Facing Our Biggest Regrets & How to Finally Let Go

What’s your biggest regret in life?

In this video, I’m asking you and reveal whether I have any regrets. You may just be surprised by my answer . . .

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Matthew :

So what is regret, but this story we keep telling ourselves that we are the person who has done this to us. When in fact, you may as well say that a stranger in the street did this to us because since then so many iterations of us have come along.

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Matthew :

Steve, we’re talking about dwelling on our mistakes. I would say to anyone out there, can you hold something to mind right now that you have as a regret? It’s very easy for regret to make us beat ourselves up and create a genuine sense of self-loathing to the point where it’s truly difficult to connect with ourselves in a positive way. And regret can also make us very resentful and angry towards the world. I can easily bring to mind people that I’m aware of in my life who were in a relationship for many years and got to the point where they realized that they had to get out of it. But then looked back on the years where they’d known something was deeply wrong, years where they knew that they had stayed with the wrong person and are now finding themselves oscillating between anger towards that person or towards the opposite sex in general and anger towards themselves for allowing it to happen.

So these things can cause a tremendous amount of pain for us in the present. They can cause an immense amount of trauma and they really can stop us from enjoying our lives in the present day. So I wanted to talk about this today and get into it, not necessarily as a specific topic about our dating lives. Although many of our regrets may intersect with our love lives, but as a general theme that I know will be affecting a lot of listeners out there of this podcast. Steve, what are your thoughts on regret as a concept?

Stephen :

Well, let me just turn this around one moment. Does Matthew have regrets?

Matthew :

Yes. Yes. Steve, did you know that we have a brand new spanking Virtual Retreat coming up? I’d said spanking. There won’t be any spanking. I meant to say brand spanking new, not brand new spanking.

Stephen :

Forget it then.

Matthew :

That was your one stipulation. Well, there won’t be spanking, but there will be a lot of really wonderful things on this Retreat. It’s a Virtual Retreat for those of you that don’t know. And you could do it from anywhere in the world. It’s three days of immersive coaching. And we have over a thousand people who join from all over the world to really discover how wonderful their life can be if they have the right tools. And for this month only, that is the month of November, so it’s almost over, there is an early bird offer for the Virtual Retreat, which means this is the cheapest tickets are going to be between now and the event.

So if you who know you want to come to this, do not delay. They’re only going to get more expensive. This is the best deal that you’re going to get. And it’s only available between now and the end of the month. This month, November go to MHVirtualRetreat.com to get your early bird special. Ticket while they’re still available. And now onto the episode.

The quick answer is yes. And I have in my life, if I added up the amount of time that I have spent beating myself up for certain things that I have done. And in my case, they fall into both categories. I have regrets that fall into the category of, I remember a very specific moment in my life where I was met with a fork in the road where I could have gone one way or the other and I wish that I had gone the other way.

And I can also look at regrets I have around things that I did for a long time that have had an effect on my life. There is a paradox to my regrets and I suppose to regrets in general. I’m sure I’ve quoted this on the podcast before, but Anne Lamott said in her book, Almost Everything I know, I think it’s called, but she says, “All truth is paradox.” And it can be true, it certainly is true for me that I both have regrets that I would be tempted if I were capable of doing so, I would be tempted to go back and do something differently, but I would also in truth, be too afraid to change it.

Stephen : Yeah.

Matthew :

Because I would be too afraid of losing all the good that has come from those moments in my life. So there is this paradox that I both have regrets, but also don’t think that I would change those things if I could, because I’d be too afraid that the life that I love today and the things that I love in my life today would be adversely affected or wouldn’t even exist if I did change one of them.

Stephen :

Well, this is where it gets sort of existential because some things, there’s a cool Mac McCarthy quote that says, “You never know what worse luck your bad luck has saved you from.” And there are certain things that you might regard as bad things befallen you, bad decisions, things where you could’ve made a more optimum decision. Say you chose somewhere different to go to school or you chose a different partner. When you were 21, you chose a different girlfriend and you go, man, if I knew, I would’ve never dated person, but you don’t know what that turned you into today, dating that person. You don’t know what forks in the road that changed. It may have saved you from some other kind of catastrophe.

