One of the least useful emotions we have is regret.

It usually comes after we’ve made a decision. Sometimes the decision was made a minute ago and sometimes it was made 10 years ago.

Maybe you missed an opportunity or you failed at some event.

As a human, you will continue to feel regret in your life.

However, you don’t have to let regret stop you from moving forward.

You can use regret as a powerful opportunity that serves you.

Listen in this week to learn about the two types of regret we typically experience, and how to stop letting regret keep you stuck. I share a concept that set me free from my regret, why I don’t beat myself up when I feel regret, and how you can use your regret as an opportunity for progress.

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What you will discover

  • The two types of regret we can have about our decisions.
  • How to deal with regret when you feel it often.
  • How to not use the decisions you’ve made against yourself.
  • The secret to not having regrets.
  • How to use your regrets as opportunities.

Featured on the show

Episode Transcript

You are listening to The Life Coach School Podcast with Brooke Castillo episode number 513.

Welcome to The Life Coach School Podcast, where it’s all about real clients, real problems and real coaching. And now your host, Master Coach instructor, Brooke Castillo.

Hi, gorgeous friends. How are things with y’all? I am coming off the most amazing, relaxing, wonderful weekend with my girlfriend, Kristine. Her husband, Joe, came into town for the weekend and we really got to enjoy our new place in Miami.

It was great. We got to play pickleball, we ate great food, we watched the Super Bowl, we hung out on the beach. It was amazing. Living here is like being on vacation all of the time. It’s so awesome in so many ways. But it’s also been not so awesome in so many ways.

And the other day, I was in here coaching and one of the students that I was coaching was really in a place of regret because of some financial investments that she had made that hadn’t turned out the way she had hoped. And she was really struggling with this idea that she had lost all this money, and that there was all this sunk cost, and that she had let her family down, and she had affected other people in her family financially because of these investments that she had made.

And it really got me – I coached her on it, of course, and we spent a lot of time thinking about how she could think about this differently because the way that she was thinking about it was causing her to be frozen in fear and not willing to make additional investments or manage her money in ways that would have been beneficial to her.

And so I started to really think about this in my own life because I was giving her some examples of terrible financial investments that I had made and letting her understand I’ve done some ridiculously dumb things with money and still am investing and showing up and doing all of the things with money because of learning from those investment mistakes and learning from those choices that I made that didn’t work out.

And so I started thinking about the two types of regret that we can have over decisions that we have made, and how do we transform or transmute regret into something more powerful? Regret is typically not a very useful emotion. It has us doing kind of unuseful ruminating. It’s usually over something that’s happened or been done. It’s like a missed opportunity or a failed event is kind of how I think about it. And the feeling is this intense disappointment over having made the “wrong” decision.

And when I first started really studying coaching and really studying the teachers that have inspired me the most, most of them taught me that there are no wrong decisions. Like everything that was meant to happen was meant to happen, and everything that’s meant to happen, does. And when I learned this concept, it really set me free.

It helped me to start thinking about my life from the 50/50 perspective and also think about my life as a series of lessons and adventures that we get wrong and right and wrong and right that lead us and correct us to the ultimate life that we’re meant to live, which is filled with a little bit of a wrong turn here, a little bit of a right turn here, a little bit of a wrong turn here. And that’s what can help us really know exactly where to go.

And for some of you, and for me, I’ve taken some really unsuccessful detours in my life that when I look back on them, I’m like, oh, that probably wasn’t the best choice. But at the time, it’s the choice that I made and I refuse to beat up on myself for any reason, especially for a reason that I can’t control anymore.

And so I think it’s important when thinking about regret and thinking about decisions that we make and choices that we make with our time, with our money, with our relationships, we have to understand that there is the regret of having done something, but there’s also the regret of not having done something.

And when we’re weighing our choices, it’s very easy to get caught up in the apparent risk of doing something and so we don’t do it. But we don’t evaluate, many times when I’m helping people make decisions, they’re not evaluating the missed opportunity. They’re not evaluating the regret of having not tried something, not done something.

So a lot of times when you look at a decision that you have made that maybe in retrospect you think wasn’t a good decision or was a wrong decision, there is so much value that can come from that realization if you don’t beat yourself up for it and if you don’t blame and complain in those evaluations.

So when I look at this penthouse that I just bought, this condo that I bought two years ago, and when I moved in here there were so many things about the way that the contract was written that were maddening to me and made me feel so helpless.

