You’re Not Broken — Success Is What’s Keeping You Empty

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Why Do the Most Successful People Often Feel the Most Unsatisfied?

Today, we’re going to have a look at why even successful CEOs, C-suite, and top leaders feel unhappy—and look at something called imposter syndrome and the paradox of success.

I’ve been coaching high achievers since 2013, and I’ve noticed trends where people who are often successful by everybody else’s standards are also often miserable. Why does high achievement negatively correlate with satisfaction and enjoyment of life?

I’ll start by sharing a story about one of my clients, Lynn, who has basically crushed it since she was a teen. She has come from a difficult home environment, and she took that as motivation and ambition to get out on her own, to be independent, to never be controlled by anyone.

And so she went out there and she crushed it, job after job. She climbed the ladder. She just got better and better at what she did. She got more and more responsibility, and of course got paid more.

It seems like every time one door closed, 20 other doors opened. She’s just kept doing better and better, and yet still she feels not good enough. Still she feels like she’s an imposter—that she’s going to be found out as being a fraud who isn’t really deserving of the success she’s had. She’s hyper-focused on her failures and weaknesses, completely dismissing or overlooking the massive achievements she’s made over decades.

So there’s a core contradiction there: achievement increases, fulfillment decreases.

Now, a lot of people who haven’t achieved highly don’t believe in this. They would mock people who would complain about being successful because they just don’t understand that the more you get, the hungrier you get. It actually gets less satisfying as you achieve more.

The Chasing Problem: “It’s Chasing That Causes the Need to Chase”

Think about money. Who do you think is more insecure and more needy about money: The guy with a stable income that doesn’t change, or the guy who keeps making more money over time?

Again your logic would tell you that the guy with the stable income would be needier for money, but actually he barely thinks about money. He’s gotten into a status quo, a plateau where everything’s just the same. Every month he doesn’t need to think about it.

But the guy who keeps adding zeros to his paycheck is constantly trying to figure out how to add more zeros. He’s actually needier, more insecure about his finances than the guy who hasn’t had a pay rise in years.

One of the most fascinating things about human psychology that I’ve ever discovered is: it’s chasing that causes the need to chase.

It was first made aware to me when I was trying to quit smoking, when somebody pointed out that my need for a cigarette was caused by my previous cigarette. If we go all the way back through the chain to before my first cigarette, there was no need. There was peer pressure and wanting to be cool and all that, but the actual need for a cigarette didn’t exist until after I’d had one, and that the need I had was from the one I’d previously had.

It became so much easier to quit because I realized it’s not the next one that’s going to satisfy me—the next one is going to cause the need for the one after that.

This applies to money, working out, eating, all these things. The need you feel was caused by the last time you chased the need. The last time you tried to fulfill it is the reason you feel hungry now.

LinkedIn, Performance, and the “I’m Okay” Mask

Now, of all the social media platforms, I think LinkedIn is by far the cringiest from my point of view. When I’m focused on integrity and honesty, that’s got to be the most dishonest platform of all of them, by far. It’s not even close.

I’m not even sure who these LinkedIn posts are for—who’s reading them and thinking, “Well, that was great that I read that.?” I mean, people are liking and commenting, “Congrats on your new job,” and all that. But when I read the post, it’s just nonsense.

Now, who’s behind those posts? Bad people? No.

Behind those posts are people who are desperately seeking the next win, and they need to project an air of confidence and success, because if you saw how they really felt, you would pity them.

They’re burned out. They feel empty. They have chronic dissatisfaction—a growing sense of dread that there is no way to be satisfied; that the more they achieve, the more they become aware that this isn’t working, and yet they can’t think of anything else to do. They’re compulsively achieving.

The more ostensibly happy someone appears on the outside, the more unhappy they are on the inside. Now there’ll be exceptions to that rule, but I did see some research that showed that the more frequently a couple posts about themselves on Facebook, the more likely they are to break up.

The more someone tries to project an image that things are going well—and you see this on LinkedIn all the time, these people try to push this image out, like, “Look how well I’m doing. I’m okay.”—the more they do that, the more I’m like, “Damn bro, you ain’t well.”

Because I work with these people. I know what’s happening behind the scenes. I know what’s behind those posts.

It’s really fascinating for me to work with a C-suite executive, somebody who’s high up in the corporate ladder, and as I’m working with them, I’m also watching their LinkedIn feed and I’m like, “Dude, what’s going on?” Because that person on LinkedIn is not the person I’m talking to every week who’s barely holding it together.

The Real Fix: The Beliefs That Make Success Feel Miserable

So let’s look at my little thesis on how to deal with this.

How is it that a high achiever can actually enjoy their life rather than getting more miserable the more they achieve?

Well, it really comes down to a lot of inner distortions—belief issues, limiting beliefs, if you want to call them—that quietly undermine your enjoyment of success. An operating system that actually makes it impossible to enjoy your life when you’re trying to achieve things, even though the whole time it’s telling you that trying to achieve things is how you’ll enjoy your life.

There are some key beliefs that you’ll need to tackle.

The belief that more is better

The quantitative belief that always chasing the next shiny object, the next win, the next finish line, the next accolade, the next pay rise—that that’s always going to be something that makes your life better.

If you just stop and look for a second, you’ll see it’s not true. I’m not moralizing here. I’ve got nothing against people doing well, but you’ll see that more does not create higher quality of inner being. In fact, it seems to correlate with the opposite. The more you get, the less able you are to be satisfied.

So there’s a belief problem there: that more is better, when maybe something else is better.

The finish line fallacy

Another belief I call the finish line fallacy: this vague sense that if I can just do enough—whatever the hell that is—I will cross this kind of finish line and all my suffering will finally end.

Jim Carrey does a great little speech about this, after being introduced as a two-time Golden Globe winner, where he says, “I dream about being three-time Golden Globe-winning actor Jim Carrey, because then I would be enough. It would finally be true, and I could stop this… terrible search.”

