You know that sinking feeling you get in the pit of your stomach when you realize you’ve made a mistake? Maybe it’s shame, maybe it’s regret. Whatever feeling that is, most of us will do anything to avoid it. Which means that we can end up making future decisions mostly on the basis of trying to avoid making a mistake and avoid feeling that feeling again. That leads to inaction, paralysis, and confusion, and we stop making the kinds of decisions that could actually improve our lives.

In today’s episode, I want to talk about a different way to think about your past mistakes, and most importantly, how to actually dissect them and learn from them so you can make better decisions in the future. This is a life-changing exercise, so let’s get into it.

Welcome to UnF*ck Your Brain. I’m your host, Kara Loewentheil, Master Certified Coach and founder of The School of New Feminist Thought. I’m here to help you turn down your anxiety, turn up your confidence, and create a life on your own terms, one that you’re truly excited to live. Let’s go.

Welcome back, my friends. Today we’re talking about mistakes, one of my favorite topics, and how to learn from them so that you don’t repeat them in the future. Learning from my mistakes is one of the most powerful abilities I have as an entrepreneur, building and leading a business, and as a human in relationship with others, and those are the two most important areas of my life. But I did not come by this ability naturally. I grew up with a very perfectionistic thought process where I had to get everything right or I was a failure and everything would end in disaster. And this meant I could only do things I already knew I was good at or was very sure would work out.

And since I was not very old or experienced at the time, that was a pretty limited set of things that I thought it was safe to do. I didn’t try things that I wasn’t naturally skilled at. I didn’t take risks, and if I ever performed anything less than perfectly, I was filled with shame and basically avoided that area forever.

For instance, I still don’t really know how to ride a bike very well because I fell off my bike a few times while trying to transition to handle brakes, and then I just never did it again. And that’s just one small example of many from items big and small that I either didn’t try at all or gave up on because I couldn’t do perfectly. And actually recording this episode is making me realize I should learn how to use handle brakes.

It wasn’t until I started to understand how my brain worked and started to be able to actually get under that feeling of shame to see what was truly going on that I began to be able to learn from my mistakes. And that turned out to be an amazing outcome because it made me better at making decisions in three core ways.

First, most obviously, I actually just learned something from what I had done concretely. So I didn’t repeat the same mistake in the future most of the time. I mean, occasionally I did. Occasionally it takes a few times to learn a lesson. I’m a human. But I just got better at making decisions because I was actually learning from the mistakes I’d made so I didn’t repeat them.

Second, though, I also got more comfortable with making mistakes and learning from them as a concept, and that allowed me to properly wait decision-making factors. When you are afraid of mistakes and failure, you overweight the possibility of failure and you underweight the possibility of success. You think you’re being responsible by avoiding risk. But actually, you’re sacrificing a lot of positive outcomes for yourself and others, which is not what I would call responsible.

Just to give you a mathematical example, let’s say you have a good shot at making $100,000 for your family. Or you can keep $8,000 you have right now. We might think, oh, it’s responsible to just keep the eight you have and not risk it. But is that responsible, especially when you look at repeat opportunities over time? Or is it more responsible to do everything we can to give our family a chance at greater financial success?

We get to decide what words mean. But we associate, for women especially, responsibility with inaction and being risk-averse. When I don’t really think that’s what it means to be responsible in the sense of responsible for living up to your potential, responsible for having opportunities to create more success for yourself, for your loved ones, right? Responsibility can mean responsible with the opportunities you have to take advantage of them.

Third, I actually got much better at making decisions because I was using my critical thinking skills to dissect what had gone wrong previously. So it wasn’t just, oh, I see that in this past mistake I did XYZ and now XYZ is happening again. That was example one, right? I got better at it just because I could see if it was obvious that XYZ was happening again to not make the same decision. But I also just got better at analyzing and using critical thinking. So, in fact, I might see a situation where it wasn’t XYZ, instead, ABC was happening, but I was able to use my critical thinking skills to understand ABC better ahead of time.

