The Entrepreneur’s Studio

The Hidden Cost of Extreme Success | Mark Manson

The Entrepreneur’s Studio

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What nobody tells you about achieving your biggest goal and what to do when the dream you built your life around suddenly disappears.

Topics Covered:

•       The three pillars of extreme success—and why they're rarer than you think

•       Altitude sickness: the grief that follows achieving massive goals

•       The two mountains of ambition—and the valley you must cross between them

What happens when you spend a decade grinding toward one defining goal and then you actually achieve it? For most entrepreneurs, that question stays hypothetical. For Mark Manson, author of The Subtle Art of Not Giving a F*ck, it became a disorienting reality. His book sold 20 million copies. He became one of the most widely read voices on the planet. And then, almost immediately, he had no idea what to do with himself.

Manson believes extreme success isn't the product of morning routines or productivity hacks. He identifies three genuine prerequisites: a contrarian idea that most people dismiss as ridiculous, the conviction that you're right and they're wrong, and the willingness to go all in—no hedging, no diversification, no safety net. The Buffetts, the Gates, the Zuckerbergs didn't spread their bets. They found the one thing and put everything on it. That's a high bar, and Manson doesn't pretend otherwise.

But what happens after the mountain is climbed? Manson describes a phenomenon named by Quincy Jones and shared by nearly every extremely successful person he's spoken to, called "altitude sickness." When you ascend too fast, your identity hasn't caught up with your circumstances. The goal that organized your entire adult life is gone. Everyone around you assumes this is the best thing that's ever happened. So you say nothing, sit in the listlessness, and quietly wonder whether you've already peaked at 32.

For small business owners and entrepreneurs, Manson offers the frame of David Brooks' Second Mountain: the idea that after you've secured the status and financial stability of the first mountain, there's a deeper climb waiting, one driven not by external validation but by purpose, contribution, and mastery. The only way to reach it is through the valley in between. That disorienting period isn't failure. It's the transition. And knowing it's coming, Manson says, changes everything.

In this episode, you'll learn:

•       Why extreme success requires a contrarian idea, conviction, and an all-in bet, not habits or hacks

•       How to recognize altitude sickness in yourself and why it's more common than anyone admits

•       The difference between first-mountain goals (resume) and second-mountain goals (eulogy) - drawing from David Brooks concepts. 

 

“When you accomplish one of those massive goals, you lose that goal. You wake up the next day and you're like, I have nothing to work on.”

— Mark Manson

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SPEAKER_02

What I eventually realized is that from age 24 to 31, the thing that got me out of bed every single day is I want to become a successful writer, I want to become a bestselling author, I want to be one of the most read people on the planet. Like this was day in, day out, year after year after year. I'm grinding, trying to like make everything work. And basically my entire adult life was geared and oriented around achieving this dream and this vision. And what nobody tells you is that when you accomplish one of those massive goals, you lose that goal.

Chris Allen

Most entrepreneurs spend their lives chasing success without a thought of what happens once a goal is realized beyond your wildest expectations. Welcome back to the Entrepreneur Studio Podcast. I'm your host, Chris Allen. Today we're joined by Mark Manson, best-selling author and one of the most widely read voices in personal development. In this conversation, Mark opens up about the hidden emotional cost of extreme success, the altitude sickness that can come from achieving massive goals too quickly, and why so many ambitious people eventually find themselves searching for meaning beyond the achievement. If you're building something ambitious or questioning whether the thing that you've been chasing is actually the thing you want, this conversation will redefine how you think about success, identity, and what it means to build a meaningful life. Let's get started. Mark, welcome to the show. It's great to be here. I'm so glad that you were able to get here. You know, there's this book, this little orange book that, you know, I've seen on everybody's shelf called The Subtle Art of Not Giving a Fuck. You wrote it in 2016 and it quickly became this best-selling book. It was a global phenomenon, 20 million copies sold. But, you know, what looked like an overnight success? I'm sure you've had uh this question, what looked like an overnight success actually preceded, you know, by a decade or more of consistent blogging, writing, often without a significant audience uh or return. So the question that I have is what gave you the drive to keep going when success wasn't really on the radar? And did you anticipate the level of success that this book had?

