Man with his head in his hands representing how to deal with regret

By Dr. Lisa Marie Bobby

We all experience regret, and that’s not a bad thing. Knowing how to deal with regret helps you build a life that is authentic, ethical, and meaningful. Without it, you wouldn’t have good information about who you are at your core, what you need to be happy and whole, and where you have opportunities to grow. 

But as positive as regret can be, it’s also true that it hurts. I’ve sat with many therapy clients who were feeling brutally painful regret about hurting people they loved, or missing opportunities to transform their lives in positive ways, or neglecting their relationships until they ended in a breakup or divorce. These feelings can be difficult to tolerate, much less process and learn from. 

When you don’t know how to deal with regret in a healthy way, it’s easy to become trapped in a vortex of unhealthy guilt and toxic shame that makes you feel hopeless and defeated. You may start believing that you are broken, perhaps even irredeemably so. You may suffer low self-esteem and stop believing that you are worthy of love and respect. You may experience depression, which can lead to more regrettable decisions, which will make you feel even worse, and on and on. To stop this cycle, you have to embrace regret as an opportunity to become stronger, healthier, and more compassionate toward yourself and others.

This article is all about how you can do that. If you’d prefer to listen, I’ve also created an episode of the Love, Happiness and Success podcast on this topic. You can find the episode on this page, Apple podcasts, Spotify, or wherever you listen.

How to Deal with Guilt and Regret

We all mess up, sometimes big time. Maybe you cheated on your partner and you’re facing the loss of your relationship. Maybe you made major decisions for the wrong reasons, like marrying the wrong person, or choosing a career you didn’t like, and now you’re looking back on a life that feels wasted. Maybe your regrets are less extreme, but they still leave you feeling bad about who you are. 

Whatever it is you regret, there are some steps you can take to deal with regret in a way that nurtures your growth, rather than feeling stuck

Have Self-Compassion

When you make a mistake, especially one with painful consequences, it can feel like you should be beating yourself up. Especially if you’ve spent a lot of time around people who can be harsh or critical, you may have a core belief that punishing yourself is the only way to learn and grow. You might be telling yourself an awful story — about how you’re lazy, or worthless, or stupid, etc. — with the expectation that this will somehow help you do better in the future. 

Take it from an experienced therapist who has listened in on many people’s inner dialogues and witnessed how their narratives either help them succeed or hold them back — there is zero benefit to having a relationship with yourself that is abusive, critical, or disrespectful. It does not help you become your best self. In fact, it does the opposite. 

When you are unkind to yourself after a mistake, you’re more likely to feel paralyzed and defeated than to feel hopeful and confident in your power to create positive change. It makes it more difficult for you to brush yourself off and learn from your experiences. Over time, a critical inner voice can even breed depression and anxiety. Having healthy self-esteem and self-compassion helps you feel strong enough to face your regrets head on. It helps you believe in yourself enough to do better today than you did yesterday. 

To practice self-compassion, first stop judging yourself. There is a reason you did what you did when you did it, and the reason is not that you’re a terrible person. Enter into your past experience with curiosity and empathy — What else was going on in your life at the time? What stress were you under? What happened before that led you to the place where you made the mistakes you made? What did you believe then that you don’t believe now? 

It can also be helpful to acknowledge the complexity of your choices, rather than placing them into categories of “good” or “bad.” Often, there is no perfect choice. Any decision you made may have led to one form of regret or another. 
This is not about being self-indulgent or making excuses. It’s about being honest with yourself, and creating the inner safety you need to turn your mistakes into something useful. Unfortunately, people with low self-esteem who don’t know how to treat themselves with compassion can feel too fragile on the inside to make positive changes in their lives.

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How to Deal with Regret: Have a Growth Mindset 

Having a growth mindset means understanding that challenges, setbacks, failures, and mistakes are the path to personal growth. We don’t grow when we’re comfortable and everything is going well — we grow when things are difficult and we’re forced to do the hard work of change.  

The opposite of a growth mindset is a fixed mindset, which says that who you are today is who you will always be, and that your mistakes and successes are reflections of who you are at your core. If you failed your algebra exam, a fixed mindset tells you that you’re just bad at math, and there’s not much you can do about that. If you lost your job, you’re just not smart or talented enough to compete in your chosen field. You are who you are, so bother trying to change?

Even if you don’t believe these messages intellectually, you may have self-limiting beliefs about how much change and growth is possible for you that are operating on a deep level of your subconscious mind. When you intentionally reframe your regrets as part of your personal growth process, you reject these messages and give yourself permission to try, fail, and try again. 

Here’s an exercise that will help you do this. Get out your journal and answer the following questions: 

  1. What was your mistake exactly? 
  2. What led you to make the choice you made? 
  3. What did it teach you about yourself and your values? 
  4. What outcome did you want that you didn’t get? 
  5. How can you create that outcome going forward?

Approaching regret with a growth mindset helps you shift from feeling bad about yourself and helpless to make things better, to feeling empowered to take control of your own future.  

Create Closure

Of course, you don’t always have the opportunity to fix your mistakes or change the situations that you’re feeling regret over, and this can be especially hard to accept. Many people find themselves ruminating for months about all of the mistakes they made that led to the failure of a relationship, for example. If you’re dealing with grief and loss after the death of a loved one, it’s very common to feel regret about things you did or didn’t do within the relationship. 

