In short
Building “unshakeable” self-confidence by stopping people-pleasing, accepting failure as the price of progress, and grounding confidence in meaning/purpose rather than constant positive feelings. Also covers boundaries, the risks of online therapy labels, and why dating apps often fail.
Guest background
Mark Manson is a best-selling author (The Subtle Art of Not Giving a F**k) and long-time writer/blogger (first post in 2007). He’s known for ethical, psychology-focused advice and for running “experiments” with fans to face fears (e.g., walking in a chicken costume; later hot-coals challenge).
Key claims
Confidence = comfort with failure, not guaranteed success. People pleasers should find “hills they’re willing to be disliked for.” Boundaries should be framed as rules (e.g., “I don’t do interviews after 3 p.m.”). Therapy/identity labels can become self-fulfilling limits; be careful about adopting them as identity. Dating apps optimize for superficial filters, missing hidden compatibility traits; apps have negative ROI. Success is better defined by meaning/purpose (deathbed question), not money/happiness alone.
Notable examples
“Paradoxically, the less you try to convince people to like you, the more likable you become.” Chicken costume and Malibu hot-coals; his burnout after Subtle Art success, then reframing back to entrepreneurship.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Nature of Confidence
0:50 to 1:27
Understanding how real confidence is about comfort with failure rather than constant positivity.
“You'll learn the psychology behind real self-belief.”
The Influence of Perception
1:27 to 3:37
Exploring how trying too hard to be liked can actually push people away.
“then how do you get more comfortable with failure?”
Evolution of Dating Advice
3:37 to 5:44
Mark discusses his journey through dating advice trends and generational shifts.
“You know, it's interesting because we've had many a walk on whatever Venice Beach Boulevard or whatever that is, the boardwalk.”
Critique of Dating Apps
5:44 to 7:46
Analyzing how dating apps can hinder authentic connections and relationships.
“And it's primarily because they're optimizing for the wrong things.”
Defining True Success
7:46 to 11:24
Mark reflects on the meaning of success beyond wealth and happiness.
“So, I mean, I think in a lot of ways everything you're talking about is about this.”
Building Confidence in a Modern World
11:24 to 14:01
Discussing the current confidence crisis and how online scrutiny affects self-esteem.
“I think predominantly a lot of young men on the internet, and I love your YouTube videos, by the way.”
Understanding Confidence and Failure
14:01 to 15:18
Explore the relationship between confidence and comfort with failure.
“Yeah, I feel like people definitely feel more scrutinized and judged these days.”
The Importance of Experiencing Failure
15:19 to 16:46
Learn how small failures can build confidence and resilience.
“We were literally just talking about it and whether that's inherent or not.”
Experiments in Overcoming Fear
16:47 to 19:38
Discussion on practical experiments to face fears and build confidence.
“Like it's every answer is actually just, do you want to go get somebody to date you that you like?”
The Dangers of Success and Comfort
19:39 to 22:08
Examine how success can lead to existential crises and loss of purpose.
“I almost, I was supposed to go to Tony's show the other week.”
Show all 32 chapters
The Dangers of Success and Comfort
25:52 to 26:25
Examine how success can lead to existential crises and loss of purpose.
“the website, logo, email, marketing, all at once.”
Reflections on Success and Happiness
26:32 to 28:00
A look into the paradox of happiness in relation to success and expectations.
“That book was so big, The Subtle Art of Not Giving a Fuck.”
Understanding What to Care About
28:00 to 30:25
Explore the balance between caring too much and having meaningful priorities.
“So the question is— It's called being human.”
Setting Boundaries Respectfully
30:25 to 32:56
Learn how to establish and communicate personal boundaries effectively.
“in a boundary way or when somebody else is trying to make you work outside of something that you feel comfortable with?”
The Impact of Labels on Identity
32:56 to 36:25
Examine the effects of self-labeling and its implications on mental health.
“Like what is going on with all these labels we're placing on ourselves?”
The Dangers of Overdiagnosis
36:25 to 40:24
Discuss the consequences of overdiagnosing mental health issues in society.
“But the best part about the test was at the end, I didn't believe it when somebody sent it to me.”
The Power of Self-Definition
40:24 to 42:00
Discover how the way we define ourselves influences our success and limitations.
“To say, you know, instead of saying, I have ADHD and, well, actually there's a bunch of contexts and situations that ADHD can actually be an asset.”
Mark Manson's Author Journey
42:00 to 44:31
Learn about Mark's transition from author to entrepreneur and the challenges he faced.
“And I was happy and everything was going great.”
The Importance of Self-Reflection
44:31 to 45:38
Understand the significance of self-reflection in avoiding burnout and aligning identity.
“which is I think one of the reasons why so many people follow you online, but why I like talking to you, you're really self-reflective.”
The Importance of Self-Reflection
45:42 to 46:05
Understand the significance of self-reflection in avoiding burnout and aligning identity.
“It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50 page restoration block, or finally break down that long article you've had open for weeks.”
Managing Emotions in Productivity
46:28 to 53:51
Explore how to view and manage emotions as a vital system in productivity.
“So a drum that I will bang on until my death.”
The Role of AI in Therapy
53:51 to 56:03
Discuss the implications of using AI like ChatGPT as a therapist and its limitations.
“And so what concerns me with some of my friends is these are like amazing people who will tell me that they'll have an argument with a man that they're dating and then go feed their side into ChatGPT.”
AI and Mental Health: A New Approach
56:03 to 57:50
Discussing the potential of AI in mental health and personal growth.
“The problem is that your average layperson has no idea what the difference between those two things is.”
Purpose: A New AI Mental Health App
57:50 to 59:46
Introducing 'Purpose', an AI app designed to provide tough love in mental health.
“And turns out he had identified the exact same problem.”
The Honest Conversations with AI
59:46 to 1:02:23
Exploring how users are more forthcoming with AI than therapists.
“So generally speaking, we see people are much more forthcoming with it.”
The Ethical Responsibility of AI Development
1:02:23 to 1:04:19
Debating the ethical implications and responsibilities in AI development.
“I was like, don't you think we should worry a little bit about what we're building with AI?”
Choosing the Right Partner
1:04:19 to 1:09:28
Insights on the importance of character and values in partner selection.
“So like we're, we're constantly testing it.”
Key Questions for Finding Your Ideal Partner
1:09:28 to 1:10:00
Advice on essential questions to ask when dating to find the right partner.
“What advice do you have for a young person that is looking for what you have, which is somebody that is all of those things?”
Finding Compatible Partners
1:10:00 to 1:11:52
Learn how to identify potential partners by asking the right questions.
Understanding Sacrifice in Relationships
1:11:52 to 1:13:26
Discover the inherent sacrifices in relationships and life choices.
“I also love the question too, because it, if you ask it and the person kind of freaks out and gets really uncomfortable, that's also a signal, right?”
Embracing Pain and Struggle
1:13:26 to 1:15:45
Understand the importance of recognizing the struggles you're willing to endure.
“I always say with goals, like don't tell me what you want.”
Passion for the Grind
1:15:45 to 1:16:34
Mark shares his joy in pursuing his ambitions as if playing a video game.
Transcript
Automatic transcript. May contain errors.0:00Thinking about refreshing the carpet in your home? Now's the time to do it. For a limited time at the Home Depot, get 10 % off installed carpet projects on trusted brands like LifeProof, LifeProof with PetProof Technology, Home Decorators Collection, and Traffic Master. Plus, with installation starting at just 49 cents per square foot, upgrading your space is more affordable than ever at the Home Depot. Offer valid June 11th, 2026 through June 28th, 2026. Exclusions apply. For licenses, see homedepot.com slash license numbers. Generally people who feel like they give a f**k about way too many things, it's not an issue about the caring, it's the extent of how much they care.
0:38It's not about not giving a f**k what other people think, it's about finding something that is more important than what other people think. If you don't have anything more important going on in your life, then what other people think about you is going to dictate everything else. Mark Manson, the best-selling author of The Subtle Art of Not Giving a F**k, is here today to break down how to stop faking confidence and start earning it. You'll learn the psychology behind real self-belief. Why trying to feel good all the time is actually what's holding you back. If you've ever second-guessed yourself or talked yourself out of taking a shot, this episode is your playbook for unstoppable confidence built from action, not affirmation.
