#105 The Confidence Expert: How To Build UNSHAKEABLE Self Confidence | Mark Manson

Summary

Podcast Summary: BigDeal with Codie Sanchez

Episode #105: The Confidence Expert – How To Build UNSHAKEABLE Self Confidence | Mark Manson
Release Date: December 4, 2025

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Episode Overview

In this engaging episode, Codie Sanchez sits down with bestselling author Mark Manson ("The Subtle Art of Not Giving a F*ck") to unravel the truth behind confidence, happiness, and success in the modern world. The conversation gets honest about the pitfalls of current self-help advice, the psychology of self-belief, the downside of therapy culture, navigating meaning and relationships, and the real ways to build unshakeable confidence through habits, risk, and embracing failure. The tone is candid, humorous, and packed with actionable insights.

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Key Topics & Discussions

What Is Real Confidence? (00:30–04:00)

• Mark opens by debunking the myth that confidence is about "not caring what others think." Instead:
  • "It's not about not giving what other people think. It's about finding something more important than what other people think." – Mark (00:30)
• Codie asserts that confidence is earned through action, not affirmation.
• Mark: The more you try to feel confident all the time, the more aware you become of your insecurities. Comfort with potential failure is actual confidence.

Notable Quote:

“When you stop trying to be confident all the time, you actually feel comfortable in your pursuits, knowing it might not work out, which is confidence.” – Mark (01:17)

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The Paradox of Likability & People Pleasing (01:45–04:32)

• Codie references Mark’s tweet: “Paradoxically, the less you try to convince people to like you, the more likable you become.”
• Mark explains that trying to control others’ perceptions is off-putting; we subconsciously respect those who respect our agency.

Notable Quote:

“At some point… you realize, ‘I’d rather be disliked for who I am than liked for something I’m not.’” – Mark (03:07)

• People-pleasing is often childish and unsatisfying; authenticity attracts more meaningful connections.

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Dating, Apps, and Our Misguided Pursuit of Happiness (05:00–08:45)

• Mark discusses his past (and resurging) men's dating book “Models: Attract Women Through Honesty.”
• Gen Z men are re-discovering “how to actually connect” amid a messy digital dating environment.
• Dating apps select for superficial traits, missing critical compatibility factors (values, sense of humor, intimacy).

Notable Quote:

“The apps have sorted for the wrong thing. People don’t know what they want—the apps supply a demand that’s not solving the problem.” – Mark (07:24)

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What Is Real Success? (08:16–09:46)

• Money and happiness are like oxygen: crucial when lacking, irrelevant in excess.
• Lifelong satisfaction comes from the sense of having spent time well, pursuing meaning and purpose.

Notable Quote:

“If you zoom out and look at your entire lifespan... the best way to define success is simply to feel as though you spent your time well.” – Mark (09:13)

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Finland’s Secret: Low Expectations (09:46–11:20)

• Mark shares insight from Finland ("happiest country"): underlying ethos is satisfaction with enough, not endless striving.
• Americans differ in overvaluing big goals but end up essentially the same after achievement.

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The Essential Habits for a Successful & Happy Life (11:45–13:03)

• Mark’s #1 advice for young people: Start with social skills.
  • Quality relationships (intimate, trustworthy) are the biggest predictors of long-term happiness and professional success.
  • "Nobody ever did anything great by themselves." (12:30)
• Codie references studies showing EQ (emotional intelligence) > IQ for career outcomes.

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The Real Foundation of Confidence: Comfort with Failure (13:39–17:14)

• Social scrutiny (especially online) creates a confidence crisis and risk aversion.
• Mark:
  • “Confidence isn’t about believing you’ll succeed; it’s being comfortable with possibly failing.”
• The only way to get comfortable with failure is to “fail”—especially small, manageable failures.
  • He shares his early dating advice: “Go get rejected five times, then we can talk.” (16:23)
• Codie reframes: Success in love, money, business—it’s all about quantity, enduring more failure for the one win.

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Mark’s Experimentation with Failure & Embarrassment (17:14–18:57)

• Mark’s personal approach: Running real-life experiments (sometimes donning a chicken suit!) to build “scar tissue” against embarrassment.
  • “By the end, there was nothing that could embarrass or scare me.” (18:44)

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Progress, Struggle, and the Easterlin Paradox (22:03–25:52)

• The wealthier people become, the harder it is to define meaningful progress, leading to existential malaise (higher suicide rates in affluent groups).
• Mark shares his own post-success depression after hitting “every goal at once.”