If you’re feeling a lot of regret, and it’s not possible to fix your mistake or heal the relationship, then creating closure will be an important part of moving forward from regret. To create closure, you need to construct a narrative in your mind about what happened, and put it into context within your own life story — where you’ve been, where you are now, where you’re going, and what you’ve learned along the way. This work helps you make peace with the past, so you can heal, grow, and move forward. 

Have Hope to Deal with Regret

Regret can only be beneficial to you if you have hope — and as long as you’re still breathing, you have every reason to hope. You always have opportunities to grow and change, no matter how old you are, and no matter how many mistakes you’ve made. You have opportunities right now to create different experiences for yourself, and for the people you love. 

I mean this in a very real way. Even if you have late stage cancer and only a few days to live, there are notes you can write, amends you can make, and internal work you can do that can transform your regrets into something that is healing and positive for yourself and for others. Redemption is real, and so are second chances. In my time as a counselor, I’ve witnessed a few miracles of redemption myself.

Our mistakes will always be a part of our stories, but they’re not the last chapter as long as we’re still alive. So don’t get defeated. Take wisdom from your regrets and allow them to guide you toward greater growth, integrity, and love.

Support for Dealing with Regret

If regret is standing in the way of a healthy, supportive relationship with yourself, it’s time to get some help for dealing with regret. You deserve the opportunity to learn and grow from your mistakes, rather than feeling trapped or defined by them. If you’d like support from a compassionate counselor or coach on our team, I invite you to schedule a free consultation.

With love, 

Dr. Lisa Marie Bobby

P.S. — For more advice on making friends with dark emotions like regret, check our “emotional wellness” collection of articles and podcasts. 

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How to Deal with Regret

The Love, Happiness & Success Podcast with Dr. Lisa Marie Bobby

Music in this episode is by Nico with their song “These Days.” You can support them and their work by visiting their Bandcamp page here: . Under the circumstance of use of music, each portion of used music within this current episode fits under Section 107 of the Copyright Act, i.e., Fair Use. Please refer to if further questions are prompted.

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Lisa Marie Bobby: Hi, this is Dr. Lisa Marie Bobby, and you’re listening to The Love, Happiness and Success podcast. On today’s episode, we’re talking about how to deal with regret. Regret is probably the most difficult, but also the most wise and powerful of all the dark emotions. And it’s vital that we all learn to make friends with it, so that we can use regret to propel ourselves towards a better future. All of that and more on today’s show.

When I was thinking about the musical feature we should have on today’s episode, there was really no other choice. This is of course, Nico, aka Nico Icon, with the song These Days from her 1967 album, Chelsea Girl. Fascinating person, she was a German supermodel in the 60s. And then she started doing interesting things with Andy Warhol and the Velvet Underground. And then, and then did a solo career, all of it fascinating. So I believe she passed away in the 90s, according to her Wikipedia page, but definitely worth checking out her work.

On today’s episode, we are talking about regret. We’ll be talking about why we feel regret, how to not just live with it, but how to really use regret in order to grow and develop and not just understand yourself, but actually create better things for yourself. Lots of good stuff here. And this is how, you know another very, very important topic, and one that came from you. You know, I think that regret is something we don’t talk enough about, particularly you know, what to do with it in productive ways. But this episode also is in response to your comments, your questions, your needs.

I’ve gotten a number of questions related to this, those of you writing in who are expressing feelings of regret about, you know, the way a relationship may have ended, because of things that you did or didn’t do – so feeling badly about that, you need to know how to deal with it.

Also, more than one comment or podcast request from those of you who are in a life space that you don’t like, particularly around being single, missing the opportunity to have had biological children. So hard things that you guys are dealing with. And thank you, first of all, just for letting me know what’s on your mind, and giving me the opportunity to address it. We’ll be talking about your questions today. Even share some personal stories, and we’ll have hopefully a good conversation that will help you get some clarity, some direction. And honestly, I hope some, although the sounds weird, real appreciation for the power and the opportunity that feelings of regret brings.

I think all of the dark emotions we are socialized to, if not reject them outright, be very suspicious of them. Not enjoy them, wish they would go away, including anger, grief, you know fear about. Regret is some of the hardest and we can either be consumed by regret, you know, just steamrolls us and we lay there and can’t get up again. Like that’s awful. But there are other things that we can do with regret and I’m pleased to share them with you today.

Okay, what is regret? You know, regret is that feeling that I think is universal. The only people who have not experienced regret are generally quite young, and they haven’t experienced regret yet. Nobody is getting out of this without having a regret show up and make itself at home in your headspace. And guess what happens when we look back on choices that we made that didn’t work out well for us, or, you know, things about our current reality that we do not like. And understand that we had missed opportunities. We made choices, we did things that, in retrospect, may not have been the right choice or the best choice. You know, maybe it’s sometimes that we didn’t do anything at all, you know, that can be a source of a lot of regret for people.

It can be a very helpless feeling. Particularly because it can be so past oriented, right? If the past is done, we can’t undo it, we can’t change what happened. That can feel disempowering. And no matter how much we might want to go back and make a different choice, we really can’t. And there is also opportunity in that, that we’ll be talking about later. But I also think it’s fair to sit with and acknowledge the validity of that reality, of just how badly it feels to feel like we’re out of time. You know, we missed it.

