How to Live With Regret

Regrets. I’ve had a few.

But then again, maybe I’ve just kinda teetered at the edge.

There are a few decisions I’ve made that I might not make again if I had another run at them; things that would be all too easy to regret.

I could easily regret not moving to the USA.
I could easily regret not socialising more with classmates at college.
I could easily regret telling Vanessa I loved her.
I could easily regret the debts I racked up.
I could easily regret not getting weirder sooner.

As sucking chest-wounds go, regret is pretty sucky

It’s complex, full of emotion, confusion and blind alleys. It can swallow you if you wallow in it too long. It can deceive you if you follow it blindly. It can drain the colour out of your life if you let it.

Regret is one of life’s most potent pollutants.

I’ve seen it weigh heavy on people and get in the way of creating and sustaining meaningful change, but I wasn’t sure what was really going on behind the scenes, how it sucked people in and what could be done about it.

So like a dead frog in biology class, I opened it up to see what made it tick.  I found 5 types of regret, each of which can be transformed into an extraordinary opportunity…

1. Regret for the things you’ve done

“…We don’t have to be defined by the things we did or didn’t do in our past. Some people allow themselves to be controlled by regret. Maybe it’s a regret, maybe it’s not. It’s merely something that happened. Get over it.”
― Pittacus Lore, I Am Number Four

You’ve just done something that’s royally screwed up. Kaboom.

You now have a choice to make. Either you get over it and keep on going, or you keep comparing what happened to the picture you’d created in your head of how things would go.

And so you stare into the gap between what happened and the picture you had, still wishing that it had gone differently.

It’s entirely pointless, of course. What’s done is done. You know this, so why is it so damn hard to break away?

Once a compelling picture of a specific outcome is in your head, it’s hard to get rid of it. You grow attached to the picture of how you want things to be before an outcome arises, and once it arises you keep looping back to how things should have looked.

The stickiness of the picture is what keeps regret closeby

To unstick that picture, take out and keep the elements that truly matter to you from the specifics of the outcome, environment and circumstances – stuff like how you still want to feel, how you want to look at the world and how you really want to expres yourself. Then throw away the rest.

The parts that have real meaning live beyond any specific outcome. You get to honour those things no matter what happens.

2. Regret for how you’ve treated someone

“It’s unfair.”
As a rule, life is unfair,” I said.
Yeah, but I think I did say some awful things.”
To Dick?”
I pulled the car over to the shoulder of the road and turned off the ignition. “That’s just stupid, that kind of thinking,” I said, nailing her with my eyes. “Instead of regretting what you did, you could have treated him decently from the beginning. You could’ve tried to be fair. But you didn’t. You don’t even have the right to be sorry.”
― Haruki Murakami, Dance Dance Dance

Ever said the wrong thing to someone and wished you hadn’t? Ever made someone feel small and then felt terrible? Ever been mean to someone and later regretted it?

In the heat of the moment you might say the wrong thing out of anger, bitterness, frustration, envy or jealousy. Sometimes those emotions can drive you purposefully towards treating someone badly in order to exact some kind of revenge or in the pursuit of some kind of “fairness”. Both situations can end up hurting someone, and in my book that’s inexcusable. No exceptions.

Regret for how you’ve treated someone stems from the knowledge that you’ve done wrong by them, and there are 2 scenarios here.

1. You’ve actually hurt someone.
Regret about hurting someone is living in the detail of what happened and wishing that it hadn’t happened at all, and all the time you’re stuck in that place it won’t change anything.

So you need to accept that your behaviour lead to someone getting hurt, and own your part of it. The aim is not to label yourself as a bad person, but rather that your behaviour lead to something bad happening. Big difference.

The former sees you judging yourself and beating yourself up for who you are; the latter sees you being honest with yourself about what you did which gives you the chance to apologise, make amends or otherwise move on.

Here’s the strange thing about it though – being regretful about hurting someone means that you give a shit. It shows that you care about them. Rather than wallowing in regret, what’s a better way of demonstrating that?

2. You just think you’ve hurt someone.
Regret about hurting someone when you haven’t actually hurt them is a dangerous fantasy.

This can be a simple misunderstanding that can be cleared up quickly, or it might be coming from a place that posits the case that “I’m not okay“. Thinking you’ve hurt someone when you haven’t is about how you see yourself; casting yourself as the wrong-doer and the other person as the innocent.

