Staring into regrets

[Content note: This post is about staring into your regrets. It's always a little painful, but if you think it would be actively harmful for you, then you may want to skip this post.]

Do you know those shameful memories? The ones that make you cringe every time you think of them, the ones that your stomach drops to remember, the ones that fill you with regret?

Today, going along with the theme of my last few posts, we're going to turn regrets into a source of power.

Before I tell you how and why I enjoy the feeling of staring into my most painful memories, I'd like you to take a moment to figure out your own method for doing the same. Can you find a way to steer towards those aversive memories in a way that makes you stronger? Can you find a way to enjoy it?

SMBC #2347 Source: SMBC, by Zach Weiner

I'm going to start with an example given by Ben Hoffman, a friend of mine. He describes, on his blog, a childhood misconception of his:

Back in the 5th or 6th grade my science teacher was telling the class about sharks. She said something about how sharks are an example of a perfected product of evolution, and that some sharks have been around basically unchanged for thousands of years. I'm now quite sure that she meant, some species of shark. But at the time, I thought:

If she meant “species,” surely she would have said “species.” Therefore, if she didn’t, by modus tollens, she must mean that some individual sharks have been around for thousands of years. Unchanging. Undying. All-consuming.

This led him to some embarrassment in college, when he boldly confronted a teacher who said that all animals age and die.

Despite the embarrassment, Ben survived to tell the tale, and nowadays he tells it in jest. But it's easy to imagine the mortification that Ben might have felt, revealing ignorance to a class full of peers. Social gaffes before peers are not always a laughing matter: people have been traumatized by less.

We can imagine what the moment of mortification may have felt like: The awkward silence, the immediate cloistered feeling of being estranged, the sensation of a stomach dropping, a desperate desire to take the words back. The stares and giggles of classmates. A teacher confused, or perhaps derisive.

Up the stakes a bit, by making the gaffe occur in front of a crush, or by having the gaffe result in a missed opportunity, and a memory like this could quickly become a Regret. (In fact, even without raising the stakes, I'm betting that this memory was at least somewhat painful to remember before Ben got some distance and learned how to use it in jest.)

Let's pretend, for a moment, that this had become a full on Regret for Ben. Pretend he made this social gaffe in front of a crush, and spent two whole days running over the scenario in his mind wishing that, at that crucial juncture, he had just kept his mouth closed. Pretend that, two years later, he still occasionally remembered that memory (whenever he heard a passing reference to sharks), and it ruined his day as in the comic above.

What, then, could Ben do? How could this painful regret be turned into a useful tool?


My answer, as usual, comes in two parts: (1) it's possible to mine old regrets for useful tools; and (2) it's possible to enjoy the opportunity to do so. So, as usual, I'm going to suggest that you steer towards the aversive memories. (Respecting obvious boundaries, of course — please don't do anything psychologically dangerous on my account.)

First things first. Let's talk about how those old regrets are useful.

I don't know about you, but when I make a big mistake, my mind tends to fixate upon the moment where everything went horribly wrong. Over and over, the crucial moment runs through my head. Running on automatic, my brain keeps wishing I had done something different, it keeps fantasizing over how much pain could have been avoided if only I had done something else.

But the simple fact of the matter is, I couldn't have done something else: that past version of me, thinking as he did, in that precise situation, made that sort of mistake. My mind, reaching back in time and wishing to change the outcome, does little good to consider a version of me that thought the same thoughts, but somehow spontaneously generated a different answer.

Think not of what you could have done differently, think of how you could have thought differently.

What patterns of thought could you have been using, which would have systematically generated a better outcome in situations such as yours? What mental process could have saved you your trouble? Answers to these questions are the tools your regrets can give you.

Consider Ben, who embarrassed himself in front of his class, and pretend again that he made his gaffe in front of a crush. It's easy to imagine his brain in a loop, after class, chastising him, worrying over the moment of choice, replaying it and wishing each time that he had kept his mouth shut.

What could Ben do with this regret? He could look, not for different actions he could have taken (such as keeping his mouth shut) but for different ways he could have thought to avoid the whole mistake entirely.

By what mental process could Ben have avoided his gaffe?

As I see it, there were three different points of failure that led to Ben's embarrassment: the first failure occurred in grade school, when Ben adopted the false belief. The second failure occurred between grade school and college, when Ben failed to reject the false belief. The third failure occurred in college, when Ben spoke the false belief without rejecting it. Dwelling on any specific point of failure (such as by reciting "I wish I had never believed that teacher in the first place!" over and over) is fruitless; in order to become stronger from this regret, Ben would have to identify a different process of thought that would have avoided one of these points of failure.