Regret can be especially intense in the aftermath of a loss, a breakup, a divorce, a death, you know, many people who have lost a loved one, or are also facing the end of their own lives can have a lot of intense regret. Because whenever there has been a loss, a death, a relationship, a career, the loss of health can be a big one for people. And even just the experience of aging, there can be a lot of regret associated with that. Because regret happens to us when it feels like a door has closed. And isn’t going to open again, that’s kind of what regret is. It is a feeling, the experience of not being able to go back and fix something that was important, say things that needed to be said, show up differently, do things differently, maybe have the chance to create different outcomes. And now we are experiencing the reality of that ship having sailed. 

These are difficult lifespaces But again, can bring so much wisdom. Regret is also quite complex. Regrets, like all dark emotions, is multifaceted and contain a lot of different components. It can include things like disappointment, sadness, guilt, shame, anger, paralysis, hopelessness, grief, despair. I think the worst part can be, at least when I have experienced regret, which I have, I think like the anger or disappointment with myself for not having seen things more clearly or understood things differently. You know, just when I had that chance to do things differently, I didn’t. I’m feeling kind of mad at myself about that. That’s really hard. And when regret is active for us, you know, like all the dark emotions, regret is really good at knocking on the door pretty persistently. I think it does that because it’s showing up because it wants to teach us things. It wants us to know things. It wants us to process stuff. But before we do that, because it is persistent, it can show up like ruminating, you know, like thinking a lot about the past or replaying things in your mind wishing you done things differently.

Thinking about what might have been, you know, imagining the future that you might be experiencing right now, if you had acted differently in the past. And regret can make you feel badly about yourself. It can take a toll on your self esteem, especially if it turns up into that like, “Why was I so stupid?”, “Why didn’t they see this when I do this?”, it can damage our trust in ourselves. And it can also carry with it feelings of hopelessness, or particularly about the future. You know, if you feel like you’ve ruined your life, it’s over. You can never get what you want now. You can never make whole what has been broken or if it feels like it’s too late to do something different. That is a bad feeling.

And, you know, if you have experienced that in the past, intensely as most of us have, it can also lead to the kind of paralysis in the present. If we’re afraid of regret, if we perceive it as being, you know, this dangerous, scary, hard, awful thing that we need to avoid at all costs. We can feel paralyzed or are anxious about making present moment choices, because of our fear that it may lead to future regrets. This is especially true if we haven’t yet learned how to work with regret, make friends with it, allow it to help us because I believe that is here to help us actually. But this fear of regret can really be worse than the experience of regret, because it can lead to things like indecisiveness in action, which ironically, breeds regret when we don’t act when we should have.

But it’s also true that people can overestimate the future regret they’ll feel if they do take an action, and it winds up not being the right action. And they underestimate the amount of regret they will feel if they don’t act, and that winds up being the wrong thing. There is a fancy term for this: behavioral psychologists call this an omission bias. And it’s important to understand this because what it’s saying in layman’s terms is that we are all more likely to experience big regret, because of not doing something we’re much less likely to experience regret from taking an action that wound up to be the wrong action. But that, when we are living in fear of regret, it creates paralysis, inhibition, indecision, that makes it less likely that we will act.

Remember, when any of us are feeling fear, the natural response is to avoid hide, withdraw, retreat. When we are feeling afraid, it feels safer in the moment to not act. But if you really want to avoid regret, the right thing to do is to do what you think is probably the right thing, in that moment, make thoughtful choices. But action is always more protective than inaction, in most situations. So, something to think about, “why it’s so important that we’re getting comfortable with regret and understanding how to work with it”.

But the other pieces of regret is that and this is the part that I think people don’t fully appreciate, is that even though it feels like this dark, horrible thing at your door, it is bearing gifts, it is your friend, it is here to help you and teach you, help you learn, help you grow, right, because it’s like shining a flashlight into things that you wouldn’t have known or understood, had regret, not helpfully shown up to assist you. And that can be things like illuminating areas of your life where you maybe in retrospect, had more control or autonomy, more ability to make decisions or take action and maybe you knew at the time.

It is also the most powerful and important, in some ways, way of understanding our values, understanding the things that are most important to us. You know, we only feel regret about losses or outcomes that are highly significant. You know, if I did x, y, z, I wouldn’t have lost my relationship, lost my job, lost my health. If I had made different choices at an earlier stage in my life, I would have been able to shape my life in such a way that it had more meaning for me, more connection, more joy, right? And I think it also pulls into stark relief, you know, not just our opportunities, not just our value, but it gives us clarity. And it gives us direction about the actions that we can take in order to have different outcomes in the future. Because we are learning from our past mistakes.

Once we kind of put those pieces together, regret can also be highly motivating. Because it’s an emotion that helps us understand what it is that we want so much. And how vitally important it is to be making values based, intentional decisions and taking action that is congruent with what it is we really want, what we are trying to create. It shows us what we need to do, what’s important to us, and if you allow it, what are the steps forward from here, so that we can move you in a new direction now. Lots of motivation comes from regret. But it is, it is a challenging ally for. Regret is not an easy, easy thing to have a positive relationship with because it can be so consuming, and it can be so painful. And you know, because of what it can do to us mentally and emotionally.