So it is a little difficult to play as Niall Ferguson calls it, “counterfactual history” with your own life. There might be obvious ones, right? Maybe some people regret they didn’t quit smoking earlier. It’s hard to say there’s going to be an upside to having been smoking for an extra 20 years. So there might be obvious ones where you go, ah, I should have done that sooner. Or people go, why didn’t I start working out when I was 20? This is great. I love doing this. I should have enjoyed it then or I would’ve enjoyed it.

Matthew :

In the smoking example and in any example like that, it’s always so easy to say, oh God, if I knew then what I know now I wouldn’t have smoked or I wouldn’t have dated that person. I wouldn’t have married that person. I would’ve changed. And you go, yeah, but you weren’t ready. That wasn’t who you were then. You weren’t ready. If you were ready to hear what you’re hearing now and acting on now, you would have done something different. And, but you can’t play that game because you weren’t that person. So it would literally, you would be reinventing the universe. If you really do that thought experiment of trying to go back to another time in your life, you don’t even truly know that person anymore.

Stephen :

Yeah.

Matthew :

You only know your memory of that person because over time you’ve changed. You’ve evolved.

Stephen :

And like you say, sometimes it’ll hit you if you go back and see an email you wrote when you were 18 and you’ll be like, what cringey idiot wrote this?

Matthew :

Yeah. You think who was that?

Stephen :

You won’t even recognize it. And you’ll be like, what is this cringey crap I’m writing?

Matthew :

Try reading an old journal. If you have ever kept a journal, try reading an old journal. And some of those things, you laugh because you’re like that’s so funny. I thought that. I did that. We shift. Our memories shift, our memories of our memories shift, our personality shifts. For all intents and purposes we are no longer the same person that we were. And so when we regret something, all we’re really doing is holding onto a story, a memory of something we wished we’d done differently, but was done by a person we no longer are. So what is regret but this story we keep telling ourselves that we are the person who has done this to us. When in fact you may as well say that a stranger in the street did this to us because since then so many iterations of us have come along.

And that’s why when I say regret not only kills our happiness but blinds us to our potential, I sincerely mean that we have no concept of just how much we’re capable of today. We have no concept of what is possible for us of what we can do. I went to Poland with Wim Hof and a group of 10 people for an ice retreat, where I was jumping off of cliffs into frozen lakes, doing 10-minute ice baths, climbing up a mountain in nothing but my shorts in the snow for hours on end. I would’ve thought that I would get hypothermia and die previously in my life if I attempted that. And I did that, and that was something that I’d never imagined I could possibly do. I was someone that, you know me Steve, we would go skiing when we were teenagers and my hands would freeze. And that was underneath two sets of gloves.

Stephen :

You were a right little shivering mini in your big onesie, scared of the cold. Couldn’t hack it on the chair lift. And I’m saying that in the nicest way possible.

Matthew :

No. Yeah, no. I appreciate you handling that delicately. No, I was. Well, mum used to have, is it Raynaud’s? Where you have bad circulation. And I seem to have inherited that from her. My fingers would go yellow in the cold. And then I-

Stephen :

Oh, now you make me sound like a jerk, because you have an actual condition. So don’t do that.

Matthew :

And that is chess. But it was something that I never would’ve thought I could do. And then I went and did this thing and it’s completely, here’s the thing. The literal thing is, oh, it changed my relationship with the cold and what I thought I could do in the cold. But it did so much more than that. What it did is it made me realize what else in my life am I capable of that I’ve been telling myself I can’t do? And I would say to everyone out there listening right now, if you’re listening to this in your car, on the train, wherever you listen to this, in your house, think right now, have you ever had a moment where you did something that previously you thought you couldn’t do or you thought you wouldn’t enjoy and it made you realize, oh my God, just the logic of this means that there must be so many other things in my life that I can do. The world just got so much bigger because there’s all these things I told myself I couldn’t do and that was a lie.

