This week, I’m bringing you a replay episode of a tool that I have used to accomplish amazing things in my life. Whether you identify as a perfectionist or swing the opposite way where you’ve never really dreamt of a bigger future for yourself, this concept of setting and achieving impossible goals is going to be a complete game-changer. 

If you have been socialized as a woman, you likely tragically underestimate what you’re capable of achieving and creating. We’ve absorbed so much about knowing our limitations and not wanting or having too much, so there’s truly nothing more fun than using the concept of impossible goals to expand your vision of what’s possible for you.

Listen in this week as I give you the framework for setting and achieving impossible goals. I’m laying out the pitfalls we want to avoid when using this tool, why this can be such a tricky concept for perfectionists, and the guiding questions to ask yourself when implementing it so you’re not doomed before you even start.

Clutch College Live is launching today! If you’ve been waiting for a reason to join The Clutch, this is your sign. Click here to join to have a chance to grab the last few spots at Clutch College, or text your email address to +1-347-934-8861 and we will text you right back with a link to all the information you need! 

What You’ll Learn From This Episode:

  • The pitfalls we want to avoid when it comes to setting impossible goals. 
  • Who this concept can be so revelatory for. 
  • How the idea of an impossible goal can fall apart for perfectionists. 
  • What an impossible goal is and how to set it in a way that serves you. 
  • 2 things perfectionists need to consider when setting an impossible goal. 
  • The difference between an impossible goal and a perfectionist fantasy. 

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

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

My Clutch chickens, listen up. We are launching Clutch College Live today. If you are listening to this podcast in the morning Eastern time, it hasn’t happened yet. You still have a chance to come to the webinar and learn all about goal setting and Clutch College Live.

If you are listening after about midday on this Thursday that this podcast is released, don’t worry. I’m sure there are still a few spots left. If you log into the membership site and go to Clutch College on the left-hand side, you will see all the information.

I am so excited for this Clutch College. We are going to be talking all about how to set big, juicy, audacious, impossible goals. And since we are Clutch chickens, we are going to talk about how to make sure that they are not perfectionist fantasies that you will fall off the wagon or never start.

So I cannot wait. We have done single-day parts of other Clutch Colleges in this, but we have never spent three whole days really digging in to how to set and achieve big goals and how to plan for them. A lot of us are good at making concrete plans for the how, the steps we need to take, but we don’t plan for the mental and emotional challenges that come with setting and achieving a big goal, and that’s really what knocks people off their game.

So this is obviously teaching that I have used in my own life and I cannot wait to really dig into it with every single one of you who attends Clutch College and really make sure that you have an awesome, mind-blowing goal in place and an action and a thought plan when you leave.

So if you’re in The Clutch, go check it out. These events usually sell out in a day or two. So if you are at all interested, you need to go hurry over there now. If you are not in The Clutch but this sounds like exactly what you need, we do allow you to sign up the same day you join The Clutch if there’s spots left.

So you can go to You can join The Clutch, and then you will be able to see in the membership site the information about Clutch College. So excited, cannot wait to set some big, amazing, mind-blowing, life-changing goals with those of you who attend.

Today I want to talk to you about the idea of an impossible goal. So this is a concept I learned from my teacher, Brooke Castillo, and I don’t know where she got it. She learned it from someone else or she made it up herself, but that’s where I learned it. And it’s a tool or an exercise, whatever you want to call it, that a lot of coaches trained by The Life Coach School where I was trained teach.

But I actually usually don’t teach this goal that often and I’m going to explain why before I do teach you about it. So even if you’ve learned this tool somewhere else, if you’ve ever had trouble with it or found it challenging, or if you’re a coach and you teach it to your clients, I recommend that you listen to this.

Of course, if you’ve never heard of this, definitely listen. But even if you think you know what it is, I teach it a little bit differently. So I think this is an amazing tool. I have used it to accomplish amazing things in my life. I also think it’s a tool that can be tricky for perfectionists, and most of my listeners and students are perfectionists.

If you’re new to the podcast, perfectionism does not mean you’re actually perfect. That’s what we think it means, that we actually do things perfectly. That’s not what it means. What it means is that you think you should be perfect. It means you think you’re never good enough and you’ve never done a good enough job and anything you’ve done, it could have and should have been better. That’s what being a perfectionist is. And so most of you are in that category.