This idea that if you almost feel like you’re satisfied—almost feel like you’re good enough—then maybe the next thing is what will get you over the line, rather than realizing there is no line. There’s no place where you are satisfied. The human brain cannot be permanently satisfied.

So constant achievements actually erode your ability to be content.

The fear of happiness (cherophobia)

The fear of happiness—cherophobia, as it’s known.

A lot of high achievers are driven by an actual fear that enjoying yourself too much will cause some kind of disaster to come your way, like you’re tempting fate. This idea that it’ll all be taken away if you sit still and relax and enjoy yourself. That you must always be stressed, always be moving on to the next goal, never really sitting around and smelling the roses.

Basically, this idea that if you’re happy, you’ll be punished.

Real vs imagined danger

The distortion between real and imagined danger—not knowing the difference between something that’s an actual threat that you can see and measure and verify versus one you made up in your head and get anxious about, even though statistically it’s very unlikely.

Quite often, overachievers are trying to prevent all sorts of anticipated imagined disasters from happening, and none of them are really ever going to come true. And even if they did come true, they wouldn’t even be that bad.

Emotional attachment to outcomes

And of course, what I simply call emotional attachment to outcomes: having your sense of worth and your sense of quality of life attached to things you don’t actually control that much, but you have some influence on—like how much money you make, who likes you, how much status you have, or how well the project went.

All these things somebody else could ruin for you, they’re not entirely under your control—that your whole sense of who you are as a person, your identity, your worth, is all attached to it going well.

This is a recipe for disaster, no matter how competent you are.

So if you want to be successful and enjoy your life, you’re going to have to tackle your beliefs about what it actually means to be successful, and have a deep, dark, honest look at why you feel so motivated to achieve so highly all the time.

Cherophobia in Real Life: The “If I Relax, Fate Will Crush Me” Pattern

What if the reason that you’re unable to enjoy your success is because you have a secret fear of being happy?

I’ve been coaching people for a long time, and this is one of the hardest belief shifts they ever have to make, because everyone seems to truly believe they are trying to be happy.

The idea that they might actually be trying to prevent happiness seems so ridiculous that they’ve never considered it, and yet it perfectly explains their patterns of behavior.

So we’re going to have a look at this weird belief, this weird fear, and try to figure out: why is it that people achieve to keep themselves unhappy?

Now, this one applies to nearly every client I’ve ever had, but I want to tell you about one called Andy.

If you met him and heard about his life circumstances, you would probably be jealous. He’s in the top 1% of pretty much every category there is: financially; he’s got a wonderful family; he’s in fantastic physical shape; he’s an endurance athlete. There is pretty much nothing this guy doesn’t have. He’s living the dream.

But if you knew what it was like inside his brain, you would be shocked at how unhappy he is. He’s ticked all the boxes you’re supposed to tick, and yet he spends a vast majority of his time—or at least before working with me, he did—feeling incredibly anxious and catastrophizing disasters in his imagination.

So let’s have a look at what’s going on in Andy’s mind that stops him from enjoying doing everything right.

Just recently, I came across a term that finally defines something I’ve known about for decades, which is cherophobia.

Short version: the fear of being happy, being content—an aversion to anything that might lead to you enjoying yourself.

People who have this tend to behave in a way that actually prevents long-term happiness or pleasure or celebration. While it might look like they’re striving to succeed and make their life better, if you look closely—especially at their micro behaviors—they really don’t let themselves actually have any fun.

Most of my clients describe it as a sense of fate. This idea that there are scales of judgment out there, and if you enjoy yourself too much—if you get too far ahead of yourself, get too complacent with how well things are going—there will be a reckoning. A balancing act, where everything will be taken away, and you’ll be severely harmed in some vague way.

A sense that so long as you’re stressed and worrying and not really enjoying your achievements, you’ll be allowed to keep them. But if you chill out and go, “I’m crushing it. I’m a really good person,” God or fate or something will look at that and say, “Right, this guy needs some humbling. I’m going to crush him.”

Generally, that’s what they have in common: this idea that they’re being judged, there is some sort of karma out there, you can’t enjoy yourself too much, and the punishment for enjoying yourself too much is it will all be taken away—whatever that means.

This leads them to basically really never feel enough. They set up systems where they’re never good enough. They always have to keep moving. They can’t stop and chill out. Nothing’s ever finished. No achievement is high enough. There’s always a sense of lack.

And they actually prefer having that sense of lack. They get anxious and worried when there’s nothing to do and things are going well and everything’s on point. They will self-sabotage to create new problems just to get rid of the unease of everything going so well.

This is one of the reasons they’re so successful, and why they achieve so much: they’re constantly solving problems. They don’t let anything get carried away, because what happens to high achievers when things start going well? They get paranoid and suspicious—just a sense that this ain’t right, something bad is going to happen.

They feel very reluctant to enjoy anything or accept accolades. They’re resistant to compliments and praise. They push back on these things. They can accept those things and they can occasionally enjoy themselves, sure, so long as they know there are problems still unfixed—so long as they can play false-humble or self-deprecating in a way that balances it out.

But they can’t just keep cruising and enjoy themselves. They can’t acknowledge that they are crushing it and doing really well consistently over time, and they’re a great person. They would feel like that’s too much of a provocation—it’s going to lead to some sort of disaster.

Essentially, this is a superstitious belief, which is quite ironic, because high achievers are quite rational, creative people. They’re usually good at solving problems in a way that actually solves the problem. Otherwise they wouldn’t be so successful.

But then they have these weird superstitious beliefs like, “If things get good, something bad must follow.” The idea that the universe is wired in some way to balance things out. There’s zero evidence for this whatsoever, but they believe it very strongly.

I think it comes from childhood conditioning—they’re raised in such a way where this was true. Anything good was followed by bad, so it usually meant that good and bad were actually the same thing.