And it was based on this idea that I had of myself, which is all wrapped up in our regrets and our self-loathing and what I’ve done in the past. This idea of what I’m capable of, this idea of what my limitations are, that is only based on looking in the rearview mirror. It’s not based on the future. This isn’t some, I really want people to understand this, this isn’t some motivational kind of rant I’m going on. I’m saying that the sheer logic checks out. That what we know ourselves to be capable of today is only based on what we’ve done before. It is not based on what’s possible in the future, on what we haven’t done yet. And if we want to do more, then it starts by saying like, it’s almost like here’s a formula that we can all use. Okay. I have regrets. Wonderful. As David Whyte, the British poet said, “If you don’t have any regrets, where have you been?” The art when someone says no regrets. No. Regret nothing. Where have you been?

Stephen :

Yeah. In Little Miss Sunshine, Steve Carell says, Proust said about suffering. It’s like, that’s where he learned everything.

Matthew :

Right.

Stephen :

All that suffering, that’s where he learned all the richness, all the stuff of life was in that.

Matthew :

And David Whyte mentions, if you bullied someone at school and you regret it, that regret changes the way you treat people for the rest of your life. Without the regret, where’s the impetus for change? Where does the fuel come from? When you regret something, it gives you an opportunity to change. So if we take our regrets from the past and we say, okay, the first part of my formula is to use this regret as fuel. What is it I want to do now? What is it I want to do differently? And if you’re telling yourself, oh, but I don’t have much time left or I’ve already wasted so much time. There’s not that much left on the clock. Well, guess what? You’re still here, which means you can still suffer from making the wrong decisions. So if all you want is to avoid suffering, it still makes sense to do things differently. Christopher Hitchens said, “Choose your regrets in life.” Choose your regrets. See we’re all going to have them.

Stephen : Yeah.

Matthew :

Choose your regrets. Now, are you going to live to regret this moment where you found something out and then still ignored it and you still had all this time left on the clock where you could’ve made a shift, where you could’ve done something different. You could live to regret spending more years beating yourself up instead of more years living or making an impact. But we use that regret to go out and do something. And I believe that even though change is a slow process, we wildly overestimate how much time it’ll take to feel better. I’ll repeat that. Change is a slow process. Getting different results in our life can be a slow process. Whether it’s the path to building financial independence and freedom, whether it’s the path to building a great relationship, whether it’s the path to having a great body, whether it’s the path to having strong friendships, whether it’s the path to just being a better person.

These things don’t happen overnight. We know that because we know how hard it is to change our habit. Changing our habit is a difficult thing. We have our reflexes, we have our wiring and it’s about unwiring and rewiring. And that takes time. But feeling better doesn’t take nearly as much time as we think it will. I am always surprised when I’m feeling terribly low, or when I’m feeling behind, or when I feel overwhelmed and I am telling myself that I’m going to have to move a mountain in order to get out of this situation. Part of that has some truth to it. In order to fundamentally change the situation that I’m overwhelmed by, usually it is going to mean a lot of work over time. The part that I’m miscalculating is how quickly I can feel better. It’s like writing a book. If I feel overwhelmed by the prospect of writing a book, the feeling that writing a book is going to require a ton of hours is appropriate. It will. What I’m underestimating is how good I’ll feel just by writing for one hour.

Stephen :

Absolutely. 100% agree.

Matthew :

Because you write for one hour and you get this immediate feeling of empowerment and satisfaction in your day. And even a kind of, you know it Steve, that writing euphoria you get after you’ve done a writing session. Just the mere act of having written gives you a kind of euphoria that is detached from whether you may have only got half a percent closer to finishing the thing, but the euphoria is actually attached to more so to just having been the person you wanted to be in that hour than it’s attached to the progress you made.

Stephen :

Oh, for sure. And I think people get way too bogged down in the, oh, I made these mistakes earlier. Way too bogged down and overestimate the cost of that. And they underestimate everything they can do now and the possibility now, the next month ahead, the next year ahead, 10 years ahead. There’s so much you can do to change how you feel that there’s so little value in being bogged down in that mistake.

