This week, we’re covering one of my most-requested topics: regret.

Regret is any thought about how you should have been different in the past and any kind of outcome for which you’re taking responsibility.

But the past is over so why do our brains get so fixated on these actions or events that are no longer under our influence to change? Because we want to feel better now.

Join me today as I break down the three elements of a regret thought pattern and share how you can start feeling better today by changing your thoughts. You don’t have to change what happened in the past. You only need to change how you think about it.

Join me in Boston on March 23, 2019 as I deliver the keynote address at the Boston Glow Career and Empowerment Conference, an amazing conference all about empowering women, LGBT people, and non-binary people… Basically, anybody in any marginalized community to glow up their career, to feel empowered and to approach their career with more intention and skills. Use the code FRIEND to get $35 off the full ticket price. I would love to see you there for this great cause!

What You’ll Learn From this Episode:

  • How I define regret a little differently than the dictionary.
  • Why we spend so much time thinking about our own past.
  • How our brains interpret the past, present, and future.
  • The three elements of a regret thought pattern.
  • Why you need to give your brain useful problems to solve rather than letting it expend useful energy on unsolvable puzzles.
  • That you can choose to think kinder thoughts about yourself no matter what you’ve done.
  • The two poisonous elements of regret.

Listen to the Full Episode:

Featured on the Show:

  • Join me at the Boston Glow Career and Empowerment Conference on March 23, 2019! Use the code FRIEND and get $35 off price of admission here.
  • Follow me on Facebook!
  • Come hang out on Instagram with me!
  • If you want to start building your confidence right away, download a free Confidence Cheat Sheet.

Full Episode Transcript:

Welcome to Unf*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard law school grad, feminist rockstar, and master coach, Kara Loewentheil.

Hello chickens. How are you all? So today, we are going to talk about one of the most requested topics I get, but before I do that, I want to tell you about an opportunity you have to come hear me speak live, which is so exciting.

So I’m going to be giving a keynote address at a conference in Boston, so it’s on March 23rd 2019 because who knows when you’re listening to this, and it’s called the Boston Glow Career and Empowerment Conference. It’s an amazing conference all about empowering women and LGBT people and non-binary people. Basically, anybody in any marginalized community to glow up their career, to feel empowered and to approach their career with more intention and more skills.

So, obviously a topic super close to my heart. It’s a one-day conference and I’m giving the keynote address, so that’s first thing in the morning. And my talk is called The Secret to Authentic Confidence: How to Deprogram Patriarchy from Your Brain and Succeed Beyond Your Wildest Dreams. So it’s obviously going to be amazing.

And I actually have a code you can use to get $35 off the conference registration and just to be clear, I’m not selling these. I’m talking for free. This is – the conference organizers have to sell tickets to pay for putting on the conference. It’s a non-profit I think. So normal tickets I think are $65 but you can $30 or $35 off. I think it’s $35 off so you can get tickets for $30, which is such a good deal. And the code is “FRIEND,” because we’re all friends.

So we’re going to put the link to the conference and the code in the show notes because it’s too complicated for you to remember listening, but all you have to do then is go to or you just go to /podcast and scroll down until you find 68.

And of course, I’m not the only speaker, there are a lot of great workshop sessions happening the rest of the day. So there are sessions about how to negotiate free equal pay, emotional labor in the workplace, entrepreneurship, health, finances, work boundaries, how to promote yourself. So much good stuff. It’s a total steal.

I’ll just be giving that speech in the morning and then there’s lots of other amazing speakers and facilitators teaching the rest of the day. So, coming out this March 23rd in Boston, and I would buy your tickets soon because the conference is capped at I think 200 people and it usually sells out, and you don’t want to regret missing it, which leads me to today’s topic.

And of course, I’m going to teach you how to deal with and avoid regret, so if you don’t come to the conference, you can still apply today’s teachings. You don’t have to regret anything, but I think you should come because it’ll be fun.