1:12The more you try to feel confident all the time, the more aware you become of all of the different areas that you're actually not confident. It's when you stop trying to be confident all the time, that you actually feel comfortable in your pursuits, knowing that it might not work out, which is confidence. If confidence is really just the comfort with failure, then how do you get more comfortable with failure? I will say this. I would say probably. I hate this answer. If you want to change your life right now, these are the habits that you need to start adopting. What are they? I think it's.
1:46I want to start with some of my favorite tweets of yours. I just went down a deep rabbit hole. I haven't been in your tweets in a minute. I guess it's called the X's. X's. I don't even know what we're doing. I know. And so there were a bunch, you had one that you pinned that's like a new favorite of mine, which is you said, paradoxically, the less you try to convince people to like you, the more likable you become. Is that true and why? I think when people try to make you like them, when they try to control your reaction to them, it is like inherently off-putting. I think we generally respect people who are, we generally respect people who respect our agency right so if i come in here and i just start saying all the things you want to hear and trying to impress you and like be like all what i think you want to see it actually puts a lot of pressure on you to make me feel happy and okay and paradoxically that makes you feel bad so and do we not even realize that like do you think people don't even realize the things they're doing to turn off other people i think so if you think about it it's like a very childish kind of tactic like i think when we're young it's it's intuitive it just feels intuitive of like oh i want people to like me so let me just like agree with what everybody says at some point that stops working and you kind of realize you're like oh i'd rather be disliked for who i am than liked for something i'm not right because you just you you start feeling like even if you do get somebody to like you it feels icky and it's uh it doesn't feel like you're being appreciated for who you authentically are.
3:22And I think this takes place on a lot of, I mean, obviously this is like a social phenomenon, but people do this in dating. People do it with coworkers. They do it in business. It's like all the ass kissing, the yes men, like it backfires eventually. You know, it's interesting because we've had many a walk on whatever Venice Beach Boulevard or whatever that is, the boardwalk. And I think one of the reasons, you know, I like talking to you so much is you have this weird experience, which is that you've been on the internet for how many years now? I wrote, published my first blog post in 2007. In 2007.
3:59And you've obsessed kind of this entire time in varying ways, it seems to me at least, about human psychology. And once through the lens of like men and dating, and you saw one whole era, which was like the, how do I get girls to like me era, right? it. And then you went through an era of like, I don't care if anybody fucking likes me, fuck all of you guys. And also how do I become confident with that and whatever. And so I've really appreciated your advice. So I'm excited that you're here because man, we've both met a lot of people on the internet. Some of the advice is like, sounds really good that it's terrible advice.
4:32And you have like a very strong moral compass, an ethical and moral lens, which you're like, no, I will not give that advice anymore because it's not real. Or, oh, hey, I did mess up on that. Sorry about that, which is also really rare on the internet. So I want to go through like a bunch of questions that I think about and then a bunch of questions from people who are listening. And I want you to take it through like a couple different eras. Like even the era of like, you know, now we're almost back again to how do I get women to like me? It's been weird, honestly. It's funny because I self-published a men's dating book back in 2011.
5:10And I just thought that era of my life was closed. And it's funny because like Gen Z men are showing back up and that book starting to sell really well again. No way. So it's like, what was that one called? It's called Models Attract Women Through Honesty. And, uh, and I wrote it, I really wrote it to kind of be the antidote to all the pickup artist stuff back in the day. You know, like, dude, you don't need to wear a fuzzy hat and like do magic tricks in a bar. Like you can just be a good human being. Yeah. and it's interesting because it's kind of catching a second life with uh the next generation yeah because they're they're having less sex they're it's a mess really yeah it's a mess right now yeah what what what is out there in dating right now what are you hearing from your millions of followers on all different platforms from what i can tell it's so i have a couple theories but I would say the primary one is, I personally think that the apps are negative ROI for people's dating outcomes.
6:09And it's primarily because they're optimizing for the wrong things. If you think about it, I don't know how long you've been with your husband, but if you think back when you were single, you probably had the experience of you would often meet somebody and it wouldn't immediately occur to you. You wouldn't immediately be attracted to them. Like maybe you would talk to them for a little bit, get to know them, and then they'd kind of like, they'd win you over. Like you'd have to like kind of warm up to them a little bit. And the reason that happens is just that like we're poor judges of who's going to make us happy in a relationship.
6:43Like we often don't understand the traits in a person that is compatible with us. And so when you get on an app, the app asks you for all these superficial traits that you want. It's like, oh, I want somebody who's, you know, six foot five and in finance and like all this stuff. And it's like it's all the resume shit that doesn't actually generate any sort of chemistry or connection with somebody. Whereas all the things that actually do matter, you know, the personality traits and the background and the personal values and how the person experiences intimacy, the sense of humor, like all those things, they're hidden.
7:19So you can't match for those things. You have to meet the person first to understand if you actually have those things, if you're compatible with the person in that way. So I just think the dating apps have sorted for the wrong thing. And it's a classic case of people also not, because people don't know what they want, the dating apps are supplying a demand that is actually not solving the people's problems. Oh, man. So, I mean, I think in a lot of ways everything you're talking about is about this. Like people want to find love because they're chasing happiness. You know, people want to find relationships because they don't want to be alone.
7:56Like it's all sort of about what do we want as a human? It's like part of this human experience. And I'm wondering like, I don't know, I think I read somewhere that you had written between books and blog posts. It was something wild. You're like 17 ,542 blog posts. I don't remember the number, but it's a lot. and one of the lines you said is that real success isn't actually about making money or being happy. What do you mean by that? Both money and happiness are they're like oxygen. When you don't have any they solve everything but when you have some it solves nothing, right? So yeah, if you're broke go get some money.
8:41That's definitely going to solve your problems and if you're really miserable or depressed and like yeah obviously get some happiness but if you're already kind of at a steady baseline like you're in a stable position chasing more it's inefficient in a lot of ways like it's not actually going to satisfy you in any meaningful way um i personally think that like on the long term like if you look at the if you zoom out and look at your entire lifespan from beginning to end um the best way to define success is simply to feel as though you spent your time well? It's the old deathbed question, right?
9:15It's like when you're 80 and laying on your deathbed, are you going to look back and say, like, I'm glad I did that? Or are you going to say, like, wow, I wish I didn't do so much of that? And to me, that boils down to meaning and purpose, right? If you have meaning and purpose, if you are finding something meaningful and purposeful in your life to pursue and to chase after, whether that's building something or, you know starting a family or giving yourself to a cause generally speaking like that's the sort of stuff that decades later we look back on and we're like I'm really glad I spent time doing that and do you think this is like a global phenomenon like you went to and spent time in the happiest country in the world right what what did you find like what do the happiest people in the world have or was it something totally else you found there well the funny thing so the happiest kind of the happiest country in the world is Finland.
10:03And if you talk to the Finnish, they're like, what? Really? And the conclusion I came to is that I think Finnish culture has this, they have this ethos of kind of low expectations, which is very opposite of how Americans are. but there's this this sense of just being satisfied very easily like it's it's kind of a good thing to be satisfied and I think that there's some wisdom in that right like it's this isn't to say that you shouldn't chase things or you shouldn't have goals or dreams or whatever but it's it's also like have those goals and dreams but also while understanding that they're not going to solve anything like it's a fun game you're playing chase after that 10-year goal hopefully you achieve it that's great but just understand that like once you get on the other side of achieving it you're still going to be the same stressed anxious person who has problems and gets in fights with his mother and like it's like it's all the you're going to be the same person with the same shit going on so um you need to like ultimately find something that's that's worth that's worth the struggle.
11:21It feels like it makes the struggle worth it. When you're talking to, I think predominantly a lot of young men on the internet, and I love your YouTube videos, by the way. Thank you. Yeah. But you have quite a few where you talk about the habits that lead to successful or happy lives. I know there's no hacks to any of this. And at the end of our three-step process, their life will probably be totally fixed. Yeah, yeah. But if you had to give somebody, man, if you want to change your life right now, if you want to be more successful in life, these are the habits that you need to start adopting.
