How to Never Regret a Decision Again
Ep. 174
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“Do you regret going to law school?” I get this all the time.

Why would I waste a single second regretting something I can’t change? 

No matter how much I replay it, beat myself up, blame other people, think about how much better my life would be if I didn’t go…

It won’t change the fact that I went to law school. 

So instead of wasting my time on something I can’t change, I focus on what I want to do with my life from here on out. 

That doesn’t mean that I can’t learn from my past decisions.

I look back and evaluate why I choose to go:

where was I abandoning myself for other people’s approval?

where was I seeking validation instead of listening to my gut?

where was I simply doing what I was told instead of questioning it?

I do all of that so that I can make better decisions in the future.

But that doesn’t mean I ever spend the time regretting my decision.

Because it is done.

And I had my reasons (even if I wouldn’t choose those reasons now).

And I can have self-compassion for the old me who didn’t know any better.

And I gain nothing by torturing myself with regret.

Because regret comes from a thought.

The thought: “If I hadn’t made that decision, my life would be so much better.”

And that’s a lie.

I have no idea how my life would have turned out.

So I choose not to think that thought.

And you can choose the same thing. 

Because regret is a choice.

Show Transcript
We think like well now I have this 300 pound gorilla sitting on my chest and I'll never get rid of it. And I'll just keep going over and over again about how stupid I am and how much I should have known. And should've made a better decision.

Hey, welcome to Lessons From a Quitter where we believe that it is never too late to start over. No matter how much time or energy you spent getting to where you are, if ultimately you are unfulfilled, then it is time to get out. Join me each week for both inspiration and actionable tips so that we can get you on the road to your dreams.