First, before we talk about, you know what to do next, I would like to talk about how to manage the feelings of regret, how to deal with regret in an emotionally healthy way, so that you’re able to take the benefit from it. And the first thing to know about regret is that it’s really important to stop beating yourself up. Regret when you feel it, it makes all of us want to do that. You know, “I should have done this”, “Why was I thinking”, and being mean to yourself is not helpful. There is no benefit to having an abusive relationship with yourself. As I have discussed in great length of previous podcasts, I would refer you back to how to love yourself. That’s a good one to start with. But it is 100% okay to feel regret. It is 100% okay to take influence from regret.

You know, I wish I had made a different decision. If I had to do that over again, here’s what I would do differently. But no value from being hostile, abusive, self critical, demeaning, disrespectful towards yourself. In contrast, if you tolerate that kind of self abusive inner voice, it will be paralyzing, defeating. It breeds depression, anxiety. And it will make it much less likely for you to be able to get back up and brush yourself off and say thank you very much regret for helping me understand what’s so important to what I need to do differently going forward. If you are consumed by anxiety and fear and loathing and self hatred, you can’t do that.

Because taking action, having hope, you know, taking steps in a different direction requires us to feel good enough, to feel competent to feel somewhat able, you know, that takes energy to have hope. And if you are stuck in self loathing, you will not be able to experience yourself in a competent, effective way, and you won’t be able to take any action. You’ll just lay there.

Regret is not doing this to you. It is learning what do I do with self criticism, beating myself up with self hatred. And it’s also validated by science. There is a study I found that people with greater self compassion, are actually better able to learn and grow from regrettable life experiences, which makes a lot of sense, because really what we’re talking about right now is resilience.

To make use of regret, and allow it to help us develop positive things in our present and in our future, we need to have a certain degree of resilience and self flagellation is the opposite of what we need to be doing internally in order to experience resilience. You know, it’s also true that many people, particularly who grow up in families with harsh parenting styles, believe that there is something helpful about being critical. And that it may feel self indulgent, to be kind or compassionate to yourself after you realize that you made a mistake.

If we grew up in homes that were punishing, we think, on an emotional level, that the right thing to do is to punish ourselves for having made a mistake, having done the wrong thing, right? And that is A: not a helpful parenting style. But B: if you notice that you’re doing that to yourself, time to make a change, because we need to have inner safety in order to be mentally and emotionally well, to be resilient enough to allow regret to help us learn and grow.

Having compassion for yourself is a very important component of resilience of, of dealing with regret. And I have also recorded a podcast on this topic, too. And let’s see, what do we call that Mindful self compassion, I think it was you want to check back on that the feed or in, you know, the content collections that I put together for you at

The core core components of compassion, I think, are, you know, rooted in radical acceptance. Being able to say, “I do not like what happened, I wish it were different. And here is my reality.” And to be able to accept that in a reality based way, so that it’s not emotionally activating, or traumatizing to the point where it’s difficult to function, difficult to think difficult to be the person that you want to be now, right. There needs to be a degree of radical acceptance. And there also needs to be kind of new dialogue, in your mind, I found to be very helpful to, you know, have an inner narrative, I think, for myself also for clients.

I didn’t know then what I do know now. I think it was Maya Angelou, who said, “When we do the best we can with what we know, at the time. And then when we know better, we can do better”. I think to have some compassion, some forgiveness, for the person that you were. And I think it can be helpful to talk with a good therapist about the context, right? Like, what was going on in your life, when you did the things you did? Or didn’t do the things that you didn’t do? Like, why did that make sense? Because when we do that kind of exploration, we develop a fuller picture and more comprehensive understanding.

The outcome typically, is that there were lots of reasons for why you did what you did, or didn’t do, that make a lot of sense when we explore them. And that even though in retrospect, you would have liked to have handled it differently, to have compassion for the person that you were to, you know, enter back into their experience, empathetically, to understand why they did what they did, can really be quite healing. And also growth-promoting, truly, because the other thing too, is that, in the moment, and I don’t think that we give ourselves enough recognition or credit for this life experience. But in the moment, in the present moment, we all often have a range of choices of actions that we could take. And many of them are not just plausible, but reasonably okay options. Like there’s almost never some, you know, the beam of sunlight, you know, shines directly on the shaft of the sword sticking in the side of the stone, like it’s not that obvious.

We are all kind of groping around. And we have many, many, many different choices and paths and directions that we can go on and is really not clear from where we stand right now. What the end result of that choice, that action that inaction are going to be a year from now, five years from now, ten years from now. There is not a perfect choice. There is almost not a universally bad choice. There are many shades of gray, and there’s a lot of ambiguity, when it comes to many things in life. I think, you know, to be able to appreciate that, understand that, and also, you know, the fact that right this very second, all of us are literally, you know, making small or major choices, sometimes without understanding the impact of the choices. But also, you know, we’re just doing the next probably best thing from the vantage point that we have now. It’s really only when we look back and see the outcomes that were able to understand, but I’m just having compassion for that fact, I think can be very, very healing.

Additionally, and I think the thing that can be most beneficial for us, both with dealing with the emotions of regret, but also being able to start using the power of regret, is to very actively and deliberately cultivate a growth mindset. And a growth mindset, I’m sure heard me talk about this on on other episodes if you’re a regular listener, but it is this very intentional, just way of thinking about yourself, the world, others as being constantly developing, I think is the right way to say it, you know that what we all do is learn and grow all the time.