And I haven’t taught it until now on the podcast because I try not to teach this tool too early to people who are not really ready for it and are going to misuse it against themselves or who are going to just suck it into their perfectionism.

And I’m going to explain what I mean in a minute, but it’s like I imagine the cyclone of the perfectionism, this tool just gets sucked up into that and it never really gets understood or used because it just becomes one more way to set impossible fantasy goals and never live up to them and then beat yourself up about that.

So if you’re new to the podcast, you can totally listen to this episode, but then I really want you to go listen to the episode on perfectionist fantasies right after, and that’s in the title. It’s Perfectionist Fantasies and Tomorrow Thinking.

Because here is the pitfall we want to avoid. An impossible goal is basically a big goal you set that you don’t think you can accomplish. And I’m going to get into a lot more how and why we would do that, but just for this beginning part, it’s a big goal you don’t think you can accomplish. You think it’s impossible.

So here’s the thing; I think this tool can be revelatory in the first instance, like without any nuance, for people who just have never set goals for themselves. There are a lot of people in the world who because of whatever, how they were raised, what they were taught was possible for them, what they saw around them, they’ve just never really tried to do anything big or change something in their lives.

For people who don’t have big dreams or who tend to just really operate in the day to day and people who’ve never really thought about their future, who don’t really – who just are like, I just go through my life and whatever happens happens, and life happens to me and I don’t give a lot of thought to where I’m going to be in five years, or 10 years, or what I want to accomplish. Life if just whatever happens to you.

For people who are in that mindset, and that’s not bad or good, it’s not better or worse than being a perfectionist. It’s just different. I’ve coached people who are like this, I have friends and employees and people who are like this. None of these are better or worse than the others. It’s just a different way of thinking.

So for people who are in that kind of mindset, setting an impossible goal can really be mind-blowing because they’ve never really thought about who they want to be or what they want to do in the future. They’re not very future-oriented, people like that. They aren’t future thinking.

So adding future thinking as a skill, as a tool blows their minds and changes their whole life. Or people who maybe have sort of thought about the future or wanted to, but don’t believe they’re capable of achieving something, and so they’ve never really even declared to themselves that they’re going to try.

The problem is that for perfectionists, we have the opposite problem. A perfectionist doesn’t have the problem of never thinking about the future. The problem with the perfectionist mind is that it’s constantly thinking about the future and how perfect the future’s going to be, how one day we are magically going to become this perfect version of ourselves, and that our lives will finally be amazing and wonderful and we’ll always feel great because we’re finally perfect.

Perfectionists live in the future all the time in our minds. So perfectionists are actually constantly setting impossible goals. Like I want to weigh half of what I weigh now, or everyone needs to like me at all times, or I’m going to vow to never yell at my kids again, or I’m going to set up this complicated morning routine and then I’m going to do it perfectly so that I always feel great and I never feel bad again.

Perfectionists are constantly thinking about the future and coming up with fantasies about how to do things perfectly in the future so they can finally be good enough. And I think that sometimes the way that impossible goals is taught as a concept doesn’t make this crucial distinction.

And so what happens is that perfectionists just kind of end up absorbing the idea, mis-absorbing it, it’s like an amoeba that eats another amoeba. Just suck it into what they’re already doing. So they just take whatever self-improvement perfectionist fantasy they already had that they’d been vowing to do forever and thinking they need to do to be good enough and imagining being perfect at and never actually doing, they just make that fantasy their impossible goal.

So somebody who has a weight loss fantasy their whole life and has never lost the weight but is constantly thinking about how they’re going to start tomorrow or on Monday or in January and then they’re going to lose weight and then everything will be perfect and they will always feel confident and everyone will love them and life will be amazing, the person who’s been vowing that to themselves for 20 years, they learn about impossible goals as a concept and they’re like, great, my impossible goal is to lose the weight.

Nothing has changed here. When you do that, nothing has been learned. You just take your perfectionist fantasy you already had, you slap a sticker called impossible goal on it, you still don’t achieve it because you haven’t changed your thought patterns, and then you feel shitty about yourself just like you did for all the other years when you just called it a regular goal.