Hello my friends, welcome to another episode. I hope that you are well. I just got back from a week-long vacation in New York. Vacation is a strong term but I would characterize it as a vacation. Traveling to a city with two young children is um exhausting to say the least but it was super fun and wonderful and also required a lot of thought work on my part. So I got to practice that. It is 50/50, it was good and bad but on the whole, it was a great trip. I'm glad we did it mostly because one of my goals this year was to take off a week every quarter. And to really like do something on those weeks, go on vacations, do… rest, do things that I put off typically. And for me, that's a bigger goal than a lot of the revenue goals I have. I want to build this business as big as I can within the parameters of what I want to be doing. And I think that a lot of times it's really easy to get led astray, to get caught up in what everybody else is doing, to just start doing things because everyone else tells you you should and it's never enough. And we always need more. I am not immune to that. I get very caught up in wanting, you know, seeing other people and thinking I should be further along or I should be making more or I should be launching more or whatever the shoulds are. I always have to recenter myself and bring it back to my own north star and really get an understanding of like why am I doing this? What is it that I want? What do I consider successful? What were my goals for this year? And I had all those kind of thoughts come up when we were planning this trip, I kept saying like we're going to, I need to launch. It's going to be the middle of a launch. I don't have the time. And when you have that north star, it's really quick, it's easier to stay in your own lane. It's easier to bring yourself back when you start doubting it. And you have the uncertainty, which you always will to say like yeah, it might be harder and there might be more work and it might disrupt my launch, but I had made a deal with myself to take a week off. So that's what we're going to do. And so I'm proud of myself for doing that. And I think it was quite the experience for the children as well. I think they were exposed to a lot of things that they don't typically get in Orange County, California. So all in all a success and speaking of a north star or figuring out what it is that you want, I've mentioned before, but I'm doing a free training next week and it's called Bridge the Gap, the three steps that you need to go from the career you have now to the career you want. And it's really about this, like figuring out where you are now, where you want to go and how to get there. And we're going to dive into each part of that and really understand like where are you right now? Which one of those three steps are you kind of focusing on? What should you be doing? And how do you start building that life that you want? How do you start figuring out what that life is? So I would love for you to join me. As I mentioned, it's free. It's on November 3rd and don't worry, if you can't make it at the date or time, I will send a replay to everybody that has registered, but you have to register in order to get that replay. So go to And I hope to see you there. On today's episode, I want to talk to you about regret because I hear this question all the time. And I know that it's something that plagues most people who want to make a big decision, including making the decision to walk away from a career that you know, you're successful in. The only one that you've known. And one of the biggest things I hear in my coaching calls is this concern of like what if I regret leaving? Right? Or I hear a lot of people even talk about the regrets that they already have about their careers. Like I wish I hadn't gone to that school, wish I hadn't taken out that much debt, whatever the circumstances, it's this mental energy that we give to ruminating over why it was the wrong decision and how much we wish it would have been different. Right? I think a lot of why we don't make decisions or make decisions quickly or we agonize over decisions forever is because of this fear. Like the fear of what if I make the quote unquote wrong decision and then I regret it. And I think a lot of times people say it as if it's just a fact like regret is just something that you can't get around if you make the wrong decision. The sun will rise, you will be filled with regret, right? And regret feels terrible. That longing and that feeling that you made the mistake in that somehow you should have known better or whatever the thoughts are that go with that, it feels terrible. And the thing is, is that there's no way for it to go away because you can't change the past. We just keep ruminating over something that we're never going to change.
And when I say that like if you think about other negative emotions, let's say guilt, right? Like guilt might serve a purpose because maybe if you're feeling that, I mean, you have to decide why you're feeling it. Oftentimes we feel it for really ridiculous reasons. But if you read like like your reasons, you want to keep your thoughts and you feel guilty, it might be that like you can rectify it, right. That might be the feeling that leads you to apologize, make up with someone, mend relationships, show up better, whatever it is, it can help you align more with the values that you want to have. Right? And so in that sense, even though guilt feels terrible as well, it may serve a purpose but regret just does not serve any purpose. Right. There's nothing you can do about it. It's done. And that's why it's so scary for so many of us and so heavy because we don't know how to escape it once it's there. We think like well now I have this 300 pound gorilla sitting on my chest and I'll never get rid of it. And I'll just keep going over and over again about how stupid I am and how much I should've known. And should've made a better decision. I want you to think about where do you think regret comes from? It's not like some fact out in the world where like you make decision A and of course that's going to lead to regret. Like nothing you can do about it. That's, it's, that's not the way it works. Right? It's a thought, it's a thought you're choosing to think. That's it. Two people can make the same decision and it could be a decision that they decide later is wrong, right? Like two people can make a decision that they would not make in hindsight. And one cannot regret it. Another can, right? Let's say like as an example two people get married. And then they later go through divorces, right? Nobody wants to go to through divorce. Nobody would choose to be in that situation. And yet there is somewhat, one of them could regret the decision that, regret getting married, regret everything that, you know, came along with it and beat themselves up. And the other person can see that as a chapter that happened and the purpose that it served at the time and learn from it and not regret that it happened. Right. And I just say this to say, to show that it is just a thought, it is a thought that causes the feeling of regret. And the thought typically is something like my life would be so much better if I hadn't done X. If I hadn't married that person, if I hadn't gotten that degree, if I didn't spend that money then my life would be so much better. And then you feel regret. And what do you do? You think about it. You obsess over it. You ruminate over it. And you look for evidence that proves that. You're you start seeing all these other people who didn't get that degree, who went and did really the things that you wanted to do or whatever or you know, people who ended up not getting married at all and staying single. And you look at that and you're like you reinforce the thought see, my life would have been so much better if I hadn't done that. And it's only because you keep