Alright, so I get a lot of questions about regret in the past and I think regret is such an interesting concept. I actually did a listener Q&A about this recently, so if a little of this sounds familiar, that’s why; but I want to devote a whole podcast episode to it because it’s such a big problem for so many people and I think in all the excitement of the listener Q&As and all the different topics, sometimes some of the subtleties of a topic get lost.

So, let’s start. You know I love to start with the dictionary. I think I learned this from my judge when I was clerking. He would always start with like, “What does the dictionary say about this word or this phrase?” Let’s define what regret is. Regret is a feeling caused by your thoughts.

And I think regret is what I call kind of a second order feeling, which means it’s not one of the five primary feelings like anger, happiness, sadness, joy, I think disgust is the fifth one. But it’s a variation on one or more of those. It’s sort of a feeling that in our body might be similar to one of the primary feelings but because we know it’s caused by thoughts about a certain topic or kind of topic, we give it its own name.

So, I think we use regret to mean basically the feeling created by thoughts about wishing the past were different. And I think that’s mostly a form of sadness. So it’s like, thoughts about wishing the past were different that creates sadness. And sometimes it might create anxiety. I mean, I think there can be some anxiety around regret, but I think it’s mostly a version of sadness.

And I think regret is almost always thoughts about our own behavior in the past. So this is where I’m splitting from the dictionary a little bit. I think the kind of regret that causes a lot of emotional suffering is about our own past words or deeds, or lack of works or deeds. You feel regret about something you said or did, or something you didn’t say or didn’t do.

I don’t think we really regret that someone else acted a certain way. We can use the word that way, but I don’t think it really causes that same feeling. So I’m really focusing on that. I don’t think you regret that there was a car accident that had nothing to do with you, right? You might feel sad about it, but I just don’t think it’s regret.

But you do regret things you said or thought or did in the past, and you regret any kind of outcome for which you’re taking responsibility. So it’s like you wouldn’t regret a car accident that had nothing to do with you, but you might regret the fight that led somebody to get in the car to drive that had the accident, because you’re taking responsibility for it. You’re like, connecting it to the thing you did and that’s why you regret it.

So you regret how you acted in a love affair, you regret the way you spoke to your sibling before they died, you regret how you showed up to a job from which you were fired, you regret failing to show up for a friend. Fundamentally, I think regret is a thought about how you should have been different in the past.

So it seems obvious to us that humans spend a lot of time thinking about the past and wishing things had happened differently. But it’s actually not obvious why we should do this because the past is totally over. As I’ve said on the podcast before, what happened yesterday is as over as ancient Rome. You can change what happened in your past just as much as you can change who killed Caesar in the Acropolis.

I actually just realized that I don’t know if Caesar was killed in the Acropolis. I think he was killed in the Senate actually. I studied classics at Yale and my professors would be really upset about this. I think he was stabbed in the Senate. Just as much as you can change who killed Caesar, wherever he was killed. Don’t tell my dad that I don’t remember how that went.

But you spend a lot of time thinking about your past and you don’t spend much time thinking about the ladder unless you’re a Roman history buff, in which case you’re going to write me angry emails about how I got that wrong. And I just had to Google, by the way, to make sure that I was right that Caesar was Roman, not Greek, and I didn’t even remember to Google where he was killed.

Anyway, the point is the past it over. It can’t be changed. It’s as good as gone, it’s as over as the pyramids. We don’t spend a lot of time being like, man, I wish I hadn’t put that fifth brick in the pyramid in that way. But we spend so much time thinking about our own past and that’s because I think our brains are not actually good at understanding the difference between past and present and future.

And here’s why; because our experience of all those things, the past, the present, the future, our experience of any of that only exists in our own mind. The past exists only as we are thinking about it. Now, I’m not talking about like, complicated quantum theory, in which all time exists at once. Maybe that’s true. It’s still our way of thinking about it.

But I mean for us humans, the past only exists for us as we’re thinking about it and the present only exists as we’re thinking about it and the future exists as we’re thinking about it. Our whole experience of it is still mediated by our brain even though we are actually in it, as opposed to the past and the present.