The opposite of the growth mindset is what Carol Dweck who wrote this fantastic book, “Mindset” called a fixed mindset. And a fixed mindset tells us that we are all we are you ever going to be right this very second, you’re either good at math, you’re bad at math, you handle yourself well, in relationships, or you don’t it’s like, you know, it’s like there, there are limits to what you’re capable of, if you have a fixed mindset.

In terms of your intelligence, your capacity, the outcomes, that you’re going to get that sort of like the roll of the dice, the luck of the draw. There’s no use in trying to make that bee different. And if you experience yourself as having made a decision that didn’t get you the outcome that you wanted, or if you made a mistake. This is a statement of who you are, and how much you’re worth, and what you’re capable of. Try to hide failures from others. Try to avoid making mistakes at any costs, and have a sense of inflated pride in yourself when things go well for you. Because that means it is because you are smart and competent and worthy. And you know, either look down on or have pity for people who have bad things happen to them, because clearly that means that they’re, you know, a bad person.

Don’t do that. That’s all examples of a fixed mindset. And it’s not helpful for anyone. It’s not helpful for kids, it’s not helpful for us as adults. What is helpful is the cultivation of a growth mindset, which says, “We are all existing right now at various levels of development. And the more eagerly and openly, we seek out opportunities to learn about ourselves, have new experiences, allow our experiences to teach us to learn from mistakes, and to really apply ourselves to actively be working on developing new skills, developing new strategies, practicing things that we don’t feel like we’re really good at right now. The more we do that, the more and more quickly we will develop”. And a growth mindset tells us that it is not a straight line. And that practicing learning, trying new things, will always have variable results, especially as we’re learning. And that it is from the things that didn’t work out the way we wanted to that we learn what to do a little bit differently next time.

Sometimes I just watch my kid play the guitar. He’s so interesting, and he will play a song and watch him listening to himself. He has a fantastic ear. And he’s playing along and I can’t even hear it. I mean, his ear is that good but how like, here’s something and I’ll stop and I’ll try it again. Try it again. Get it right, and then practice that. That’s the sound. That’s the sound that I wanted it to make. they’ll do that a couple times. And then he’ll keep going. And I’ll do the song again. And that little micro process happens 50 times during the same song, especially if it’s a song that he’s learning, because he is playing along. Nope, that doesn’t sound right. And then what do I need to do differently? Yep, that’s what it was in keeping on going. 

It’s such a simple example. But it’s so obvious when it comes to like, you know, learning how to play a piece of music on an instrument. But we do not give ourselves that kind of grace for our own learning process when it comes to so many other things, be it, how we show up in relationships, how we take care of our health, what we do on the job, what we do to stay organized, what we do to feel okay, you know, that people don’t appreciate the fact that as we go on, like, “Oh, no, I just ate a whole bag of Cheetos. And I don’t feel good right now”. I’m not going to do that, again, like, you know, this little micro course correction, rather than “What is wrong with me?” “Why did I do that?” “Oh, it’s disgusting. I’m like, terrible”.

A growth mindset helps us stay in this space, where we’re able to be in the world do our things. Notice how things we are feeling are impacting us as we’re going along, and learn from it. And also like value, the experience of learning and understand that it is a fundamentally non-negotiably important part of being a healthy, happy and effective person, if we are not allowing ourselves to learn and grow, bad things happen to us. That’s really why regret is here. It is just showing us on a dramatic, painful kind of level, what our real opportunities for growth and learning are.

It’s very important that we reframe our experiences of regret through that lens, and understand that regret is part of that growth journey. It shows us things that we would like to change about ourselves. It shows us our opportunities for development, for continued development, you know, like, why did you do the things that you did? That, you know, you’re unhappy with the outcomes, we’re going into compassion? Like, there were reasons why you did what you did. Maybe it was the best that you knew how to do at the time. And regret is here to inform you that it’s time to figure out how to do that differently. “Is it a relationship skill? “Was it an emotional reaction to something that made a lot of sense in early childhood?”

But now, as an adult, it is time to figure out what to do instead and stop getting triggered and stop, you know, reacting to things in that situation. That’s, that’s why regret is here. It’s time to learn how to do that differently. And so to be able to look at something that you know, what was regrettable that you were unhappy about and reframe it, you know, in the context of your own growth, and learning as a positive thing, maybe something that needed to happen. Maybe, even though it wasn’t a great feeling experience, maybe it happened because it was protecting you from something else. Or maybe you needed to have that life experience in order to continue growing and developing.

This also can tie into a spiritual belief system that can be really helpful for you to tap into, if you’re dealing with regrettable situations, but only if it is healthy and helpful for you. You know, it can kind of go both ways with spirituality. For some people, a belief system can turn into a fatalistic kind of worldview, that is actually not conducive to growth and emotional wellness. But if you have a way of making meaning, that makes you feel safer in the world, protected, cared for. That can be really helpful too, because it ties into your ability to support yourself, to have compassion for yourself, and to feel like you’re worthy of better things, right? 