For example, they expected us to close on this house and have it not be completely done and need to wait 30 days before we could even think about moving into it because they would still have so much construction to do. And I thought this was insane. I’ve bought many houses before. Usually when you close on a house, you can move in literally that day or the next day.

You don’t have to wait 30 days and pay 30 days of payments or fees or living costs at the place and not be able to live there. I couldn’t wrap my mind around it. So I went back and looked through this contract that I had signed, and not read very thoroughly, and it was right there in black and white that this was totally what they expected us to do.

And then another example is as part of purchasing this place, you purchased and chose all the furniture that went into the place. And so the whole marketing behind it was like, hey, just bring your toothbrush. You’ll be ready to move in and it’ll be so great.

So when I got here and they delivered the furniture, what I realized is that half of the rooms didn’t have lighting in them. No chandeliers, just light bulbs. We’re calling them serial killer light bulbs. In this beautiful penthouse, you go into one of the bedrooms, there’s just a light bulb sticking out. And I asked them, I said, where are my lights?

They’re like, oh, you didn’t get the lighting package. What do you mean the lighting package? Like I thought I was just bringing my toothbrush. They were like, oh, well you had to make sure you got the lighting package. And so I go back and I look and I didn’t really read through that.

And I’ve spent a lot of time this past month learning about my own personality and how I deal with things not working out. And I’ve been talking to a lot of my students who are entrepreneurs and we talk about this idea that we naturally either freeze or we fight or we flee.

And I am typically a fighter, and not in the sense that I fight with people, but in the sense that I advocate for myself to get what I want and I stick with something until I get what I want. And in this situation, it’s been impossible to really do that because of how these contracts were set up.

And it’s kind of like, hey, this bed is broken or this furniture isn’t what I ordered. And they’re just kind of like, well, this is what we have on the sheet, this is what you’re dealing with. And having no recourse, because I bought this house like two years ago. It’s not like you can just go back to the store.

So everything is very complicated in terms of getting any kind of momentum around justice, is what I would say. And being what I would say is mistreated, but they wouldn’t see it that way, right? And so everything they’re doing is by the book, but I am astounded at what is actually going on in terms of how much I paid for this place and what is actually happening.

So I’ve been thinking a lot about how do you advocate for yourself in a way that serves everyone around you and makes sense and isn’t just banging your head against the wall? And then how do you deal with regret if you are having to coach yourself through it constantly?

I keep saying to myself, what were you thinking when you bought this place? What were you thinking when you didn’t read through that contract? I was telling my friend, Kristine, I’m like, I feel like so much of it was pretty reckless when I signed up for it. It’s just like, oh my God, it’s so beautiful. I love it and we get to get all the furniture. And not being really thoughtful about the whole situation.

I just assumed that it was like any other house that I’d ever bought, right? That the contracts would all just be the same. And the crazy thing about this purchase is I bought it two years ago and then there was a conflict in the building. There was a conflict between the developer and the builder, so there was an incredible delay.

The house was supposed to be done in eight months and it took almost two and a half years to get it done. And so there was a part of me that’s like, how do you put all this money down on a house and they say it’s going to be done in eight months and it’s not, it takes two years to do it, and you have no recourse and you can’t get your money back? You can’t get your money out of it. It’s insane to me how they had set it up to do that and there was nothing we could do about it.

But then on the other hand, the value of the place as it was being built kept going up. So I had invested a certain amount of money and I had already made that much money back because time had passed and the property value had gone up.

And so I was thinking that I’m very glad that I made this decision financially. It’s been a very good financial investment, thank goodness. And I’m very glad that I made this decision kind of in this reckless way and that I’m paying the price for it.

I know that sounds crazy, but I have no regret in the sense that this has been an extraordinary time for me to learn about myself and who I am and who I want to be when entering into contracts and doing business deals and making big decisions for my life and making sure that I don’t get in a position that I can’t get out of.

And so when I think about the decisions that I’ve made and I don’t use them against myself, I feel like I learned so much and I get to understand my tendencies and adjust for them in the future. I’ve had many examples of this.

There have been masterminds that I signed up for. Like last year, I signed up for some very high-end masterminds that were like $200,000 to join into a mastermind and then go and be with other people that were making similar amounts of money and talking about business.

And I signed up for this mastermind, super excited about it, really had a lot of promises about what I’d be able to do and what I’d be able to learn. And I went to the mastermind and it wasn’t what I had expected and it wasn’t what I had wanted it to be.