For example, if you succeeded, you’d still get punished for the success. Let’s say a child wins the race. If they’ve got hyper-critical pressure-parents, then the parent might say, “Well, you didn’t win it by much, and so that wasn’t really a win.”

They actually got criticism for the win, but of course they’d get a much more brutal criticism if they lost the race. So they’re stuck in this rock-and-a-hard-place situation where they have to win, but it’s not going to feel like a win.

I see this even in general culture-norms. Like when I came to the Czech Republic, if you’re talking to someone, the first question is, “Are you married yet?” So that’s the first achievement you’ve got.

So you think, “Okay, I’ll go get married.” Then on your wedding day, they’ll ask, “So when are you going to have a kid?” You’re still not finished!

And on the day that you give birth to your first kid, they’ll say, “Are you thinking about a second kid?” And this shit just never ends.

There is no accomplishment that satisfies anyone for more than a couple of hours before you get this criticism disguised as curiosity or caring: the sense that you lack something, that you failed.

So success and failure become combined as a single thing. You can’t have one without the other. But you can also still have total failure without any success. So your choice is really: do I have a win-fail, or a fail-fail? It’s not a hard choice to make, but there’s no win-win. There’s no just, “I get to enjoy something, and nobody takes anything away from me.”

There’s also the problem where every time you succeed, it resets the bottom line. When a high achiever succeeds, that quickly becomes the new expectation.

Your personal best becomes the thing you can’t go below, which, of course, is very hard to do, and eventually you are going to slip. Your personal best won’t be something you can always beat the next day.

And now you feel like a failure, even though your original starting position was much worse than where you are now.

Somebody who goes to the gym and they can’t quite lift as much as they lifted last week feels like an abject failure, and they fail to notice they’re lifting twice as much as they did just two months ago. That doesn’t matter to them, because the new baseline means all taste and enjoyment is taken out of anything that isn’t a win.

And so people start to do this weird correlation thing where they link things that aren’t actually linked, and they create these partnerships of good and bad.

Let’s say you’re sick. It would be because you were happy last week. You’ll think, “Oh, see, I deserve this. I knew this was coming.”

If your birthday sucked, it was because you got too excited about it. And if the client quits, it’s because you’re happy that you signed up a client last week.

This idea that these are connected—that you’re getting punished for each win—knowing that, of course, you could also just plain lose all of them. So you’ve only got this choice of win and lose together as a combo. You actually start creating that combo by just arbitrarily connecting events that have nothing to do with each other.

So this fear—cherophobia—keeps high achievers and leaders stuck on this horrible treadmill where the faster you run, the more you stay in the same place.

You never feel safe to relax, enjoy whatever it is you’ve achieved, to just chill and go, “You know, I’ve done enough for quite a while.” It just always feels like you’ve got to keep moving just to stay in the same place.

There’s a sense of competition. You can’t relax because it will be taken away by some other. Sometimes it’ll be quite specific, e.g. at work, if you take a week off, somebody else will steal your job or your clients. And other times, it’s just a vague sense as you’re relaxing—this agitation where you just feel like you should be doing something productive or else something bad will happen.

I remember seeing an interview with Will Smith, the actor, way back in the day where he was saying that he will outperform anybody else, that he doesn’t care if you’ve got more talent than him, because he’ll just stay on the treadmill longer than you and outpace you.

Everyone praised him for that advice or wisdom. That was before we realized how badly he’s doing. I mean, if you read the book Will (as told to Mark Manson), you’re reading the book of a high achiever who cannot be satisfied—a person who won everything and still never felt good enough and still had a disastrous home life and family life, because he was so obsessed with his success.

He looked like he was having a good time all the time. But if the book is even half true, behind that was just this constant need and anxiety and desperation.

Sure, he often felt triumphant, but he felt the need to brag about his wins all the time as well. And that’s not what a satisfied person does.

How to Break Cherophobia Without “Tempting Fate”

The solution to cherophobia is deep and dark, but it’s essentially about breaking patterns and behaving as somebody who’s not superstitious.

It will feel like massive risk-taking—like a leap of faith—where you’re going to actually sit back and rest and relax and enjoy yourself, and tempt fate into punishing you for doing so well.

One of the ways to do it is set hard time limits. Working eight hours a day, for example, five days a week—most of you probably do far more than that.

Make it there’s a certain time where work stops and you are not allowed to achieve anything. You’re not allowed to be productive. Your phone’s off, you don’t check emails, you’re not available—and just let the world burn without you.

Let it all come crashing down, if that’s what’s needed for you to have some time out to enjoy the fruits of your labor.

Of course, redefining achievement will go a long way. Achievement is not about the so-called productivity of quantity—of just doing more and more and more and win, win, win, up, up, up all the time.

Achievement should be about quality of life over quantity of accomplishments.

You having a wonderful half-hour with your daughter where it’s just you and her together, building memories, is such a bigger win than you getting the next contract with the big client who you’re never going to remember when you’re old.

You also need to face your fear by actually taking on compliments and accolades. When somebody says you did well, just say thanks. Don’t push back on it or try to undermine it.

Be aware and shameless about your strengths. When someone asks what you do, tell them that you do it well, if you do it well. And don’t try to appear to be humble and modest and qualify yourself to try to prevent fate from finding you.

Just go, “Yeah, I’m doing well. I’m happy.”

You know that guilt you get when you’re doing really well, and then you’re around someone who’s not, and you feel the need to outdo them with how much you’re suffering? You make up a big song and dance about how it looks like you’re doing well, but you’re actually not.

How about just saying you’re doing well—even if it makes them envious or resentful of you—just hold it instead of trying to downplay it.

And what’s really important is measuring your skills and your efforts, rather than your accomplishments—your results.

What did you do and why did you do it? Not what did it cause. Because the results aren’t actually under your control.

You can do everything right and lose, and you can do everything wrong and win. It’s not really an accurate measure of who you are as a person.