So if you’re a perfectionist, meaning you often set goals for yourself that you can’t achieve, that hinge around you doing something perfectly to finally feel good enough, you have to be very careful with setting an impossible goal to make sure you’re doing it in a way that serves you.

So let’s get down to business. What is an impossible goal and how do you set it in a way that serves you? An impossible goal, like I said at the beginning, is just a goal that you want to achieve that seems impossible to you.

But especially if you’re a perfectionist, you need to make sure you understand two things. Don’t just pick a goal and run with it. You need to make sure you understand number one, why do you want this goal? Why did we pick this goal? And number two, why do you think it’s impossible?

If either of the answers to these questions – and I’m going to give you an example in a minute, but I just want to give you the framework. You have to understand why you want the goal and why you think it’s impossible. And if either of those answers has to do with your own self-worth or your own lovability, you’re setting yourself up to fail and it’s really more of a perfectionist fantasy.

An impossible goal should not be a goal that you set because you think once you have or can do whatever the thing is, once you’ve achieved the goal, you will finally prove something about yourself, or you will finally feel good about yourself, or you will finally be worthy.

An impossible goal cannot be tied to your worthiness. If you tie it to your worthiness, you are dooming yourself before you even start. When you make your worth conditional on achieving any goal, whether you label it impossible or not, you make it impossible to achieve the goal, and not in a good way.

Because you have now put so much weight on the goal that any failure on the process becomes excruciating. When you make your worth conditional on whether you can achieve a goal, any failure in the process of achieving the goal means to you that you are not worthy and you may never be worthy, and that is excruciating.

And any big goal does require failure along the way. That’s one of the big differences between a real impossible goal and a perfectionist fantasy. In a perfectionist fantasy, you never think about failing. It’s just oh, on Monday I’m going to be a completely different person who can magically do it perfectly.

When you really set an impossible goal, you know there’s going to be so much failure along the way. And if you’ve made your worthiness part of it, you are guaranteeing that you will feel terrible and suffer so much and probably quit because it’ll be just too painful.

Similarly, if you think a goal is impossible because you believe you aren’t good enough to do it or not worthy enough to have it, then again, your motivation for doing it is to prove to yourself that you’re worthy. So I said there were two questions. Why do you want it? If you want it so you can finally feel good about yourself, then you’ve tied your worthiness in it.

And I said you need to ask yourself why do you think it’s impossible. If your answer to that is because you aren’t good enough to do it or not worthy enough to have it, then again, you’ve got your worthiness all mixed up in it.

So those two questions can kind of collapse into each other. Why you think it’s impossible or why you want the goal, but that’s fine. If the answer to either one or both has to do with you finally feeling good enough, you’re coming at this from a perfectionist point of view. It’s not going to work. And in that case, you really are just having a perfectionist fantasy and you need to listen to the whole episode I did on those and how to handle them.

So what are some examples of good answers to one and two when you’re setting an impossible goal? What would a kind of – I don’t really use the word healthy because I think it means so many different things to different people and it becomes its own kind of perfectionism.

But what are kind of reasons that set you up to have a useful experience when you’re picking an impossible goal? And why should we do this at all if it’s so fraught and complicated and easy to fuck it up for ourselves?

The reason to set an impossible goal is to blow your own mind with what you can accomplish and who you can become in doing that. It’s not to finally be good enough or worthy. And it’s not to obtain an outcome. If you’ve achieved a goal, that achievement becomes the new circumstance. If my goal is to run a marathon, once it’s over, it becomes a circumstance that I am someone who ran a marathon. That’s a fact now.

We don’t set an impossible goal to get an outcome, to create a new circumstance because we think it’ll make us happy. Circumstances don’t make us happy. Running marathons is not what makes us proud of ourselves. Getting married is not what makes us feel loved and good enough. Circumstances don’t cause our feelings.

The reason to set an impossible goal is because the most fun thing about being a human is doing something you didn’t think you were capable of and expanding your vision of what is possible for you. That is, if not the most fun thing, one of the most fun things.