We create our whole experience of life with our brain in our minds. So our brains can’t really tell the difference between past and present and future. They all feel equally real because when we think about them, they are happening to us right now, at the moment we think about them. Whatever happened in the past, it’s happening again for us as we think about it because when it happened in the past, it was still just happening as we thought about it because the present is still just happening as we think about it.

So it all feels the same. All feels equally real. The brain isn’t less worried about things happening in the future because they’re in the future. When it thinks about them, it feels like they’re happening now. That’s why anxiety about the future is so debilitating. And similarly when your brain thinks about the past, it all feels like it’s currently happening because what happened only exists inside your head.

Now, I’m not saying that certain actions did or didn’t take place. If you hit someone with your car, that happened. I mean, side note, philosophically, there’s a big debate about whether we really can prove that anything happened but we’re just going to assume that there’s real things that happen for the purpose of the podcast.

If you hit someone with your car, that happened. But your experience of that happening in the present is only created by your thoughts. So outside of the moment in which the car was hit, if you were not thinking about it, then it is not happening for you at that moment. It is not impacting you.

So what does this all mean? It means that the reason you want to keep going over the past, trying to change it by thinking about it is that you want to change how you feel about it now in the present. It’s so important to understand. The only reason you want the past to be different is you think you would feel better now if it were different.

But circumstances don’t cause your feelings, right? Your thoughts do. So the past doesn’t need to be different for you to feel better. Only your thoughts have to be different. The problem is your brain does not know that. It thinks that what happened in the past causes the feelings that you have today in the present. So your brain think if it keeps replaying the past over and over in your brain, it can change it and you’ll feel better.

What’s ironic is that your brain is actually right that thinking about it is the key, but it’s not just replaying what you think you did wrong or wish you could change. That’s what the brain does is just go over and over and over it again. That never works. You don’t ever come up with new thoughts about it that way or feel any better because you’re just replaying the old thoughts you had.

What you have to do is change what you’re thinking about the past. If you change the way you’re thinking today about what happened in the past, you will feel better today. The past does not have to change at all. So when you feel regret, it’s because you’re thinking that you should have been different in the past.

And I kind of like to break down three elements of a regret thought pattern. They all work together and kind of happen at the same time, but it just helps you think through what’s going on in your brain. So number one is you think that you caused a circumstance that you have negative thoughts about. Something you don’t like.

So let’s say you cheated on a partner and the partner broke up with you, and you don’t like not being with that partner. So you regret the cheating because you think that if you’d acted differently, you’d still have the partner. And you think if you had the partner, you’d be happier than you are now. So you regret the action you took because you think it caused the circumstance of not having the partner that you don’t like.

The second element is that you’re thinking negative thoughts about yourself now based on those past actions or inactions. And this doesn’t always happen but I think it’s pretty common, especially among women who are kind of socialized or people identify as women, whoever it is, people who are socialized to take more responsibility for things, to blame themselves.

So let’s say the same circumstance, you cheated on a partner and the partner broke up with you. Now, on top of believing that you’d be happier if you still had the partner, you have a lot of thoughts about what a bad person you are for doing that and you regret the action because you think the action is what makes you feel bad about yourself.

And you think if you could change that action, you would feel better about yourself now. So you think you’d have something you wanted and you’d feel better about yourself. And the third, which is kind of implicit in both of those, but it’s useful to just see it on its own, break it out, is that you think life would be better now if the past were different.

This is crucial to recognize because it’s why your brain is so fixated. You think that if the past hadn’t happened the way it did, your present would be better. Either material conditions would be different, like where you live or who your friends are, who your partner is, whatever, or you believe your mental conditions would be different. Like you wouldn’t be constantly criticizing yourself or you would feel good about yourself.

So what all these three elements of regret have in common is that you can change all of them right now simply by changing your thoughts. You do not have to change what happened in the past. You only need to change how you think about it.