SPEAKER_02

Well, I I always tell people that anybody who anticipates that level of success is probably an asshole. So uh I I I expected it to do well, but that I mean, it exceeded all expectations. Um and in terms of like what kept me going early on, you know, it's I actually recently got a an email from a from a fan, and he was telling me that he was dreaming of writing online and he had all these ideas that he wanted to share, and he wanted to do the thing that I was doing, and he wanted to write books. And and he asked me, he said, Well, what gave you permission to start? And I I was thinking about it and I was like, I never felt like I needed permission. I just had low expectations. Like I never expected anybody to read anything beyond like my roommate and my mom. So it's like when the bar, I ironically, when the bar is low, it kind of frees you to just do the thing that you think needs to be done. And and you you don't get caught up in like, oh, how many clicks did I get this week? Or, you know, how many is our editors at publishers gonna approve of this title or not? Right. Like it's just you just get on with it.

Chris Allen

Yeah. It's one of those things that uh as a marketer, I'm like, I wonder if there was any receptivity testing on the title or not. You're like, the title's kind of like it, I don't care. So there probably wasn't any.

SPEAKER_02

It's interesting. It you're gonna laugh at this, actually. So the biggest concern. So when when when I went and shopped around the book, um, by that point I had built a blog with a couple million monthly readers, so pretty large internet audience. And so we got we got interviews with uh we got meetings with eight different publishing houses, all the big ones and then a couple of the smaller ones. And so I went to New York City, spent two full days just going office to office with my agent, you know, 29-year-old kid, bright-eyed, like no idea what's going on. And uh, and it was funny because a lot of them really pushed back on the title. And the reason they gave, you you'll never believe this, was that Walmart would not stock it if it had the F-word on it.

Chris Allen

No way.

SPEAKER_02

Which is hilarious in 2026 because it's like, who buys a book at Walmart? No doubt. But but this was the biggest concern among all the publishers at the time. You know, they're like, we get it, it's your whole profanity, like you've got this edge to you, we'd love it, but like we can't do the F-word because Walmart's not gonna stock it. Um, and then to Harper's credit, uh, Harper Collins, who I ended up going with, um, you know, they they said, screw it, we're we're in. Like, let's see what happens here. And uh now there's like 25 different fuck books in every airport.

Chris Allen

Kind of a good uh kind of a good icebreaker in the sense that like, you know, it's not a popular word to put in print, uh, especially the cover. But listen, the thing that's wild is you know, I spend a lot of time on video calls. I see a lot of libraries, and there's always that little orange book on somebody's shelf. And you walk through the airport and you see it, right? It's just it, it's a it's become an icon, right? Like uh, and business people talk about it, right? You know, it it's uh the self-help for people who hate self-help, it's it's pretty remarkable. And the thing that was wild about the, you mentioned the blogging, right? You know, just in the pre-conversation, I was like, you know, there's this blog that you wrote, and you're like, there were a lot of those. Yeah, I don't remember every single one in particular that I I thought would uh be apropos to really have kind of like center this conversation around. And it's really this idea of extreme success. Right, right. And really at the end of the day, that book really has catalytic extreme success. And where did that blog kind of come from? And what made you sort of make the three pillars thing a thing?

