How to Deal With Regret

Learning From Your Regrets

What’s the difference between a mistake and a regret?

I would argue a regret is simply a mistake that we haven’t learned the proper lesson from yet. Often, we regret because we did something so cataclysmic that it’s difficult to learn the appropriate lesson. But often, we regret not because our actions were so heinous, but simply because we lack the imagination to pull some productive meaning out of them.

Learning from our mistakes is such a fundamental component of not being a shitty person, that I don’t even know where to start. But let’s put it this way: if you do something wrong, but you learn from it, then suddenly that mistake becomes helpful.⁵ Developing a habit of learning from our failures is like this magical elixir that transmutes all of the embarrassing cringey shit of our lives into making us better. And while that might not remove all our negative feelings, it certainly prevents things from getting worse.

Regret serves an adaptive purpose. It can help us or hurt us. When we feel regret, we can either wallow in our past mistakes or we can take steps to ensure we don’t repeat our past mistakes.

Maybe you fucked up a relationship years ago and it still stings when you think about it. Instead of beating yourself up, use it to identify the issues underlying your fuck ups:

• Maybe you were a little too absent.
• Maybe you were a little too selfish.
• Maybe you were a shitty communicator.
• Maybe your love comes with impossible conditions.

The way you move on isn’t by rationalizing all of these uncomfortable feelings away—by blaming yourself or the world for your misfortune—it’s by accepting your mistakes, by understanding what happened and integrating that experience into your understanding of who you are today.

This forces you to take responsibility for your fuck ups, and if you truly take responsibility for your fuck ups, you don’t repeat them—that is what regret is for.

But, of course, this is much easier said than done.

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Questioning Your Narratives

In my book, Everything is F*cked: A Book About Hope, I explained that our minds are always constructing narratives to explain our feelings and experiences. These narratives are rarely accurate and often unhelpful, yet, we need them because they hold our sense of self in place.

By learning how to question our narratives, we can gain greater perspective on how bad what we did actually was. And if we’re honestly questioning ourselves, we’ll often find that it wasn’t nearly as bad as we thought.⁶

For instance, let’s say Timmy wasted his life savings in a pyramid scheme. Timmy feels awful. His wife hates him. His friends ridicule him. He can’t pay his rent. Everything is falling apart.

In the moment, due to how painful the event is, Timmy constructs a narrative for himself, “I wasted all our money because I’m an idiot and I ruined our lives. If only I could go back and do it over again.”

Timmy now has a regret.

What’s dangerous about narratives like this is that they self-perpetuate. Our minds are meaning-making machines⁷, and negative narratives are particularly pernicious.⁸ If Timmy believes he’s a piece of shit and horrible with money, then whenever he has new experiences, he will interpret them through the “I am a piece of shit and terrible with money”⁹ lens. He will also interpret good things that happen to him as simply good luck, and bad things that happen to him as his own fault.

The problem with our narratives is that they are chronically short-term, emotional, and self-centered.^{10, 11} What Timmy’s narrative doesn’t consider is that losing your money can have some subtle long-term benefits.

Aside from learning to never invest in a shady Las Vegas timeshare, his experience will test the commitment of his marriage, and it can alter his own relationship and philosophy with money for the better. It can teach him that he needs far less to live and survive than he had expected.¹² It can root out all of the superficial materialistic values he had been carrying around his whole life and help him replace them with healthier, non-material values. It can stress test his friendships and bring him closer to certain family members who help him out in a time in need. It can give him a useful cautionary tale, teaching others lessons so that they don’t repeat his same mistake.

If he extends the timeline long enough and zooms out on the lens wide enough, Timmy may one day look back and say, “That was the best thing that ever happened to me.” And in fact, most people, if you talk to them, say that their most painful experiences were often their most important experiences.

But to get to that point, you have to get out of your own way. You have to wipe away your own bullshit narratives.

Listening to Our Worst Hits Album, On Repeat

When we experience regret, we are choosing to relive our past. We are replaying our broken narrative over and over again. We are living as though the past is still true, even though it has long stopped explaining the world well for us, and even though the broken narrative continues to hurt us.¹³

The problem is that we identify with these lost opportunities—we take these failures on as our lost identity, the person we should have been but never were. And then we torture ourselves with that idealized image.

Let’s say you’re in a dead-end job. And maybe you’re not the young gunslinger you once were, so you think it’s too late to do something different. You’re too old to go back to school, too far into your career to change paths, and too settled in your life to make changes that will affect others, like your family.

(All of these narratives are probably wrong, by the way.)

So you have constructed this ideal self that reflects who you wanted to be 10, 15, or 20 years ago rather than who you are today. Your ideal self is:

1. Young, because that’s when you’re supposed to go to school;
2. Single and responsibility-free, because that’s when you’re supposed to develop the foundation of your career.

As Shakespeare once said (probably) “How is this fucking stupid? Let me count the ways.”¹⁴ First, and foremost, youth is just this made-up thing you decided was important. You don’t have to think it’s important if you don’t want to.

I used to think I was going to be a musician. Then I dropped out of music school. I don’t sit around thinking, “Oh man, if only I hadn’t dropped out, I could have been a musician—what’s wrong with me?” No, I realized that my desire to be a professional musician was a totally arbitrary ideal in my mind and I could change it.

The second reason this obsession over our idealized self is dumb is that even if you did somehow revitalize your sense of youth, it would probably require deluding yourself in some other harmful way.¹⁵

Meanwhile, with each passing year, you get a little older and take on a few more responsibilities and you grow further and further away from this idealized youthful self. As it becomes less and less attainable in your mind, you feel your idealized self slipping away. And you regret it. You regret it so much—so much time lost, so much time wasted.

But fuck it. Let that narrative die. It’s no longer serving you. And it’s not, nor was it ever, necessarily true.

Let it die.

Instead, choose the right career as the older and wiser version of yourself now that you have an idea of what the hell you actually want. Being older has so many advantages! Use them and move on.

By moving through your regrets and accepting the falsity of your ideal selves, you free yourself to take responsibility for the present.

Regrets and Responsibility

I’ve said before that in order to let go of a relationship, you have to accept that a part of you—the part that was born and only lived when you were with that person—is now dead and gone.

Well, the same goes for regrets. Finding closure for your regrets means letting your lost self die off once and for all. That death is necessary so you can learn what your regret is trying to teach you.

Here’s the irony: at the Cocktail Party of You, the only version of you that can teach you something you don’t already know is the Regrettable You. It’s the one version of yourself that can show you where your narratives have gone wrong, where your understanding of yourself has faltered, where you are refusing to take responsibility for your life and your pain.

We often hold onto our regrets as another way of avoiding responsibility. And confronting our Regrettable Self makes that responsibility unavoidable—we have to face and accept who we really are. And that’s probably going to hurt.

Regret can take us through a whole spectrum of emotional states. One side of the spectrum is the dark lament we feel when we’re reminded of how fucked up and flawed we are. But the other side of regret, the side that makes it all worth it, is the light it shines in. That light guides us to a better understanding of ourselves—and ultimately to a place of acceptance of how fucked up and flawed we are.

In the end, the slow burn of regret that carries on for years is really just a death by a thousand tiny cuts. So let your regrets turn into a raging wildfire that kills everything in its path.

You can sow the seeds for something better in the ashes.