11:56What are they? If I had a 16-year-old in front of me and my job was to optimize them to have the most healthy and successful life possible, I would actually start with social skills. Because it's on the psychological side, pretty much all of the research around happiness essentially boils down to the quality of your relationships. do you have people in your life a and then do you have trusting intimate relationships with those people like do you have people in your life that you feel like have your back that you can trust that you can go to with a problem who aren't going to judge you for making a mistake and on the psychological side that's like the 80 20 and then on the professional side as you know like relationships are also everything like it's nobody ever uh did anything great by themselves Like there's no incredible successful business story that they did it alone.
12:55It's like you either built an amazing team or you had an amazing team of people backing you and helping you and supporting you. Yeah. I was reading a study the other day about how there's something like a 20 to 30 percent increase in salary just from thinking about increasing your EQ and really ignoring IQ that IQ almost has no correlation between monetary success. Yeah. Do you find also in personal relationships, like I think a lot of people these days, you know, some of our top videos on YouTube lately, I was talking to the team about them. They're all about confidence. And I thought that was really interesting because I feel like confidence usually goes away when you like, or a lack of confidence goes away when you work a lot.
13:40Like the more you work, the more confidence I have. I rarely am like, we're not going to be able to do it. I'm like, we probably haven't prepped. We haven't done sufficient things in order to have this outcome. And so I'm not confident we're going to hit it. But it does seem like we have like a confidence crisis. Do you see that with a lot of people saying, I do not feel confident in myself. I'm not going to be able to do it. I don't believe in myself. I have imposter syndrome. Yeah, I feel like people definitely feel more scrutinized and judged these days. And I think a lot of that is just how online and permanent everything is.
14:12You know, I think when you and I were young, if you kind of made a fool out of yourself, people would forget about it within a week or two. Now it lives forever on the internet. and people can like, you know, it's just everybody has a phone in their pocket. So it's anything dumb you do or say can potentially last forever. So I just think people have become much more risk averse and they haven't built that muscle of taking risk. But the other thing too is I think, you know, I've always said that confidence isn't about believing you're going to achieve success. It's a comfort with failure. It's knowing that you're going to be okay if it doesn't turn out okay like that's actually what makes you confident in a situation it's like i'm gonna take a stab at this and if it doesn't go all right that's fine i'm gonna learn from it right and i just think a lot of people have that backwards so they focus on like the the guaranteeing of success and so they they become a perfectionist and they try to control everything which then just makes them more anxious and more stressed out and they get into kind of a downward spiral that's a good point.
15:18I was really struggling to like nail what confidence is exactly the other day. We were literally just talking about it and whether that's inherent or not. But if it is, if confidence is really just the comfort with failure, then how do you get more comfortable with failure? Again, I hate this answer. I hate this for me. I hate this for everybody listening. Is this the only, is there not a three-step framework? God damn it, Mark. Sorry, but really like, okay, so let's get granular then. Like big failures, little failures, any failures, daily failures? All the above. And I will say this, I would say probably little failures first.
15:58I think it's because big failures, if you're not used to failing and if you're not used to failing publicly, like it can overwhelm you and kind of wipe you out. But yeah, definitely you want to get lots of little failures in, lots of little embarrassments, lots of, you know, coming back to the dating coaching thing. One of the first things I used to tell people, I would say like how how much have you gotten rejected lately and You know most people would say not at all because they didn't ask anybody out I'm, like well, that's your first problem Like go get rejected five times and then we can talk about what went wrong, you know, and People just don't think about it in those terms.
16:37They just think about it in terms of Give me the thing to say that is going to guarantee that this person likes me and The world doesn't work that way It really doesn't and it's almost like that in everything it is Like it's every answer is actually just, do you want to go get somebody to date you that you like? Go eat shit at least a hundred times to find one. And it's like, and if you want to get rich, go talk to a hundred customers that tell you no to get one. And if you want to buy a business, go look at a hundred deals to find one. Like every answer is basically quantity and more. And if you don't pile on more pain and failure, you're never going to have the thing that you want.
17:14Yeah. Which is crazy. And you know, it's kind of interesting about you too. like you've done these experiments with people. So as opposed to a lot of people who talk about things online, you're like, all right, I have a theory. And we're going to go test this theory live and see if the theory actually works and whether it breaks down. And you've done it, as far as I can see, with people who have lost weight, you know, one way or another, people who were scared of failure. Like maybe you could talk about one of the times that you walked in a chicken costume down Venice Boulevard, which I remember, and why?
17:45Because you put yourself through the experiment. at first right yeah yeah one of the things i i've always believed very strongly like i i've never never wanted to be the guy on stage like telling this is what you should do these are the five things that are going to change your life i've always liked the idea of like i'm in the trend i'm in the shit and the muck with everybody else you know i i go through this stuff too so in the videos i do the same i i basically took fans with various anxieties or personal issues and and kind of ran them through a gauntlet of different challenges or having them face their fears and whatnot.
18:19But I made myself do it too. And it's, it was a good exercise, right? It's like one is just, I should be able to walk the walk of, of what I say. But it's, it's also, I think it comes back to like building that, you can call it scar tissue or you can call it the muscle but it's basically it's like that accumulation of failures embarrassments etc um and it's funny because doing that series of videos by the time we got towards the end like i i honestly reached a point where i'm like i don't think there's anything at this point that could embarrass me or like or scare me careful if you put it out there you know i know um it was funny actually so we just shot one a few weeks ago um and i it was funny i i basically hosted a dinner for a bunch of of people in my audience and uh and went through worked on a bunch of stuff with them and then took them outside and we're on the beach in malibu and took it took them outside and then uh had everybody walk on on hot coals and uh which is like a classic tony robbins thing and uh and it was really funny because uh the the attendees like looked at me and they're like, oh, well, you do this all the time, right?
19:29And I'm like, no, I've never done this before. You're like, it might work. You might die. They were all looking at me. They're like, what the fuck is wrong with you? And I was like, I don't know. I don't know what's going to happen, but we'll find out. Are you okay? Yeah. Yeah. It was fun. But I like that. I almost, I was supposed to go to Tony's show the other week. Oh yeah? Yeah. I've never done it. Actually, that would, that gives me anxiety. Like I've like, we've got fire stuff or or being like hugging random people jumping up and down smiling like i don't know i'm an opt out and i say that with a lot of love to tony who's going to come on the pod and he was like come and you know what his selling point was be in the front row i was like tony not a selling point i want to be in the back i'm unsure about this you know but i i couldn't end up doing it because i had some health stuff but um i do think that it would have probably been good for me because I hate that.
20:20I hate the idea of hugging strangers and jumping up and down. Maybe. You know, it's funny, like a huge part of those seminars is that kind of like synthetic fun. And it's easy. I think it's one of those things where it's like easy for you and me, because I have the same feeling. Like I look at it and I'm like, really? Like we're going to dance again? Like what? Come on, man. Public dancing. Yeah. It's like, no, I don't want to give another back rub. Like it's just, you have to do back rubs. Yeah. I'm like, I'm good, man. Like I'm, I don't, but it's funny because I think it's ultimately we're not the target market.
21:01Like if you think about somebody who's extremely depressed, extremely lonely, like hasn't gotten out much, has kind of lost touch with most of the people in their lives, an experience like that can be very powerful um but yeah if you do have like a bunch of you know a bunch of good relationships in your life you're pretty happy like it is kind of just it's synthetic fun interesting so you almost have had to stair step your way up the embarrassment ladder too oh yeah you're like you know now now chicken costume is like that's a tuesday oh yeah i could put one on right now i was like no problem So it's, I mean, it's like anything though, right?
21:42Like, I mean, it's, it's, you, you, you climb that ladder with money too, right? Like, it's like the first time you have a five figure deal, you're sweating bullets. You know, now it's like, you don't even, probably don't even get out of bed for a five figure deal. So it's, it's like anything in life is like that. You just, you, you get that progressive desensitization that happens over time. Yeah. That's probably actually bad in a lot of ways and why really rich people go crazy. It can be, you know, they like can't find the new adrenaline rush. Because you have a line actually that I like, which is like, happiness comes from progress, therefore happiness requires struggle, which I think lends itself to this.
22:19Because what if you can't find something to struggle on anymore? What does that quote mean to you? Well, it's paradoxical because the more successful you become, the harder it is to know what progress is or what progress is worth having. So, and this is why you see, so in my second book, I talk about this, that there's, there's, uh, I believe it's called the Easterland paradox in psychology, which is essentially that you find that the poor, the country or the poor, the, the neighborhood, the lower the suicide rate and, and the more affluent the country and the more affluent the neighborhood, the higher the suicide rate.