Those are all things to consider. When we put these things into place, we can then really actively use our regrets to promote our wellness and our growth. If regret is there, knocking at your door and saying you made a mistake. The helpful response is “I did make a mistake.” And then have that turned into a growth process for you. What was the mistake specifically? What did you do that created that outcome? And also why? You know, why did you do what you do? Was it because you didn’t know what else to do at the time? Was it because you didn’t have the skills or strategies to handle a difficult situation in a better way? Is this illuminating a growth opportunity for you? And if so, what is that? Because when you get clarity about what that is, then you can begin taking action on that.

I want to have a different outcome in the future. So what do I need to do? What do I need to learn? What do I need to practice so that I can handle this differently in the future and make a different choice in the future? Additionally, talking to regret about what did this life experience, teach me about myself? About my values, about my patterns? What are the things that I need to know about me, in order to handle this differently next time because I don’t want to feel this way again. Thank you regret, for helping me understand.

Also, too, I think, to be clear about what your more preferred outcome would have been like, if you did have a magic wand and could have created a different outcome. You know what, let’s play that out. What did you want? A relationship, a different life experience, different career? So many different things, but like use that thought experiment, to help create clarity about what is important and what you would like to have, you know, maybe starting now. Because it allows you to think about how you could build that in your future. 

Furthermore, to be thinking deliberately, about the opportunities with, if we allow regret to steamroll us, that is where we stop. But if we make it our friend, and it’s illuminating all these things, to be able to say, What could I do to make this different starting today, is incredibly powerful. Right? I can’t go back and rewrite the past, I don’t have a time machine. And what did this just teach me about myself about what is so important to me like that maybe I didn’t understand or appreciate at the time, but that I know, now, it feels like my life is almost meaningless without it like it’s that important to me.

What does that mean about what I need to be doing today, in order to be actively building this into my life? Even if it’s not, you know, exactly what I originally wanted? I need to have this in order to feel okay. Right. And that’s when we allow regret to transform into motivation. “Who do I want to be?” “Who do I need to be? Where am I currently in my developmental stage, between becoming the person that I want to be and that I need to be in order to get a different outcome next time”, then the actions, “What do I need to be doing are learning how to do right in order to to be creating different outcomes in my life going forward?”

Here, I think it’s very important to construct a new narrative and new way of thinking about time, and about where we are and the opportunities that we have. People who get stuck in debilitating regret, think, feel, believe that it’s over, that whatever positive outcome they may have experienced is over, it is no longer possible for that thing to happen. And that was the only thing that could have happened that would have been positive or helpful. It was a one shot, you blew it, it’s over. And there’s, you know, no sense in trying.

That is when you will be defeated. Right. And so we can’t go there. Because it’s also not true. It is not ever true. Redemption is real in a spiritual sense, in a psychological and emotional sense. Redemption is always possible. Second chances are real. Just like you didn’t really know what the outcome was going to be when you did whatever you did originally. You also don’t know what the outcome is going to be by doing things differently from here forward.

You always, always have opportunities to create different experiences for yourself. What you lived through is part of the book, it’s always going to be part of the book. But as long as you’re breathing, it is not the last chapter. As long as you are still alive, that last chapter has yet to be written. Where there is life, there is hope. If you have terminal cancer and a week to live, there are still things that you could do today that create a positive impact in the world and that help you feel better and take action that is in alignment with your values.

If you are about to die, and wishing that you had the opportunities to tell certain people that you loved them, get somebody to bring you an audio recorder and record those messages, make those calls, send those notes, have those visits. And for those of us who hopefully have more time left in this world, it’s very important that we use this in a constructive way, and get to work like today.

It is also very important to be considering the big picture here. We can get hyper focused on our regrets, the things that we wished we had done differently when they feel like, you know, they’re still open loops. I recorded a podcast for you on creating your own closure. I hope you listen to that. I think it will be helpful for you in doing some of that psychological work of creating closure, because that is important. But it’s also really important that you are thinking about the big picture regrets of, you know, maybe right now you’re in your 40s, or your 30s. And you’re fixated on something that happened five or ten years ago: a lost relationship, whatever it was, but you know, not really appreciating the fact that you may have 30, 40, 50 more years ahead of you, and that you, like me, like all of us are going to die.

You are going to be that person on your deathbed. Eventually, not all of us go out like that. Not all of us have the gift of time, you know, knowing that we’re dying. For some, it’s swift and more sudden, but to use this very powerful idea that I have talked about on past podcasts of memento mori, remember that you will die, in order to create clarity around what we need to be doing with ourselves in an intentional way. And where we need to be focusing, in order to avoid the biggest, biggest regrets in life.

There’s a hospice nurse, Bonni Ware, who spent her career doing hospice work, working with the dying, and wrote a book about it called Five Regrets of the Dying. And I think it’s instructive because it is when people are close to death, that they have the most clear vision about what was most important to them about how they lived the day to day choices that they made that in retrospect, may not have been in alignment with our highest and best and are sitting with the outcomes of those choices in a very final way. Like even though we can always always do things in service of our values and achieve redemption and make things right, as long as we’re living. When you’re close to the end. You don’t have as many options, right?

It’s important for us to be thinking about what those most important things are, what she lists in order number one, people saying I wish I had the courage to live a life true to myself, rather than the one other people expected of me. And that can show up in different ways, right? Who we marry, where we live, the kind of career we pursue, the lifestyle that we do, the inner narrative about who we are and who we should be, can be externally defined. And so it’s really important for all of us to be doing a lot of work around who you really are, what is most important to you, and what kind of life you want to create so that you’re not saying that to yourself at the very end of your life when you’re 90 years old. What do you need to be doing today?