If this is a pattern, working on the regret won’t help – there’s work to be done on your thoughts about yourself first.

3. Regret for the things you didn’t do

“Take the stupidest thing you’ve ever done. At least it’s done. It’s over. It’s gone. We can all learn from our mistakes and heal and move on. But it’s harder to learn or heal or move on from something that hasn’t happened; something we don’t know and is therefore indefinable; something which could very easily have been the best thing in our lives, if only we’d taken the plunge, if only we’d held our breath and stood up and done it, if only we’d said yes.”
― Danny Wallace, Yes Man

Holding back from something you want to do, talking yourself out of something that might be amazing or limiting your view of what’s possible will do one of 2 things.

Either you’ll end up regretting the things you haven’t done and the risks you didn’t take, or you’ll mold your thinking to the point where you believe you made all the right calls and where reinforcing your belief about being right becomes more important than being happy.

Both routes are shitty, giving you ample help in becoming sad, small and quietly desperate.

The second route just adds a little self-delusion into the mix

I’m not saying that you should do everything you think of, because that can be equally damaging. What I am saying is that you need to listen. Really listen.

To what matters. To what’s worth the risk. To what might make you come alive.

Then take a breath and act.

4. Regret for the things you didn’t pay attention to

“Over the last couple of years, the photos of me when I was a kid… well, they’ve started to give me a little pang or something – not unhappiness, exactly, but some kind of quiet, deep regret… I keep wanting to apologize to the little guy: “I’m sorry, I’ve let you down. I was the person who was supposed to look after you, but I blew it: I made wrong decisions at bad times, and I turned you into me.”
― Nick Hornby, High Fidelity

The years roll by. Seasons change. You change.

Sometimes it happens so slowly that you don’t even notice. Suddenly it’s 20 years later and you’re half the person you were. Suddenly all the wrong things matter to you. Suddenly you’re not the person you wanted to be.

Regret for the things you didn’t pay attention to is waking up one morning and saying, “What the hell happened to my life?” and not even being able to think of an answer.

Just like the Grand Canyon has been eroded and shaped by the waters passing through it, over time, incremental shifts in thinking and behaviour can drastically alter the landscape of your life.

Don’t let the wrong things get worn

Letting time slowly erode what matters is guaranteed to stockpile regret for your later years. So gently watch what you dismiss and what you embrace. Gently watch the judgment calls you make and the resultant impact on what you believe. Gently watch how much value you’re creating.

5. Regret that isn’t really regret

Ever got stuck on something that’s happened in your life and had it weigh heavy on you? Regret certainly falls into that category, but so do 2 other things that can get confused with regret.

1. Sadness.

“The soft strings of the lute rippled with memories, and the maid’s lilting voice made Mary sigh as she closed her eyes. She fell asleep filled with sadness, but without regret.”
― Margaret George, Mary Queen of Scotland & The Isles: A Novel

Sadness is about loss, regret is about behaviour.

Loss is natural, it’s part of life just like breath and birth and bills. Regret is thinking that’s layered on top of your behaviour that can lead to further behaviour (like wallowing).

Be sad, feel grief, experience loss. Don’t regret it.

2. Shame.

“When I was young, I spent my days and nights trying to impress future generations. I spent them. They’re gone. All because I was deathly afraid of being forgotten. And then came the regret. The worst things of all worst things.”
― Miguel Syjuco, Ilustrado

Brene Brown describes shame as being that feeling that washes over you and makes you feel small, less than, not good enough. Those feelings can be magnetic, drawing your attention to them time and time again and making you wish something had never happened.

But wishing you didn’t feel small or not good enough is about how you see yourself and wanting to escape from your belief that that you’re less than the sum of your parts. It’s about self-worth, belonging and a desire to be enough.

As Brene puts it – you’re already worthy of love and belonging.

You’re already enough.

Ceaseless curiosity always beats away regret

Regret can’t be born or survive when you’re asking the right questions.

Ask questions about what’s fun, resonant, playful, daring, meaningful or even silly, and regret has no place to live.

And should you find yourself with the experience of regret, see it for what it is – the realisation that you didn’t listen to yourself.

Do you have any regrets?