choosing to think that thought that you keep feeling that regret and you keep creating that cycle. But as you know, if you've listened to this podcast for awhile and if you haven't, you may want to start with another episode, you get to decide what you think. I know that sounds so foreign to so many of us, but you have that role. And so here is my big punchline of this episode: regret is a choice. It's just a decision to keep thinking that thought, that's it. And if you could go back and change whatever that circumstance was, fine. Keep thinking it like if that was like hey, if I keep beating myself up over this and telling myself how terrible of a decision I made and how wonderful my life would be if I hadn't done that, I would say, you know what, go for it. Have at it, go back and change it. But you can't. So it's literally just a waste of your time and your mental energy. Just takes up all of this room in your brain and does nothing. So I want you to walk you the three mistaken assumptions that you have to make in order to think the thought that leads to regret, right, in order to have this thought. Because the reason you get there is based on faulty thinking. Okay. So just stick with me. This is what happens which leads to this thought. The first mistaken assumption is that had I not made that decision, had I made another decision, my life would have turned out better, right. That situation would have turned out better. And that's a lie because you have no idea how else it would have turned out. Right? Like we love to believe that if I didn't go get that degree, if I didn't spend the hundred thousand dollars on my law degree, my life would have been so much easier. But how could I know that? If I hadn't gotten my law degree, I have no idea what else I would have done. Maybe I would have gone gotten my psychology degree. Maybe that would have turned out better. Maybe it would have turned out worse. Maybe I would have hated that even more. I can never know. And in order for regret to work, it's this just like we just take it for granted that like oh yeah, there was this wrong decision. And if I hadn't made it, then everything would be great. Right. Even with mare, anything, like marriage, whatever. Like if I hadn't done this, then I would be so much happier. Would you? How can you tell? There is no way to know. People ask me a lot like if I regret going to law school and I, I mean, I just chuckle about it because I'm like why would I waste my life thinking about that? Like I went, doesn't matter. Even if I think a million different ways about it. And if I go back and I regret it's only because of this mistaken assumption that somehow it would have been better, but would it have? Because it seems like my life has kind of led me to a place I want to be. So maybe it was the best decision for me. And maybe it wasn't, who knows. I recently actually, it's funny. I was doing this mental work on this trip to New York because I was finding myself having a little bit of regret about how long we stayed in New York, from Friday to the following Saturday. And that is a long time with, like I said, two young kids in a city and the kids were worn out and melting down and we were exhausted by the end. And I started realizing I was having this thought loop that was constantly like in the back of my mind, I wasn't really even conscious about it, saying like we shouldn't have stayed this long. We should have gone back earlier. We should have had a shorter trip. And it was like as if it was fact in my brain, right. It was creating so much negative emotion for me because I was thinking I did something wrong. I was thinking like I planned this trip wrong. My kids are now worse off for it. We're not having fun or whatever. And it was creating the whole situation that I was not having fun because I kept thinking this thought ugh… I should have. Why did I think that we should stay this long or whatever, but when I thought it, I immediately started thinking like that's only because I'm assuming that if we went back earlier, it would have been better. And that's a mistaken assumption because had we had a shorter trip, there would have been different stresses. I would have been stressed out that we didn't get to like see all the things we wanted to see. And we would have packed in seeing more people in less amount of time. And I would have been more stressed about, you know, how much we have to do each day. And we would have been dragging the kids out for longer periods of time every day in order to see everything and see everyone and make every plan work. And I know that that would have stressed me out more too. And when I instantly like saw that reframe, I was like oh, the only reason I'm regretting that choice that I made is because I'm lying to myself and I'm thinking the other way would have been perfect. Had I gone a couple of days less, it would have been the right way of doing it but I don't know that. That would have been a different trip and it doesn't serve me to think that cause this is how long our trip is. Right. So instead of me wasting my time, maybe I can figure out how do I make it so that the kids get some more rest or that we're all kind of in a better place, like enjoying it. So that's number one, like really understanding, like asking yourself, like what am I thinking would have happened if that didn't happen and how am I lying to myself? Thinking like it would have been rainbows and butterflies. Everything would have been perfect. It would have been the perfect amount of time that we'd gone on this trip and everybody would be happy. And you know, there would be no other hiccups. It's like clearly that's a lie but that's the way our brain subconsciously is thinking. Like ugh there was this perfect decision and you ruined it and you picked the wrong decision. So that's one, two is that it's possible somehow to always make the right decision. Regret is this indication that you're giving yourself that like something went wrong, you did something wrong. Right. I shouldn't have ignored that red flag. I shouldn't have given into what my parents wanted and I should have chosen the field that I wanted to go in. I shouldn't have gotten caught up in the hype or, you know, whatever what society told me is the right thing to do. Whatever the thing is. And so we use this sort of as like oh yeah, clearly there was something, there was a right choice. And then I did something wrong. And I think intellectually, we understand that of course, we're not going to be happy with a hundred percent of our choices. In hindsight, we're going to look back and be like huh, I probably would have done something different in that situation, right. So we realize this intellectually but then in practice, we never want to make a mistake. And as soon as we do make a mistake, we beat ourselves up with the thoughts that lead to regret. We constantly like engage in self-loathing and tell ourselves this lie that we can't trust ourselves or, you know, whatever. Instead of really understanding that like of course, I'm not going to make the right decision all the time, of course, some things are not going to turn out the way that I want them to because I don't have all the information when I take the first step. Sure, like when I go on this trip to New York, this is the first time I've traveled to a city with kids. I'm going to learn a lot and I might do things differently next time, right. The next trip we take, I will take into consideration the time that we fly with the children or how long we go for or whatever. But how could I have known that when we haven't done something like this? And so I think the more you kind of understand that like there's nothing that's gone wrong when you make a choice that you're, you later would decide you wouldn't make again. That's quite literally just being a human and that it's not possible to always make the right choice.