Notable Quote:

“The more successful you become, the harder it is to know what progress is, or what progress is worth having.” – Mark (22:29)

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The True Meaning of "Not Giving a F*ck" & Establishing Boundaries (27:55–32:11)

• True "not giving a f*ck" is about prioritizing meaningful things over others’ opinions—not becoming a sociopath.
  • “If you don’t have anything more important than what people think about you, then what others think will dictate everything else.” – Mark (28:49)
• Advice to people-pleasers: Find what you’re willing to be disliked for and pursue it. That’s meaning.
• Boundaries: Reframe boundaries as personal rules. “People respect rules… if they don’t, it makes it easy to know this relationship won’t work.” (31:43)

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The Double-Edged Sword of Therapy Culture & Labels (33:03–41:44)

• Mark discusses the rise of “overlabeling”—identity around being avoidant, ADHD, narcissistic, etc.
  • Labels can help raise awareness but become self-fulfilling prophecy when adopted as identity.
  • Internet/society incentivizes broadcasting (and clinging to) negative labels, which can entrench issues.
• Example: Mark himself was diagnosed with ADHD, but warns against overdefining oneself by such terms.

Notable Quote:

“As soon as you adopt the label as an identity… you start imposing that on all your experiences and relationships.” – Mark (35:10)

Self-Definition:

• Mark recommends avoiding labels altogether (“Buddhist school of not labeling yourself—your potential is then infinite”).
• His story: He became unhappy after labeling himself only as an “author” instead of entrepreneur, after rapid success. Very easy to unconsciously reframe identity for external rewards—with a heavy emotional cost. (43:06–44:35)

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The Power of Journaling & Emotional System Management (46:44–50:48)

• Mark: Your emotions are a system to be managed (like any business resource).
• Use journaling to ask “why” repeatedly about negative feelings or outcomes.
  • “Start with the basics: What do I feel about this? Why do I feel this way? … And follow the chain until you hit the real root cause.” (49:01–50:48)

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Dangers of Over-Corrected Boundaries, Family, & Therapy Apps (51:01–56:00)

• Mark worries about “over-corrected” boundaries leading to rising trend in cutting off family, especially among Gen Z (20–25% have ceased contact with a parent).
  • Cautions against going “no contact” as a first step when intermediary boundaries can be set.
• Discussion on AI therapy: ChatGPT and similar LLMs often just validate, never challenge, users—mirroring the worst of “therapy culture.”

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Mark’s Solution: Building “PRPS”—An AI That Tells You the Truth (57:03–61:47)

• Mark has co-founded PRPS, an AI platform trained specifically for mental health and true psychological improvement (rather than just validation).
  • “Instead of just trying to make you feel better all the time, [the AI] is designed to actually make you better—to tell you the things you need to hear, point out your blind spots, and challenge your bullshit.” (59:16)
• Users are more honest with AI, reaching deeper insight quickly.

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Tech, Happiness, and Dangerous Optimism (61:47–67:30)

• Codie questions the tech industry’s blind optimism, especially regarding AI’s effect on happiness and social well-being.
• Mark affirms that, having worked directly with LLMs, he sees limits to AI’s abilities; moral panic is premature.
  • “They’re brilliant idiots… able to do multivariate calculus, but with their shoes on the wrong feet.” (64:47)
• Effective use of AI demands as much from users as from the tech itself.

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On Choosing the Right Life Partner (67:31–72:47)

• Mark reiterates: Who you marry is the highest-leverage decision in your life—for better or worse.
  • Look for character, integrity, decision-making, values (not just romance).
• Top first-date question: “What did you learn from your last relationship?”
  • Red flag: If they only blame their ex.
  • Green flag: Balanced reflection and personal accountability.

Notable Quote:

"A good spouse makes everything better and a bad spouse will make everything worse." – Mark (69:15)

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The Inevitable Sacrifice & Embracing the Struggle (72:48–76:44)

• Every choice comes with inherent sacrifice; every dream comes packaged with its own pain.
  • “Whatever makes us feel good will also inevitably make us feel bad.”
  • Important question: “What pain do you actually want? What struggles are you willing to put up with to get your goals?” (73:47)
• Mark’s personal "struggle of choice": Relentless work and embracing the grind.

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Most Memorable Quotes

• “Confidence isn’t about believing you’ll succeed; it’s being comfortable with possibly failing.” – Mark (14:03)
• “If you don’t have anything more important than what people think about you, then what others think will dictate everything else.” – Mark (28:49)
• “People generally want the same things—the real question is, what pain do you want?” – Mark (73:47)

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Timestamps for Key Segments

• 00:30: Mark's principle: it's not about shutting out opinions, it's about having a higher purpose.
• 03:00: Likability paradox and people-pleasing.
• 07:24: The failure of dating apps and real compatibility.
• 09:13: Lifelong success is about time well spent.
• 13:39: The real roots of confidence and fear of scrutiny.
• 16:23: Embracing small failures as confidence training.
• 28:49: The truth on "not giving a f*ck"—purpose over public opinion.
• 31:43: How to tactically set boundaries without drama.
• 35:10: Label identity as a psychological trap.
• 43:06: Redefinition of self—and the cost of the wrong label.
• 49:01: Journaling for emotional problem-solving.
• 59:16: Why Mark’s AI project, PRPS, is designed as tough-love advice (not just validation).
• 69:15: On marriage as the ultimate “force multiplier.”
• 73:47: “What pain are you willing to live with?”—the question behind any meaningful pursuit.