This allowed me to get a better handle on my strengths, my weaknesses, how I learn best, what kind of support I need from myself and others to follow through on things, what unknown thoughts and feelings were driving my actions without me being aware. I got practice in logically evaluating potential risks and benefits rather than just acting from emotion. And over time, that literally taught my brain how to make good strategic decisions and make hard calls, which has made me much better as an entrepreneur and a leader. And it’s also made me better in my personal relationships because I see when something’s important or when it’s not. I can see past the emotion or heat of the moment to see whether whatever is happening on the surface is indicative of a true problem or not. When I can solve something in a relationship myself, when it is a dual responsibility to solve, when we need outside support, etc.

This is what I want to teach you how to do today. To understand how to actually make better decisions based on our past mistakes, we have to first understand what impact our mistakes have on our brains and how they impact our decision-making as we move forward from them.

If you think about it from an evolutionary perspective, when we lived as hunter-gatherers, mistakes could be dangerous or even fatal. If you eat a poisonous berry and you’re lucky enough not to die, you better remember which one it is so you don’t eat it again. If you accidentally stumble into a wild animal’s den and get attacked and are lucky enough not to die, you better remember where it was. People who forgot those things and kept making the same mistake were more likely to die without passing on their genes.

Evolution is selecting for people who imprinted strongly on negative experiences and who played it safe when it came to avoiding potential mistakes. That’s one of the hypothesized reasons for why humans have a bias for the negative, right, meaning our brains are naturally wired to retain unpleasant memories and negative experiences more than pleasant memories or happy experiences. When we make mistakes, our brain encodes them as dangerous and potentially even threatening to our survival, even when they really aren’t.

Now, rationally, if we slowed down to learn from our mistakes, that should improve our survival chances, right? But that’s not how our brain works, and I think that this comes down to the difference between primitive survival and the kinds of mistakes we make now. This is just my hypothesis. If you accidentally eat something poisonous or stumble into an animal cave, you don’t need a lot of nuanced analysis to figure out what went wrong. Your brain just needs to encode, “Don’t eat that thing. Don’t go into that cave.” So that’s what was selected for, was just the strong, immediate association of, “ah, danger,” with that thing. But we bring that same avoidance strategy, right, just avoid, to our modern-day mistakes.

If we have made a mistake or believe we’ve made a mistake, and we had negative emotions or felt bad about ourselves or experienced pain or loss, we associate that thing with the threat, and so we just avoid it. If we had a bad relationship or bad breakup, we may just avoid dating, or avoid really investing or really getting intimate. If we failed out of college, we may just avoid going back or avoid any scenario where we’re going to have to learn and demonstrate our learning.

If we spent money on something and then later we told ourselves it wasn’t worth it or that we made a mistake, we may just avoid ever trying that thing again or even just spending money on anything similar again. If we try something, a hobby, a course, an activity, and then we don’t do it forever, or we change our minds, or we aren’t amazing at it right away, and we shame ourselves for that, we may avoid trying new things in the future. In business, if we try a strategy or hire a consultant or invest in an idea that we try to bring to market and it doesn’t work out, and we feel shame and that we failed, we may just avoid taking risks in our business or hiring help in the future.

We’re just operating on this primitive brain understanding that if something hurt in the past, the best course is to simply avoid it now, that’s how we get to safety. And our brains may come up with all sorts of complicated cover stories about this and justifications and tell us we’re being responsible, we’re just taking our time thinking things through, right? We’re just really waiting to feel certain. But most of the time we’re not actually being responsible because we’re not actually analyzing what went wrong to know why things failed in the past so we can improve. That’s what responsible would be, right? We’re just avoiding the trigger altogether.

Like any strategy, this strategy has a benefit, which is we probably won’t make the exact same mistake again if we avoid ever trying the thing again. But it has huge hidden costs because there are so many incredible outcomes in life—relational, experiential, economic, self-development-wise—that we miss out on when we don’t take action because we’re so afraid of making a mistake.

If I had not been willing to try being a life coach, I would never have had this career. If I had not been willing to make investments in training and consultants in my business and programs, even though some of them were flops, I would never have made the amount of money my coaching business has made, which I think at this point is $26 million since we started. If I had not been willing to keep trying to date after a string of failed relationships, I would have never met my husband. If I had not been willing to keep trying to heal my body image, even after missteps and backsliding into diet culture and binging and purging, I would never have reached body and food freedom.

The key, though, is that I was not just taking blind action over and over again, even though it kept not working. I was analyzing my mistakes and failures to see where I went wrong so I could adapt going forward. That’s what I want to explain and teach you how to do after this quick break.

