Paul Graham on Doing What You Love

Image by DuffDudeX1, via Wikimedia Commons, public domain.

PETER

Our high school guidance counselor used to ask us what you would do if we had a million dollars and didn't have to work. And invariably, whatever we would say, that was supposed to be our careers. If you wanted to build cars, then you're supposed to be an auto mechanic.

SAMIR

So what did you say?

PETER

I never had an answer. I guess that's why I'm working at Initech.

MICHAEL

No, you're working at Initech because that question is bullshit to begin with.

-- Office Space (1999)

***

In an essay he titles "When To Do What You Love," venture capitalist Paul Graham considers a dilemma just about every thoughtful person faces regarding work in the long term.

He begins:

There's some debate about whether it's a good idea to "follow your passion." In fact the question is impossible to answer with a simple yes or no. Sometimes you should and sometimes you shouldn't, but the border between should and shouldn't is very complicated. The only way to give a general answer is to trace it.

When people talk about this question, there's always an implicit "instead of." All other things being equal, why wouldn't you work on what interests you the most? So even raising the question implies that all other things aren't equal, and that you have to choose between working on what interests you the most and something else, like what pays the best. [bold added]

Note the careful consideration of this advice, which is so common as to be effectively devoid of meaning and subject to the kind of ridicule we see in the movie quote above.

Whether you're young or simply someone who has struggled with finding the right career, I highly recommend reading the whole piece. I'm from the latter camp, so I recognize lots of the pitfalls Graham discusses, and I am in awe of the creative ways he offers around some of them:

One useful trick for judging different kinds of work is to look at who your colleagues will be. You'll become like whoever you work with. Do you want to become like these people?

Indeed, the difference in character between different kinds of work is magnified by the fact that everyone else is facing the same decisions as you. If you choose a kind of work mainly for how well it pays, you'll be surrounded by other people who chose it for the same reason, and that will make it even more soul-sucking than it seems from the outside. Whereas if you choose work you're genuinely interested in, you'll be surrounded mostly by other people who are genuinely interested in it, and that will make it extra inspiring.

The other thing you do in the face of uncertainty is to make choices that are uncertainty-proof. The less sure you are about what to do, the more important it is to choose options that give you more options in the future. I call this "staying upwind." If you're unsure whether to major in math or economics, for example, choose math; math is upwind of economics in the sense that it will be easier to switch later from math to economics than from economics to math. [footnote removed, bold added]

All I would add to this is that the advice is synergistic: Young Me nailed uncertainty-proof only to get mired with exactly the wrong set of colleagues for who he was then, by hastily choosing an ill-fitting job right after college.

The time I could have saved!

Oh, and yes: He does advise not waiting until you're done with college to start getting an answer to this question.

-- CAV