Another common regret that I think many of us, myself included, can relate to a regret of I wish I hadn’t worked so hard meaning I wish I hadn’t organized my life around a career that at the end of the day, didn’t really provide that much satisfaction or meaning, I spend a lot of time at work in service of this company away from my family. It can also mean I wish I didn’t work so hard to keep my house clean, keep my car clean, do the little tasky-task, things that, you know, I spent so much time and energy doing at the expense of other things that were really more important. 

And if you guys saw Marie Kondo, the sparkling joy decluttering guru has announced that she is not actually focusing so much on keeping your house clean lately, so that she can spend more time playing with her kids. Like, you know, hats off to her. But another really common regret people have at the end of life, I wish I’d had the courage to express my feelings to somebody that I loved them. While I still had the chance to. Tell somebody how mad I was at them. And legitimately so because you know what? I needed to say that to them.

Another common regret that people often experiences, I wish I had stayed in touch with my friends. I wish I had cultivated more positive relationships with nice people, you know, but letting friendships kind of drift. It’s easy to do, we all do it. But that’s one of the big regrets that people have at the end of life. And then the last one, you know, I wish I let myself be happier. And that one is very instructive and very relevant to our topic today. I wish I’d let myself be happier. I wish I hadn’t let myself be consumed and beaten down by regrets. Instead of figuring out how to find pleasure in my life. How to be happy, how to create a life that felt more meaningful to me. I wish I’d let myself be happier. And so to be thinking about what gives you joy, what gives you pleasure, what is meaningful to you, what is connected to your values? And how is your experience of regret showing that to you right now.

So, that you can, by the time you’re 93, by the end of your life and say, I did it, I figured out how to be happier. And thank you so much regret for showing me the way. Those are all, I think really powerful and important ideas about what to do with regret, the kinds of regret, how to handle the emotions that come along with regret. And now, as promised, I do also want to briefly address some of the specific questions that have come through because I want to give us all the opportunity to hear these stories, and then, like, be able to apply the things that I was talking about today to these different situations.

One person wrote in saying, you know, I have a lot of regret right now, I ended a relationship with somebody that I loved very much. And I didn’t want to end the relationship. But there were issues that I didn’t know how else to deal with this person that I was in love with how to substance use problem. We had value differences that I didn’t know how to square. So I ended the relationship.

But now I feel so much regret. I’m so angry with myself. I long for her I crave contact with her. She has moved on. It is over. And now I’m sitting with this regret. How do I forgive myself for making this life changing decision that I wish I could take back? Okay, I hear that there is regret over the experience of the loss of somebody who you had an attachment to. This person was precious and important to you. And now the regret is saying could you have handled that differently related to the values differences to the substance use disorder? What could you have done in order to work through that in such a way that it maintained your relationship with this person?

The work here is a few things. Your values are really around connection and attachment and having strong and enduring relationships and that is something that’s really important for you to know. You will also, obviously, need to grieve and heal from that breakup and do the closure work, which is a separate thing. But when it comes to the regret parts, what this is saying is, if you are going to have a relationship that endures, which we’ve established is important to you, you will need to learn how to either find someone from the get go that has more congruent values to you avoid getting deeply involved in falling in love with people who have untreated substance use disorders.

Those are growth opportunities that then have a next step. Figuring that out is how do I learn how to do that in terms of choosing partners? But also, how do I maintain a relationship with somebody who maybe is struggling? Who does have a problem? How do I maintain that connection, while also maintaining my own boundaries? Because I bet if you had the opportunity to kind of do some of that context work that we were talking about going back into the past. You know, right now you’re sitting with the outcome that feels bad the relationship ended. But I bet if we went back into the time as it was living, you are experiencing things on a day to day basis, that probably felt pretty bad for you.

Living with somebody who has an untreated addiction is really hard. Trying to figure out how to plan a life with somebody that has very different values, or hopes or dreams for you, is very difficult. And, you know, what you may discover is that you actually made the right choice. Don’t do not want to define this for you. But that regret is also showing you another opportunity, which is I have so much regret over this relationship ending. You know, if you go back and do that exploration work, and at the outcome of that say, “No, that was actually probably the right thing to do”, then, regret is also showing you, how do I learn how to create closure, to honor and respect my own decisions, how do I figure out how to go through a grieving process effectively. How do I learn how to release an attachment to somebody that I loved, but they really wouldn’t have made a good partner for me?

Regret is providing you with that opportunity, as well. There are lots of options for you here. And I hope that you consider, you know, what I just said is not the end, my friend, that’s just the beginning. Now, go do some journaling, get involved with a good therapist or a good coach who can help you continue doing that growth work. Because there’s a lot ahead of you, I can hear that. There’s another listener question, actually two that are similar. We’ll talk about these back to back.

Another person wrote about having a reaction to a podcast that we launched. I think it was February around how to be happy being single. And what they brought up is the fact which I think is a reality for many people. Yes, I can be, you know, air quote, “happy as a single person”, but I’m also experiencing a lot of grief and a lot of regret that never gets acknowledged. And it’s so painful. I long for a partner. And I’ve just always been single, I’ve never had that I regret that so much. I have never had children, I am getting older. I feel like this is slipping away.