Most of us drastically tragically underestimate what we are capable of achieving or creating. Because we are mostly being driven by our unconscious thoughts. And we’ve absorbed so much socialization from our families, our teachers, our friends, popular culture, society, especially for women.

We’ve absorbed so many messages about knowing our own limitations and not getting too big for our bridges and not wanting too much and not having too much and not thinking we’re special and not standing out and not making a scene and not thinking too highly of ourselves. And we’ve been raised with ideas of what we are or aren’t good at, which often have literally nothing to do with what we actually could be good at or not.

So to give you my kind of example, the story in my family growing up was always that I was bad with money. And now I’ve created six million dollars total in revenue in my first ever business, in its first five years, with a very healthy profit margin and very healthy taxes that I pay.

So possibly, I’m not actually bad with money. Turns out that might have been a story about me that wasn’t true. But the only reason we know that is because I set the impossible goal of making a million dollars in revenue in one year in my business.

And that wasn’t my first impossible goal. My first impossible goal was to make $100,000 in revenue in one year in my business. That didn’t seem possible to me when I was starting out. But then I did that twice over in my second year, and then I set the next impossible goal.

And now, making a million dollars in revenue a year is easy to me. Making several is. So I have to set a new impossible goal. Your impossible goal absolutely doesn’t have to be money related. But my first ones were because that’s where I was in my life and my business when I learned about this concept and that’s what seemed truly impossible.

I had always believed that I would be successful professionally in some way. I had tons of imposter syndrome still, but I believed that I would have a career. That didn’t seem crazy to me. But I had such a strong story that I was bad with money and that I was kind of spent frivolously and I was – whatever the opposite of thrifty is, profligate. And that I didn’t know how to make money.

And so to me, the idea that I would be able to make money and not just enough to basically live on but actually create an enormous amount of revenue, and then to be able to create all of the work in the world that that allows, to have a business and run a business and be able to employ women and give them amazing jobs making change in the world that pay well and have benefits, and to be able to reach all the students that I can reach, all of that seemed impossible, but the money was the concrete thing that seemed impossible.

And again, that has nothing to do with money itself. It’s just a function of where I was. I think if I had – I did most of my body image work, the real bulk of it before I trained as a coach. I was using thought work, but it was before I got certified. And I think if I’d known about impossible goals back then, the idea of not binging and purging and being done with that forever, that would have seemed impossible.

That probably would have been an impossible goal for me to set. When I was in that life, that was just something I had been doing forever, for 20 years. It seemed impossible. The frequency varied and after a height of disordered eating in my college years and early 20s, it had kind of slowed down. So it was in a fucked up way kind of sustainable.

It was not causing me major health problems; I probably could have kept going like that forever. And when I think about what it was like to be living in that mind, where this just seemed like something that was impossible to stop, I think that would have been an impossible goal. So stopping that behavior would have been an amazing impossible goal. Not trying to lose weight and loving my body.

Loving my body without losing weight, that would have seemed like an impossible goal. Any of those could have been my impossible goals. I just didn’t happen to know this concept at the time that I was working on those things.

So it does not at all have to do with money or business or your professional life. It can be anything in your life. Just because of where I was when I got certified as a coach and when I really learned this tool, those financial goals in my business were what seemed impossible.

Because I didn’t believe that I was the kind of person who could do that. That’s what is mind-blowing about an impossible goal. It’s not just like, oh, well I don’t know the how of making a million dollars, I don’t know which buttons to press, but when I figure that out it’ll be fine. It was my identity.

Like my identity was as someone who was bad with money and didn’t know how to make money. So the idea that I could become someone who could create a million dollars in revenue in a business in a year seemed impossible. That’s what made it an impossible goal.

And it’s important to know why you want to achieve it and why you don’t believe you can. So let’s use that example. Setting the impossible goal of making a million dollars in a coaching business or making $100,000 in a coaching business or making $20,000 in a coaching business is not a good idea if the reason you want it is because you think that once you make a million dollars, you’ll finally feel like you’re a good coach.

Or that once you make a million dollars, you’ll finally feel like you’re good enough to success, or once you make a million dollars, you’ll finally feel like you’re as good as your older brother who has an MBA. Whatever it is. That’s not my story. I don’t have a brother with an MBA.