But why did you do the thing, and how did you do it? Are you putting in efforts that you’re proud of? Are you doing it for reasons that feel honorable to you?

If that’s the case, then that’s what you measure. And you train yourself out of measuring the outcomes and results.

High Achievers Are Afraid of Ghosts: Real Risk vs Imagined Risk

After coaching high achievers for so long, I’ve come to the opinion that they are afraid of ghosts.

Which is to say, they live in a world that is largely fictional—their imagination—and most of the problems they’re trying to solve and most of the worries they have are about things for which there is no evidence.

It leads highly successful people to be oddly superstitious and irrational, which makes no sense given how successful they are. But you’ll notice, if you pay attention, the more successful someone becomes, the crazier they get.

So we’re going to have a look now at how our mind fucks with us by keeping us in a near-constant fight-or-flight state, even though our lives are relatively safe. Let’s talk about why high achievers and top leaders are often in constant fight-or-flight—very stressed—even though they might not appear to be on the outside.

Now this isn’t exclusive to high achievers. All humans have a problem differentiating real risk from imagined risk.

You could describe it as the difference between fear and anxiety, as they talk about in the movie Inside Out. Fear is dealing with the threat you can see. Anxiety is dealing with the threat you can’t see.

The higher you achieve, the more potential “can’t-see” threats you start to imagine—which is ironic, because you actually have less of them.

Somebody who’s in poverty without much support in a dangerous country has far more real threats to deal with, but ironically, they are often going to be less anxious than the CEO of a Fortune 500 company who has good health and a wonderful family.

Their perception of what’s real and what they should be responding to is very difficult to manage, because in their mind, they are one and the same.

As Jim Carrey also once said: we don’t know the difference between a dog that’s going to eat us in our mind and a dog that’s actually going to eat us, and so we’re constantly in fight-or-flight response.

As you imagine something really badly happening, this emotional reaction happens inside you. According to your mind, it is happening, you’re actually now creating memories of a bad thing that never really happened.

And even though, in some rational, vague way, you know that this is just a prediction, it feels like a very accurate prediction. It’s not just a possibility of what might happen. It’s more a case of, “This is going to happen, so I must respond.”

The problem with high achievers is because they are actually aware of their success and their accomplishments - they’re used to being the big fish in the small pond and outdoing their peers and so on - they come to believe that their mind must be somehow much more accurate than other people’s minds—their thoughts and their ideas and beliefs must be very helpful and accurate because they’re so successful.

They become more likely to believe what their mind says than somebody else, and that actually puts them at risk of being manipulated by their mind so much more powerfully—that is to say, manipulated by their imagination.

When you believe your mind, you won’t challenge its lies, and then you will fall for them, and you will react to them as if they are true.

Some common fears that come up:

The fear of failing publicly.
The fear of slowing down.
The fear of complacency.
The fear of losing it all due to some freak occurrence.

Again, we have those two questions we must answer: is it likely to happen? And even if it did, would it be that bad?

For most high achievers, the likelihood that you are actually going to fail in some big, disastrous way is so much less now than it ever was.

Even though you are in the spotlight and you’ve heard of scandals of people like yourself crashing down, unless you got there by being very deceptive and breaking laws and being a fraudulent person—in which case, my material is not for you, because I’m all about integrity—it’s very unlikely that you’re going to have some big public fall.

And even if you did, you would probably survive it and rebuild successfully later.

Think of someone like Paris Hilton with her sex tape, or Louis CK with his harassment scandal. Both of them bounced back wonderfully from those things, even though that’s about as disastrous as a fall as you can imagine, publicly speaking.

The likelihood that you’re going to have a fall as bad as they did is very unlikely, and yet even they bounced back from those. So why would we be scared of that?

The fear of slowing down—the fear that if you back off the pace a little bit, relax and enjoy yourself, then you’ll be quickly overtaken by the pack and left in the dust.

One of my clients often wakes up in the middle of the night afraid of being homeless, even though he is so far away from homelessness it’s ridiculous. He would have to actually want to be homeless for it to happen.

He’s got so many skills and resources and support people in place that he wouldn’t fall that low. He just couldn’t.

And yet he worries about it all the time, as if it’s likely—as if him slowing down would mean he’ll suddenly be homeless.

The irony here, of course, is that some of the most successful people in the world do very little because they understand the difference between leverage and productivity.

The Tim Ferriss Four Hour Work Week thing—most of the highest achievers just know which levers to pull, and they can do just a couple hours’ work a day. They can live life quite slowly.

Whereas the people who are busting their ass 12 hours a day are simply being inefficient. And it’s ironic, because being that busy is much more likely to lead to failure than slowing down, relaxing, and doing things smart rather than hard.

Fear of complacency: this idea that if you enjoy success, something bad will happen to you. You’ve always got to be burning hard, worried and stressed.

Again, you must ask yourself: where’s the evidence that somebody enjoying their success is met with serious punishment of some kind?

Who’s more likely to suffer—the person enjoying their success, or the person burning themselves out and stressed out to fuck because they never stop to enjoy things? Who ends up having the heart attack and the stroke?

Slowing down and enjoying yourself is going to cause problems? No. Not doing that is going to cause problems.

You look at someone like Ricky Gervais, the comedian. He’s constantly doing whatever the hell he feels like doing. Sometimes he does big, hard bits of work. But other times, he coasts and just does what he feels like doing.

He bathes in his success. He even brags about it, or sort of jokes about it, quite often. He’s certainly not humble about it, and the guy just keeps on winning, right?

How do you explain him?

And of course, the fear of just losing it all due to some freak occurrence—as if being stressed and busy would prevent that from happening.

You’re more likely to make mistakes and have accidents if you’re not relaxed and your mind isn’t clear and your body isn’t in good shape.

