On making sloppy mistakes

I made a mistake the other day.

Like everyone, I make mistakes all the time—it’s part of being human.

Most of these mistakes are not a big deal. (In fact, I catch many mistakes—though not all of them!—before anyone else does.)

But some mistakes are a big deal. Some mistakes have a lifespan to them. You can’t just fix them and make them go away. They hang out with you.

My recent mistake was of this unfortunate variety, which led me to start thinking about how there are different categories of mistakes.

There are several ways that people have categorized mistakes, but I like the breakdown from Eduardo Briceño, who sorts mistakes into four categories:

• Stretch mistakes. We make stretch mistakes when we are trying something new. When I flub a note while I’m learning a new song on guitar, that’s a stretch mistake. These are good mistakes, because without without them, we cannot learn and grow.
• A-ha moment mistakes. You could categorize a-ha moment mistakes as a variety of stretch mistake. These mistakes involve a collision between “how the world works” and “how I think the world works.” These mistakes force us to adjust our mental models. When I bake according to sea level instructions at high altitude, there’s nearly always an a-ha moment mistake lurking in the final product.
• Sloppy mistakes. We make sloppy mistakes when we’re not paying attention. We know what to do and how to do it, but—somewhere in the doing—we fail. “Fail” sounds harsh. I don’t want to imply that sloppy mistakes imply total failure. That’s not usually the case. More often, sloppy mistakes are a messy partial failure. Sloppy mistakes are typos rather than missing the deadline. Missing the deadline because you misread the date falls into the last category.
• High-stakes mistakes. We avoid these mistakes at all costs. High-stakes mistakes have consequences. These mistakes are catastrophic—meant less in the natural disaster sense and more in that of Greek drama, where a catastrophe represents a sudden end or overturning of our expectations. There’s no Ctrl+Z for high-stakes mistakes. You make one (no need to make multiple, usually) and it’s over.

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High-stakes mistakes are interesting for a few reasons.

Firstly, this category of mistake is inclusive of the other categories. A stretch mistake, a-ha moment mistake, or sloppy mistake can also be a high-stakes mistake.

Briceño mentions the Olympics (or any high level competition), and that’s an apt example: you don’t make mistakes in the Olympics, period. You have reached the summit of achievement in your sport. Stretch mistakes should happen in your training. (Olympians shouldn’t be trying out untested moves in their Olympic routines.) The same goes for a-ha moment mistakes. (Olympians should carry a highly-developed mental model for their sport.) And, obviously, sloppy mistakes have no place in the Olympics.

Any of the above mistakes, made in Olympic competition, is a high-stakes mistake.

But what does a high-stakes mistake look like for the rest of us?

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The stakes are pretty low in my life.

Olympians must execute highly complex and technical movements, honed over years of training, on an international stage, where failure carries what I’ll call an “obituary risk.”

Will the mistake be mentioned in your obituary?

Bill Buckner, an outfielder and first baseman whose long, solid career was overshadowed by a crushing error that cost the Boston Red Sox Game 6 of the 1986 World Series against the Mets, who went on the win the championship in seven, died on Monday. He was 69.

It’s baseball, not the Olympics, but you get my point. The New York Times obituary for Buckner leads with his mistake, one of the most infamous errors in sports history—a high-stakes mistake if there ever was one.

In my day-to-day life, there really aren’t opportunities to make mistakes of that magnitude.

The challenge for me—and for most of us—is that we have to define the stakes for ourselves. We must define catastrophe.

So what does catastrophe look like for you?