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Final Thoughts & Tone

Throughout, Codie and Mark maintain a witty, direct, no-bullshit style filled with self-awareness, gentle self-mockery, and practical wisdom. Listeners are challenged to confront failure, embrace discomfort, reject superficial fixes (like affirmations and endless self-labeling), and instead pursue meaningful risk, reflection, and relationships—both with others and deeply with themselves.

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Takeaways for Listeners

• Confidence is built in small, repeated failures and a healthy relationship with risk.
• Authenticity, not people-pleasing, breeds both self-respect and external respect.
• Rethink goals: Seek progress and meaningful struggles, not just “happiness” or external metrics.
• Boundaries work best as respectful “rules”—and reveal who truly respects you.
• Beware of adopting negative labels as identity (on TikTok or elsewhere).
• Use journaling for radical self-inquiry and emotional management.
• AI therapy is only as good as its programming—seek feedback, not just validation.
• The partner you choose shapes literally everything in your life; select for character, not just chemistry.
• The inescapable pain of pursuit is where meaning is found—choose your struggles wisely.

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Transcript

[A]

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[B]

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[A]

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[B]

Generally, people who feel like they give a F about way too many things, it's not an issue about the caring, it's the extent of how much they care. It's not about not giving 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.

[A]

Mark Manson, the best selling author of the Subtle Art of Not Giving a 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.

[B]

The 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 in. 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.

[A]

If confidence is really just the comfort with failure, then how do you get more comfortable with failure?

[B]

I will say this, I would say.

[A]

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?

[B]

I think it's.

[A]

I want to start with some of my favorite tweets of yours. Okay, I just went down a deep rabbit hole. I haven't been in your tweets in a minute. I guess it's called 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.

[B]

I think when, 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.

[A]

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?

[B]

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 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, it doesn't feel like, like you're, you're being appreciated for who you authentically are. So. And I think this, this takes place on a lot of, I mean, obviously this is like social phenomenon, but people do this in dating. You know, people do it with co workers, they do it in business. It's like, you know, all the ass kissing, the yes men, like it, it backfires eventually.

[A]

You know, it's interesting because I like, we've had many a walk on whatever, Venice Beach Boulevard or whatever that is. The boardwalk.

[B]

Yeah.

[A]

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?

[B]

I published my first blog post in 2007.

[A]

In 2007. And 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. 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. And man, we've both met a lot of people on the Internet.

[B]

Yeah.

[A]

Some of the advice is, like, sounds really good that it's terrible advice.

[B]

Oh, yeah.

[A]

And you have, like, a very strong moral compass.

[B]

Yes.

[A]

You know, 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?

[B]

Because it's been weird, honestly. Like, it's funny because I self published a men's dating book back in 2011, and 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's starting to sell really well again.

[A]

No way.

[B]

So it's.

[A]

What was that one called?

[B]

It's called Models Attract Women Through Honesty. And. 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.

It's interesting because it's kind of catching a second life with the next generation.

[A]

Yeah. Because they're. They're having less sex. They're.

[B]

It's a mess. Dating's a mess right now. Yeah.

[A]

What, What. What is out there in dating right now? What are you hearing from your millions of followers on all different platforms?

[B]

From what I can tell, it's. So I have a couple of theories, but, like, I would say the primary one is I personally think that the apps are.

Negative ROI for people's dating outcomes, and it's primarily because they're optimizing for the wrong things. If you think about it, like, I don't. I don't know how long you've been with your husband, but, like, if you think back to when, 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 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 gonna make us happy in a relationship. Like, 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 tr you want, it's like, oh, I want somebody who's six foot five in finance and all this stuff, and 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, the personality traits and the background and the personal values and how the person experiences intimacy, the sense of humor, all those things, they're hidden so 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.

[A]

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. Like, 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 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?

[B]

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. Like, that's definitely gonna solve your problems. And if you're really miserable or depressed, then, like, yeah, obviously get some happiness. But if you're already kind of at 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. 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, the best way to define success is simply to feel as though you spent your time well.

It's the old deathbed question, right? It's like if you, 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 did. 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 were 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.

[A]

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 did you find? Like, what do the happiest people in the world have? Or was it something totally else you found there?

[B]

Well, the funny thing, so the happiest, technically the happiest country in the world is Finland. And.

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 sense of just being satisfied very easily. Like, 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 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 gonna 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 gonna be the same person with the same shit going on. So you need to like, ultimately find something.

That'S worth the struggle, that feels like it makes the struggle worth it.

