Any advice about procrastination that concentrates on crossing things off your to-do list is not only incomplete, but positively misleading, if it doesn't consider the possibility that the to-do list is itself a form of type-B procrastination. In fact, possibility is too weak a word. Nearly everyone's is. Unless you're working on the biggest things you could be working on, you're type-B procrastinating, no matter how much you're getting done.

In his famous essay You and Your Research (which I recommend to anyone ambitious, no matter what they're working on), Richard Hamming suggests that you ask yourself three questions:

What are the most important problems in your field?

Are you working on one of them?

Why not?

Hamming was at Bell Labs when he started asking such questions. In principle anyone there ought to have been able to work on the most important problems in their field. Perhaps not everyone can make an equally dramatic mark on the world; I don't know; but whatever your capacities, there are projects that stretch them. So Hamming's exercise can be generalized to:

What's the best thing you could be working on, and why aren't you?

Most people will shy away from this question. I shy away from it myself; I see it there on the page and quickly move on to the next sentence. Hamming used to go around actually asking people this, and it didn't make him popular. But it's a question anyone ambitious should face.

The trouble is, you may end up hooking a very big fish with this bait. To do good work, you need to do more than find good projects. Once you've found them, you have to get yourself to work on them, and that can be hard. The bigger the problem, the harder it is to get yourself to work on it.

Of course, the main reason people find it difficult to work on a particular problem is that they don't enjoy it. When you're young, especially, you often find yourself working on stuff you don't really like-- because it seems impressive, for example, or because you've been assigned to work on it. Most grad students are stuck working on big problems they don't really like, and grad school is thus synonymous with procrastination.

But even when you like what you're working on, it's easier to get yourself to work on small problems than big ones. Why? Why is it so hard to work on big problems? One reason is that you may not get any reward in the forseeable future. If you work on something you can finish in a day or two, you can expect to have a nice feeling of accomplishment fairly soon. If the reward is indefinitely far in the future, it seems less real.

Another reason people don't work on big projects is, ironically, fear of wasting time. What if they fail? Then all the time they spent on it will be wasted. (In fact it probably won't be, because work on hard projects almost always leads somewhere.)

But the trouble with big problems can't be just that they promise no immediate reward and might cause you to waste a lot of time. If that were all, they'd be no worse than going to visit your in-laws. There's more to it than that. Big problems are terrifying. There's an almost physical pain in facing them. It's like having a vacuum cleaner hooked up to your imagination. All your initial ideas get sucked out immediately, and you don't have any more, and yet the vacuum cleaner is still sucking.

You can't look a big problem too directly in the eye. You have to approach it somewhat obliquely. But you have to adjust the angle just right: you have to be facing the big problem directly enough that you catch some of the excitement radiating from it, but not so much that it paralyzes you. You can tighten the angle once you get going, just as a sailboat can sail closer to the wind once it gets underway.

If you want to work on big things, you seem to have to trick yourself into doing it. You have to work on small things that could grow into big things, or work on successively larger things, or split the moral load with collaborators. It's not a sign of weakness to depend on such tricks. The very best work has been done this way.

When I talk to people who've managed to make themselves work on big things, I find that all blow off errands, and all feel guilty about it. I don't think they should feel guilty. There's more to do than anyone could. So someone doing the best work they can is inevitably going to leave a lot of errands undone. It seems a mistake to feel bad about that.

I think the way to "solve" the problem of procrastination is to let delight pull you instead of making a to-do list push you. Work on an ambitious project you really enjoy, and sail as close to the wind as you can, and you'll leave the right things undone.

To do something well you have to like it. That idea is not exactly novel. We've got it down to four words: "Do what you love." But it's not enough just to tell people that. Doing what you love is complicated.

The very idea is foreign to what most of us learn as kids. When I was a kid, it seemed as if work and fun were opposites by definition. Life had two states: some of the time adults were making you do things, and that was called work; the rest of the time you could do what you wanted, and that was called playing. Occasionally the things adults made you do were fun, just as, occasionally, playing wasn't-- for example, if you fell and hurt yourself. But except for these few anomalous cases, work was pretty much defined as not-fun.

And it did not seem to be an accident. School, it was implied, was tedious because it was preparation for grownup work.

The world then was divided into two groups, grownups and kids. Grownups, like some kind of cursed race, had to work. Kids didn't, but they did have to go to school, which was a dilute version of work meant to prepare us for the real thing. Much as we disliked school, the grownups all agreed that grownup work was worse, and that we had it easy.

Teachers in particular all seemed to believe implicitly that work was not fun. Which is not surprising: work wasn't fun for most of them. Why did we have to memorize state capitals instead of playing dodgeball? For the same reason they had to watch over a bunch of kids instead of lying on a beach. You couldn't just do what you wanted.

I'm not saying we should let little kids do whatever they want. They may have to be made to work on certain things. But if we make kids work on dull stuff, it might be wise to tell them that tediousness is not the defining quality of work, and indeed that the reason they have to work on dull stuff now is so they can work on more interesting stuff later. [1]

Once, when I was about 9 or 10, my father told me I could be whatever I wanted when I grew up, so long as I enjoyed it. I remember that precisely because it seemed so anomalous. It was like being told to use dry water. Whatever I thought he meant, I didn't think he meant work could literally be fun-- fun like playing. It took me years to grasp that.

By high school, the prospect of an actual job was on the horizon. Adults would sometimes come to speak to us about their work, or we would go to see them at work. It was always understood that they enjoyed what they did. In retrospect I think one may have: the private jet pilot. But I don't think the bank manager really did.

The main reason they all acted as if they enjoyed their work was presumably the upper-middle class convention that you're supposed to. It would not merely be bad for your career to say that you despised your job, but a social faux-pas.

Why is it conventional to pretend to like what you do? The first sentence of this essay explains that. If you have to like something to do it well, then the most successful people will all like what they do. That's where the upper-middle class tradition comes from. Just as houses all over America are full of chairs that are, without the owners even knowing it, nth-degree imitations of chairs designed 250 years ago for French kings, conventional attitudes about work are, without the owners even knowing it, nth-degree imitations of the attitudes of people who've done great things.