22:58And I think it, it comes from the fact that when you don't have anything in life, like when you're struggling on a day-to-day basis, meaning is very simple. It's like get to tomorrow, get the rent paid, get some food on the table. Like there's no ambiguity of what you should be doing to be improving your life. If you're like kicking it in a Bel Air mansion, you know, with like some crazy nine-figure exit or something and you're 32 and you have nothing to do all day, like that is an existential crisis. Like nobody's going to shed a tear for you, but it's not obvious what progress is. It's not obvious what you should do next.
23:44In fact, the fact that you can do potentially an infinite number of things actually makes it even harder to figure out what progress looks like or what you should be doing next and so you you often see so it's funny like i there's a i don't know if it's a national network or if it's just like a california thing but there's there's a network uh it's it's called the post exit founders group or network or whatever and it's um and i've got some friends who are in it and it's i've talked to them before and they're like yeah dude it's like when we do our events and everybody gets behind closed doors it's like half the people there are like in an existential crisis because they just had this massive check hit their bank account and they're not working anymore.
24:26And sure, you can like splurge on a boat and go to Greece or something, but like that gets old after a month or two. And then you're just sitting around being like, oh shit, what next? Especially if entrepreneurship is a trauma response, which I think it is half the time. I'm like, what sane person would do this? That's not normal. And so if that's true, and so like half the reason you keep going is because you're kind of self-masochistic and you like the struggle and figuring out what to do next. If I only had the option of sipping sipping Mai Tais all day and you got to look at yourself in the eye and nobody else yeah that could become problematic for sure it's funny like the one of the most depressed I've ever been is after my first book blew up and it was because basically everything I'd been working for towards the previous 10 years all happened and got accomplished at the same time and so then I just kind of sat around being like well I guess I'll play some more video games because I don't know what else to do.
25:25And it was like a very bleak six months. It was very strange, which is weird because everybody's patting you on the back and saying, oh my God, you must be living your dream. And you're like, yeah, this is my dream, but I'm the same dude with the same problems and the same anxieties and the same bad habits. And except now I have nothing to look forward to. I have no definition of progress in my life. Buying a business or launching your own venture can feel impossible if you're stuck figuring out the website, logo, email, marketing, all at once. But here's the good news. GoDaddy Arrow is here to help.
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26:35Obviously, we talked about it in the beginning of this in the intro, but it was so big. It is so big. I mean, one of the most sold nonfiction copies books of all time. 20 something million copies at this point. Which is insane. Also an incredible documentary on Netflix. I remember when that came out. Great thumbnail too. Was that you? Weren't you at a floaty at a pool? Yeah, they put me in a pool. There's this like crazy surreal opening sequence that involves me sitting in a pool drinking out of a pineapple while like people die and emergencies happen around me. It's like this very dramatic sequence.
27:13It was shot. It was like 45 degrees in New Zealand when they shot that. So I was freezing my ass off the entire time. But, you know, I got to have my little Hollywood moment. It did not look like that. It looked lovely and happy. So cold. There was like a, there were a bunch of PAs with like mountains of towels on the side. So as soon as I got out of the pool, they just like draped all these towels over me. So it was so cold. But you know, what's cool about that book that I think is really resurfacing for people. Boundaries are really big with the kids these days. Yes. You know, not giving a fuck, having confidence.
27:43That book, again, is like, I feel like even having another resurgence moment. I'm sure there are many people out there right now thinking about what other people think more than those other people are ever actually thinking about them. Oh, like all of us. Right. Like you're talking about me? So the question is— It's called being human. The book's not that long, which I also love about it. But if you had to distill for somebody who hasn't read it yet, what do you do when you give too many fucks? so the the paradoxical thing and this is this is laid out in chapter one is is the whole idea of not giving a fuck it's a bit of a misnomer like this idea that things are just going to roll off your back and nothing's going to faze you like it that there's a word for that in psychology it's called a psychopath so it's we don't want that you do want to care about things obviously you do want people in your life that you you do care about their opinion right like it should upset me if, I don't know, my parents are mad at me.
28:46So the question is, how much should we care? So generally people who feel like they give a fuck about way too many things or what way too many people think, it's not an issue about the caring, it's the extent of how much they care. So the point I make in the book is that it's not about not giving a fuck what other people think, it's about finding something that is more important than what other people think. Because if you don't have anything more important going on in your life than what other people think about you, then what other people think about you is going to dictate everything else. And that's just like a shitty place to be.
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29:20It's nothing good's going to happen. But if you have, this comes back to the meaning and purpose thing. If you have something very meaningful, something you're giving yourself to, something you're willing to sacrifice for, something you care very, very deeply about, then suddenly it's okay if some people don't like you. It's okay if some people don't get it if some people judge you or disapprove of you so what what would you say to somebody that's like i just want to stop being such a people pleaser find the hills that you're willing to die on like find like ask yourself what are you willing to be disliked for and for a people pleaser that's going to be a very hard question to answer they like they might not actually have anything that they can answer and to which at that point your job becomes to find something find something you're willing to be disliked for and then go do it because that that's your thing that's that's that's the piece of meaning and purpose that's going to be more important than other people's opinions as long as you're driving towards that then everything else will kind of fall into place what is sort of the right way to respond when somebody else is like coming at you in a boundary way or when somebody else is trying to make you work outside of something that you feel comfortable with?
30:37How do you keep boundaries, but not look like a dick? I think it's, I think tactically speaking, it's, it's always great to frame things like rules. So, you know, for instance, if I, if I was like, like, let's say your producer emailed me and it was like, you know, come in at whatever o 'clock. And I was like, no, that's preposterous. I like, I refuse. Like, then it creates this ugly situation, right? Whereas if I'm just like, hey, man, I have this rule. I don't do interviews after 3 p.m. Sorry. Maybe we can find another time. Like, when you frame things as a rule, it's like, hey, this is just a rule I have in my life.
31:19I just don't do this thing. And it's just to take care of my own health and my own sanity or whatever. People respect it. And then if they don't, it actually, it makes it very easy to be like, oh well then fuck them like they're not respecting my rules so this is just not going to work out so i i always encourage people like frame whatever boundaries you want to have frame it as a rule it's like hey i don't um you know i i don't talk about this subject uh with people who aren't part of my family nothing personal you know and then it's like then things become very clear it's so because it's shifting the no to you to like, oh no, it's not about you.
32:00It's about this thing under here that already exists. It's like you get to use a shadow influence without even having one. And then you get to deflect in a respectful way whatever somebody else is trying to push on you. That's so good. Yeah. And what's interesting too is that it also clarifies for you the caliber of the relationship you have, right? Like if the person doesn't respect your rule, then by extension they're not respecting you so it makes it very clear of like okay this is i have somebody in my life who is not respect who doesn't respect me what am i going to do about that whereas if you're kind of in this people-pleasing mode and you're like well i don't want to upset them so i'm going to like hint and like maybe like be a little passive-aggressive drag my feet pretend like i forgot then you just end up in this like murky gray area where it's like nobody nobody's really happy with how how the friendship's going or the relationship's going but like you're you're kind of going through the motions and like it just yeah it doesn't doesn't end well do you think that we are like over labeling ourselves such as like these days i was like watching something online it's like i'm an avoidant i'm a this i'm a you know i'm With a passive aggressive person.
33:19He's definitely a narcissist. Like what is going on with all these labels we're placing on ourselves? Are these real? Are they that black or white? Yeah, they are real. They're not necessarily black and white. And I have mixed feelings about it. Like I think it's a sword that cuts both ways. So I do, and I do think there is a bit of an over labeling that has been happening. So I'll make the bull case first for all this labeling. and and i guess we could call this just kind of like therapy culture in general you know so it's like the all of the language that permeates tiktok and instagram and and youtube these days and people talking you know about being neurodivergent and avoiding and attachment types and dealing with narcissists and all this stuff like there's all this like kind of clinical therapy language that has entered into the mainstream so on the one hand it represents just an awareness of like a lot of these dynamics and issues, right?
