that will be enough to make you say, for a while at least, wow, that’s pretty cool. What there has to be is a test.

So one thing that falls just short of the standard, I think, is reading books. Except for some books in math and the hard sciences, there’s no test of how well you’ve read a book, and that’s why merely reading books doesn’t quite feel like work. You have to do something with what you’ve read to feel productive.

I think the best test is one Gino Lee taught me: to try to do things that would make your friends say wow. But it probably wouldn’t start to work properly till about age 22, because most people haven’t had a big enough sample to pick friends from before then…”