The crazy thing I see quite often with high achievers is they’re so worried about something at work going wrong that they end up sacrificing their family. The big thing really goes wrong when they don’t have a relationship with their son when he’s in his 20s, and it’s too late to do anything about it, and the whole time they were worried about that email at the workplace, which actually didn’t matter at all.

And even if you did lose it all, do you really think you’re also going to lose all your skills and your drive and your pattern recognition and intelligence—like you wouldn’t be able to start over again?

Have you ever looked at a list of top actors who started late in life? Morgan Freeman, I think, was in his 40s when he started acting. There’s others—top businessmen who were in their 50s and 60s before anybody ever heard of them.

The idea that you’ve got to make it happen now is total crap—you could restart any time. The fact that you’ve made it here means you have the skills. It wasn’t luck. You could do it again.

So it doesn’t matter if you lost it all. It would be painful, but not horrific, and yet you stay up at night worrying about it.

The tragic irony is that one of the reasons people are high achievers is because they have very active imaginations.

Problem-solving really takes place in the imagination—the ability to see potential pathways into the future, to correlate patterns and events. So generally, that’s the kind of intelligence that successful people have in common.

But it’s a double-edged sword. It will cut you as well, because if you feed negativity into that imagination, you’ll get catastrophic cinematic dramas in your head that will crush you emotionally.

This thing that’s your greatest weapon is also the thing that will hurt you the most.

Your imagination is actually more powerful than your rationality. Rationality is facts-based. Rationality is less compelling.

Rationality will say to you, “Look, statistically speaking, here’s the most likely thing that’s going to happen.”

But then your imagination goes, “Oh no, what if this big fucking horrible emotional bad thing happens?” Then you’re like, “Oh geez, he’s making a much louder point. Maybe he’s more accurate.”

And that’s what it feels like.

Most of you know that you’re being irrational when it happens. Like you know that those great disasters you’re imagining are not going to happen, and yet you pay no attention to that logic, and you just bathe in the kind of misery your imagination comes up with.

Basically, there’s a failure to engage in critical thinking. You’re all creativity and no editing.

Your mind says you’re going to end up homeless, and you don’t start with going, “That sounds unrealistic. Let’s pull that apart a little bit.” You just go, “Oh no, homelessness,” - there’s no challenge.

And again, I’ve talked about this before: high achievers often trust their minds, because their minds were always there while they were achieving.

They give credit to their mind for the successes, and don’t see that, hey, maybe the mind can be wrong sometimes. And actually, maybe you’re successful in spite of your mind, not because of it.

I’ll put it out there: you succeed in spite of the voices, not because of them.

Managing Your Mind Like a Known Liar

The solution to getting out of this constant, stressful state driven by your imagination is to become essentially a faithful loyalist for rationality.

To start understanding: your imagination, your mind, is just a tool. It is not the Truth. You can use it to solve direct problems that you point it at, but if you’re not doing that, it will just go fucking wild on you, and it needs to be managed.

You can’t let the dog off its leash. It’s got a job to do. It’s a hunting dog. It’s not a “run into the sea and do whatever the fuck it wants” dog.

When your mind starts coming up with stuff randomly—to worry about problems that are not directly in front of you that actually need to be solved, anxiety rather than fear—you need to get super skeptical.

You know how you are with all those salespeople that are approaching you and pitching you all the time? All those emails you get from people claiming that they want to help you, but you know they just want to get something from you?

You know how you look at every word as if it’s full of shit? You need to do that with your own head.

One of the reasons you’re so successful is because you’re good at being skeptical. You know what to say No to. You know who to not believe. You know who to be suspicious of.

You need to apply those skills to yourself.

When your mind says, “Oh no, what about this?” you go, “Wait, what sales pitch is this? What kind of bullshit is this? Where’s the evidence? Point to it. Where’s the thing I have to solve? How are you so sure it’s a bad thing? Even if it did happen, isn’t what I’m doing already going to prevent that anyway? So why are we talking about this? Is this the most important thing to solve? Is there something that’s more obvious and real that I should be dealing with first?”

Take a critical approach to your thoughts, where you treat them like they’re coming from a known liar who only occasionally tells the truth.

I suggest, when you’re really ruminating on something dramatic, write it out like it’s a legal argument.

Start with the devil’s advocate approach, where you write out the argument from your mind saying, “Okay, you say I’m going to be homeless. Explain to me how that’s going to happen. Why you think that’s going to happen? Justify this as a genuine risk that needs to be dealt with immediately .”

And listen to it. “Okay, you just make your points, and then we’ll see.”

Then, once you’ve written out those points, attack them like a fucking lawyer. Pull them apart.

Go, “Where’s the evidence for that? How come that contradicts that thing? That’s never happened before! Why are we treating it like it’s an immediate threat? What would I actually do to prevent this happening before it got anywhere near that level of disaster?” And so on and so on.

Just attack it so hard with logic and rationale that it feels ridiculous to believe it.

Do this again and again and again, to make up for all the years that you haven’t done this.

Eventually it will become your default, where you’ll be skeptical first as soon as your mind speaks, rather than just embracing every noise that comes into your head.

Perfectionism: Why Nothing Ever Feels Good Enough

Why do successful people accomplish more than most and yet nearly constantly feel like they’re failing?

Let’s talk about the perfectionism trap. That is: why nothing ever feels good enough, especially for high achievers.

There’s an inverse relationship between actual achievement and sense of achievement. We’re going to explore why that happens and what you can do about it.

One of my clients, Anthony, when he was younger, has a very clear memory of winning a spelling bee at his school. He was in a spelling test, and he got like 99%, I think, on the test, and beat everyone else in the class by a lot. And he came home to a super-critical, high-pressure father and said, “Look, look, 99%!”

No smiles, nothing. His father just looked at it and said, “Where’s the other 1%?”

This is a very common experience for high achievers in their childhood. This idea that whatever you accomplished, the focus was on the little bit you did not do—quite often an imagined failure.