34:18Which I don't think that's a bad thing. Like if you go back a couple generations, like people just buried shit for decades and it only come out after - Like adults, you know? Shove it down. Just keep shoving it down. Yeah, don't deal with that. And hope it doesn't come out after nine or 10 drinks. So I do think it's good that these things are being talked about. The problem is that there's a very fine line between labeling a problem and adopting a label as an identity. So as soon as you adopt a label as an identity, like the way our minds work is whatever I've defined myself as part of my identity, I'm going to defend it.
35:04And I'm going to become emotionally attached to it. So if I decide that, let's say I'm ADHD, which I am diagnosed as ADHD, but if I decide to make that a core part of my identity, like it defines who I am and my relationships and how I see the world and interact with the world, then I'm going to start imposing that on all of my experiences and my relationships. and then you get this kind of self-fulfilling prophecy, which is that because I'm approaching every experience in my life is like, well, as an ADHD person, I can't really handle this. And as an ADHD person, you need to talk to me this way and not that way.
35:44You actually amplify how serious the condition is. Whereas if you just said like, okay, this is a thing I have and I'm just gonna manage it and I'm not gonna make it part of my identity, you can use that awareness to diminish how much it affects your life. So the problem I see is that adopting these labels as an identity is being rewarded online. And so the more it's rewarded, the more people like cling to them, which the worse they feel for having them. Great point. I've also been diagnosed as ADHD from an online test I did once. Very clinical. Yes, it was super. But the best part about the test was at the end, I didn't believe it when somebody sent it to me.
36:32But at the end, there was a literal link to talk to, I guess it would have been a psychiatrist because they could prescribe, and consider some sort of option, which I believe was some variant of Adderall that I hadn't heard of before. So like, you may need to get on a person with this one. And some of your treatment options. So it was like kind of an ad. And I thought, for the love of all the Tully, in a 15-question interview online, you're going to diagnose me as X thing and give me a pill? Seems flawed. Yes. You know? There's a whole overdiagnosis issue, and that's just across the board. Anxiety disorders, depression, PTSD.
37:16Probably all of those are being overdiagnosed to a certain extent. I mean, the problem is just without getting down too much of a tangent, there's always been kind of the pharmaceutical incentive, right, to diagnose people. And I think for many, many decades, the population was underdiagnosed. So like that incentive was aligned with the public good. but I think probably in the last 10 years 15 years um we're we're getting to a place where there's an over diagnosis and now that incentive is an issue and then on top of that you have kind of the social incentives of well if I start making tiktoks talking about my adhd then I'm going to get a following and all these other adhd people are going to follow me or if I talk about my anxiety disorder or my panic attacks like all these other people are going to follow me and then that becomes just a core part of who I am, which psychologically promotes, subtly it promotes a greater propensity for anxiety attacks and panic attacks, right?
38:20So like self-definition, I probably should have said this earlier, like self-definition has a huge impact on our mental well-being, right? Like there's so much research about this on both good and bad labels. So like for instance, if you set out and start a new challenge, say it's a business challenge or it could be anything, it could be running a mile or whatever, simply deciding, like simply believing that you are capable of doing it, that you will be successful at it, like increases your odds of success substantially. it's it's the self-fulfilling prophecy aspect of life right like if i tell myself that uh my new business venture is going to fail it makes it more likely it's going to fail because it's going to prime my brain to start looking for all the ways it could screw up and and then when it does screw up i'm gonna be like see i always knew it was going to screw up so it's like this is why you often see like founders and entrepreneurs are delusionally optimistic and overestimate themselves consistently because it's actually very useful in a certain context.
39:30You see this with the athletes. You generally see this with a wide range of highly successful people. The opposite of that is true as well. So if you believe, I can't do this because I'm an anxious person. I can't do this because it's going to be too stressful. I'm going to have panic attacks. you make it more likely that you are going to succumb to stress and panic attacks. That's not to say that it's the only thing causing your stress. People do legitimately have anxiety disorders and panic disorders and all sorts of things. But the language you use with yourself can move the needle in terms of the likelihood of it holding you back or not.
40:16And so the other concerning part of therapy culture is that it is, I think it is subtly reinforcing people to place limitations on themselves. To say, you know, instead of saying, I have ADHD and, well, actually there's a bunch of contexts and situations that ADHD can actually be an asset. that it's encouraging people to say, I have ADHD, so I'm just never going to be like a normal person. And there's all these things I can't do. And there's a bunch of things I'm probably going to fail at. And then it becomes the self-fulfilling prophecy. If you're listening, how do you integrate this into your life?
40:54What should you do instead of labeling yourself as negative things? How do you change and prime your brain so that you can label yourself a winner? It's a great question. I also think there's potentially issues with labeling yourself a winner so I I'm I'm of the Buddhist school of like don't label yourself anything you don't know who the fuck you are because when you don't have a label then your potential is infinite right like you could potentially become anything or anybody you want so I just I recommend people shy away from labels as much as possible. And if you do adopt one, like be very conscious of why you're adopting it and like what the consequences of adopting that label are.
41:44I'll use kind of a superficial example or it's not really superficial. It might sound superficial, but it was actually very profound for me. So I started, as we talked about earlier, I started blogging 2007. my first business was dating relationship coaching. And that actually did pretty well. And I was happy and everything was going great. And I decided to write a book to kind of promote my online coaching business. That book eventually became Subtle Art. Subtle Art went on and sold a bazillion copies. And sure enough, next thing I know, all these big book deals are showing up. all these publishers want to work with me, all these incredible opportunities are knocking on my door.
42:32I got to do a book with Will Smith. And it was super exciting. For the next five years, I was working just as hard as I had always worked. But it was feeling like, I guess I would say, it started to feel like a grind. It started to feel like, obviously, it wasn't a day job. But the feeling that people get when you're just doing something for a paycheck, it started to feel like that towards the end and and it really started to like grind me down and i i got pretty burnt out and i took a sabbatical in 2022 and and my big realization on the sabbatical was like i thought i was an author like all of this shit all the burnout and the stress and like long long miserable hours the problem was i thought i was an author I'm an entrepreneur this is like I I was creating a media and coaching business I lost track of that because people showed up and started offering me like more money than I'd ever seen in my life to play as an author and so I I told myself I'm an author I do author things now and I started living an author life and it was like I don't know it was like walking around in clothes that are the wrong size like it's just very uncomfortable and eventually like starts to wear you down.
43:47And so on my sabbatical, I was like, I completely forgot. The way I got here is because I'm an entrepreneur, I should go back to being an entrepreneur and building online media and coaching businesses. And that's what I did. And I'm like happy as a pig in shit. So I haven't written a book in five years. So it's a simple shift in definition. And I think, I guess my story like the lesson from that is that it's very easy to unconsciously change how you see yourself based on the financial opportunities that show up it's very tempting to do that and um and i did that and it like i ended up paying the consequences so um so yeah i'm back to being an entrepreneur and i'm very happy comma author yes sometimes author well you know you are really good at which is I think one of the reasons why so many people follow you online, but why I like talking to you, you're really self-reflective.
44:44Like almost every time we've talked, you've been like, I'm thinking about this. I tried this. I didn't like it. Like it didn't sit well with me. And so I thought about it and I, and I changed it. And I think a lot of us in life, we just keep going. We're like, you know, don't pay attention, keep going. And that's why burnout comes. There's no self-reflection. There's no review, but like, you're quite good. I think it taking a step back and going, okay, let me think about this. And even a reframe like I did there, you would have been very tempting for you to go like, oh, well, here's how you should label yourself.
45:16You accept somebody else's frame. That's actually, it's really hard to not do, especially in an interview. To go instead, you said dumb question, this is what you should do instead, right? So for somebody listening, what is the way that you should self-reflect to even figure out, oh, I'm unhappy because I've labeled myself improperly? properly. Yeah. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50 page restoration block, or finally break down that long article you've had open for weeks.
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46:04Mark Manson:Good sleep is everything. That's why Oli's science back support is made with a blend of melatonin and L-theanine for both kiddos and grownups. So when your mind won't switch off, you've got something that can help. Erasing thoughts and restless nights won't stand a chance. Find Oli's sleep solutions for the whole family at Oli.com. That's O-L-L-Y dot com. So a drum that I will bang on until my death. I keep pushing this message into the productivity space and I feel like nobody wants to hear it but I think it's extremely important so for people who care right now or in a phase of their life that they care very deeply about success, productivity, achievement, all those things you have to view your emotions as another system to be managed most people just like you said push the emotion that they compartmentalize they're like we're not going to think about that now.