[A]

When you're talking to like I think predominantly a lot of young men on the Internet and I love your YouTube videos by the way, but. Yeah, but you have quite a few where you talk about the habits that lead to like successful or happy lives. I know there's no hacks to any of this. And at the end of our three step process, sure, their life will probably be totally fixed.

[B]

Yeah, yeah.

[A]

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. What are they?

[B]

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 did anything great by themselves. Like there's no incredible successful business story that they did it alone. It's like you either built an amazing team or you had an amazing team of people backing you and helping you and supporting you.

[A]

Yeah. I was reading a study the other day about how there's something like a 20 to 30% increase in salary just from thinking about increasing your EQ and really ignoring IQ. That IQ almost has no correlation between monetary success. Do you find also in personal relationships? I think a lot of people these days, um, 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.

[B]

Yeah.

[A]

Like the more you work, the more confidence I have. I, 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.

[B]

Right.

[A]

And so I'm not confident we're going to hit it. Yeah. But it does seem like we have like a, a confidence crisis. Do you see that? With a lot of people saying, I do not feel confident in myself. I'm not gonna be able to do it. I don't believe in myself. I have imposter syndrome.

[B]

Yeah. I feel like people. People definitely feel more scrutinized and judged these days. And I think a lot of that is just how online and permanent everything is. You 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 gonna 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 guaranteeing of success. And so 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.

[A]

That's a good point. I was really struggling to 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?

[B]

By failing.

[A]

I hate this answer. I hate this for me, I hate this for everybody listening. Is this the only.

[B]

Sorry, everybody.

[A]

Is there not a three step framework? God damn it, Mark.

[B]

Sorry.

[A]

But really, like, okay, so let's get granular then. Like, big failures, little failures, any failures, daily failures, all the above.

[B]

And I will say this, I would say probably little failures first.

I 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, I. One of the first things I used to tell people is 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. And 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. They 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.

[A]

It really doesn't. And it's almost like that in everything.

[B]

It is like, it's.

[A]

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 100 customers that tell you no to get one. And if you want to buy a business, go look at 100 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.

[B]

Yeah.

[A]

Which is crazy. And you know what'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. I have a theory.

[B]

Yeah.

[A]

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? Because you put yourself through the experiment first, right?

[B]

Yeah.

[A]

Yeah.

[B]

One of the things I've always believed very strongly, like, I've never. I've 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, in the muck with everybody else. You know, I go through this stuff, too. So in the videos, I do the same. I basically took fans with various anxieties or personal issues and kind of ran them through a gauntlet of different challenges or having them face their fears and whatnot. But I made myself do it, too, and.

It was A good exercise, right? It's like one. It's just. I should be able to walk the walk of what I say. But it's also.

I think it comes back to 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. And it's funny because doing that series of videos, by the time we got towards the end, I honestly reached a point where I'm like, I don't think there's anything at this point that could be embarrass me or like. Or scare me.

[A]

Careful. If you put it out there, you know? I know.

[B]

It was funny, actually. So we just shot one a few weeks ago, and I. It was funny. I basically hosted a dinner for a bunch of people in my audience and went through, Worked on a bunch of stuff with them and then took them outside. And we were on the beach in Malibu and took them outside and then had everybody walk on. On hot coals. And. Which is like a classic Tony Robbins thing. And. And it was really funny because the. The attendees, like, looked at me and they're like, oh, well, you do this all the time, right? I'm like, no, I've never done this before.

[A]

You're like, it might work. You might die.

[B]

Yeah. They are all looking at me. They're like, what the is wrong with you? And I was like, I don't know. I don't know what's gonna happen, but we'll find out.

[A]

Are you okay?

[B]

Yeah.

[A]

Yeah.

[B]

It was fun.

[A]

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. It actually, that would. That gives me anxiety. Like, I have, like, we feel the.

[B]

Fire stuff or being at a Tony.

[A]

Robbins, hugging random people, jumping up and down, smiling, like, I don't know. I would 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 couldn't end up doing it because I had some health stuff. But I do think that it would have probably been good for me because I hate that. I hate the idea of hugging strangers and jumping up and down. And maybe.

[B]

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 gonna dance again. Like, what? Come on, man.

[A]

Public dancing?

[B]

Yeah. It's like, no, I don't want to give another back rub. Like, it's just.

[A]

You have to do back rubs.

[B]

Yeah, like, I'm good, man. Like, I don't. But it's funny because I think it's ultimately, we're not the target market. Like, 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.

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.

[A]

Interesting. So you almost have had to stair step your way up the embarrassment ladder too.

[B]

Oh, yeah.

[A]

You're like, you know, now, now chicken costume is like, that's a Tuesday.

[B]

Oh, yeah. I could put one on right now. I was like, no problem. It's. I mean, it's like anything though, right? Like, I mean, it's.