I see this happen sometimes with my students. I think that we discover thought work and we apply it to our thoughts going forward, but we ignore everything that came before it. Like, we just assume all of our analysis and story about the past is true because we developed those thoughts before we knew about thought work. But that’s not true of course, that doesn’t make any sense, right?

Your thoughts weren’t any more true when you had them in the past then they are now, or any more helpful. So if you experience regret about the past, it’s so essential that you rewrite your story about what happened. Otherwise, you’re draining so much brain energy because you’re spending it on puzzling over a problem that can never be solved.

Remember, your brain is a problem-solving pattern-seeking machine. So much power up there. It wants something to do. It’s like a bored super computer. But because we don’t tell it what to do, it does totally useless things and even harmful things, and one of those is puzzling over how to change the past, which is completely impossible except by changing your thoughts.

But your brain will never come up with that on its own. That’s why you’ve got to give it the problem. You got to tell it, hey brain, listen, your job with the past is to change your thoughts about it, let’s think about this a different way. That’s what I want you to solve.

Because the funny thing is that your brain is right. You can change the past by thinking about it, but you can’t do that by thinking all the same old unintentional unmanaged thoughts that you’ve been having about it this whole time. You have to come up with new thoughts on purpose. That’s what you have to tell your brain to do.

Your unintentional thoughts are producing regret, so you have to come up with a new set of intentional thoughts if you want to produce a different emotion. So remember, I said there were three elements of regret thought patterns, which is one, taking too much responsibility for a past outcome, or two, judging yourself for your past behavior, and number three, thinking that your life would be better if it were different now. That if you hadn’t taken that action or that inaction, that your life would be better now, you’d be happier.

So, if we’re going to reverse engineer this, if we’re going to change these three pieces of the pattern, we got to go one by one. So number one, you need to recognize that your actions were only one element of what happened. No matter what happened, a lot of things went into it.

I actually was coaching someone about this recently and she’d slept with someone who was not her partner and when she told her partner, her partner broke up with her and she was consumed with regret about having caused the break up. She was taking full blame for what happened. But the truth is her partner was also part of the break up.

Her partner could have decided to give her another chance. I’m not saying it was her partner’s fault or blame where they should or shouldn’t have. It’s not about fault or blame or should or shouldn’t. It’s like a math equation. She took an action, her partner took an action. The break up resulted from the sum of those actions like a math equation.

She didn’t singlehandedly cause it. She cheated, she took responsibility, she apologized, her partner still chose to not be with her. That’s totally her partner’s prerogative. I’m not saying that was wrong. But it’s just important to see that it was her partner’s free will and autonomy in action that impacted the outcome just as much as her cheating. And when we take full responsibility for things that we don’t control, we end up feeling all of this blame and shame that totally holds us back and keeps us trapped obsessing about it.

The second step is to look at your thoughts about yourself in light of those actions you regret. Nine times out of 10 I find when we’re dealing with regret, there’s a heavy element of self-judgment and shame built in. You’re believing that you were a bad person or you acted badly in the past or even worse, you’re believing that because of your past, you are a bad person now in the present.

So you keep replaying the past because you think if you could change it, then you could feel okay about yourself now. But the circumstance of the past doesn’t determine your thoughts about yourself now. You can choose to think kinder thoughts about yourself no matter what you’ve done. I truly mean no matter what.

And here’s what’s kind of mind-blowing. I want you to really ponder. In the past, you had thoughts, feelings, and actions, just like now. So if you did something you regret, why did you do it? Because you had a feeling caused by a thought, and that feeling drove a particular action. Just like now.

This is another place that I see my clients learn how thought work works and they apply it going forward. Like oh okay, today I snapped at my kid and I felt bad about it but then I looked at my thought and I saw how I was thinking they should be different and I was feeling angry and I snapped and now I know how to change that.