47:02I've got meetings to go to. And you can do that for a while. You can do that for a year, maybe a couple of years, but like at some point it's going to come back and it's really going to bite you in the ass. And I think that the thing that doesn't get talked about enough is that your emotions are another system to be managed to. And as soon as you feel yourself getting off track emotionally of like not enjoying what you're doing, not being excited about the people you're working with, not getting along with your team. Like these are all signals of like something's off and sure, maybe it's not showing up on the balance sheet and it's not showing up in the PNL, but like it matters because if you're miserable, like that's, that's fucking terrible ROI long-term.
47:52Like you don't want to be stuck in a business. you don't want to build your own prison essentially so it's it's the first thing i would say for people who like you know really care about uh that stuff is is like to just acknowledge that this matters that it like it does affect everything and the second thing i think once you once you realize that it is an important facet of of everything that you're doing it is another system to be managed then you can start looking at it and thinking about it like you look at and think about other systems in your business or your career of like, okay, where's the bottleneck?
48:28You know, where's like the poor ROI? Like where's the place or the person that I'm putting tons of energy into and I feel like I'm getting very little out? Like it's the exact same principles that you're applying in all these other areas of your life. You can look at your emotional life in the exact same way. In terms of tactically, I think journaling is by far probably the easiest lift, the highest leverage activity for people who haven't thought about this stuff a whole lot. Just get yourself an empty notebook and start asking yourself a lot of these questions. And really starting with the basics.
49:08What do I feel about this? How am I feeling in this moment? How am I feeling today? How am I feeling about what I'm working on? How am I feeling about the people around me? And then once you've identified those feelings, then ask yourself, why? Why do I feel this way? Why does it feel so draining when I'm working on this part of my business or on this part of my career? What is it about it? And then really explore that. you know, give yourself the freedom to, to write pretty liberally until you, you find something. That's really good. So no screaming manifestations in the mirror and journal just kind of briefly about the things that we feel and ask why.
49:52That seems reasonable for like internet people. It's funny too. Like it's such a basic thing. I used to call this the why game and it's, um, you know, so you just take something, take something you're struggling with and say like, how do you feel about that uh or like why are you struggling with it take that reason and then you take that reason you say okay why is that reason a problem and then you get another reason and you say okay why is that reason a problem and it's just like layers of an onion and you just keep going going and going and going and usually you'll you'll get to a point where it gets circular and um and and like that circularity is usually like okay that's that's actually the real problem That's the thing that you actually have to focus on, not this surface layer shit that, you know, you've been thinking about.
50:38That's so good. You know, on the same vein, you were talking originally about, hey, like, I think people get this wrong and they're not listening to this, but I'll scream it from the rooftops. What else do you think that young people today just have so wrong? Yeah. Well, we've definitely hit two of them. Like the failure piece is, that feels very particular to Gen Z, I think. It's just the... I'm alarmed by the amount of risk aversion. I think the other thing that people, you know, we talked about boundaries a little bit earlier. I do feel like there's maybe an overcorrection that's happening there.
51:16Again, it's great that people are becoming aware of boundaries and speaking up for themselves and being willing to say no. But I think, again, coming back, there's so much shitty advice on social media But it's just like, if they don't respect you, then they can get the fuck out of your life. And it's like, well, no, actually, some people you don't want to do that with, right? Like some people, some people you maybe want to stick it out and, and try to work with them or, or put some time into it. um i i do there's some alarming we did a we did a podcast last year on um uh kind of some alarming statistics on on people people cutting family members out of their lives what's happening it's i forget the exact numbers because it's been a while but it was an it was an episode we did like probably like early 25 um and it's yeah it's it's shocking it's way more people and you think it's something like 20-25 % of Gen Z is like willingly chosen not to speak to at least one parent.
52:22A lot of siblings being cut off you know a lot of stuff and again I think it's it's like well-intentioned therapy culture type stuff of like you know well my mom is toxic or my brother never respects my boundaries or whatever and I get where it's coming from but I also think that there are i i feel like cutting family members out of your life is is a a move of last resort like there's a lot of intermediary steps you can go you can doesn't need to be step one you can manage you can manage exposure to people you can manage like you know set boundaries around which topics you you'll talk with how long you'll spend with them you know what conversations you'll indulge which ones you won't um yeah there's there's just a lot of managing that you can do in between.
53:09I mean, I always go back to the quote. It's like an African proverb about you can either pave the world in leather or you can wear leather shoes. And I think there is, I totally agree with you. Sometimes that person that's problematic is there to teach you something. And if you just avoid everybody that you don't like or everybody that is even toxic or everybody that is pushing boundaries, then that means you don't get better at holding them. You don't get better at keeping things out of your perimeter that are toxic because you're so hard to push through. You know, if you don't allow these people in to teach you lessons in some way, you never get better because you expect the whole world to be paved as opposed to wearing the shoes.
53:51And so I think, you know, it's cool because what you're building right now that I want to talk about is a pushback to the thing that scares the hell out of me, which is I have like multiple girlfriends who have turned ChatGPT and named it into their therapist. Okay. And the problem, as my friend Arthur Book said better than I did, and I'm not going to say it as eloquent, is that he says the problem with chat GPT is it is a malignant narcissist in that it is just trained to read back to you the things that it thinks that you want to hear. Yes. And to agree with you by and large. And so, and it has no emotion.
54:27Yes. It is psychopathic in its tendencies. And so what concerns me with some of my friends is these are like amazing people who will tell me that they'll have an argument with a man that they're dating and then go feed their side into ChatGPT. And ChatGPT will confirm every single thing that they're doing. Of course. And I love you friends, but some of you guys are fucking psychos too. Like, you know, we can get crazy relationships, me included. Of course. And I'm wrong all the time. And so if I only feed my side in and then ChatGPT is always telling me I'm right, that seems bad. Yes. And I don't know.
54:58you're the expert in this. Like what is happening? Is that bad? Should people be using chat GPT as a therapist? What is your thought? And then I want to talk to you about your counterpoint to it. Deeply concerned as well. You know, I started noticing in my life, same thing, a bunch of friends, family members started using chat GPT as a therapist. I went, this is maybe a year, year and a half ago, I went and started experimenting with it, you know, kind of And I'll say this. It's very uneven. There's some things that it's much better at than, say, your average therapist, and then some things it's much worse at.
55:40So the thing you pointed out is what it's much worse at. It just validates. It doesn't think critically. It doesn't challenge you. It wants you to feel happy. It kisses your ass way too much. the thing that it's good at is it is in its data set is the entire wealth of knowledge the entire field of psychology essentially every research paper is in there every finding is then in there every branch of the the topic is in there all like there's i think there's um over 3 000 hours worth of therapy transcripts like in the foundational model so if you get it away from if you approach it with any problem that's not about validating your feelings, like if you actually ask it for some sort of tangible feedback or advice on a more specific problem, it will actually be extremely well-informed on the research in that area and will generally give you some good direction and good advice.
56:44The problem is that your average layperson has no idea what the difference between those two things is. And so yeah, that becomes very problematic for sure. Yeah. And isn't, I mean, I was reading the other day that like 60 % of LLMs are off of Reddit, which is, I think where dreams go to die. So that like those people being my therapist is my personal nightmare. That would be horrific. Yes. But like, I guess my point here is you're building something that's a counterpoint to this, which is don't just go to, like, if you actually want to change your life or fix your life, you don't just want to be told you're right.
57:19And that's like my husband and I always say that to each other. We say, do you want to win or do you want to be right? Right. Exactly. And often winning doesn't mean me personally winning. It might mean our relationship winning. You know? Do I want our relationship to be good or do I want to say, you are wrong. I am right. Tell me. Tell it back to me. Yes. You know? Yeah. And if that's what you want, then I guess go to ChatGPT. Yeah. But if not, there's not a lot of other places to go to where somebody will kind of give you a little tough love. Yeah. And so you came up with something that I think is really clever.
