The Importance of Saying “Oops”

I just finished reading a history of Enron’s downfall, The Smartest Guys in the Room, which hereby wins my award for “Least Appropriate Book Title.”

An unsurprising feature of Enron’s slow rot and abrupt collapse was that the executive players never admitted to having made a large mistake. When catastrophe #247 grew to such an extent that it required an actual policy change, they would say, “Too bad that didn’t work out—it was such a good idea—how are we going to hide the problem on our balance sheet?” As opposed to, “It now seems obvious in retrospect that it was a mistake from the beginning.” As opposed to, “I’ve been stupid.” There was never a watershed moment, a moment of humbling realization, of acknowledging a fundamental problem. After the bankruptcy, Jeff Skilling, the former COO and brief CEO of Enron, declined his own lawyers’ advice to take the Fifth Amendment; he testified before Congress that Enron had been a great company.

Not every change is an improvement, but every improvement is necessarily a change. If we only admit small local errors, we will only make small local changes. The motivation for a big change comes from acknowledging a big mistake.

As a child I was raised on equal parts science and science fiction, and from Heinlein to Feynman I learned the tropes of Traditional Rationality: theories must be bold and expose themselves to falsification; be willing to commit the heroic sacrifice of giving up your own ideas when confronted with contrary evidence; play nice in your arguments; try not to deceive yourself; and other fuzzy verbalisms.

A traditional rationalist upbringing tries to produce arguers who will concede to contrary evidence eventually—there should be some mountain of evidence sufficient to move you. This is not trivial; it distinguishes science from religion. But there is less focus on speed, on giving up the fight as quickly as possible, integrating evidence efficiently so that it only takes a minimum of contrary evidence to destroy your cherished belief.

I was raised in Traditional Rationality, and thought myself quite the rationalist. I switched to Bayescraft (Laplace /​ Jaynes /​ Tversky /​ Kahneman) in the aftermath of . . . well, it’s a long story. Roughly, I switched because I realized that Traditional Rationality’s fuzzy verbal tropes had been insufficient to prevent me from making a large mistake.

After I had finally and fully admitted my mistake, I looked back upon the path that had led me to my Awful Realization. And I saw that I had made a series of small concessions, minimal concessions, grudgingly conceding each millimeter of ground, realizing as little as possible of my mistake on each occasion, admitting failure only in small tolerable nibbles. I could have moved so much faster, I realized, if I had simply screamed “OOPS!”

And I thought: I must raise the level of my game.

There is a powerful advantage to admitting you have made a large mistake. It’s painful. It can also change your whole life.

It is important to have the watershed moment, the moment of humbling realization. To acknowledge a fundamental problem, not divide it into palatable bite-size mistakes.

Do not indulge in drama and become proud of admitting errors. It is surely superior to get it right the first time. But if you do make an error, better by far to see it all at once. Even hedonically, it is better to take one large loss than many small ones. The alternative is stretching out the battle with yourself over years. The alternative is Enron.

Since then I have watched others making their own series of minimal concessions, grudgingly conceding each millimeter of ground; never confessing a global mistake where a local one will do; always learning as little as possible from each error. What they could fix in one fell swoop voluntarily, they transform into tiny local patches they must be argued into. Never do they say, after confessing one mistake, I’ve been a fool. They do their best to minimize their embarrassment by saying I was right in principle, or It could have worked, or I still want to embrace the true essence of whatever-I’m-attached-to. Defending their pride in this passing moment, they ensure they will again make the same mistake, and again need to defend their pride.

Better to swallow the entire bitter pill in one terrible gulp.