But they don’t apply that to their past. So whatever they did in their past, they continue to believe means something about them as a person. But the truth is, you’re always having thoughts, feelings, and actions. You just didn’t know it. So if you did something, you did it because you had a thought, a feeling, and an action. It’s not because you’re a certain kind of person. It’s not because you were bad or selfish or terrible. It’s because you had a thought that created a feeling and the feeling created an action. That’s all that is ever happening.

And when you see it that way, it’s so much less dramatic and morally fraught. You can understand why you took the actions you did and you can start to cultivate compassion for yourself. You probably didn’t even know about thought work back then. You did the best you could with the tools you had at the time.

And that’s true now, even if you do know about thought work now, we’re all still just doing the best we can with the tools we had at the time. I really think there are very few, if any, people who think, I could do better than this but fuck it, I don’t care, I’d rather do some dumb shit. We’re all doing what seems to make sense to us at the time, based on what our thoughts and feelings are.

So when you practice thinking about your past self this way, you will find you are much less obsessed with regret because you’ll be judging yourself less and you’ll feel better about yourself now. So you won’t have to keep obsessively replaying the past to try to feel better about yourself.

Okay, so we talked about your judgment about yourself, we’ve talked about taking too much responsibility for outcomes that had a variety of factors, and the third element of regret is the implicit assumption that your life would be better now if the past had been different.

Sometimes that’s because you think you’d have something you don’t have now, like a person in your life, or you think you’d no longer have something you don’t want, like you regret not having left your job to join that start up or something like that. Sometimes it’s just you think your life would be better if you weren’t feeling so regretful all the time. It can be kind of about the regret.

It really doesn’t matter. The solution is the same. Changing your thoughts. Because your current circumstances don’t create your feelings, nor do your past ones. Your thoughts do. So maybe you’re single now or maybe you’re married, or maybe you’re not in touch with a friend, or maybe you don’t have children or you do, or you’re in one career instead of another, or someone has passed away that you can’t speak to again.

But none of those things cause your feelings. Whatever resulted from the words or actions you regret is actually a neutral circumstance. Your thoughts about it are what create your feelings about it. Full stop. So if you want to feel free of past regrets, you have to take responsibility for your life now. You have to really understand that you get to choose your thoughts and feelings on purpose.

And there’s nothing wrong with your life other than your thoughts about it. You don’t have to change the past. If you want to feel better now, you have to change your thoughts now. And you want to be also clear that there’s differences in negative emotion and some negative emotions you might want to have.

So let’s say that the thing you regret is that you never went to see someone before they passed away and you’re judging yourself about that. So you’re taking responsibility for how they would have felt, which is caused by their thoughts, taking responsibility – you’re making it mean something about yourself as a person, you’re thinking you’d be happier now if you’d done it.

Undoing all that regret, working through that thought pattern doesn’t mean that you’re not allowed to feel sad that the person passed. Or even sad that you didn’t speak to them. You’re always allowed to have any negative emotion. You just want to pick it on purpose.

Regret is really about stopping that shame-based spin and stopping that spin that’s based on believing that if only the past were different you could enjoy your life more now. Those are really the two poisonous elements of regret I think, that’s what keeps us trapped in fixation.

Sadness or loss or grief are a natural part of life and they flow through and they change over time. Regret gets stagnant and stuck because it’s just repeating the same thought patterns over and over, trying to produce a different outcome, which will never come.

You don’t have to change the past to love the life you have now. You just have to change your thoughts. Your life would not be better if the past were different and it wouldn’t be worse if the past were different. It would just be different. What creates the meaning, the better, the worse, that’s all your thoughts.

Alright my chickens, that’s the story with regret. So remember, you do not want to regret missing my talk in Boston, so hop over to the show notes, to get the link to the conference and the discount code for the half price tickets.

It’s going to be $35, $30 – probably should have checked that before I recorded but it’s in between. You’ll figure it out when you get there – for the whole day conference, so much goodness on top of my talk and I hope to see you there.

Thanks for tuning in. If you want to start building your confidence right away, you can download a free confidence cheat sheet at

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