Consider the first failure. By what process of thought could Ben have avoided adopting the false belief about sharks in the first place? Perhaps this failure stemmed from a lack of skepticism. Perhaps it stemmed from too much trust in authority, or from an underdeveloped ability to parse the intended meaning from a sentence. In these cases, the problem may already be fixed: children tend to gain skepticism, lose respect for authority, and improve their ability to parse meaning as they age. But it's also possible that Ben remembers a specific type of discord that arose when he noticed an ambiguous sentence and sided with the teacher's specific wording instead of his intuition. If this is the case, then Ben could train himself to notice similar notes of discord and pay more attention to them in the future.

Now consider the second point of failure. By what process of thought could Ben have rejected his false belief between grade school and college? The universe undoubtedly presented Ben with lots of subtle opportunities to do so: the movie Jaws had no puns about immortality; popular science articles rarely talk about life extension research that focuses on sharks; friends likely never mentioned immortality during "shark week." However, noticing and using this weak evidence is completely unrealistic. Claiming that Ben should have been able to do this spontaneously (for a belief that is inconsequential in day-to-day life) is absurd at best. I doubt there is a mental process Ben could have implemented in a human brain that would have systematically allowed him to avoid the second failure.

And what of the third failure? By what process could Ben have rejected his false beleif in the moments between the objection coming to mind and reaching his lips? What thought process could have systematically prevented the gaffe? There are simple solutions ("never think you should talk in class") that would work, but would do far more harm than good. More complicated suggestions depend on Ben's specific experience. Was there a note of dissonance, flavored like "I remember this belief being adopted while mentally uncomfortable", that Ben could train himself to pay attention to, next time? Was there a feeling of oldness to the belief, that Ben could hook into, so that next time an old belief pops up he can remember to check whether or not it is stale? If yes, Ben could use that remembered discord to train his mind and grow stronger.

Notice how we can harness that compulsive desire to run over the memory a thousand times and use it to identify solutions that can be adopted in the present to preemptively avoid all future variants of the same mistake.

(Remember, in all things, the goal is not just to solve the problem. The goal is to solve the problem so hard that next time you encounter one of that problem's distant relatives, it's already solved.)

When I pick apart a regret at the mental process level, one of three things tends to happen:

  1. Sometimes, I realize that there was no realistic way to avoid the mistake. It was just part of the normal human experience, and mostly unavoidable given the mental hardware I'm running on. This is more or less the case in Ben's scenario: younger people, by default, are more succeptible to authority and more prone to misinterpretation. Furthermore, it's unrealistic to expect childhood misconceptions to be cleared before they come into contact with reality. It's useful to train yourself to notice when your beliefs are stale, but this is a high-level skill, and one that is difficult to perfect. Gaffes such as these are not errors, but causes for celebration. Indeed, others will probably empathize with you: notice how when Ben tells his shark story, it is funny and it reflects well on him. (Notice, too, how many comedians make a living telling embarrassing stories that ring true to the audience.)
  2. Occasionally, I realize that there was no realistic way to avoid the mistake, because my evaluation was sane given the information I had at the time. For example, imagine that I lost $100 due to some unfortunate event, but that looking back, I see that I had correctly weighed the odds and calculated the risks. This isn't enough alone to eliminate the sinking feeling of loss, but it sure helps, and it takes the sting out of the memory if ever it arises again.
  3. But most of the time, I realize that there were ways I could have forseen the failure; thinking patterns I could have used to avoid the mistake. In this case, I adopt new ways of thinking and acting.

I have found that, once a regret causes a tangible shift in my thinking, the memory defuses and loses its ability to ruin my day. Imagine that Ben spent some time learning how to notice old beliefs and check them for staleness reflexively, enough time that this is now a part of Ben. Now, the next time that the shark memory resurfaces, it contains within it a pointer to a new pattern of thought that Ben can recognize within himself. In my experience, this transforms the aversive memory entirely: where once it came with a stomach-wrenching shame, it now comes with a soft regret for the pain that had to be suffered by an earlier version of me, one who did not have all the abilities that I possess now.


It is telling, I think, that almost everybody views childhood misconceptions as cute, funny, or endearing. Here's a reddit thread on childhood misconceptions — go ahead and read three, and notice how none of these gaffes make you think less of the person who committed the gaffe.

Why is it that we view our early childhood mistakes with fondness, but we view the teenage and adult mistakes with nigh-crippling shame? I think it is in part because we understand that young children are hardly at fault for their misconceptions: their brains are still in training; they can't be expected to correctly parse the meaning out of every ambiguous sentence, they can't be expected to understand every implicit social rule by magic. Children aren't "finished people" yet, they're expected to fumble around a bit.