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. Now it's like you probably don't even get out of bed for a five figure deal. So it's like anything in life is like that. You just, you get that progressive desensitization that happens over time.

[A]

Yeah, that's probably actually bad in a lot of ways. And why really rich people go crazy. It can be they can't find the new adrenaline rush because, you know, 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.

[B]

Yes.

[A]

Because what if you can't find something to struggle on anymore? What does that quote mean to you?

[B]

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, I believe it's called the Easterland paradox in psychology, which is essentially that you find that the poorer the country or the poorer the neighborhood, the lower the suicide rate and the more affluent the country and the more affluent the neighborhood, the higher the suicide rate. And I think it Comes from the fact that when, 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, get some food on the table. Like it's, there's no ambiguity of, 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, that is an existential crisis. Nobody's gonna shed a tear for you. But it's not obvious what progress is. It's not obvious what you should do next. In 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 often see. So it's funny, 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 a network, it's called the Post Exit Founders Group or network or whatever. And I've got some friends who are in it and I've talked to them before and they're like, yeah, dude, when we do our events and everybody gets behind closed doors, it's like half the people there are in an existential crisis because they just had this massive check hit their bank account and they're not working anymore. And, and 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, yeah, what next?

[A]

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 the half, the reason you keep going is because you're kind of self masochistic and you like the, you know, struggle and figuring out what to do next. If I only had the option of sipping, sipping my ties all day and you got to look at yourself in the ey and nobody else. Ooh, that could become problematic for sure.

[B]

It's funny, one of the most depressed I've ever been is after my first book blew up. And it was because basically everything I had 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. And 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. Except now I have nothing to look forward to. I have no definition of progress in my life.

[A]

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[B]

20 something million copies at this point, which is insane.

[A]

Also an incredible documentary on Netflix. I remember when that came out. Great thumbnail too. Was that you? Weren't you at a floaty pool with.

[B]

Yeah, they put me in a pool. There's. There's this like crazy surreal opening sequence that involves me sitting in a pool drinking out of a. A pineapple while like people die and emergencies happen around me. It's like this very dramatic sequence. It 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 it, you know, I got to have my little Hollywood moment.

[A]

It did not look like that. It looked lovely and happy.

[B]

It was so cold. There was like a. There were a bunch of pas with like, 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 because I'm so cold.

[A]

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. You know, not giving a. Having confidence. That 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.

[B]

Oh, like all of us, right?

[A]

You're talking about me.

[B]

So the question is, it's called Being Human.

[A]

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?

[B]

So the paradoxical thing, and this is laid out in chapter one, 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 phase you. There's a word for that in psychology. It's called a psychopath. So we don't want that. You do want to care about things. Obviously. You do want people in your life that you do care about their opinion. Right? It should upset me if I don't know. My parents are mad at me. So 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. Nothing good is 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.

[A]

So what would you say to somebody that's like, I just want to stop.

[B]

Being such a people pleaser.

Find the hills that you're willing to die on.

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 might not actually have anything that they can answer, 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's your thing. 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.

[A]

What is sort of the right way to respond when somebody else is 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? How do you keep boundaries not look like a dick?

[B]

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, if I was like.

Like, let's say your producer emailed me and 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 3pm Sorry, maybe we can find another time. Like when you, when you frame things as a rule, it's like, hey, this is just a rule I have in my life. I 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, 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.

You know, I, I don't talk about this subject with people who aren't part of my family. Nothing personal, you know, and then it's like, then things become very clear.

[A]

It's so good because it's shifting the no to you to like, oh, no, it's not about you. It's about this thing other here that already exists. It's like you get to use a shadow influence without even having one.

[B]

Yeah.

[A]

And then you get to deflect in a respectful way whatever somebody else is trying to push on you. That's so good.

[B]

Yeah. And it's what's interesting too is that it also clarifies for you the caliber of the relationship you have, right. Like it's, 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's really happy with how the friendship's going or the relationship's going. But like, like you're, you're kind of going through the motions and like it just, yeah, it doesn't, doesn't end well.

[A]

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. I, it's, he's definitely a narcissist. Like what, what is going on with all these labels we're placing on ourselves? Are these real? Are they that black or white?

[B]

Yeah, they are real. They're not necessarily black and white. And I have mixed feelings about it.

I think it's a sword that cuts both ways. 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 I guess we could call this just kind of like therapy culture in general. So it's.

All of the language that permeates TikTok and Instagram and YouTube these days and people talking about being neurodivergent and avoidant 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. Which I don't think that's a bad thing. Like if you, if you go back a couple generations, like, like people just buried shit for decades and.

It only came out after.

[A]

Just shove it down, just keep shoving.

[B]

It down and you know, 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 the 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 and 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 like 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. You actually amplify.