None of those are good reasons because those are all about believing that you’re worthwhile, believing that you’re good enough, believing that you have to catch up to someone else or you have to manifest something outside of yourself in order to believe in your own potential.

That’s backwards. You cannot achieve an impossible goal to make yourself believe in yourself. I’m going to say that again. You cannot achieve an impossible goal or any goal in order to make your brain believe in you, to make yourself believe in yourself, to give yourself evidence that you’re worth believing it. It has to be the other way around. You have to believe in yourself first.

The good reason to set an impossible goal is honestly almost always the same, regardless of the goal. It’s that you don’t believe you can do it, and it would blow your mind in an awesome way if you did, or you’re curious to find out who are you going to have to become and how are you going to have to evolve, or you’re just curious to experience it. What is it like to be that person?

And similarly, you have to ask yourself why you find the goal impossible right now. If your answer is I’m not good enough, I’m not a good coach unless I make this amount of money, it’s going to be an uphill battle because you’re trying to achieve the goal in order to feel okay about yourself.

Or if your answer is well, if I make a certain amount of money then I’ll never have to worry about money again and I’ll be happy, or if your answer is well, if I can change my body this way, then I’ll always feel good and confident about my body.

Those are not good reasons because you’re wanting a change in circumstance to create an emotional state and that isn’t how it works. And you’re never going to get there thinking that way because along the way, you’re going to feel terrible. And then you’re going to be like, well, why should I bother? The whole point of this goal was to feel good and I don’t feel good now, so I’m just going to quit.

That’s not how it works. But let’s take my example. The reason I thought it was impossible was my thoughts about money are that I’m not good at making money. Now, that is sort of a negative thought about myself, and so we have to be really clear. I’m not saying you can’t set an impossible goal that has to do with limiting beliefs about yourself.

Every impossible goal involves limiting beliefs about yourself, otherwise, you’d already believe you could do it and it wouldn’t seem impossible. And some people might have self-worth tied up in that. So some people’s thought might have been, “I’m not good at making money and that means I’m not worthy.” And then that would be a problem for this project, right?

But I did not have my self-worth tied up in it. I thought I was bad at making money the same that I would say I was bad at tango dancing. It was just a statement of fact. It was limiting my life in that it was keeping me from creating wealth and creating the impact of this business, and just like thinking I’m bad at tango keeps me from spending time dancing tango, it was having an effect on me, but I didn’t think it meant I wasn’t a worthy person.

In fact, ironically, like many of you, I had a lot of thought about people who were good at making money being bad people. So it was almost a badge of honor. In my mind, it was like, well, people who want to make money and are good at making money, that’s suspect. Those are bad people. So when I say I’m bad at making money, that’s kind of awesome about me.

That’s how my thoughts were all tangled up. Now, I could have gone through my life with that thought process just fine if I’d stuck with being a public interest lawyer or an academic, but then I went and quit the law and became a life coach and started a business, so it was not a helpful set of thoughts to have if I was trying to run a business.

So you see what I’m saying. I was not thinking I’m bad with money and so I’m not worthy and I need to make this money to prove my worth. In fact, it was kind of the opposite. I had my worth tied up in the idea that I don’t really care about the money, I don’t want to make money.

And so my reason for setting that impossible goal was to really challenge myself. I really wanted to blow my own mind with how wrong I was about what I was capable of. I came to this point of being like, you know what, let’s see if I can, and then I can decide if I want to believe it’s a bad thing to do.

But coming at it from this place of just assuming that it’s bad and I can’t, I’m not learning anything or growing. I really wanted to experience that shift in identity and self-conception. Like, what is it like to go from being someone who believes she can’t make money and isn’t good at making money, and takes some pride in that in a way, to being someone who can make a million dollars in a year as a life coach?

What is that journey? How did my conception of myself have to change? How did my thinking have to change? What kind of negative emotions and discomfort and cognitive dissonance did I have to be willing to feel and work through to make that shift?