57:47Yeah. so i i i felt very strongly so i again i felt this tension i'm like it's definitely not meant for this purpose but the potential is there like it is it is trained on so much wealth of psychological knowledge and data um and coincidentally it's funny i was actually at a poker game i sat next to a guy and um started talking to him and uh his name was raj and he founded a ai business have you ever checked in a hotel and you get like a like a text message and it's like an ai concierge you can say like oh i want towels or whatever so yeah he created that um he's probably doing okay yeah he he had like a very big exit and took a year off and had just just finished his sabbatical like when he went to that poker game so i started talking to him he's like yeah i'm just wrapping up a sabbatical i'm trying to figure out what's next i was like oh cool like what are you thinking about and he said well i i really want to do something in ai mental health.
58:43And I was like, no shit. Been thinking about this too. And turns out he had identified the exact same problem. He's like, there's so much potential here, but there's no LLM that has been optimized for it. There's nothing that's been trained for it. There's nothing that's like been specifically created for this purpose. So he and I became co-founders and he's, we've been working together since February. And as of this week, we were in full V1 launch of our app called Purpose. And the goal of it is to essentially be that counterpoint, the ChatGPT, instead of just trying to make you feel better all the time.
59:24The goal is to actually make you better, right? Tell you the things, the hard things that you need to hear, you know, point out your blind spots to you, challenge you on your bullshit, say like are you really sure about that or like maybe like your shit stinks too um and it's been great like it's it's because here's the funny thing that we've actually noticed with a lot of our early users as well is that like people are way more honest with an ai than they are with a therapist like if you i don't know about you but like my experience in therapy like it often takes like four or five six sessions just to get to the point where i'm like okay I'll actually say this thing to her right and you want them to like you more than your partner that's like the natural inclination it's all about your perspective but it's you know when it's an AI it's just like well fuck it whatever this is what I'm thinking this is who I'm kind of screwed up but like here it is it never judges you it's like you never have to worry about it's gonna like hold something against you or it's like secretly thinking something about you.
1:00:30So generally speaking, we see people are much more forthcoming with it. And you actually get to that clarity extremely quickly, like sometimes in a matter of minutes. It's like pretty crazy. Is there like a Mark Manson button or Mark Manson? Is there a button where we can get your voice to talk back to us? Not yet. Maybe, maybe. That might be coming. Or is it really nice still? It is nice. Does it cuss? No. I have a lot of user feedback. I feel like this is a mess. I wanted to be able to talk shit to me from the author of The Subtle Art of Giving a Fuck back. We actually talked about this. Okay.
1:01:15And one of the things I told my co-founders, I was like, look, I'm under no illusions that I'm the right person for everybody, right? So it's, I actually think if we put my personality on it, we would be limiting it. It would help fewer people. So it is not limited to me, but, you know, maybe we will get a Mark Manson button. Just a little button. Yeah, that's what. Just be like, hey, fuck face. Yeah, exactly. Pull your head out. Also, talk about viral feedback loops. Yes. You know, can you imagine those screenshots? Yeah, it'd be fun. Yeah, come on. All right, let me on the cap table.
1:01:49Mark Manson:I've got feedback. Okay. But I really like the idea and I really commend my husband's, the smarty on AI. It's not me. But just this weekend, I was with, yeah, last weekend, whatever, whatever ASL was. And I was with all these guys who like the guy who started Aptronic, the robot company. And well, I won't say the, anyway, like just a bunch of really big names in robotics and AI. And I had the funniest conversation. It wasn't from the CEO of Apptronic. And the conversation kind of went like this. I was like, don't you think we should worry a little bit about what we're building with AI? Because seems like happiness, gone down.
1:02:30Sex, gone down. Marriage, gone down. Like social media has like, by and large, us gluing our faces to the phones, by and large, incredible for productivity and GDP growth. Not so great for just being happy, like as humans, it seems like, or even procreating. Like the data is kind of hard to refute, I think, on that. So if that's true, I'm like, maybe, you know, if they like neurochip ads into our brains, it would be not great. And so anyway, like that seems like reasonable to me. And as I was talking to this guy, who's a really nice guy that I like, he was like, well, I'm a tech optimist. And I thought, yeah, like I'm an optimist too, but you could be cautiously optimistic, which also seems rational.
1:03:11And he's like, no, we'll just like figure it out. I go, well, we haven't exactly figured it out. So shouldn't we have these conversations and say, what are we building? Is this really a good idea? And how could we try to take all the knowledge we have of human psychology for millennia and realize that if this is an extension of human psychology, it's probably good to put some guardrails on it if at all humanly possible. For sure. So I commend that you're doing it. Because his response was hysterical. It was like maximum mansplain. He goes, listen, come on Monday. I'll explain AI to you. I was like, get the fuck out.
1:03:44I was like, that's what I was like. I was like, I want to have my big dick energy. I'm like, I want to open my legs wider than you. But I know it's not funny. I mean, and I'm not pretending I know very much about AI, but we've invested in a slew of companies and even the best founders are concerned. Oh, we spend like a ridiculous amount of time. The two big things we spend most of our development time on is privacy and guardrails. Because it is such early days and we are still learning so much about what is an appropriate use of this technology and what's not. And, and, and yeah, it's hard. It's, it, there's some scary shit.
1:04:22So like we're, we're constantly testing it. Like it's, it's very, very high on our priority list. The one thing I will say to what you just said is, and this actually like relieved me, it's going to sound a little bit funny when I explain. When I went in, when I started this company, you know, I was very like, Like basically we, you know, Raj is the engineer, the builder, you know, built the team, built all the development team and everything. And then I was kind of the product guy. So I had a rough idea of like how this thing should talk, what it should sound like, what good tough love advice is and, you know, what is just kissing your ass.
1:05:01and so I spent a lot of time working with the LLM directly like on the the eval system the training data all the system prompts like trying to trying to squeeze out of it like what should come out of it and I will say after working very very closely directly with an LLM for over a year now I've actually my estimation of what they're capable of has dropped considerably like they are they're like brilliant idiots. Like they, they will, they will do multivariate calculus while doing a backflip and like spinning two plates on their fingers. But then, you know, like their shoes will be on wrong. Like it's, there's like so many situations like that, that, uh, you know, there've been so many times where I've just been trying to get, uh, get it to do like such a basic thing and it'll take an entire afternoon.
1:05:55And I'm like, okay, there's no way this thing's taking over the world. Like it's just like the fact that it can't even give me this like one text response when I specifically asked for it, you know, it's like, okay, we're probably going to be okay for a while. So I do think there's a lot of, there's a little bit of, of moral panic going on around it. I don't think they're quite as capable as, as most of, I mean, I don't know how much you guys have been using AI in your business, but it's, it's like a year ago I was like, so on the train of like everybody on my team, you got to get good at AI right now.
1:06:30This is going to be part of every workflow. And six months later, we're like, oh, half of it is just trash. I do think garbage in, garbage out. Yeah. And it's actually very, very hard to, you have to be extremely skilled to get it to do what you want extremely well. And oftentimes the amount of effort it takes to get it to do something you want extremely well, you might as well just do it yourself. Yeah, I'm still there. sometimes too. But I do have, we hired a whole AI specialist team. So it's actually so fun to work with them because they're just, they're also smarter than me at prompting. And because with AI too, you have to know, I mean, to go to your part about beautiful idiots or brilliant idiots, you know, there's like, there is the plate spinner that is the best plate spinner of all time, but that you have to match with the back flipper sometimes.
1:07:17And you're like, oh, okay, the two of you together do some magic, but independently, Jesus, you know? There's like one other place I want to go with you today. Totally unrelated to AI, hard pivot, but you did start in dating and I've always like respected the conversations we've had about you and your wife and how you choose partners. So I want to read you a couple of quotes and get your feedback. You said, choosing a romantic partner isn't just about romance. You're also choosing a confidant, counselor, career advisor, therapist, investor, teacher, travel buddy, roommate and business partner.
1:07:51Choose wisely. And the question I think is, does that still hold true for you? That was from quite a few years ago. And how exactly does one find this type of partner? It's funny because when I posted that, I got a bunch of blowback of people like, oh, you shouldn't hold people to such high expectations. And I think what gets missed is that it's not that you should go looking for all those things. It's when you choose to marry somebody, that's what you're getting. Whether you want it or not, that person, your spouse becomes that, all of those things for you. So you have to vet them beyond just how is the romance or how spicy is the sex.