  • G’day Steve,
    I am having a major problem with regret. As a teenager I had an overbearing father and neurotic mother and because of this combination I had absolutely no social life. Then I got in a relationship very young (around 18) with an older woman I thought I loved but who, when looking back, was emotionally abusing me. After 20 years of devoting every waking moment to her and our Children she just said out of the blue one day “I don’t love you anymore” and left. I am well and truly over her leaving but realise I spent my whole life making sure everyone else had a good time without worrying about my own needs. I am 50 have never been on a holiday, got drunk, gone to a party, never let loose, never even been allowed to sleep in a single day. I am now with a woman who loves me dearly but I just cannot get over not having had a youth, I dearly want to have memories of youth, having seen the wonders of the world through a young man’s eyes, gone out with women my own age (or they may not have been interested but it would have been nice to find out) on a basal level I may miss the sex drugs and rock and roll teenage years, but I think I never had a chance to find myself. It hurts

    • Hi Mark. First of all, thanks so much for sharing some of your story. Secondly, you sound like a smart, well-adjusted and loving guy. Please don’t sell yourself short. You may not have had the “conventional” kind of youth that’s often expected, but what if the path you’ve taken has brought you to where you are today, so that you’re in the perfect place to find yourself. What if now, today, was exactly where your life wants you to be in order for you to move forward meaningfully.

      50 is not old these days, you probably know that. Maybe it’s time to put yourself first?

  • Thanks Steve I wish we could talk together some more. I’m going through some things now with all of these things pulling my life apart. It’s hard to stay positive sometimes.

  • I regret not marrying someone who asked for my hand. I somehow think my life would’ve been better had I done it you know went through with it. I’m nothing I ever wanted to be in life. I smoke cigarettes I’m an addict I live with people who don’t care for me I’m alone lonely and regretting the past. I’ve done things I’m not proud of. I miss this person. They’ve married someone else. They have two children they’ve moved on. I can’t seem to let go. It still hurts me to this day. Should I have married them. We shared so much. I can’t believe they’re actually absent gone from my life. It kills me. I hate my life. I hate myself for not marrying them. I’m so stupid.

    • You’re not stupid Ashe. You may have done something you regret, something that people might label “stupid” even, but there’s a huge difference between doing something dumb and being stupid.

      There’s no answer to the “should I?”, “what if?” of course. That’s where the work is for you, learning to let go of those questions while working to build something you can care about now.

  • Sadly,

    There is nothing anyone can do about regret. You just live with it. We can rationalise and keep playing the scenes in our heads. Consciously or unconsciously? In the end of the day it won’t go away, so we accept it and live with it. We made our beds, now we have to lie in it. Decisions weather they were fair/unfair/considerate/inconsiderate/Hurtful/Intentional or unintentional. You can’t run away from it, repress it or ignore it. It’s always going to be there. But would you rather have something there called “Experience”?

    Lets just say, we’ve all done stupid messed up things, i mean small to massive errors but what matters is sometimes boundaries are always pushed and broken. And that’s the way you just have to live life. This whole live life with “No Regrets” thats aloud of BS…..

    Everyone can live how they choose, there are people who have killed someone else. But turned there life around. People who lost everything regardless of there fault or not. “Wives, husbands, girlfriends, boyfriends, children, family, friends, jobs…. The list is endless”. But what have they done? They kept moving on……

    And eventually, they manage to change there life around even better “adapt” to life with this so called “experience”.

    My motto regardless of things if they can be fixed or not.

    -“Mess up, Fess up, Grow up”

    “I made bad decisions because i never knew any better, maybe i did but never listened to myself. What has that taught me? No matter how old i am, I’m growing as a person good/bad and i must always listen to what i feel is right even if i’m wrong….” – Myself

  • Hi Steve,
    Thank you for that passage.
    A life with regret and loss is a hard one to navigate, so any help with directions is much appreciated.
    Thanks again.

  • Very interesting article, I have quite a few regrets and as I was reading this article it made me see a way forward, where as when I’m at a crossroad or have to make a decision, I will ask myself which choice would I regret more. Once again, great article, good food for thought.

    • Yeah, regret’s one of those things that can keep on sucking away at you. Great to hear that it was food for thought for you. Let me know what you do with it.

  • Great article, Steve. I agree with your ideas about regret. The two emotions that are most toxic are regret and guilt.
    When I notice these feelings I intentionally let them go by reminding myself that I did the best I could at the time with the tools I had available. It’s my way of releasing that negativity that used to permeate my days.

    • Being kind to and forgiving of yourself surely has to be one of the most beneficial and hard things to learn in life, don’t you think?

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