Matthew :

And decoupling the results that you’ll get in your life from changing something now from the feeling you can have now by doing something different.

Stephen :

Yeah.

Matthew :

The results may be slow, but the feeling doesn’t have to be. The reward of doing something different and the pride that that creates, the feeling of I’m finally living or I’m finally being the courageous person I wanted to be, or I’m finally having difficult conversations that I’ve been putting off forever. And the pride that gives us and it’s not, oh, I’m finally proud of the person I hated before. No, it’s you’re not the person you were before. Stop associating with that person. You’re a new person.

Stephen :

Yeah.

Matthew :

And you get to be proud of this brand new person today. You get to be that. It doesn’t mean that that new person today is going to have wildly different circumstances from the person who woke up yesterday. Because the circumstances take time to change in most situations. But you can have a completely different feeling about the person who woke up today just by doing something different. And when you get a different feeling that starts to breed confidence. Because when you feel like man, I just went for a run this morning and my weight didn’t change, but I’m really proud of myself. I went for that run. I did a hard thing. That gives us confidence. You start thinking, what else could I do today? I get the same feeling when I tidy the house. It’s a small thing, but I tidy a room in the house and I suddenly go, what else could I do right now? Or when I complete a piece of work, or even make progress for an hour, or do something difficult, I think what else do I want to take on today?

You get momentum. The feeling creates momentum and momentum creates consistency and consistency over time creates results. And so that is the formula. Let your regret have you make a different decision right now. I want something to be different. I want to have a different feeling about the person I am today. Well, what does that mean I have to do today? Go do that thing. Even if you don’t get results, get the feeling. When you get the feeling, you start to get that confidence. And when you get that confidence, you get momentum. Momentum is consistency. Consistency is results. You’re alive today. So don’t let your regret blind you to how happy you can be right now by being the person you want to be. And that also starts by changing the meaning for ourselves of the word regret. When I say I regret things and people may have heard me say that earlier in this episode and thought, man, that’s really sad that Matt wishes he could go back and do things differently.

I want to make it very clear to people. When I say I regret something, that’s not imbued with all of this emotion and the poison that we associate with regret when we just keep drinking this poison of self-hatred. It’s not that. It’s really me saying I wouldn’t do that today. I wouldn’t do that today, but I don’t hate me today for something that a past me did. I wake up today and get to be who I want to be. And instead of seeing it all as wasted time and oh, look at all that’s been lost, I can A, look at what’s been gained through the insight and also acknowledge that I literally wouldn’t have that insight without that regret. So to wish to not have the regret is to also rid yourself of the insight.

But also to realize that if I just take on the attitude that I am a brand new person today, I don’t actually think in this timeline of, let’s say you were 70 years old and you were going to die at 80. And you only had 10 years left and you’d been doing something your entire life and you looked at the calculation of your life and said, this is so sad. I’ve missed out on 50 years of a certain thing because of what I’ve done. And I only have 10 years left.

I want to offer a different perspective. What if the life of that 70-year-old began today? What if instead of thinking about yourself as someone who’s been alive for 70 years that’s going to be alive for 80, what if instead, you said I’m a person who was born today who has 10 years to live. You’d have a completely different… But you inherited all of the insights of someone who’s been alive for 70 years. So I am being born today and I have 10 years to live as hard as I want, as much as I want, as richly as I want, as enjoyably as I want. I have 10 years to live. Not I’ve got 10 years to live, but I have 10 years to live as much as I want. This is a gift.

I woke up today and I have 10 years to live, but I also inherit the insights of this other dude who’s been around for 70 years. What do I want to do with these 10 years? Now you don’t think of it as I’ve got 10 years left. You think of it as I have 10 years starting from scratch now to go hard and live the way that I want to live. That to me is exciting.

Stephen :

Yeah.

Matthew :

And that’s the game we all get to play with ourselves starting today. Love the person who got you the insight and make the person proud who started today.