How serious the condition is. Whereas if you just said like, okay, this is a thing I have and I'm just going to manage it and I'm not going to 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.

[A]

Great point. I've also been diagnosed as ADHD from an online test I did once.

[B]

Very clinical.

[A]

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. But the end there was a literal link to talk to psychology. 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. It was like kind of an ad and I thought for the love of all the Tolle In a 15 question interview online, you're gonna diagnose me as X thing and give me a pill. Seems flawed.

[B]

Yes. You know there's a whole over diagnosis issue. I mean and that's just across the board. You know, anxiety disorders, depression, ptsd, like there's probably all of those are being over diagnosed to a certain extent.

I mean the problem is, 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 under diagnosed so that incentive was aligned with the public good. But I think probably in the last 10 years, 15 years, 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, 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? So 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 like if you set out and start a new challenge, you know, 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 the self fulfilling prophecy aspect of life, right? Like if I tell myself that 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 going to 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. You see this with the athletes.

You generally see this with like a wide range of highly successful people.

The opposite of that is true as well. So if you, 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 and pain. Like people do legitimately have anxiety disorders and panic disorders and all sorts of things. But the, but the language you use with yourself can move the needle in terms of the likelihood of it holding you back or not. And so the other concerning part of therapy culture is that I think it is subtly reinforcing people to place limitations on themselves to say instead of saying I have ADHD and well, actually there's a bunch of context and situations that ADHD can actually be an asset. 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 so. And there's a bunch of things I'm probably going to fail at. And then it becomes the self fulfilling prophecy.

[A]

If you're listening, how do you integrate this into your life? Like what 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?

[B]

It's a great question. I also think there's potentially issues with labeling yourself a winner. So 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, what the consequences of adopting that label are.

I'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 like 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. I 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 like the feeling that people get when you're just doing something for a paycheck. Like it started to feel like that towards the end and it really started to like grind me down and I got pretty burnt out and I took a sabbatical in 2022. 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 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. And so in my sabbatical I was like, I completely forgot, like I, the, 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, 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 I did that and I ended up paying the consequences.

So yeah, I'm back to being an entrepreneur and I'm very happy, comma, author. Yes, sometimes author.

[A]

Well, 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. Like almost every time we've talked you've been like 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 at taking a step back and going, okay, let me think about this. And even a refra frame like I did there, you would have been very tempting for you to go like, oh well here's how you should label yourself. Yes, you 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 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. Yeah.

[B]

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[A]

Listening to this podcast.

[B]

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[A]

So you're about to make a trade based on a friend's text, but which u do you listen to? Is it we could buy a house.

[B]

In Tulum.

[A]

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[B]

I will bang on until my death.

I keep pushing this message into kind of 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, are 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 emotions. They compartmentalize. They're like, we're not going to think about that now. I've got meetings to go to. And you can do that for a while. You can do that for a year, maybe a couple 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. And as soon as you feel yourself getting off track emotionally of not enjoying what you're doing, not being excited about the people you're working with, not getting along with your team, these are all signals of something's off. And sure, maybe it's not showing up on the balance sheet and it's not showing up in the P and L, but like, it matters because if you're miserable, like that's, that's Fucking terrible roi. Long term, like. Like, 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 that stuff is like, to just acknowledge that this matters, that it, like, it does affect everything. And the second thing, I think once you realize that it is an important facet 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?

Where's the poor roi? 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 of. 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, like, the basics, like, what 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, like, explore that. You know, give yourself the freedom to. To write pretty liberally until you. You find something that's really good.

[A]

So no screaming manifestations in the mirror and journal. Just kind of briefly about the things that we feel and ask why that seems reasonable for, like, Internet people.

[B]

It's funny too. Like, it's such a basic thing. I used to call this the why game. And it, it's, you know, so you just take something, take something you're struggling with and say, like, how do you feel about that? 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 get to a point where it gets circular 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.

[A]

That'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.

[B]

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 is. Again, 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 that is 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.

I, I do. There's some alarming. We did a, we did a podcast last year on.

Kind of some alarming statistics on.

People cutting family members out of their lives.

[A]

What's happening?

[B]

I forget the exact numbers because it's been a while, but it was an episode we did probably like early 25. And.

It'S shocking. It's way more people than you think. It's something like 20, 25% of Gen Z is like willingly chosen not to speak to at least one parent.

A lot of siblings being cut off, you know, a lot of stuff. And again, I think it's like well intentioned therapy culture type stuff of like, you know, whoa, 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 feel like cutting family members out of your life is a.

A move of last resort. Like there's a lot of intermediary steps. You can go, you can, it doesn't.

[A]

Need to be step one.

[B]

Yeah, 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.

Yeah, there's, there's just a lot of managing that you can do in between.