SPEAKER_02

Well, the blog article. So a lot of my work is in many ways, it's kind of reactionary. It's uh against like traditional self-help and like typical work and productivity advice, just because it all most of it's bad. Yeah, most of it's really it's trite, it's like platitudes and obvious shit packaged, you know, oversold and overhyped. And I remember at the time, uh, there were a number of very prominent productivity YouTubers, bloggers, kind of business gurus. Um, there was this thing going around of the uh how to be more successful than 99% of people, how to achieve extreme success. And they would have these big talks and 40-minute videos and like a 20-page PDF or whatever. And you would read it, and it was like all the typical shit like get up at 5 a.m., like you know, put butter in your coffee, take an extra creatine, uh, work out before you go to the office. And I'm like, if that worked, like everybody would be a billionaire. No doubt. Right? Like that, there's nothing like Warren Buffett is eating McDonald's to this day every morning. He's not going to the gym in the morning, I'm pretty sure. Seriously, like some of some of the most brilliant minds in history were were just degenerates and addicts and like complete messes in their personal lives. Uh, and and so it it forced me to actually really ask myself, like, okay, what actually generates extreme success? And the three things that I landed on is first, you have to have a contrarian idea. So by definition, extreme success demands that you there is something that most people are missing or that most people are not aware should exist, right? Some value out there, something of value or some something that could be created that just everybody's missing right now. And so by definition, you need to find something that most other people are gonna look at and think is ridiculous. Why would you ever focus on that? That's where the biggest opportunities are, by definition. The second that that by itself is hard enough. Like most of us really struggle to do something that our peers and our friends and our family like laugh and shake their head and they're like, Why are you doing that? Uh pillar number two is you have to be right about that contrarian thing. So not only do you have to find the thing that 99% of other people think is ridiculous, but you have to be right and they have to be wrong. And that is extremely unlikely. Like those sorts of opportunities don't come around very often, maybe a handful of times in each person's life. And that's if you're looking for them. And then pillar number three is you just have to have the guts to go all in on it. So if you if you're lucky enough to find that contrarian idea that other people are missing out on, and you you've like properly spotted it and you're high conviction on it, you have to be willing to sell the farm and and put in a big bet on it. And that that's that that's the interesting thing is that if if you look at these types like like the Warren Buffett's or the Stan Druckenmillers or like uh Bill Gates or Zuckerberg or whatever, like they are all in on one thing. Yeah, they didn't diversify across 20 things, they didn't play it safe and you know, uh, you know, sock away an extra five percent in their 401k. Like they found one thing that they were like, if this wins, nothing else matters, and then they just put everything on it. Yeah.

Chris Allen

You know, uh you've heard maybe a songwriter say, like, the song wrote itself, or I would just happen to be listening, right? And that's the thing that I I love about having that contrarian idea, right? There's an aha moment, you know, that you, you know, everybody's if if you're gonna go all in on something and and you have conviction, but you gotta be sort of attuned to something, right? Because not everything has, you know, this wonderful orange book uh success, right? Yeah. So the thing that I thought was awesome that uh just in sort of getting to know each other on the pre-call, you talked about this idea of altitude sickness. And I was like, okay, I we gotta we gotta have some sort of time dedicated to that one because I really enjoyed, you know, where that came from, how that showed up, and uh, you know, just to hear from your standpoint, because there's there's a high and a low.

SPEAKER_02

Yes, absolutely. Um, so to give some context on this, and and we'll knock out the uh the overnight success uh piece as well. You know, so I started I started blogging writing online in 2008. Um originally it was kind of a lark. It was just like, hey, you know, the economy was in the toilet. I just gotten out of school. Yeah, I didn't have a job. I'm like, can't hurt to write online, right? No, never killed anybody. Um what were you writing on? You were like medium or something like that? Or no Medium didn't even exist. Yeah, yeah. Blogspot.

Chris Allen

All right. Yeah, yeah.

SPEAKER_02

Shout out to uh yeah, the uh everybody over 35. Um Blog Spot was was the place to be. Um and it it it actually by 2009 it started to get a little bit of traction. And I read Tim Ferris's four-hour work week, and I was like, you know, like maybe I make a go at this, right? Like let's just see what happens. And then for the for the next six, seven years, I wrote at least one article every single week. I launched probably four or five different courses. I self-published one full book, multiple like short PDF books, guides. Um, I probably wrote hundreds of thousands of words and published online hundreds of thousands of words before I even like anybody in a publishing house knew my name. Uh but then of course I get the book deal, it goes supernova, and and then I start getting it invited to all these swanky industry parties, and I'm introduced as like the the overnight success debuted author. And I'm like, and it just feels it felt. Yeah, it felt weird because I'm like, dude, I've been writing every day for a decade. Yeah. Um, this is not, this was not an accident. Um so the flip side of that, obviously that's hugely exciting. It's very satisfying. You you feel validated, you feel, you know, it's you took this contrarian bet in 2009, and by 2016, it's paid off in a massive way, right? So it's like you you get to kind of feel that satisfaction and and that excitement. But then something else happens, which I didn't expect at all. And it's interesting because since then I've talked to many extremely successful people, and to a person, every single one of them experiences it, which is there is a sense of loss or or almost grief or depression that comes afterwards. And what I eventually realized is that from age 24 to 31, the thing that got me out of bed every single day is I want to become a successful writer, I want to become a best-selling author, I want to be one of the most read people on the planet. Like this was day in, day out, year after year after year. I'm grinding, climbing the mountain, trying to like make everything work. And my basically my entire adult life was geared and oriented around achieving this dream and this vision. And what people know what nobody tells you is that when you accomplish one of those massive goals, you lose that goal. You wake up the next day and you're like, I have nothing to work on. I have nothing to do. Which may sound nice for like it's nice for like a week or two, right? You know, you have to put your feet up and you know, take the wife on a nice trip or something. But you get like three months in and you're like, wait a second. I still have nothing to do. And I'm 32 and I may not ever have anything to do again. You know, like what do I dream for? I can't there is a loss, right?