You won the running race, but you didn’t run fast enough. Even though it was fast enough to win, somehow it wasn’t fast enough for some other vague goal.

It’s this idea that no matter what you do, it just never quite crosses the line. It’s close—close enough to give you hope that maybe next time, if you tried harder, you’d cross the line—but you always seem to imagine how it could have or should have been better.

Whenever you accomplish something, even if you win, even if you outdo anyone who’s ever done it before, you always imagine it being better, and that makes it feel like a failure.

You could call this maladaptive perfectionism, which is: you have unrealistic standards to begin with, and then harsh self-criticism after the event.

That makes it nearly impossible to feel like you’ve done something well or good enough.

At the start, we get what I call the Everest effect, where you ask too much from yourself.

If you imagine: there’s not doing the thing at all, there’s too much, and somewhere in between is ‘enough’.

Now a perfectionist would look at “enough” as a failure, and they think everything must be achieved to an exceptional standard, even though this is excessive and might actually do more harm than good.

Let’s say, for example, I go to the gym and lift a certain amount of weight. At any given time when I go to the gym, there’s the right amount of weight to lift to keep me healthy for as long as possible. There’s a kind of longevity lift.

I won’t always know what it is, but if I pay attention to my body, my body will tell me, “Yeah, stop about now.”

But then there’s the amount I wanted to lift, which is usually so much higher that if I actually did it, I would injure myself. And yet I think of myself as a failure for not lifting that much.

That’s what we’d call the Everest effect. You’re actually asked to do too much—or at least more than is enough. More than is the maximum efficiency.

You’ve almost got no chance of achieving it.

And then if you did actually happen to achieve it, or come close, your brain will still go, “Yeah, but…”

It’ll say, “Yeah, but you didn’t do this,” or “it wasn’t fast enough,” “wasn’t good enough,” “wasn’t slick enough,” “could have been better.”

Sometimes just vaguely: a sense it could have been better. And other times it’s a very specific unit or quantity of measure that defines what “better” means.

Quite often it even measures something that has nothing to do with quality anyway.

Let’s say you go talk to a woman you’re attracted to, and it turns out she doesn’t like you, and she’s also really nasty and rude. You measure that as a failure, where actually getting someone who’s nasty and rude out of your life is a good thing.

You’d say “I got rejected” rather than “I kept a bad person out of my life.”

So it’s measuring all the wrong things in the first place.

But mostly what I see is people just measuring what did not happen. What they did not do that could have been better, even though it didn’t need to happen, and it’s all in your fictional imagination anyway.

Perfectionism turns every win into not good enough, and just puts more pressure on you for the next time.

You end up with this history where you never appeased your mind—where nothing you did was ever really applauded and encouraged by yourself. It’s like you’re living with this bully in your head who just always says, “Is that the best you can do? That fucking sucked,” no matter what it is you did.

You can’t ever win. You can’t ever please that voice.

Hint: it’s not really your voice. I bet you can figure out whose it is though. Mummy, daddy, your teacher? You know who it is.

You end up realizing there’s a pattern here: the end result of you doing anything is a sense of failure, and no matter how much you achieve, the final result will be a sense of not feeling good enough.

And yet you keep doing this, because it’s either that or feel really not good enough. You’d rather feel the least amount of not good enough.

You’ve got this kind of false hope: maybe this time, if I just tweak this thing and do that a bit more, then I’ll finally be enough—even though that’s never happened, and I’m always trying my best. But this time…

Achievements do come with little wins and little pleasures. Don’t get me wrong. I know you’re not suffering nonstop.

But the problem with those little pleasures—those little dopamine rushes from instant gratification—is it gives you a sense you’re actually on track, that if you got the dials tuned correctly, you could feel like this all the time.

Except, of course, you can’t. It’s not physically possible for a human being to feel happy and satisfied all the time. You’re never going to cross that line.

You create a personal history of failure because you only track your losses, most of which are imagined.

You go to the gym and you do seven pull-ups instead of 10. You track it as minus three pull-ups when actually you didn’t fail at all. You did seven more than zero. That’s great! You’re a strong person, probably in the top 10% of strength in the whole world. And yet, as far as you’re concerned, you failed to do three pull-ups. That’s how you measured it.

You measure everything like that, so you’ve just got this track record of being a fucking loser who never gets anything right.

While at the same time, you’re somehow contradicted and aware that you are exceeding most people’s standards and beating most people and in the top percentile for most of the things you do.

You try to reconcile that, but you know that cognitive dissonance doesn’t sit well with you. You’re just so sure that you’ve actually failed all the time because you imagined it.

And even when you do actually win—you occasionally meet your standards or exceed your standards—and the voice in your head does say that’s enough, it just becomes a new expectation.

So there’s this burden with winning.

You’ve probably seen that at work. Maybe you got some great sale on a really hard-to-get client, and now everyone thinks that you’re going to get those sales all the time, and you feel like you have to, rather than seeing it as a one-off fluke.

Even when you do win, it just makes you more anxious, because now you feel like you’ve got this new standard you have to uphold.

You’ve just got pressure, stress, no enjoyment, constantly running on that treadmill, and you can’t stop yourself. It’s like you’re a glutton for punishment. It’s almost like you want to be miserable, isn’t it?

It’s one of the weirdest things, working with my clients and just seeing human beings in general, is this idea that we actually want to be happy. Our behavior contradicts that. We seem to be working very fucking hard to be as miserable as possible.

Happiness is almost like a random event that sneaks through all the self-sabotage we’re doing.

If you want to stop self-sabotaging yourself and actually enjoy being who you are, get in touch—[email protected]—and I’ll help you out.

So you’ll know that you are a maladaptive perfectionist if you have any of these symptoms:

Exhaustion—constantly feeling like you’re worn out from performing all the time.

Shame—a sense that there’s something wrong with you, something unfixable, completely broken, that you have to hide from the world.