I have a secret for you: adults aren't finished people yet either.

Being a person is hard. We're implemented in brains, and brains act in strange ways. We never get told all the rules, we're systematically and fundamentally biased, and it's inherently unreasonable to expect us to be able to act as we'd like to be able to act while constrained by human psychology.

The same adults who smile at childhood misconceptions tend to beat themselves up about their old regrets. But beating up on a past version of yourself for not magically having all the right thought-patterns is like beating up on a child for misinterpreting an ambiguous sentence.

It's not that the child has no responsibility. It's not that children are incapable of gaining the right thought-patterns while young. You could have trained me to guard against over-trusting authority long before fifth grade. I could have trained myself to raise a red flag whenever the default interpretation of the teacher's words was very surprising, and I could have done this before I turned eleven. Children aren't silly aliens that can't know better, they're people. They just aren't finished people yet. For any class of misconception, you could have tought me how to systematically avoid it before I turned eleven — it's just completely unrealistic to expect me to have any given defensive thought-pattern by the age of eleven.

But it's similarly unrealistic to expect an adult to have any given defensive thought-pattern! We aren't taught these things in school; we have to learn how to avoid the standard human blunders, and we have to do it the hard way. Just as there's no shame in a child who hasn't got around to learning appropriately defensive thought patterns yet, there's no shame in a human who hasn't got around to learning the right mental processess to avoid one particular mistake.

It's easy, after doing something we regret, to run over the action again and again in our heads. It's easy to visualize, over and over, what would have happened if we hadn't taken that stupid action, if only we had taken some other action instead.

Look not at what else you could have done, but at how else you could have been thinking.

And why stop there? Once you've identified a way you could have been thinking differently to avoid an entire class of mistakes, ask yourself what mental process could have led you to adopting that thought-pattern earlier. Can you adopt that second-level mental process today, and then preemptively adopt thought-patterns that eliminate whole classes of mistakes before they arise? This is the road that leads to the study of rationality.

My advice here is not new: "Make sure you learned your lesson" is Old Wisdom. But too many people hear that old wisdom on the wrong level of generality: they say "Ok, I learned my lesson, and it was 'Chris is a bastard.'" For better results, you have to look at other ways you could have been thinking, you have to look at ways you could have seen the whole debacle coming in advance and cleanly sidestepped the entire problem.

(Warning: I have met a lot of people who, when prompted to learn the general lesson, do it with bitterness and a hint of violence. "Ok", they say, "I learned my lesson, and it was 'never speak up in class ever again, not even when I think I have a legitimate question.'" Avoiding shooting your foot off immediately after making a mistake is an important skill beyond the scope of this post, but in the meantime, be very skeptical of "solutions" laced with despair, bitterness, or helplessness, or which otherwise seem to come at a high cost.)


Being a person is hard, and, spoiler alert, you're never going to be able to avoid mistakes entirely. You are going to need to continually update your patterns of thought, as you learn what works and what doesn't.

Aversive memories, visceral regrets — they aren't land mines cunningly placed to ruin your day, as in the comic at the top of this post. Rather, they're goldmines.

Try as we might, it's often hard to see which thought patterns we need to change in order to become more the people we wish to be. School isn't very good at teaching you how to think about shifting our thought patterns in useful ways. Usually, it takes a whole lot of information to convince us that we've been thinking ineffectively — it usually takes a giant, harrowing mistake to get us to even notice. The clearest signal you ever get that your thougth patterns aren't working out is everything going horribly wrong. Gaining that information is possible, bit it usually hurts. The universe occasionally lets you know when your ways of thinking need a change, but those messages are expensive.

Aversive memories and crushing regrets are messages about how to change your thinking that happened in the past. They're an extremely valuable signal that comes for free, without the usual price of everything going wrong again.

Realizing this is the second part of my advice. You can enjoy the opportunity presented by those regrets; you can even grow to treasure them.

Next time an aversive memory surfaces, it will probably still come with gut-wrenching regret. But it doesn't need to come with that crippling shame.

Instead, it can come with excitement. It's an opportunity, a message from the universe, a message containing information about how to become more the person you wish to be.

Next time this happens, I urge you to find some quite time and some mental space, and pop that memory open. But this time, instead of calibrating your what-ifs to "what if I had done something else?", calibrate them to "what if I could have thought differently?". Look. Learn.

Once you have the answer to that question, once you have adopted a new way of thinking, the memory will be defused, and you will be stronger.