Chris Allen

Right. Like it's the box is checked, but it's it's not like something was taken away. It was something was achieved.

SPEAKER_02

It it was achieved and and the achievement of it is what took took it away, right? Like it is like that that I think as humans, we are just deeply wired to to uh to want to pursue something. And um, and once you kind of hit that top of that mountain, you don't you have nothing to pursue after that. Yeah. And so there's kind of this listlessness and this like, whoa crap, did I have I peaked? Like, is this it? Is it just all downhill from here? And when you're like 30 something, that's that's a terrifying prospect. And the worst part about it is that everybody you in your life is like thinking this is the best thing that's ever happened to you, right? So you you never feel uh at liberty to um uh to to to to complain about it, to to tell people how you're actually feeling, you know, saying, like, actually I feel pretty lost and I don't I don't know what to do with myself. Um there's a lot of imposter syndrome, right? Of like, did I just get lucky? Like, do I actually deserve this? Um, is it gonna go away? Right. Like, is this is somebody it it is this just my 15 minutes and I'm gonna wake up in a year and this is all just gonna be kind of a um a joke? And um, and so it it's very disorienting and it's interesting because I eventually um the first person I met in my life was uh I had a friend in New York who was um co-founder of a uh very, very successful unicorn startup. And he had a massive exit for like nine figures. And it was funny because the entire time I knew him, all he did was sit around and play video games. And I never put two and two together. And and I remember hanging out with him after after the book was kind of number one everywhere. And I too had been sitting around and pretty much doing nothing but playing video games for a few months, and I'd gained a bunch of weight, and I was like, you know, just like I was kind of a mess. And I I saw him and he was like, Are you okay? And I and I was like, Yeah, yeah, yeah, everything's great, man. You know, the book's crushing, you know, got this like tour coming up, everything. And he's like, Yeah, yeah, yeah, but but really, are you okay? Um and I was like, actually, no, I'm like completely, I don't know what to do next. And he was like, that's normal. That's he's like, nobody tells you, but this is part of it. And the the best name I've heard for it, I was when I was doing Will Smith's book. I I actually asked him about it because he had this kind of insane rise to fame. Um he he had a more he didn't experience it exactly because he had kind of a complicated path in the 90s, but he said that Quincy Jones, who was kind of his mentor when he was in his 20s, um, had actually seen it happen to so many people that he actually had a name for it, which he called it altitude sickness, which is basically the idea that if you climb the mountain too fast, you get sick and can actually die because your brain is not acclimated to the to how thin the air is up there, right? And what Quincy said is that he noticed that people when they ascend too quickly, if they can't acclimate to the new reality, they will find ways to sabotage themselves so that they can come back down the mountain.

Chris Allen

Wow. That had to be a pretty like uh maybe a sense of maybe loneliness where you're like you're wandering, you felt lost. Like because the people around you, they don't they don't connect to what's happening. And then you have somebody else, you know, that has you know had the nine figure exit and they're like, yeah, so you're yeah, been been through it. And you're like, yeah.

SPEAKER_02

Yeah.

Chris Allen

So probably, you know, this sense of loneliness, you probably like somebody gets it.