What happens if we experience a mistake or a failure and we are not conscious of our minds and managing our brains is that we just feel shame. So we avoid thinking about it. And then we feel fear anytime in the future we face any kind of decision or opportunity that seems like it could bring up a similar shame if it goes wrong. And we intellectualize this by telling ourselves that we’re being responsible by not taking chances, or that we can’t trust ourselves to make the decision because we’ve made a bad one in the past.

All of this kind of mystifies decisions, failure, and success into something that just happens to us that we don’t control and that we can’t do anything about. And that means we never get any better at making decisions.

If we want to improve at making decisions and be able to trust ourselves to make them, we have to know how to actually learn from them so we can start to develop our own personal criteria or checklist for decision-making. Now, I want to be clear, this doesn’t guarantee that all decisions will be successful, right? Not every decision can be engineered to produce exactly the outcome if you want, if you just do enough self-reflection.

There is a large piece of this that is about risk tolerance, decision-making, managing your mind around failure, and I’ve talked about those elements multiple times on the podcast in other episodes. But it’s also true that if you never actually analyze why you made past decisions and what went wrong, you’re certain to have a higher proportion of failures going forward.

And I count it as a failure if I don’t make a decision out of fear or I don’t take a risk out of fear. I’d much rather try and fail than fail by not trying. I just personally respect myself much more when that’s how I live my life. But no matter how much mind management you’re doing, you can’t absolutely guarantee the outcome of everything. But it is also true that if you try to actually concretely learn from your failures, you will reduce your failure rate and you will make fewer mistakes going forward.

Here are a few questions you can ask yourself when you’re contemplating what went wrong in a past outcome that will allow you to take responsibility for what you contributed and see what you can change going forward. This doesn’t mean you caused everything that happened to you. It just helps you take responsibility for the parts that you can control or impact.

Pick a mistake you’ve made or a decision you regret and ask yourself these questions. First, what were the thought and feelings that led you to take that action? Often when we take an action that doesn’t work out well, we are being motivated by negative emotions and thoughts we aren’t even aware of. Maybe we make an impulsive purchase or investment out of scarcity without running the numbers, with the belief that we’re bad with money or that we need the thing to feel okay about ourselves.

Sometimes we’re settling for a relationship we don’t want or we’re ignoring red flags because we feel pathetic when we’re single, and we fear there’s no one else out there for us, so we overlook all of the signals that were telling us that this wasn’t a good connection. Maybe we’re moving across the country not because we really know we would love living in a new place and have thought about what matters to us in a home, but because we think that if we can just get out of our current town, we will magically feel better, have better friends, be a different person.

In these scenarios and others like them, we are making decisions based on trying to get away from an emotion that we don’t like. This will lead to a much higher failure rate for two reasons. First, you’re not analyzing the pros and cons logically. You’re just trying to get away from a feeling that is probably sending your nervous system into overdrive.

Second, these decisions don’t work. You can’t get away from the feeling. The feeling comes with you. And then as soon as you realize that your feelings didn’t change, you just throw your hands up and give up and call it a failure without trying to see what you could do to improve your situation.

Sometimes we’re trying to change circumstances in order to change our thoughts and feelings when we make a decision, but that doesn’t work. We think if we spend a lot of money on a gym membership, that will motivate us to work out more, right? That will magically overcome the thoughts and feelings that keep us from working out. But of course it doesn’t, and then we tell ourselves that we can’t trust ourselves to invest in our physical health or fitness or any other kind of commitment because we won’t follow through. And we just think that’s a character flaw as opposed to understanding what was actually keeping us from working out, in which case we would understand why, of course, just spending money didn’t resolve it. Or we think if we get divorced, we’ll be magically happy, and then when it doesn’t change our entire emotional state, we think we made a mistake.

It is true, as I have taught on this podcast many times, that regret is created by our thoughts, and no matter what has happened, you can choose how to think about it after the fact, which is very important. But if you look at the thoughts and feelings that preceded decisions that you later regretted, you can also start to discern patterns that tend to drive you personally, specifically, to make decisions that aren’t really aligned with your values or aren’t deeply considered or are coming from an impulsive or compulsive place. You can start to see when you’re making decisions to get away from a feeling or when you’re avoiding making a decision, avoiding taking a risk, settling for the status quo to try to avoid a feeling.

