There’s a great meme that goes around on occasion, which is a motivational poster of some kind with the words:

We do these things not because they are easy, but because we thought they would be easy.

If you’re not familiar, it’s a reference to a line from JFK’s famous speech, justifying the moon program:

We choose to go to the Moon in this decade and do the other things, not because they are easy, but because they are hard; because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one we intend to win, and the others, too.

There is truth in Kennedy’s approach—it is the basic foundation of how we teach children—but it is extremely rarely done by adults for the simple reason that adults usually have better things to do. The truth is that the moon shot program wasn’t really about human advancement. It was a massive game of capture-the-flag played with the Soviets as a PR stunt, which is why we and they both stopped shortly after the US captured the flag (by which I mean, planted a flag on the moon).

Which gets us back to the original quote: there are a lot of times when somebody does something useful because he thought it was going to be a lot easier than it turned out to be, but by the time he put a lot of time into it he found that the harder version was actually worth doing, especially because he was now in a place to do it with a lot less work than if he was starting from scratch. And this is an example of what I would call a useful mistake. Another example would be what Larry Wall, inventor of the Perl programming language, famously called the three principle virtues of a Perl programmer.

Those virtues were: laziness, impatience, and hubris. These are, of course, rhetorical, since laziness, impatience, and hubris are actually vices. What Larry meant (and explained in his own words) was that there are things that look like these things, but are actually good habits. What he called laziness is really foresight; good design so as to avoid having to do excess work in the future. What he called impatience is really ambition, or the desire to solve problems—to not be willing to sit through endless drudge-work when it was possible to write a program to do the drudge-work instead. And what he called hubris was really faith—the faith that one could see the task through to its conclusion. “I can do this,” in spite of not (yet) being able to point to conclusive evidence that you can.

The ideal would be, of course, to have a perfectly accurate estimation of both the amount and difficulty of the work to be done, and also of one’s ability to get it done. We very rarely achieve perfection, though, and so choosing the kind of failure mode we want is important. Would we prefer to fail at our estimations in a way that makes us start more projects, or start fewer projects? That is, is it better to waste time when we make imperfect estimations of difficulty and our ability, or to leave undone things we could have accomplished? I think that there is much to be said for the former, because we can always give up when it turns out that something was too difficult for us, and this will help to refine our skill at estimating difficulty. If we bias our failures towards leaving things undone, there’s no reason we’d ever decide to start up, and there will be nothing giving us feedback about our accuracy of estimating difficulty.

So I think that there’s a lot to be said for slightly under-estimating how hard things will be; your life will tend to be better off for it. And to counter-balance people saying that you should be humble about your abilities, this is just being humble about your ability to estimate how difficult something is. Ultimately, when it comes to worthwhile things, we never know what we’re getting ourselves into, so we have to live by the faith that something good will come of our efforts. This is really just making the decision to have some faith.