SPEAKER_02

Yeah, it it is hard to find. Obviously, it's hard to find people who have been through it, but like it's interesting. I think, I think it it is a variation of kind of the classic midlife crisis. Um, so David Brooks is a friend of mine, and he wrote a phenomenal book on this topic called The Second Mountain. And he it's the second mountain is a metaphor that um we each climb two mountains in our lives. And the first mountain is kind of status, professional success, financial security, right? It's like let's make more money, let's get a better job, better title, better house, like all those things. And what happens is that if if you know, a lot of people, not everybody, but a lot of people, they eventually kind of reach the top of that first mountain, right? They they reach a point where they're like, okay, I'm like secure and I've got a good career and I've got a lot going for me. And um, I've got I've got a family and my kids are taken care of and everything. And what he observed is that it's it's there's a second mountain behind that first mountain, which is uh the thing that you actually want to pursue for yourself, but you never gave yourself the liberty to pursue that thing because you needed to climb the the first mountain first and secure your future and secure your family's future. And he it's such a beautiful metaphor because he said that the only way to get from the first mountain to the second mountain is you have to descend into a valley. And that valley is like kind of an existential vacuum of like, why am I here? What am I doing? How much like is is was any of this worth it, right? And um and it was interesting because he said that when when that book came out, first of all, he didn't expect anybody, he wrote it because he had a similar kind of experience. He didn't expect anybody to resonate with it. And he said that he went to his first book reading uh in New York, and it was like the entire line was a bunch of guys in like suits and ties, you know, mid-50s, corner office, CEOs, CFOs, uh VPs, right? And every single one of them was like, I'm so lost, man. And this this book is the first thing that ever showed me, you know, that this is normal, right? This is I'm not alone.

Chris Allen

Yeah. So then, you know, it gives people this encouragement to keep going. Um, there's probably more meaning in the second mountain.

SPEAKER_02

There is. And, you know, I went through my own path and my own journey, but it it's funny because it's, you know, the thing I eventually recognized is like, you know, the the obviously money's great, status is great, right? Accolades, all that stuff. It it's awesome. But really, the value of that is that it buys you the freedom and security to actually go do the things you want to do with your life. And I think what makes it so hard for people is that most of us, we spend our entire lives just focused on that first mountain, right? It's like when you're a kid, you gotta get into a good school. And then you go to the good school and it's like, all right, I gotta get my degree, I gotta get a good job. And then you get the job and you're like, all right, I gotta build my resume and my portfolio and you know, climb the corporate ladder and all this stuff. And so once once people even ask this question, they're like in their 40s or 50s, yeah, and they've never thought about it. And that is just that there's a certain element of just terror that comes with that of like, my God, I'm 40 and I've never actually asked myself, what do I want for no other reason than I want it.

Chris Allen

It's uh, I mean, definitely have been through that uh before. It it's one of these things where um there's this part of your life that you're, I don't know, not quite pen noticing everything because you're so focused on this thing. And there's different reasons for it, right? Like mine was uh, you know, I had identity issues. I was like, I'm, you know, only loved if I'm good and right. You know what I mean? And so these are these are some of the things I was like, I gotta have a green scorecard, I gotta have all this stuff. And then you kind of hit this sort of thing that you're like, okay, well, I'm a mess and I gotta sort this thing out, right? Because, you know, I have a lot of kids and they're uh trying to find their way to and they need a dad that's gonna show up for them.

SPEAKER_02

Right.

Chris Allen

Right. And that's one of the things that I think is is really powerful about what that whole Second Mountain thing. I I love the this idea, right? Because I do think it's a I don't know if it's a rite of passage. I don't know if it's it's like you said, you know, the I the guy saying to you this is normal. Right. It it's a high quality problem, but it's it is a problem.

SPEAKER_02

Yeah. You know, and it is something that if you are a very ambitious person, very successful person, you will probably experience it at some point, or you probably already have experienced it at some point. But because it is caused by success, and you we're all told 24-7 that success is just a good thing and you should only want success. And success is gonna fix everything in your life. Because this problem is caused by success, it I think it just discombobulates us. And we don't know how to talk about it, and we don't know how it's very hard to relate to people who are going through it.

Chris Allen

You know, the wild part about this idea is like it's probably unless you've experienced it, you don't really know about it, right? But there's gotta be an altitude sickness of falling too fast. Yes. And that's the one I think many of us have observed, right? You know, people getting canceled, or you know, uh, I'm sure there's the inverse of that that we don't even see, you know, there anyway. But I think one of the things that I I this whole sort of self-help idea and this uh the nucleus of it, you know, is maybe some motivation or inspiration. What what are some of the things, right? On the the first mountain are some motivations, right? Which is the success. What do you think are some of the motivations for success in the second mountain?

