How to Deal With Regret

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Imagine this, you’re at a cocktail party where every person there is a past version of yourself. There’s a kid’s play area with all the little kid versions of yourself. There’s a TV room with your angsty teenage selves watching music videos and playing video games. Then there’s dozens of adult you’s walking around, sipping whatever garbage you drank when you were young and broke, representing each of the distinct periods of your life: the insecure college you, trying to look smarter than you actually are; the frustrated and exhausted you from your first job; the doe-eyed and innocent you from the first time you fell in love.

Now, this might sound like fun. But I think this “Cocktail Party of You” would actually get quite boring. The reason is that for each version of you that you talk to, you know everything that they know, while they only know a fraction of what you know.

That’s not to say it wouldn’t be endearing. You’d hang out with your awkward teenage self and reassure them not to worry, those painful high school years will pass and things will get better. You’d talk to your arrogant 23-year-old self and compassionately bring them down a notch. You’d talk to your smitten self who had just fallen in love for the first time and bask in the feelings of a new, young relationship—while not disclosing that Mr./Ms. Perfect is about to drag your heart across the pavement and smash it a dozen times with a sledgehammer.

But then there’d be that one former self that you’d want to avoid… you know the one. That former self that did that horrible thing you’ve never quite found a way to forgive yourself for. If forced to finally speak to them, you would immediately start chastising them, “How could you?!?! What were you thinking? You are such a moron, my god.”

Then the cocktail party would be ruined. There you are, Present You ripping into Past You, with all of your past selves looking on in horror, feeling both neglected and abandoned. The Cocktail Party of You would collapse into this one pointed, awful moment in your life that would suck away the joy and vibrance of all the others.

The Cocktail Party of You is a kind of metaphor for what happens when you experience regret. You abandon and neglect the celebration of all of the interesting parts of your life to hone in on this one festering mistake that haunts you.

Regret is a form of self-hatred. If who you are today is a culmination of all of the acts that have led up to this moment, then the rejection of some past act is therefore a rejection of some part of you in this moment. Hating some part of yourself in the present messes you up psychologically.1 But hating a part of your past is not much different.2 It harbors shame and resentment. It inculcates self-loathing. And it makes you a real drag at parties, metaphorical and otherwise.

But the way to get over regret is not to ignore it. It’s to push through it. It’s to engage that former self, to talk to them directly and understand why they did what they did. It’s to sympathize with that former self, to care for them, and ultimately, to forgive them.3,4

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.

    No Ragrets Temporary Tattoo
    Live footage of Timmy and his ‘ragret’. Y’know m’sayin?

    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.


    1. Self-hatred carries a lot of negative weight, but there are ways to address it. Self-hatred might focus on self-judgment, isolation, and overidentification while self-compassion focuses on self-kindness, common humanity, and mindfulness. The latter is better.
      Neff, K. D., & Knox, M. C. (2017). Self-Compassion. In V. Zeigler-Hill & T. K. Shackelford (Eds.), Encyclopedia of Personality and Individual Differences (pp. 1–8). Springer International Publishing.
    2. The costs of regret are not nice and it has been linked to depression and anxiety.
    3. Forgiveness has all sorts of mental health benefits. It increases feelings of happiness, decreases feelings of anger and grief, helps alleviate anxiety and depression, and can improve your relationships.
    4. Coyle, C. T., & Enright, R. D. (1997). Forgiveness intervention with postabortion men. Journal of Consulting and Clinical Psychology, 65(6), 1042–1046.
      Freedman, S. R., & Enright, R. D. (1996). Forgiveness as an intervention goal with incest survivors. Journal of Consulting and Clinical Psychology, 64(5), 983–992.
      Tangney, J.P, et al. (1999). The Self-Conscious Emotions: Shame, Guilt, Embarrassment and PrideThe Handbook of Cognition and Emotion, 541-568.
    5. In fact, this is all learning is, getting feedback when something goes wrong and correcting it. Higgins, R., Hartley, P., & Skelton, A. (2002). The Conscientious Consumer: Reconsidering the role of assessment feedback in student learning. Studies in Higher Education, 27(1), 53–64.
    6. Related to this, research has shown that we also tend to overestimate our control over past situations. Thompson, S. C. (1999). Illusions of Control: How We Overestimate Our Personal Influence. Current Directions in Psychological Science, 8(6), 187–190.
    7. Meaning-making is a term used in education, psychology, and counseling, particularly during grief, to refer to our ability to how we make ‘sense’ of life events.
    8. Hit me up people if you need more dope rap lyrics like this sentence. Or a new Dr. Seuss book. Word.
    9. Actually the title of a lesser-known Platinum hit from the Notorious B.I.G.
    10. Your daily reminder that our brains are not to be trusted. Backed by science. Thanks, science…?
    11. You can find a more complete list of cognitive biases on Wikipedia’s Cognitive Biases article.
    12. Stoic philosophers used to make a practice of this, fasting, dressing up in ridiculous rags, and going out in public, asking themselves, “Is this the condition I so feared?”
    13. Roese, N. J., Epstude, K., Fessel, F., Morrison, M., Smallman, R., Summerville, A., Galinsky, A. D., & Segerstrom, S. (2009). Repetitive Regret, Depression, and Anxiety: Findings from a Nationally Representative Survey. Journal of Social and Clinical Psychology, 28(6), 671–688.
    14. If you must know, Shakespeare almost certainly never said this. And the poem to which it alludes to, “How do I love thee? Let me count the ways” is actually a poem written by Elizabeth Barrett Browning, a Victorian poet who influenced Emily Dickinson and Edgar Allan Poe. Don’t say you never learn anything on this site.
    15. See: Peter Pan Syndrome