After you’ve identified the thought and feeling that motivated the decision or the multiple thoughts and feelings that motivated the decision, the next question to ask yourself is, what went wrong? And what can I take away from that? Now, when I say what went wrong, I mean in detail.

Let’s take the example of a launch strategy if you have an online business. Just that’s one I’m super familiar with, and I’ll give you another example after this. Let’s say I try a new strategy. I try a new challenge, a new kind of email sequence, whatever. It does not work. It does not sell. People do not convert. It’s not helpful to answer, “What went wrong?” with, “Well, it didn’t sell.” Yeah, okay, right. It didn’t sell. But the point is why? What part did not work? For instance, did people open the emails but not click through to the info page? Did people visit the info page but not check out? I need to really analyze what happened so I can narrow in on what I could have done differently.

Often, we don’t want to think at all about our mistakes or failures because of the shame that we’ve been talking about, so we just ignore it, and then we actually have no idea what actually went wrong. Which means we can’t tell the difference between something that was a complete failure with 0% chance of working that never would have worked, and something that was 95% ready to work and just needed one or two little tweaks. We don’t know the difference because we’re not looking at what actually happened and what actually went wrong.

This is not only for business. Let’s apply this to a very different-seeming scenario, a relationship that didn’t work out. Now, I don’t think a relationship that didn’t work out needs to be called a mistake, right? And what does not work out even mean? Often, relationships are not meant to be forever, and we can always choose to learn and grow from whatever we experienced. But we can also look at what brought us to that relationship and how we operated in it to learn what we might need to do differently in the future to get a different result. That’s actually how we transmute the experience into learning and growth.

If you’re asking yourself these questions about a relationship, for example, answers that aren’t useful would be, “We grew apart,” or, “They were a narcissist.” Even if those things are true, okay, even if they’re true, there are ways that you showed up in the relationship and acted and reacted and thought and felt that drove your behaviors that you may be able to learn from.

For example, if you notice that you were, quote-unquote, growing apart, you had different interests or liked to spend your time differently. How did you react to that? Did you resent it? Did you ignore it? Did you try to get them to spend time with you the way you want, but weren’t willing to spend time the way they want? Or did you go too far in the other direction and you just suppressed everything you cared about and tried to turn yourself into someone who would like what they liked, only to end up feeling alienated anyway?

Maybe what you learned is that you contributed to that distance by wanting them to change to be like you, or maybe what you learned is that you went too far in trying to change to be like them and abandoned yourself, and that’s why you end up feeling unfulfilled. Or if you were willing to change and your partner wasn’t, what was your thought about that? Did you keep trying to change yourself too much because you didn’t believe that you could find a partner who would meet you halfway? Did you participate in your own gaslighting and second-guessing yourself? Was that coming from believing that you couldn’t find another partner, you couldn’t find someone who would treat you any better?

None of this is about blame or shame. It’s just about getting clear on, oh, this red flag came up and I ignored it because this was my thought. Or, oh, I don’t think I ever really felt that connected to this person, but I kept going on dates with them because this was my thought, right? It’s just looking at what was the thought, what was the thought process that drove you to make these decisions, and what actually was the breakdown in the relationship.

Let me give you one more example because people have a lot of past, quote-unquote, mistake drama around money, often. People have this completely unrealistic idea that to be good with money would mean every investment you make works out, you never spend money on something that you end up not using or not finding as valuable as you thought you would or not enjoying. We have this completely unrealistic idea of what it means to be good with money or make good money decisions. It’s perfectionism, right?

I often coach people who are considering making an investment or making a financial decision, but they’re scared to do it because they’ve lost money in a past financial investment, or they bought a house in a neighborhood and then didn’t like it in the end, or they’ve signed up for things and didn’t follow through, or didn’t get the results they wanted, right? Whether that’s a gym membership or an educational degree or a coaching program, whatever. These are people who they’ve made some kind of investment in the past, it didn’t work out the way they wanted it to, and now they feel a lot of shame or they feel defeated.

And so they don’t actually analyze what actually happened. Why did they make that decision? And then once they’d made the decision, what happened in the playing out of the decision? What actually went down? They don’t analyze that. They just start telling themselves that they can’t trust themselves to make decisions anymore. That’s a real problem because, really, listen to me when I say this, if you tell yourself you can’t trust yourself to make decisions, you are fucked. There is no way to build self-trust off of that.