This feeling of regret is not something that is like absolutely has to happen, which is the third mistaken assumption. Right? So the second one is that it's possible to always make the right choice. And the third one is that it's inevitable to feel regret if you make the right choice like you have to think it basically. And this acts sort of as like a punishment for making the wrong decision, you feel like I have to beat myself up. I'm going to constantly focus on the shoulds of what I should have done, which I shouldn't have done as a sort of a way that if I keep punishing myself, then maybe I'll make better decisions later. Which again, we know is not true because you're still going to make mistakes and self-loathing and punishment has never helped anyone make a better decision. It just doesn't work that way. And so I want you to truly understand this. You don't have to feel regret. You don't have to think that thought. You can learn from the mistake. You can understand like hey, maybe this wasn't the best decision. You can look back at what happened and gain the teachings. Right? Look back for clues of like why did I do that? Was I doing it to please other people? Was I ignoring my gut? Did I ignore some red flags? Was I not showing up the way I wanted to show up? Why not? These are all amazing things to look at. I'm not saying that you're always going to be happy with every decision. In fact, I'm saying the opposite. You won’t. There's going to be lots of decisions that in hindsight you decide okay, I probably wouldn't do that if I had to do this again. Wasn't the best decision. But me of that time didn't know better. And I was doing the best that I could and I can learn from that and I can move on. I can leave that in the past. I don't have to make it mean something about me. I don't have to beat myself up. I get to just make the next decision and the next decision. And that is the only way that decision-making becomes easy. Because as long as you engage in this kind of regretful thinking, of course, it's hard to make decisions because you're so scared about what you're going to do to yourself if that decision doesn't turn out to be absolutely amazing. Right? And so when you correct these three assumptions, you know that there is no way to know how the other way would have turned out. You just have to pick something and go down that path. You know that it's not possible to always make the right choice. Of course there's gonna be times you're going to make the wrong decision. And you know that you can just learn from those mistakes and you don't have to punish yourself. When you know those three, like when you have corrected those three assumptions, you never have to regret a decision again. I say this like I will never, I just know that I'm not going to regret decisions. It doesn't matter what I do. Will I learn from my decisions? Of course. Would I do different things differently if I was given a chance? Sure, for a lot of things. I'm sure I would have. Will I waste my life regretting something that I can never change? No, why? I, I’m way too busy looking at what I want to do in the future. I think about this a lot, like I said, with law school, because like of course, if I was going to do this all over again, I would not go to law school. Even though I met incredible people. I loved learning about the law. And I do think it taught me a certain way to think. I think given the choice to do it all again, I probably, I wouldn't do it but I don't regret it for a second because like that's the path that brought me to where I am. It's made me who I am. It forced me to learn the lessons I needed to learn and it's over. So it's also pointless for me to sit and regret it. Right. And so how I know, how I make decisions now, moving forward in my life is I just, I know there is no right answer when I'm making the decision. And I know that I will always have my own back no matter what happens. And what I mean by that is that I won't use something not going my way or instead of it not going the way I want or me getting additional information later or me figuring out like you know, maybe another path is better as a reason to beat myself up. I don't think the decisions I make is any reason for me to hate myself or beat myself or whatever. I can absolutely learn. I can absolutely admit when I'm wrong and that I will not show up the way that I want to all the time. And that I'm will make mistakes. And I can still do that from a place of self-compassion. I can do that from a place of understanding that I'm a human being who's going to make mistakes. And that I'm never just whittled down to one decision like that is not who I am. And if I learn from that, then that's good enough for me because I can then leave the past in the past. And I can use my mental energy to figure out what I want in the future. And that's what I want for you is to just understand that you can trust yourself. I'm going to do another episode on this later, more fully, but it's a lie that you told yourself that you can't and trusting yourself doesn't mean that you're going to make every best decision. Like every decision is going to be the best one. It's knowing that you'll learn from it and that you'll have your own back. And when you start really understanding that, when you start realizing that like that fear of regret is just a fake fear, it doesn’t have to exist because you never have to choose to think those thoughts to make you feel that. You can choose more loving and accepting and understanding thoughts. You can have self-compassion for you as you go through this life. You can decide to make a decision and be okay if it's wrong and pivot from there. And you don't have to spend this time and energy reinforcing that you don't know how to make the right decision.
You can't trust yourself. You're not good at X, Y, and Z or whatever. So I want you to take time to realize where you're doing that and start figuring out how much more energy you would have to look to the future and build your future if you just let go of the decisions that you made in the past. You tried your best. You have no idea how it would have turned out otherwise and you will learn from it. And when you can start doing those things, I promise you, making decisions becomes so much easier. So I hope you take this to heart and let go of whatever it is that you've been regretting and know that you can change the story you hear. Alright, you guys, I hope you join me in the class next week. And um, if you want that free class, go to and I will teach you the steps that you need to take to go from where you are to where you want to go in a regret-free way. Alright, talk to you next week.

Thank you so much for listening. If you liked this episode, share it with someone else. I promise you know somebody who also hates their job and wants to quit, so why not share the love? And if you want to come follow along for more, come join me on Instagram at LessonsFromAQuitter and make sure you say hi. I'll see you next week for another episode.