“Pain Is the Best Teacher”

I was with a friend who was going through some pretty significant challenges with his company the other day. I asked him, naturally, how he’s dealing with it all.

How does he manage to keep his head above water and find the will to fight, day after day?

He gave an interesting response: “I always try to keep that Holly Black quote: to remind me, pain is the best teacher.” He went on to explain how he tries to lean into the pain and suffering he’s going through, because he somehow knows that he’ll come out of it a stronger and better person.

And I’m sure he will.

But I also think that people have a tendency to grossly overestimate the benefits of pain.

If you can learn the same lessons without going through the pain and suffering, you should probably take that path… because for the most part, all pain does is remind you how much it sucks, and how you should avoid it as much as possible if you can.

The Silicon Valley version of “pain is the best teacher” is “fail fast” (you can always count on Silicon Valley to optimize everything, including the number of words in a sentence that conveys the same idea).

The idea here is simple: you learn more from your failures than your successes, so the more you fail, the more likely you are to succeed the next time you try again.

But I’m not so sure if that’s true.

For the most part, failure teaches you that what you did was wrong, but running a company isn’t filled with right/wrong choices; the opposite of wrong, in many cases when making those difficult decisions, isn’t right. If you didn’t make the decision you did, you could’ve made another wrong decision. The right decision may prove to be too elusive for you to find, right until the moment your company has to shut its doors.

So, an entrepreneur who has failed once may fail again, and again, and again. It sounds like a tedious process.

Success, on the other hand, is a better teacher: even if you can’t replicate your winning decision over and over again 1:1, it still shows (luck notwithstanding), that your decision framework was probably right. Often times, the decision framework that results in mega-successful (i.e. home runs) decisions are not easily teachable, or something they’d share with you in a book or MBA course. You have to discover it yourself by being successful. Once you are, success begets further success.

At the end of the day, I’m sure one can learn at least something from failures and pain. But unfortunately, it’ll only tell you what not to do, not what you should do.

But is it really worth paying that high of a price only to learn what not to do?