Which leads to imposter syndrome: this idea that you’re going to get caught for being the fraud you really are, and everyone will find out you’re actually this loser who’s pretending to be a winner.

Self-doubt—where you have to make decisions all the time, but you don’t trust the person making the decisions, that person being you. You feel like you’re taking risks all the time.

The burnout that just comes from never being able to enjoy stuff, but always working really hard—constant effort, no reward—this low-ROI life.

People-pleasing, of course—trying to get those approvals and validations from others to make you feel good about yourself, often while you sacrifice your relationship with your family and friends to appease total strangers or your boss.

And of course, eventually: heart attacks, strokes, and death. That’s where this is heading.

I say it harshly like that, because your system is really, really harmful. Perfectionism is a death sentence. If nothing else, it’s the death of enjoyment. But I think it’s actually quite physiologically a death sentence.

You’re trying to achieve something that can’t be achieved because you have a measurement system that can’t let you win anyway, and all you’re doing is burning yourself ragged, physically and mentally, and eventually you’re going to be left with nothing and wonder, what was the point?

You think perfectionism helps you—it limits you. All your successes are in spite of that perfectionism, not because of it. You’d be doing even better without it.

Isn’t that a crazy thing?

You think you’re so successful now, such a high achiever—it’s a fraction of what you’re capable of. That’s what’s really tragic about this.

This is you with a leash on. I can’t imagine how far you could go unleashed, because creativity is not something you put a leash on.

Risk-taking, authentic leadership—perfectionism does not enable those things. It disables them. Think of the difference between doing something right by the book—perfect—versus doing something freely.

One of my clients is a very high-profile writer. His name is Mark, and he’s an amazing writer, a well sought-after public speaker. His books are great.

But I sent him an exercise where he was allowed to write something that didn’t serve a purpose. Something that didn’t teach a lesson or provide value to his clients or anything like that—just something he wrote for the sake of writing.

And I can tell you right now: it’s his best writing ever.

He’s done about three or four pieces for me, and it’s better than any of his so-called great stuff that he’s ever written. All the stuff he wrote perfectly to satisfy the value and productivity urges.

When he just writes a story that he feels like writing, it’s fucking amazing. If he wrote more like that, he’d probably get to the next level.

Isn’t it interesting that we think pressure helps creativity and productivity?

Think of what the word pressure means: to squeeze, to tighten, to reduce. Of course pressure doesn’t help. Pressure is like a resistor in an electric system. It reduces the current. It doesn’t enable it.

You credit pressure for your success when really it’s the thing that’s been holding you back the whole time.

If you were free and light-hearted and enjoying yourself and going with what really interested you, and being willing to take risks and get things wrong, you’d be doing so much better than you are.

And not only that, you would enjoy it so much more.

It’s sad you’re not embracing your potential because you’d rather get things right—which you can’t do anyway, because the system won’t allow it.

Risk has inherent loss rates to it. If you’re taking risks all the time, you’re going to lose a certain percentage of the time.

Take stupid risks, you lose a lot. Take smart risks, you lose 20% to 30% of the time, right?

Perfectionism allows for no loss, so you’re restricted in your ability to take action, because you’re not allowed to take risks. You’re only allowed to do things that are guaranteed to win.

Once you think of all the masters in the world you know—think of the Beatles. How many albums flopped? How many songs does nobody listen to? It’s far more than the ones people do listen to.

Think of chess grandmasters. Do you have any idea how many games of chess they’ve lost? Almost half. In fact, think about how many moves they’ve made that were wrong, how many blunders they’ve made, and yet they’re at the top of the game.

How is that possible? Shouldn’t they have an undefeated record?

No. Nobody at the top has an undefeated record.

Perfectionists don’t get to the top because they’re not allowed to be defeated, which means they’re restricted. It’s like a chess person who only plays somebody who’s lower-rated than them. They can’t get good at chess.

Authentic leaders—especially in this day and age—are so revered. They get the best results from their teams. They get the most loyalty.

But perfectionism doesn’t allow you to be authentic. It doesn’t allow you to show weakness, to make mistakes, to hold yourself to account for getting things wrong. It prevents honesty.

And so you can lead, but not as effectively as you could if you were authentic, so you’re missing out on the leadership results you could have as well.

Take a moment. What would it look like to put aside doing things perfectly—trying to satisfy that voice in your head who can never be satisfied?

Instead, take some risks and do what you really want to do. Do what you really think is the right thing to do, and be willing to fuck up just to see what happens.

The Comparison Spiral: Why Success Breeds Misery

We’re going to talk about the comparison spiral—how success breeds misery because of you comparing yourself to your peers.

I’ve noticed that the more zeros somebody has on their paycheck, the more ambitious and unsatisfied that person is, and the more concerned they are with how many zeros their friend has on his paycheck.

So we’re going to have a look now at why your enjoyment decreases as the numbers of what you’re supposed to be doing well on go up, and how this relates to comparing to others.

I’ll share a story about a previous dance partner I had. We started as beginners together, entering beginner competitions and stuff, and we won quite early on. I think we won almost everything we ever did.

And so, as you can imagine, we just kept working hard and developing our skills. Every time we entered a competition, we were a higher level, and so every time we went in, we’d have to compete against higher-level people.

I noticed an escalation in her. The higher up we got, the more anxious and worried and distressed she became about our performances.

At the lower levels, we both really enjoyed it. But by the time we were in the advanced level, it was almost impossible for her to enjoy any form of competitive dance.

Even if we won, there was a good chance she’d spend a few hours in the toilets crying afterwards over some small flaw in our dancing.

It seemed like every level up, she compared herself to the next one up. So if we were amateur, she compared us to pros. If we went pro, she compared us to super famous people.

No matter where we got to, she was always looking up and comparing us to that, and finding us to be failures—thinking we weren’t good enough—even as we won competitions, even with gold medals on our chests.