Now, in that situation, I could have asked for my money back. I could have thrown a fit. I could have complained. I could have been super mad at myself and super frustrated with myself. But I didn’t do any of that. I just thought, okay, I know now and I don’t have the regret of signing up because I think if I hadn’t signed up, I would have the regret of never knowing that this was what I wanted or didn’t want to do.

And it was a huge pivotal moment for me to have made this investment in myself and to try to get the most I could from the situation to make it worth my money. And this is what I always say to myself whenever I invest in something or sign up for a class or something like that, I will take full responsibility for making sure this investment is worth it.

I will learn as much as I need to learn, apply as much as I need to apply, utilize as much as I need to utilize in order to make sure I get a return on my investment. And because I think of it that way, it ended up being a very powerful experience for me.

Now, I haven’t always done this well. I was recommended to sign up for a YouTube class by one of my mentors last year, or maybe two years ago now, sign up for a YouTube class. And it was like $25,000 and it was very intensive, like hands-on, create videos, get feedback, build up your YouTube audience, like all of the things.

And I signed up for the course and I never went to even one of the classes. It was such a waste for me in so many ways. And I had just decided that I wasn’t willing to put in the work. I wasn’t committed to building my YouTube channel. I wasn’t committed to doing videos. It was not something that I really wanted to do.

And I had, I think, signed up for the course in the hopes that I could force myself to do it. It’s like, well, I just paid $25,000, now what? I’m going to have to do it. And I look back with my intention and like what I thought, I thought just paying for the course would make me more popular on YouTube, I don’t know. But I didn’t put in any of the work, didn’t do any of the effort.

And I had talked to my financial people and they’re like, you should ask for a refund. You should get your money back since you didn’t show up. And I’m like, hell no. I am not going to go and ask this organization that did everything they had promised to do for a refund for something that I didn’t show up to do.

And I will tell you, by staying committed to that, I learned a lot about myself and about being careful when I sign up for things and what I invest my energy in and what I follow through on.

And I’ve coached many people inside of Get Coached in Scholars on this very thing. They’re like investing in course after course after college degree, after college degree, after certification, after certification. It’s like they’re investing all of their money in learning and they’re afraid that they’re not going to get their money’s worth or they’re afraid that they didn’t get their money’s worth in terms of the time and energy that they put into it.

And so then they beat the crap out of themselves. And the worst part about it is then they won’t allow themselves to ever invest in another course again.

And I want to speak to this because I think it is incredibly important to make sure you monitor your mind on this. One of my best girlfriends, Kris, she’s been struggling and trying and wanting to get her body in healthy shape for a long time. And she has tried a lot of things, signed up for a lot of things, invested in a lot of things.

And many times she’s like, that didn’t work for me. This didn’t work for me. And sometimes it’s the approach that doesn’t work and sometimes it’s the application because we’re not showing up and actually doing what the doctor is telling us to do or what the organization or the trainer or whatever is telling us to do.

So it’s like you have to tell yourself the truth. Am I doing everything that this teacher told me to do? Or am I not even showing up and blaming the teacher, right? And you have to be really careful with doing that because what she was doing is like, every time she would sign up, she was building evidence that nothing would work for her.

And I remember saying to her, I’m like, listen to me. It took me so many different attempts and approaches before I found freedom around food and my weight. And I don’t consider any of that money wasted. Even the money that I invested into Jenny Craig. Even the money that I invested into Weight Watchers.

All of the weight loss things that I ever did, I don’t regret any one of them because I have such a breadth of knowledge now. And I have such an understanding of what does and doesn’t work for my body. And I understand the calorie count in almost every single food in the world because I went through this process.

Anyway, Kris has actually found a situation, found a doctor, a person that’s supporting her in a way that is crazy effective. And she’s having so much success and it’s going so great for her. And I remember saying to her, I was like, I’m so glad that you didn’t give up.

Even if you feel like, oh my gosh, I invested in that and wasted money. It’s like, no, I’m going to keep trying. I’m going to keep doing this. Just because I didn’t show up for that one thing, doesn’t mean I won’t show up for this one. And just because that wasn’t a good fit for me doesn’t mean that this won’t be a good fit for me.

And it goes back to this idea that you can regret doing a bunch of stuff, or you can regret not doing a bunch of stuff. And for me, and for most of you who follow me, we’re always going to regret the stuff we didn’t do so much harder than the stuff we did do.

And I think the secret to not having regrets is to understand that every attempt, whether you succeed or fail, gets you closer to knowing. It gets you closer to knowing what works and what doesn’t. It gets you closer to knowing your own level of commitment and discipline. It gets you closer to engaging with the world.