You know, the emotions that are being described here are regret. And I think it’s very important to frame it this way. Because when we’re experiencing regret, grief, those dark emotions are saying, you don’t like this outcome. You don’t like what you have right now. You want this to be different. And so, even though you might listen to a podcast, with somebody telling you that we can embrace singleness and learn how to love ourselves and figure out how to be happy on our own and lean into it and accept it and all these things, your regret, your grief is saying, “I don’t like that, that doesn’t feel good to me. I don’t want to do that. I don’t want that to be the answer.”

And what you get back is the motivation that comes with it. You know, the values that are clarified. That understanding of “I actually think I do want to have a great relationship with somebody, and feel like I have achieved one of the most important dreams of my life”. I think that can and should be valid. And 1,000% valid to say, I want to be a parent, I want to nurture children, if there is radical acceptance to be had around whether or not you can have a biological child, you know, that’s, that is also a fact.

There are so many ways to be a parent and to have a family. And, like, let’s listen to what grief and regret is telling you. And take action from that. Like, okay, thank you regret, I understand that this actually is important to me, it is valid. And now, how do I build that? Which will require a lot of gross work around, “Okay, so what have I been doing consciously or unconsciously, that has been creating this outcome that I really don’t want?” Because, you know, we can’t just flip a switch and be like, okay, great, sign me up for a relationship or an order that on Amazon, like, it’s not how it works. There’s a reason why you have been single, and that isn’t going to change until you figure that out. 

Learning about yourself figuring out, okay, if this is what I want, what do I need to be doing differently? What do I need to work through? What are my patterns? What is my narrative, right? There’s a lot of work to be done. And those are all solvable problems. Working with, and I will qualify this working with a therapist who specializes in air quote, “dating coaching”, meaning a therapist who specializes in helping people understand who they are, and where they need to grow and develop in order to create new, healthy relationships. Part of that can be dating coaching, like we know, what are you doing on a dating profile? But the real deal, the big enchilada, is figuring out how are you showing up? What are you doing? How are you communicating? Who are you attracted to? What are your patterns? What are your imprints? What is your inner narrative? What are you doing, and then being able to correct that so that you’re developing skills and strategies that allow you to competently find somebody great, and build not just a relationship with that person, but a life with them and a family with them.

Just because you did not know how to do that previously, doesn’t mean that you can’t learn how to do that, and create this reality going forward. Where there is life, there is hope. And then the related question, you know, I think within a theme. Another person wrote in about feeling really lonely, and being unhappy about it. Asking how do I handle the pain, the emptiness, the loneliness, that comes from being single for 11 years, it feels like nobody can fill this hole. Right? And what I hear in there is regret. I am sad about this. I don’t like this, I wish this were different. And I have the same response to you that I did for the former person, like what would happen if she started making this valid and real and paying attention to it, you know, not trying to make the feeling go away. But saying like, what, what is this feeling telling me about what I want and what I need to do, and helping it turn into motivation for you and an action plan.

I have heard from other people who have experienced regrets and I have experienced my own regret. I had a terrible time with a daily overwhelming regret when I was in my late 30s and had had one child when I was 34. And because I was you know in a doctoral program and building a private practice and working so much, you know, wasn’t the right time to try to have another kid I felt like I couldn’t handle it. We felt like we couldn’t handle it and then realized, you know, four or five years out that I really did want to have another child my husband was more open to either he would have been fine with one kid he’s fine with two kids. He’s more easy going in that way. But I really wanted to have another child and could not. I had a series of miscarriages that were awful. We did fertility treatments and I had so much regret about not having tried sooner, you know, when I was still younger when we would have had a better chance. I beat myself up for being so careerist and not not focused enough on the on the family side of things. 

But thankfully, you know, in working with regret and understanding, you know what it is so important for me to parent, another child, I love being a mother. This is just like, fundamentally important. We became foster parents. We began and doing different things in terms of fertility treatments that ultimately wound up being effective, thankfully. But if I hadn’t listened to regret, and just felt sad about not being able to have another kid or feeling defeated, or feeling like it was hopeless, I would have stopped trying. And so that was really powerful. I also experienced a lot of regret, you know, when my mom died, wishing that I had handled aspects of that relationship differently. Should’ve spent more time with her, right, all these different things that were painful, and I had to spend a lot of time working through those.

You know, the gift of regret is how I show up differently now in my relationship with my father, understanding that we don’t have all the time in the world. And so I’m doing things differently with him because of what I’ve learned and the ways that I’ve grown. And also reclaiming a very positive relationship with my mother. Now, who is an angel. She was an angel, and she was alive. And she’s now a real angel. And it’s been a lot of fun for us. So that’s been cool. But like, you know, figuring out what it is that you want, what it is that you need, and how you can create it for yourself. Now regret is hard. But it is so empowering when you let it in when you have a relationship with it.

I hope that this episode was helpful to you and I hope that it gave you some new ideas that you can put into practice in your own life and I hope you stay compassionate with yourself, gentle with yourself, but also motivated and moving towards empowerment and growth. Because that’s what it’s all about. Alright, my friends, thank you and I’ll talk to you soon.

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