SPEAKER_02

It really comes down to I think purpose, contribution, um, and mastery. It's one way to think about it. This is not, this is not a perfectly accurate depiction, but it it is, I think it generally maps, is that generally the the first map mountain is uh is is chasing um external validation and extrinsic uh motivation, right? Getting people's approval, you know, winning at things, getting a bunch of money, getting a nice house, all that stuff. Um the second mountain tends to be more internal, right? It's like what what am I gonna be proud of? Um Brooks calls it, I'm trying to remember what he calls it. He has a great name for it though. He he's it he it's two different eulogy, or he's like it's uh resume goals versus eulogy goals, right? So the first mountain is um like what what's your stat sheet? What's like what's gonna go on your resume and like how impressive is it gonna be? The second mountain is what are people gonna say at your funeral and who's gonna show up? Yeah. That's powerful.

Chris Allen

Well, you know, the thing about the extreme success that we kind of started talking about, do you ever have the sense that you're living in the shadow of your own success?

SPEAKER_02

I used to. I used to. Um I actually think, and this kind of dovetails back to the to the two mountain thing, but it did mess with me a lot, the fact that I mean subtle art has sold at this point, it's sold over 20 million copies. Yeah. Which in the book world, that's like it's like a Avengers, you know, of it's unicorn level. Right. Like it's just you're not really gonna replicate that. And um, and it it's so it was really hard when I when my identity was very much based around being an author and this is what I do, this is what I'm always gonna do. Uh, that weighed very heavily on me. The the fact that it's just like, okay, no matter how well I execute the next book, it's not gonna do as well as the last one.

Chris Allen

Um so there was an acceptance that you came to?

SPEAKER_02

Yeah. I well, it's funny. I think the way the way I kind of came to terms with it is I stopped seeing myself as an author. I stopped kind of measuring myself by how well the next book did. And honestly, this pivot kind of in the business and like seeing it as a broader media business, I think has been very psychologically healthy for me. Because on the one hand, now I just look at that book as with pure gratitude. Yeah. Right. Because it's it's just bought me so much freedom and and leverage to like do so many cool things in other areas of my career. And, you know, when I do go back and write another book, I don't necessarily feel like I have to top that one anymore. Like it's just like now, now that whatever the next book is, it just gets to be whatever the next book is and serve its own purpose. I don't, I'm not depending on it for my paycheck.

Chris Allen

Well, what's next for Mark Manson?

SPEAKER_02

Uh well, I am planning to start writing another book, hopefully by the end of this year. We'll see. I'm trying, I'm in that stage of kind of the business where I'm like desperately trying to like get stuff off of my plate. Uh, you know, that the the awkward scaling. Um the other thing I'm working on, so I I co speaking of AI, I co-founded an AI personal growth coach. It's called Purpose. Um, my co-founder is just amazing. He's a genius. Um, and it's it's a super cool product. And so I've been spending about five or ten hours a week um in that office working with those guys. And um so I'm really excited about that. I I I personally think AI is just gonna eat most of the personal development market. I just think it's it's too good. And it's in terms of use cases, I think it's just like a perfect use case for you know coaching support, you know, mental health support. It's it's it's not quite there, but like it's getting very, very good. But yeah, that's that's uh, but yeah, just keep scaling the media company and um super excited about it.

Chris Allen

Keep writing great books. You know, I think um, like I said, I've seen this book all over the place. I the one of the best moments that I can remember, you know. Obviously, we're like, man, who can we talk to next? Right. And um, and somebody picked up the book and they were like, Yeah, I won't, I, I, uh, I wonder if he's like well known, right? And then they saw your Instagram and they were like, Oh my, oh my God. So it's it's really been awesome to see, right? Like uh the this sort of extreme success, your transparency about it, helping people acknowledge, you know, the reality of where they're at and this this whole sort of uh self-help for people who sit hate self-help. It's pretty amazing. And I just really enjoyed that you came here to have this conversation.

SPEAKER_02

Thanks, man.

Chris Allen

Yeah, it's been a pleasure. Awesome.

Narrator

Thank you for listening to the Entrepreneurs Studio Podcast. Check the show notes for resources and links from today's episode, and follow us on Instagram at the entrepreneurs.studio. See you next time.