And that’s what we’re talking about today: how comparing yourself to others is not only false, but the reason you don’t feel any enjoyment about how well you’re doing.

You Only Compare Up—and That’s the Problem

Choose one area of your life that’s important to you, and just rate how well you’re doing. Think of it as: how well am I doing overall in this thing?

Once you’ve given yourself a rating, review how you benchmarked that rating. Who did you compare yourself to? If you decided you’re “okay” at something, who was “good” and who was “bad”? Who did you compare yourself to in order to come up with that rating?

One thing you’ll notice is that you don’t really look down. You only look up.

You look at how you’re doing compared to people who are doing it better than you, longer than you, more successfully than you, and you come up with a rating relative to them.

You don’t do a deep dive into their overall psychological satisfaction. You don’t know how well they’re really doing internally. You just look at some arbitrary measure—some statistic relating to one endeavor—and assume they’re doing better.

Often without evidence.

Then you decide they’re better than you in general. You cherry-pick where they’re better than you and decide you’re a worse person than them, but you don’t look at how their life is actually going.

Maybe they’re making more money than you, but their family’s a mess. You don’t measure their family. You just go, “Oh, he’s making more money. He must be better than me.”

Meanwhile, there are people you look down on. Maybe you look down on a janitor working hard with his hands while you’ve got a nice office job. But if you were inside his mind, it might be a much more pleasant place than being inside yours. So who’s actually doing better?

The Toxic Achievement Cycle

As high achievers, we’re trained from a very early age to enter what I consider a toxic achievement cycle made of comparison.

We’re given a goal when we’re younger. We succeed at that goal. We get a brief high—“Yay.”

Then we compare up.

We realize someone else did it faster, better, earlier, or bigger.

And then comes immediate deflation. The wind gets stripped out of the achievement. There’s an emptiness.

So we create a new goal to fill that emptiness, and the cycle starts again.

Over time, we become addicted to external validation. And like any addiction, it becomes less satisfying over time until it becomes completely unsatisfying.

We rate ourselves compared to others because that’s how we were trained. School compares us. Sports compare us. Parents compare siblings. Society constantly shoves hierarchy in our faces.

Nobody ever steps in and says, “Yeah, he’s better than you at football, but he’s worse than you at reading. It balances out.”

They just say, “He’s better than you.”

So even when you’re at the top, there’s always fear that someone younger, faster, smarter will come and take it from you. You never get to enjoy the crown.

You’re Measuring Wrong—and It’s Destroying You

You don’t compare globally.

If you make $60,000 a year, you’re in the top 1% financially in the world. But you don’t compare yourself to the world. You compare yourself to your neighbours. So you feel like you’re failing.

You only look slightly above you, never at the massive fraction below you.

Even when you win—top sales guy of the month, best performer—the dopamine rush is brief. The next day, you have to do it again. There’s no “I win, lock it in.”

You end up in an endless chase—competing with peers, your past self, imagined versions of yourself, imagined outcomes.

You’re always looking up, so you’re always losing, even while objectively crushing it.

You’re in a Race You’re Guaranteed to Lose

Here’s the brutal truth: there is no finish line.

You will get older, slower, and less sharp over time. We all do. There will always be someone coming up who will overtake you.

So if your definition of success is “being better than others,” you are in a race you are guaranteed to lose.

And the tragedy is, you’ve been winning the whole time while telling yourself you’re losing. If you can put food on the table, put a roof over your head, do something remotely enjoyable, maintain relationships, and your body works—you’re doing incredibly well.

The bar for a good human life is actually very low. And yet you’ve convinced yourself you’re failing.

That’s not rational. That’s not intelligent.

What Comparison Costs You

Constant comparison causes:

Loss of identity
Loss of joy
Loss of meaning
Loss of relationships

You become obsessed with winning, but “winner” isn’t an identity. Winning what? For whom?

You end up burning yourself out for a game you don’t even enjoy. And eventually, it creates depression—sometimes severe. Some people even become suicidal.

This isn’t abstract. This is what I see in my coaching practice.

Intelligent Decisions vs Compulsive Achievement

Now let’s talk about decision-making.

High achievers often make unintelligent decisions, despite being intelligent people. Why?

Because they confuse compulsive achievement with intelligence.

Intelligent decision-making means choosing actions that improve long-term quality of life and align with your values. Compulsive achievement decisions are reactive, habitual, driven by fear and validation, focused on short-term wins.

High achievers often:

Chase instant gratification
Avoid discomfort
Work hard instead of working wisely
Sacrifice long-term wellbeing for short-term status

They don’t stop to ask: Does this actually move me toward the life I want?

Value-Based Living: The Missing Operating System

Most people never consciously define success. They inherit it. They’re chasing goals someone else taught them were important.

Valued-based living flips this.

Instead of measuring success by outcomes, you measure it by how and why you acted.

Values are principles you can live by regardless of outcomes. No one can take them away from you. You can be honest and lose money. You can be dishonest and gain money.

Which one do you want to live with?

Redefining Success So It Stops Destroying You

Healthy psychological habits that change everything:

Celebrate effort and integrity, not outcomes
Accept “good enough”
Allow losses as proof you’re playing a meaningful game
Rest without guilt
Stop comparing yourself to others
Challenge perfectionist thinking

Wisdom comes from mistakes.

Anyone who’s never failed hasn’t done anything worth doing.

The Final Paradox

Outward winning with inner losing is failure.

Triumph is not contentment. Contentment is stable, quiet, and internal.

If your definition of success requires you to never be satisfied, then you’ve defined failure. Success without fulfillment is not success. It’s just exhaustion with trophies.

You don’t need to give up ambition. You need to aim it at something worth living for.

Closing

If you’ve been achieving more and enjoying less, it’s not because something is wrong with you.

It’s because your system is wrong.

And systems can be redesigned.

Thank you so much for reading. I hope something useful landed for you.

I’ll see you next time.

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