[A]

That's so true. I mean, I always go back to the quote, it's like an African proverb about you can either pave the and leather, you can wear leather shoes. And I think there is, I, I totally agree with you sometimes that 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. Yeah. Because the whole world to be paved as opposed to wearing the shoes. And so I think 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 multiple girlfriends who have turned ChatGPT and named it into their therapist. 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, with ChatGPT 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.

[B]

Yes.

[A]

And to agree with you, by and large. And so. And it has no emotion. It is psychopathic and 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 chat GPT. And chatGPT will confirm every single thing that they're doing.

[B]

Of course.

[A]

And I love you, friends, but some of you guys are psychos too. Like, you know, we're all, we can get crazy in relationships, me included, of course. And I'm wrong all the time. And so if I only feed my side in and then Chat GPT is always telling me I'm right. That seems bad. And I don't know, you'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.

[B]

Deeply concerned as well. You know, I started noticing in my life, same thing, a bunch of friends, family members started using ChatGPT 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 running some life problems through it, seeing how it responded. And I'll say this, it's like, it's very uneven. Like, you get. There's some things that it's much better at than, say, your average therapist, and then some things it's much worse at. So 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 doesn't. It just. 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 in there, every branch of the topic is in there. I think there's.

Over 3,000 hours worth of therapy transcripts 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, 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 it will generally give you some good direction and good advice. The 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.

[A]

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. My personal nightmare. That would be horrific.

[B]

Yes.

[A]

But, like, I guess my point here is you're building something that's a counterpoint to this.

[B]

Yes.

[A]

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. And 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 when 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.

[B]

Yes.

[A]

You know?

[B]

Yeah.

[A]

And if that's what you want, then I guess go to ChatGPT. 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.

[B]

Yeah.

[A]

And so you came up with something that I think's really clever.

[B]

Yeah. So 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. Of psychological knowledge and data.

And coincidentally, it was funny, I was actually at a poker game. I sat next to a guy and started talking to him, and 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.

[A]

He's probably doing okay.

[B]

Yeah, he. He had, like, a very big exit and took a year off and had 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 really want to do something in AI mental health. And 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 been specifically created for this purpose. So he and I became co founders, and.

We'Ve been working together since February. And as of this week, we were in full v1 launch of our app called PRPS. 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. The goal is to actually make you better, tell you the things, the hard things that you need to hear, point out your blind spots to you, challenge you on your bullshit, say, are you really sure about that? Or maybe your shit stinks too? And it's been great, because here's the funny thing that we've actually noticed with a lot of our early users as well, is that 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?

[A]

And you want them to like you more than your partner. That's like the natural inclination. You're like, he's the.

[B]

You know, the thing is, it's all about your perspective. But it's. You know, when it's an AI, it's just like, well, fuck it, whatever. I'll just. This is what I'm thinking. This is who I. Yeah, I'm kind of screwed up, but, like, here it is, you know, like, it never judges you. It's like you never have to worry about it. You know, it's gonna, like, hold something against you or it's like secretly thinking something about you. So 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.

[A]

Is there like a Mark Manson button or. Mark Manson. Is there a. Is there a button where we can get your voice to talk back to us?

[B]

Not yet. Maybe. Maybe that might be.

[A]

Or is it really nice still?

[B]

It is nice.

[A]

Does it cuss?

[B]

No.

[A]

I have a lot of user feedback.

I feel like this is a mess. I want to be able to talk shit to me. From the author of the Subtle Art of Giving a Fuck Back. We.

[B]

We actually talked about this, and one of the things, you know, one of the things I told my co founders, I was like, look, like 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. 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.

[A]

Yeah.

[B]

Hey, fuck face.

[A]

Yeah, exactly. Exactly.

[B]

Pull your head out.

[A]

Also, talk about viral feedback loops. You know, can you imagine those screenshots? Yeah.

[B]

It be fun.

[A]

Yeah. Come on. All right, let me on the cap table. I've got feedback.

I. But I really like the idea and I really commend. My husband's the. The smarty on AI. It's not me, but, you know, I go, just this weekend, I was with. Yeah, last weekend, whatever, whenever a sale was. And I was with all these guys who. Like the guy who started Apptronic, you know, 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, but. And the conversation kind of went like this. I was like, don't you think we should worry like a little bit about what we're building with AI? Because seems like happiness gone down, sex 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 like 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 neuro chip 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. And 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 like put like have these conversations and say, what are we building? Is this a really a good idea? And you know, 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?

[B]

For sure.

[A]

So like, 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. I 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. You know, But I know, is that 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.

[B]

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 yeah, it's hard. There's some scary shit. So we're constantly testing it. 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 started this company, you know, I was very 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 about, what it should sound like, what good tough love advice is, and what is just kissing your ass. And so I spent a lot of time working with the LLM directly on the eval system. The training data, all the system prompts, trying to squeeze out of it 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 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, you know, there have been so many times where I've just been trying to get. Get it to do, like, such a basic thing, and it'll take an entire afternoon. And 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 moral panic going on around it.

