Good and bad ways to go wrong

We all go wrong, and have done so literally since Adam, unless I’m wrong in thinking there was an Adam, or in assuming there’s anything true of all of us, or if I got the meaning of "wrong" wrong.

In any case, there are right and wrong ways to go wrong. Probably.

For example, I once was at a conference of 50 people. During the opening get-to-know-one-another session, one of the participants said casually that he’s interested in studying the Internet as a type of brain. "The Net’s not a brain," I expostulated to my surprise. It’s just that it seems like such a dumb idea. Maybe if you were a brain scientist who understood the Net deeply you could make some claims about the similarities, but otherwise you’re just succumbing to a too-easy analogy. Of course, the guy who made the analogy was a brain scientist who understood the Net deeply. When a bunch of us had a beer afterward, he said that his old dissertation adviser had told him that you can be arrogant or you can be ignorant, but you better not be both. He was looking straight at me.

That’s one bad way to go wrong. In fact, it’s an example of the broader rule that where it’s OK to go wrong one way, it’s disastrous to go wrong in two or more ways. So, you may be wrong about how much a subordinate knows, which is sort of OK unless you’re also wrong about her ability to learn. You may be wrong about how your distributors are going to take to the new sales strategy, which is OK so long as you’re not also wrong about how you measure the distributors’ dissatisfaction. Those double whammies will really get you, since the second whammy covers up the error you’re making with the first whammy. Conclusion: Try to keep your whammies in the low single digits.

One of the greatest sources of error is the generalization. In fact, there’s a traditional informal fallacy that warns against generalizations. In truth, however, it warns against hasty generalizations. Generalizations by themselves are fine. In fact, much of what we call "learning" involves seeing what the abiding factors are that brought about a particular result. "Ah," you say to yourself, "every time I fire someone for blogging, productivity goes down among our new hires." You get the fallacy of hasty generalization when you generalize based on too few instances, so you pick out irrelevant factors: "That employee with tattoos is a great blogger. Jenkins, hire more people with tattoos!" That’s called being stupid.

We need generalizations, but one of the whopper ways of going wrong is to generalize about people. There you may not only get the factors wrong, but you treat people as known quantities, thus losing what is perhaps the greatest joy in life: being surprised by what people become. Twenty years ago, I worked with a brash, cocky and undeniably brilliant software engineer. I’ve watched him become a serial entrepreneur, CEO and now a philanthropist of the sleeves-rolled-up variety. Predictions about people that generalize based on their behavior here or there are not only risky, they can deny people the possibilities to become more than they are ... as we almost all do.

Being surprised by what someone becomes is a type of mistake. But, so long as it doesn’t make you stand in their way, it’s an example of a mistake we’re all bound to make (because we humans are so surprising), and that has the consequence of bringing joy in its wake.

Then there are the good mistakes. These include the ones we make because we’re trying something new. Research itself involves running down lots of blind alleys. The pace of wrongness has increased exponentially thanks to the Internet, which means the pace of rightness has also picked up briskly.

Also high on the list of good mistakes: assuming good intentions when there is in fact doubt, and assuming the possibility of change when there is little or no real possibility of it. Both of these mistakes are required for hope, and hope is required for action.

My favorite mistakes are the ones that not only teach us something, but that remind us just how miserably foolish and inadequate we are. These work best if performed in public and are more embarrassing than hurtful. I once was showing off my totally miserable command of Spanish by saying something lofty about God, except I kept calling him "Diego" instead of "Dios," pretty much equivalent to repeatedly referring to the creator as "Pete." It matters, of course, that this mistake had no bad consequences, except perhaps for hurting "Pete’s" feelings. Investing all your company’s 401K entirely in that glamorous Enron stock wouldn’t be half as amusing.

Not every mistake is a learning experience. Not every mistake is one we’ll look back on and laugh. Some are disasters that ruin lives. But if you have a choice—and, unfortunately, generally we don’t—try to make your mistakes good ones.