That is what I was interested in. I was interested in proving my own thoughts about my limitations wrong. I was not interested in proving my worth. I did not believe that how much money I made had anything to do with my worth. I struggle with my own thoughts about my worth in my human brain in other areas of my life where I have to be careful about this with my impossible goals, but not in money, which is why I was able to do it so relatively quickly. Because I didn’t have my worth tied up in it.

Any time that you are tying your worth up with a goal, you are sort of fetishizing the goal. Any time you set an impossible goal and you’re really fixated on the goal itself and you think it really matters if you hit the goal, you’re setting yourself up to fail.

We call it impossible because – or at least I do, because it truly doesn’t matter if you meet it or not. That’s the paradox. You want it to matter a lot in the sense that you want to take it seriously and do everything you can, and it doesn’t matter at all if you ever actually get there.

Because the point of setting an impossible goal isn’t the goal at all. It’s the journey. It’s who you have to become on your way to trying to achieve that goal. So I fought with my teacher Brooke a lot about this when I first learned it. I was very upset about this idea.

This was way before we got to my money stuff. This was like, in the first day of certification probably. And so this was the example I kept using that I was so mad about was I was like, what if I decide that my impossible goal is to play for the women’s NBA team or the WNBA, I guess it is.

Like from my perspective then, I was like, this is a slam-dunk argument. This is – why would that be useful or a good idea? That would be a ridiculous waste of time, it would never happen, it’s obviously impossible, this is such a stupid idea.

I’m 5’2, I’m not athletic, I have no basketball experience. But here’s what I’ve learned because my teacher was patient with me, and here’s how I think about it now. Let’s say I set that goal. What would I have to learn to try to reach that goal? Who would I have to become?

As somebody who hates sports and doesn’t think she’s naturally athletic, doesn’t think she has any sports talent, doesn’t think she enjoys exercise. I enjoy lifting and I like dancing and walking, you know, sometimes I run even though I hate it because I sort of love to hate it. But I’m not someone who says about herself, “I just love vigorous, strenuous exercise.”

So who would I have to become? So much about me would have to change. My lifestyle, my skills, my habits, my thinking, it would be a wild, incredible journey. You could imagine the book I would write at the end of it, even though I probably would never make the WNBA team. If I truly embrace that goal, I would become an entirely different person.

Now, in some ways, this is a red herring because the truth is, I don’t think we ever set impossible goals that are things we don’t really want. I would never set an impossible goal to play for the NBA, the WNBA, because I don’t actually want that.

So it’s not even really an issue. But I just share it to show you that even going to the extreme, even being like, what if I set this impossible goal that truly is impossible, I’m 39 and a life coach and I’m going to become an astronaut. The question isn’t like, well could you ever actually become an astronaut? The question is like, how much would your life change and your thought process about yourself change if you took that seriously and did everything you could do?

For me, I would have to believe I was amazing at science and also get in incredible physical shape. I would have to learn so much, I would have to change how I think about myself. Everything would change. The point is the journey always. What are you going to learn along the way? Who are you going to have to become?

I want you to consider setting an impossible goal for yourself. Not because you need to achieve something else to be worthy. Your impossible goal could be napping every day for a year if you’re someone who struggles to rest. It’s not about doing.

Not because you aren’t good enough the way you are. Not because getting the thing or doing the thing will make you happy or change your feelings. It is a terrible idea to set an impossible goal thinking that you’ll feel good when you get there because going after an impossible goal involves feeling terrible.

You have to have a lot of negative emotion. You’re changing your whole identity and challenging all these beliefs and sucking and failing all the time. You have to learn how to process that and move through it and act despite it and keep going.

So if you pick something because you think getting that’s supposed to make you happy, there’s no way you’re going to stick with it because it’s going to be so uncomfortable along the way. You have to pick something that inspires you, something that seems insane and impossible, something that would blow your mind. Who do you have to become? That’s the point.

If you’re loving what you’re learning in the podcast, you have got to come check out The Clutch. The Clutch is the podcast community for all things Unfuck Your Brain. It’s where you can get individual help applying the concepts to your own life.

It’s where you can learn new coaching tools not shared on the podcast that will blow your mind even more. And it’s where you can hang out and connect over all things thought work with other podcast chickens 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 That’s I can’t wait to see you there.

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