I don't think they're quite as capable as most. I mean, I don't know how much you guys have been using AI in your business, but it's like, a year ago, I was like, so on the train of, like, everybody on my team. You gotta get good at AI. Right now. This is gonna be part of every workflow. And six months later, we're like, oh, half of it is just trash.

[A]

I do think. Garbage in, garbage out.

[B]

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. 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. So.

[A]

Yeah, I'm still there sometimes too. Yeah. 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. Yes, that. But that you have to match with the back flipper sometimes. And you're like, oh, ok. The two of you together do some magic. But independently. Jesus.

[B]

Yeah.

[A]

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. Yeah. And how you choose partners. So I want to read you a couple quotes, 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. Choose 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?

[B]

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's the romance? Or how spicy is the sex? You 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 leverage decision of your entire life.

[A]

Life.

[B]

And also not marrying well is also a very high leverage 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.

[A]

So true. I totally agree. And I get shit about it on the Internet too. And you know what else is scary? I'm always scared to give advice, advice, because I'm like, I don't know check back in 40 years, see how we're doing. I should. This is like, I'm kind of new at this. It's only been 10 years. You know, like, let's, let's chill. But we're doing good right now. Yeah. 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?

[B]

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? How's their relationship with their family? Like, all these things matter and obviously nobody's perfect. Like, nobody's gonna check every single box but you.

Ideally, you want to find somebody who checks most of them. And the ones they don't check, like, you can work with it. You know, do you have, like, a.

[A]

Couple questions you ask? Like, if you. I know we're both like a little. We're a little baked now, but, you know, but we're boomers, basically. Fuck. 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 or five questions to sort of start sussing out, is this potentially my person or not? What are those?

[B]

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. 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.

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 was my part in it. This was their part in it.

Somebody who has perspective and an understanding of what went wrong and who also has clearly done some work since then to make sure that it doesn't go wrong again. I also love the question too, because if you ask it and the person kind of freaks out and Gets really uncomfortable. That's also a scene 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.

[A]

You know what's crazy is that's the same thing for interviewing, too. I always say if, like, the person you are 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 evident. Ever. I 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. Yeah, because I think the way that you treat the last person, the highest indication will be that you will be treated the same, right?

[B]

Yeah, absolutely.

[A]

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 is the house you repair. The dream job you take is the job you stress over. Everything comes with inherent sacrifice. Whatever makes us feel good, good will also inevitably make us feel bad. What do you mean?

[B]

You can't. You can't escape the.

You can't. You can't escape it. It's. No matter where you go, there's gonna be some. So you. You just need to make sure that it's the. You like having. It's. It's the problems you are grateful that you have in your life again. I think, think people, they think about 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.

The question is, like, what pain do you want? Like, what are you willing to give up? What. 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.

[A]

That'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, 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.

[B]

Those questions, like, what are you willing to give up?

[A]

Yeah, like, what is the pain that you want? Like, what would be the way that you would even ask those questions to some? 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. I like it.

[B]

Yeah. Like.

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 corporate conferences.

[A]

Do you say this?

[B]

You can imagine. I get invited back all the time.

[A]

Google's like, b, you.

[B]

And I probably have the most polar opposite it. Corporate speaking experience.

[A]

No, I tell all their employees to leave, and then you tell them who wants to spank them.

[B]

So you know what?

[A]

I'll start bringing you along. Let's do a road show.

[B]

Yeah, we just be the anti corporate speakers.

[A]

Exactly.

[B]

Yeah. It's. It's. I like the. 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 do you. What do you. 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.

But yeah, I think. I think. I think the answer is extremely important.

[A]

What do you like the.

[B]

The problem I secretly enjoy having?

I mean, I'm a workaholic.

Like, I actually, I. I like the grind. I like climbing the ladder. Like, it's just fun. It's like I. 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 launching a podcast and everything, my dad kind of pulled me aside and he's like, you know, why are you doing this? He's like, financially, you're. You're pretty set. And. And I told him. I was like, dad, that it's like, I found the best video game, and there's always another level. Like, you can. You never beat it.

And he got it. He was like, okay, that's cool. That's a good reason to do it.

[A]

Oh, that's such a good place to end. Mark, this was incredible. Thank you so much for being on the podcast.

[B]

Thanks for having me.

And Doug here. We have the limu emu in its natural habitat, helping people customize their car insurance and save hundreds with Liberty Mutual.

[A]

Fascinating.

[B]

It's accompanied by his natural ally, Doug Limu. Is that guy with the binoculars watching us? Cut the camera. They see us. Only pay for what you [e-mail] Liberty, Liberty. Liberty. Liberty Savings Ferry. Underwritten by Liberty Mutual Insurance Company and affiliates. Excludes Massachusetts.