So if you think about this $25,000 course that I signed up for YouTube, and I did not show up to one class, it’s maddening to me. Typically, if I sign up for something, I do everything. All the homework, everything, but I just did not want to. I signed up for the course well before the course started. So then when the course actually started, I just did not want to do it.

And I allowed myself to not want to do it and feel the pain of not doing it and paying for something that I did not do. And also knowing I can’t sign up for something like that and expect I’m going to want to do something that I don’t want to do.

It was kind of like a dig at my future self, right? It was like, well, I’m going to sign you up for this course, so you better take it. I don’t want to take it, but you’re going to have to take it in the present moment in the future. And I was like, uh-uh, I’m not doing this. It’s like my past self and my future self got in a little bit of a fight around it.

And I chose not to dwell in regret about it or get upset about it or even be responsible, so I would honor what I said I was going to do to my future self, even though I really didn’t want to. I did not respect the decision that I had made. I didn’t think it was as careful and thoughtful as it should have been when I made it.

And I learned a lot from that because typically when my past self, when my present self makes a decision, it’s very thoughtful and careful. And so I always honor it, even if it’s something I don’t want to do. But in this situation, I was a little bit reckless and careless in that decision. I do not regret making that decision because if I end up regretting making decisions, I’m going to stop making decisions.

And this is the whole crux of what I want to teach you in this podcast, is that if you end up spending time regretting decisions and beating yourself up for decisions that you’ve made and feeling like you did the wrong thing and that you’re dumb or stupid or whatever, you are going to stop your momentum and you’re going to stop making decisions and you’re going to start being afraid.

And this doesn’t mean you don’t learn from your decisions, but you don’t use your decisions against you. Even if it’s something that didn’t work out. Even if it’s something that puts you in a position where you’re now waiting for furniture that you paid for two years ago, right?

It’s like learning from what I did there and how to keep myself in a positive state of mind, be supportive to my past self, be supportive to my present self, and also not dwell in the regret of having not done something or the regret of having done something. That is the most powerful thing.

And so I will continue to buy condos and buy homes and sign up for classes, I will just be more thoughtful now. I’ll be more understanding. It doesn’t mean I won’t make decisions that don’t turn out the way that I had hoped.

But I’m not going to spend a lot of time like my student that I was coaching. She was like, I just need to forgive myself for making these poor investments. And I said, there’s nothing to forgive if you use it as an opportunity to learn and you have your own back and you use it in any way you can to propel you forward.

Now, if I had a desire to be a YouTuber and to be more popular on YouTube, I would access that class and learn from that class and honor my decision to take it. But the truth is that I bought it and I just don’t want to do it. And that’s okay. I still paid for it, right? I’m still thinking about what else I could have spent that money on, but because it’s already done, there’s no point in me being in regret.

So now I take every single thing I can from that decision and I move forward in terms of applying the knowledge of my decision making process to my future.

When you line up your opportunities in front of you and when you’re looking at what you can or can’t do as a choice in your life, please consider that there isn’t more safety in not making the decision. There is no preventative way of avoiding the desire of your brain to feel regret because if you don’t do it, you might regret it tremendously. And if you do do it, you might regret it tremendously.

So now that we know that it’s kind of an even either way, then what do you do when it comes to making a big investment, a big decision about your life? And here is what I do. I make decisions based on if both scenarios turn out awesome, which one would I choose, okay? I give equal airtime to whether it would be tremendously successful or a complete failure.

If I do fail at this, if it doesn’t work out, what can I learn? And what am I absolutely committed to doing if I sign up for this? I am absolutely committed to earning this money back to pay for it based on what I learned in this class or not.

And if I’m not, I probably won’t do it. I probably won’t sign up for it. And I tell myself the truth about what I genuinely want to do. And I don’t try and force myself. And most importantly, my friends, I do not beat myself up with regret afterward.

I move on. I learn what I can. I appreciate where I was when I made the decision. I don’t blame. I don’t complain. I do not say horrible things to myself about myself. I simply learn what I can and move forward from there.

Regret will weigh you down. The regret of doing and not doing things will weigh you down. It isn’t useful. Take the opportunity to learn as much as you can and keep moving forward.

All right, my friends, have a gorgeous week and I’ll talk to you next week. Take care. Bye-bye.

Hey, if you’ve ever wanted to work with me as your coach, now is the time to do it. You can join me in Get Coached in Scholars by going to This is going to be the best year ever. It’s your turn to change your life. Let’s go.

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