Mistakes

Mistakes are bad.

Not catastrophically bad, though they can be. But still bad — deviations from the optimal path, resulting in worse outcomes than were available. Modern sensibility has conditioned a near-reflex response against saying this plainly. We prefer the framing that there are no bad mistakes, only those you fail to learn from.

This is partially true and mostly wrong.

The learning part is right. Learning is one of the few things that lets you reach back in time and adjust the value of a past event — not by reducing the cost, but by increasing the benefit. That is a genuine power. But the frame that sanitizes mistakes into pure learning opportunities fails to acknowledge that some mistakes are genuinely bad regardless of what you learn from them. A mistake that costs someone an arm, or a life, is bad even if the lesson is absorbed perfectly. A mistake that could reasonably have been avoided — given information you already had — is bad by that fact alone.

Some learning should precede mistakes, not follow them.

Accepting that mistakes are bad serves a purpose: it gives you sufficient displeasure about them to actually work at avoiding them. You cannot avoid them entirely. But encountering fewer of them is achievable, and worth the effort.

Judging mistakes correctly

The most important thing about evaluating a mistake is also the most counterintuitive: you must judge it from the moment it was made, not from where you stand now.

Hindsight distorts. Looking backwards from a bad outcome, any decision that preceded it looks like a mistake. Looking backwards from a good one, the same decision looks fine. But the soundness of a decision is not determined by what happened next — it is determined by the quality of reasoning at the time, given available information.

A surgeon who operates while impaired on psilocybin mushrooms has made a mistake, even if the patient recovers. A person who places half their net worth on a million-to-one bet has made a mistake, even if it comes off. Drink-driving is not made acceptable by arriving home safely.

In each case, the probability structure of the decision was wrong at the moment it was made. What the future actually delivered is a separate question. Mistakes are the mismanagement of risk, not simply decisions followed by bad outcomes.

To evaluate a past decision honestly, you have to attempt to transport yourself back to the moment and look forward again — discarding what you’ve learned since, holding only what was knowable then. This is harder than it sounds, and we mostly skip it. But it is the only way to extract a true lesson rather than a post-hoc rationalization.

Not all mistakes are equal

Even among genuine mistakes, there are shades. Yudkowsky’s Fallacy of Gray makes this point with characteristic directness:

“Everyone is imperfect.” Mohandas Gandhi was imperfect and Joseph Stalin was imperfect, but they were not the same shade of imperfection. “Everyone is imperfect” is an excellent example of replacing a two-color view with a one-color view. If you say, “No one is perfect, but some people are less imperfect than others,” you may not gain applause; but for those who strive to do better, you have held out hope.

And:

“The Moon is made of green cheese” and “the Sun is made of mostly hydrogen and helium” are both uncertainties, but they are not the same uncertainty.

The retort “you’re not perfect either” — in response to a criticism — is an attempt to collapse all mistakes into a single category and thereby escape scrutiny. Reject it. Mistakes differ qualitatively (in kind) and quantitatively (in severity). Both differences matter. The goal is not perfection, which is unavailable; it is to be less imperfect in the ways that count.

Knowledge changes which mistakes you make

As you acquire more knowledge, you become less susceptible to certain mistakes and more susceptible to others. Progress is non-linear. Nate Soares captures it well: “Optimality is not a feature of the strategy, it is a relationship between the strategy and the playing field.”

What takes you from ignorant to aware is not the same as what takes you from aware to capable. What grows a business from zero to a hundred customers is not the same as what grows it from a hundred to a thousand. The underlying values don’t change; the strategy must. This is as true in reasoning and self-development as it is in business.

The implication: periodically reassess which class of mistakes you are most prone to, not just which individual mistakes you have made. The type of error shifts as your understanding does.

Don’t make peace with your mistakes

There is a trap that people fall into when confronted too long with their own imperfection: they strike a deal with it. Since mistakes are inevitable and correction is hard, they lower their sensitivity to the harm caused by their own errors. Everything becomes a matter of interpretation, or everyone else does it too, or perfection is impossible anyway.

This is the worst version of accepting imperfection. It feels like wisdom and functions like surrender.

Stay sensitive to the damage your mistakes cause — especially to others. Justification is always easier than progress. The homeostatic pressure toward the status quo is strong. But the fact that mistakes are unavoidable does not mean they are welcome, or that all of them are acceptable, or that the ones within reach aren’t worth working to eliminate.

Mistakes will occur. Do not greet them with open arms.