Stephen :

Yeah. You might like be an alien who drops in this body and you’d be like, huh? This person in some toxic, crappy relationship. They’ve wasted 10 years.

Matthew :

Yeah.

Stephen :

I’m going to go and have a conversation now and end that shit.

Matthew :

Yeah.

Stephen :

And let’s do something else.

Matthew :

That’s exactly it.

Stephen :

And it’s like, huh, we have all this to play with now. I can go and call that person, make that connection, have that adventure. It’s like my slate to paint on, instead of like carrying everything from the past with you all the time. And I remember Charlie Munger, who I see as sort of a bit of a spiritual mentor, great investor sort of wise man, 97. And he just talked about in this one meeting about the cost of bitterness and the cost of carrying, carrying any sense of bitterness of past decisions, past things someone did. He said, it’s just, it’s so, so, so fundamental to not carry bitterness with you. And it was sort of one cornerstone thing he said to drum into anyone is don’t carry bitterness from the past and past decisions, past problems with you now, if you want to be fruitful, enjoy your life, do things now.

Matthew :

That’s beautiful.

Stephen :

Really important to let go of that.

Matthew :

Guys, I hope you enjoyed that video. I hope that you are seeing with these videos we’re making that there’s a bigger conversation happening here, that it’s not just about dating advice. I love being involved in the deeper issues that affect our lives. I really believe that the only way to truly have a great love life is to love life. And the only way to love life is to begin by loving ourselves. I have coming up in March 2022, my next Virtual Retreat, where for three days of coaching immersion, I work with people to fall in love with their life and fall back in love with themselves, or maybe fall in love with themselves for the first time. It is a mind-blowing life-changing experience.

And for the month of November, we have an early bird offer. That means it’s a deep discount. If you’re coming to the Virtual Retreat in March, this is the best price you’ll get between now and the event. All you need to do to get access to that early bird offer while it’s available in November is go to MHVirtualRetreat.com. And that is not available for long now. So while it’s on your mind, if you know you’re going to come, go to that link now and grab your spot, MHVirtualRetreat.com. And I’ll see you in the next video.

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7 Replies to “Facing Our Biggest Regrets & How to Finally Let Go”

  1. Your timing with this post is perfect. Tomorrow is my 66th birthday. I’m 6 months out of a dysfunctional relationship, doing well in my recovery, dealing with the generational legacy of trauma that life handed me…..and feeling proud of my recovery progress so far.
    I had decided on my own to approach this first birthday of my new life as a re-birth day and I’m doing it all so the next 20 years that I have can be amazing. Thanks for putting it all into words for me…..spot on!

  2. Yes, regrets make us love ourselves more, how to grow up and redirect self awareness.
    And as you said, ‘not blame ourselves’, yes over respect with estimated will be neglected.

    Everything gonna be great for us.
    God bless.

  3. Your timing of this video was perfect. I have been dealing with a past regret and now know how to move forward. Love your insight.

  4. I have a big regretted entire my life,I met the wrong person and I thought he loves me. We was a long distance relationship we do video I thought his real but it turn into a nightmare because I found out his a scammer. I sent money and the name he was gave is a negerian guy. I was so frustrated because I’m a victim of scammer.

    What made me happy right now is I learned a lot and problems turned into blessings. I’m a brand new person and more aware this time.

  5. I’ve done something in the past 2 months that i was never ready to do. I have been battling with it lately, watching this video has really taught me how to look at the situation differently. Everything that has happened has shaped me to be the better person that I am today, i wasn’t aware of the changes i have now because of holding on to my past decisions. I can now say i have learned and i am a new person that i wasn’t yesterday. Therefore that was my way to growth. I don’t see myself holding to that piece of memery,that’s happened and i must be grateful because i wqs able to shift from who i was yesterday. I qm proud to say i am a new person qnd should embark on a new journey.

  6. Thank you so much for this video/ article, I’ve been living in regrets for 4months, most times it becomes so depressing and suicidal, I’ve always told myself to get myself a therapist as Soon as I get the money.. but thanks for this, I feel better.

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