If your thought to yourself is, “I can’t trust myself to make this decision,” whether it’s, “I can’t trust myself to pick the right relationship,” “I can’t trust myself to make this investment decision,” “I can’t trust myself to take this risk in my career,” because I took a risk and it didn’t work out before. I was in a relationship and I missed the bad signs and it ended badly. I made an investment and it lost money. There’s no way to build self-trust off of that. It is a dead end.

If you think you made a mistake and you do no analysis to see what happened and understand it better, why would you ever trust yourself again? In that scenario, you’re just telling yourself that mistakes just happen to you, they can’t be avoided, they can’t be prevented, there’s nothing to learn from them other than you suck at decisions, right? You are telling yourself that decisions are exploding ticking bombs that might go off and that you don’t know which ones are going to blow up. Your brain’s just going to avoid it.

And then you end up sacrificing all of the opportunities you might have to learn new skills, to grow, to evolve, to work in a different way, to have an amazing relationship, to create wealth, whatever it is, because you are just prioritizing avoiding risk instead of prioritizing learning, iterating from mistake and failure and success to get better and better at making investments and decisions or any other big moves in your life.

If you tell yourself you can’t trust yourself to make decisions, you will never feel any differently than that. You cannot build back up to trust from that because you’re not making decisions. You can’t ever accumulate any evidence that you can make decisions. That is the most poisonous thought that people have, “I can’t trust myself to make this decision.” Dead end for your life. Nowhere to go from there.

Whereas if you actually look at what exactly happened, how did I make this decision? What was my thought process? What was motivating me? What emotional need was I trying to meet or what emotion was I trying to get away from? What kind of thoughts, beliefs, premises drove that decision? And then once the decision happened, how did I show up in the aftermath of the decision? What did I do? What kind of questions did I ask? What kind of conversations did I have? What kind of things did I try? How did I react to the results of the decision as they started coming in?

When you look at all that, you will learn something that you can use to inform decision-making going forward. Maybe previously you invested in something when you didn’t totally understand the terms and you just told yourself that you were too dumb to get it or it was overwhelming or these people must know what they’re talking about. If you actually analyze and figure that out, now you’ve learned something. Now you know that you need to ask whatever questions you need to ask to understand something before you invest in it, and you can coach yourself or get coached about your fears of what other people think of you for asking those questions.

Maybe you signed up for something, a gym membership or whatever, because you felt bad about yourself and you just wanted having put the money in to make you do it. But you avoided doing it because you felt bad about yourself, and every time you went to the gym, you felt bad about yourself. Okay, so now you know that you need to make sure that if you do want to get fit and you do want to achieve an athletic goal, whatever, that you can’t just count on investing in the gym. You need to also be working on your self-esteem while you do it, right? You’ve learned something so that you can try again, having solved the flaw in the first attempt.

Whatever it is, if you pay attention to what happened, you can learn from it. If you don’t analyze what happened, you have no idea how to do better in the future. If you do analyze what happened, then you can provide whatever kind of support you need, plug the hole in the plan, fix the problem in the plan, whatever it is, to get a different outcome.

The bottom line is that self-reflection is how you learn from your mistakes so you can make better decisions going forward. And the more you do that, the more you see that failure isn’t fatal, that you can make some mistakes and also some great decisions, and that you get farther in life by being willing to make lots of both of those instead of trying to make only right decisions and therefore taking almost no risks and making almost no decisions.

The answers to these self-reflection questions are going to be very different based on who you are and what decisions you’re thinking about. There isn’t a right answer to any of them. But the more you actually stop and ask and answer those questions and analyze what has happened in the past, the better off you are going to be for approaching your future.

If you’re loving what you’re learning on the podcast, you have got to come check out The Feminist Self-Help Society. It’s our newly revamped community and classroom where you get individual help to better apply these concepts to your life along with a library of next level blow your mind coaching tools and concepts that I just can’t fit in a podcast episode. It’s also where you can hang out, get coached and nerd out about all things thought work and feminist mindset with other podcast listeners just like you and me.

It’s my favorite place on Earth and it will change your life, I guarantee it. Come join us at www.unfuckyourbrain.com/society. I can’t wait to see you there.