1:08:32You have to think through a lot of different personality traits. And I think it's absolutely true. I personally think marrying well is the single highest leveraged decision of your entire life. And also not marrying well is also a very high leveraged decision. Like it is just the force multiplier on all of your outcomes across life. And it's not just your career outcomes. It's your happiness outcomes. It's your health outcomes. It's all sorts of things, your social life. A good spouse makes everything better and a bad spouse will make everything worse. It's so true. I totally agree. And I get shit about it on the internet too.
1:09:16And you know what else is scary? I'm always scared to give advice because I'm like, I don't know, check back in 40 years. See how we're doing. Like I should, this is like, I'm kind of new at this. It's only been 10 years, you know? Like let's chill, but we're doing good right now. What advice do you have for a young person that is looking for what you have, which is somebody that is all of those things? I think the biggest thing to look for is character. it's it's again yes you want the romance you want the sparks to fly you want you want to have be swept off your feet and all like we all want that it's great don't get me wrong but you have to look a level deeper you have to look at their character their integrity how good of a decision maker are they are they dependable are they trustworthy do they share your values issues how's their relationship with their family like all these things matter and that not and obviously nobody's perfect like nobody's going to check every single box but you ideally you want to find somebody who checks most of them and and the ones they don't check like you can work with it you know and do you have like a couple questions you ask like if you i know we're both like a little we're a little baked now yeah but you know but basically shut up mark but like if you if you were given young you advice the team actually asked me this the other day i was like oh i have an existential crisis trying to answer it but like what if i only had three to five questions to sort of start sussing out is this potentially my person or not what are those well i will tell you my favorite first date question that i recommend everybody ask is ask the person you're on a date with um what did you learn from your last relationship and the red flag is if the person starts going off about how horrible their ex was and how shitty they were and oh my god i can't believe i dated them for so long like that that person run far away get as far away as you can what you're looking for is somebody who says you know it was a complicated relationship it was good for a while then things went bad here's why they went bad here's here was my part in it this was their part in it somebody who has perspective and an understanding of like what went wrong and and who also has clearly like done some work since then to make sure that it doesn't go wrong again.
1:11:52I also love the question too, because it, if you ask it and the person kind of freaks out and gets really uncomfortable, that's also a signal, right? It's a signal that this is not a person who is comfortable opening up relatively quickly, who like doesn't want to go there. You know, what's crazy is that's the same thing for interviewing too. I always say if like the person you were going to hire, if you ask them, like, tell me what happened in your last job? Like, why did you leave? Why did you choose to move on? If they start going negative, the company was terrible. The boss was awful. Everything was ever.
1:12:25I have never once hired one of those people and had it work out. Not once. Every single time I wished I didn't hire them. Because I think the way that you treat the last person, the highest indication will be that you will be treated the same, right? Yeah, absolutely. Oh, that's such a good one. Okay. Last one for you. You've also tweeted, the person you marry is the person you fight with. The house you buy the house you repair. The dream job you take is the job you stress over. Everything comes with an inherent sacrifice. Whatever makes us feel good will also inevitably make us feel bad. What do you mean?
1:12:57You can't escape the bullshit. You can't escape it. No matter where you go, there's going to be some bullshit. So you just need to make sure that it's the bullshit you like having it's it's the problems you are have are grateful that you have in your life um again i think people they think about the the benefits and the successes that they want that's actually a very easy and uninteresting question everybody generally wants like everybody wants money everybody wants a great partner everybody wants to be liked and popular and you know all these things um the question is is like what pain do you want like what are you willing to give up what struggles are you actually kind of okay having like what challenges do you seem to do better with than most people like those are that's actually where you get into who somebody is and like what makes you unique as an individual and what is ultimately going to serve you best as you move through life.
1:14:02That's so good. I always say with goals, like don't tell me what you want. Tell me what you're willing to sacrifice to get them. But I've never actually asked. I've like proselytized on the internet about that, but I don't ever think I've actually asked somebody. Like have you asked your wife or your friends or people you meet with those questions? Like what are you willing to give up? Yeah. Like what is the pain that you want? Like what would be the way that you would even ask those questions to someone? Because it's kind of hot. I want to like, I need to go around. I need to go around and you know you can take that question multiple ways but like I like it yeah it's when I give talks I always say I say like everybody everybody is secretly a masochist about something the question is just like what do you want to spank you and call you daddy by the way this goes over great at like corporate conferences you can imagine I get invited back all the time google's like pull him you and i probably have the most polar opposite corporate speaking experience no i tell all their employees to leave and then you tell them who wants to spank them so you know what i'll start bringing you along let's do a road show yeah we'd just be the anti-corporate speaker exactly um yeah it's it's uh i like that i like to frame it in those terms it is a it's a hard question like nobody i think nobody asks themselves nobody's asked it very often it's like what what do you what do you what do you actually kind of secretly like like what problem do you secretly like having it's like a very interesting question that most of us don't think about and uh but yeah i think i think i think the answer is extremely important what are you like the the problem i secretly enjoy having um i mean i'm a workaholic uh like i actually i i like the grind i like climbing the ladder like it's just fun it's like i told my dad once you know when so when i came back and i started scaling content and doing video and stuff online and uh launching a podcast and everything my dad kind of pulled me aside and he's like you know why are are you doing this he's like financially you're you're pretty set and uh and i told him i was like dad it's like i found the best video game and there's always another level like you can you never beat it and uh and he he got it he was like okay that's cool that's a good reason to do it oh that's such a good place to end mark this was incredible thank you so much for being on the thanks for having me
1:16:44you
From the publisher
Most people think confidence is about believing you'll succeed. Mark Manson knows better — it's about being comfortable with failure. After writing one of the best-selling nonfiction books of all time and spending nearly two decades studying human psychology, the author of The Subtle Art of Not Giving a F*ck has cracked the code on why Gen Z is struggling with relationships, why therapy culture might be making us worse, and why your emotions are a system that needs managing just like your business.
In this raw conversation, Mark breaks down the alarming statistics behind today's confidence crisis, why dating apps are optimizing for all the wrong things, and how adopting labels as identity actually amplifies your problems. We dive deep into the hidden costs of success, why the happiest country in the world has low expectations, and the brutal truth about why 20-25% of Gen Z has cut off at least one parent. He reveals why AI therapy is both promising and dangerous, the single question that exposes red flags on first dates, and why marrying well is the highest leverage decision of your entire life.
But this isn't just about what's broken — it's about what actually works. Mark explains why failure is the only currency that matters, how to stop being a people pleaser without being a dick, and why your bank account reflects the difficult conversations you're willing to have. If you've ever felt like you're chasing happiness instead of meaning, or if you want to build real confidence that comes from action instead of affirmation, this episode will change how you think about success, relationships, and the problems you're willing to have in your life.
Thanks to GoDaddy for sponsoring this video! Head to https://godaddy.com/codiesanchez to get started with GoDaddy Airo® today
I say it all the time: building real wealth doesn’t require a flashy startup — it just takes one boring, cash-flowing business. Join me at Main Street Millionaire Live to get my exact playbook for finding, buying, and scaling a business. Stop wondering how ownership could change your life, and come find out: https://contrarianthinking.biz/MSML26_BDYT
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00:00:00 Introduction
00:01:16 The Paradox of Being Likable
00:05:19 The Dating App Crisis and Modern Relationships
00:07:45 What Real Success Actually Means
00:09:16 The Happiest Country: Low Expectations in Finland
00:11:28 Social Skills: The 80/20 of Happiness
00:13:21 Confidence is Comfort with Failure
00:15:14 Building Failure Muscle: From Small to Big
00:24:07 The Post-Exit Existential Crisis
00:27:33 Stop Labeling Yourself: Identity and Mental Health
00:45:07 Emotions as a System to Manage
00:48:37 The Why Game: Peeling Back the Onion
00:49:45 Therapy Culture and Cutting Off Family
00:53:48 ChatGPT as Therapist: The Malignant Narcissist Problem
00:56:27 Building Purpose: AI That Challenges You
01:02:40 AI Limitations: Brilliant Idiots
01:06:21 Choosing a Life Partner: More Than Romance
01:09:37 The Best First Date Question
01:11:18 Everything Comes with Bullshit
01:12:17 What Pain Do You Want?
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