The Knowledge Project with Shane Parrish - Ryan Holiday: How to Win the War with Yourself

Episode Date: November 26, 2024

Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal missteps to famous entrepreneurial gambles, this episode is a deep dive into the art of learning from experience, knowing when to listen, and the cost of stubbornness. Plus, Holiday revisits his roots to discuss how Stoic principles can guide you in navigating feedback, balancing ambition with self-awareness, and understanding the fine line between determination and delusion. Holiday is a New York Times bestselling author. He has written over 10 books, covering both the fundamentals of Stoicism as well as key elements of modern-day marketing and media. His most recent release is Right Thing, Right Now. Holiday has been a guest on the podcast twice before. Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/ -- Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠https://fs.blog/membership/⁠⁠ and get your own private feed. -- Follow me: ⁠⁠⁠⁠⁠⁠⁠⁠https://beacons.ai/shaneparrish⁠⁠⁠⁠⁠⁠⁠⁠ -- Watch on YouTube: https://www.youtube.com/@tkppodcast (00:00) Intro (02:20) When to Ignore Advice (04:49) The Importance of Reflection and Journaling (07:26) Balancing Emotions and Stoic Practices (24:34) Misconceptions and Historical Context of Stoicism (29:53) The Pursuit of Excellence and Its Trade-offs (40:58) The Power of Saying No and Opportunity Costs (49:09) The Role of Anger and Emotional Control (52:58) Defining Self-Discipline (53:43) The Essence of Self-Discipline (54:29) Balancing Discipline and Life (55:09) Consistency and Overcoming Setbacks (56:09) The Struggle with Compulsive Tendencies (58:33) Navigating Competition and Personal Goals (01:01:22) Cultivating Discipline Through Physical Practice (01:02:15) Instilling Discipline in Children (01:04:22) Understanding Character and Virtue (01:23:32) The Impact of Modern Technology on Writing (01:35:04) Defining Success and Managing Expectations Learn more about your ad choices. Visit megaphone.fm/adchoices

You've said before that life is always whispering at you, and if you're not paying attention, it'll eventually scream at you. In sobriety circles, they talk about like two cars in the garage addicts. What rock bottom is for you is a choice that you kind of get to make? So do you realize that you're heading down a bad path after you've had to sell your house and your cars and you've lost literally everything? Or is it that embarrassing evening at the company Christmas party that serves to send the message. How are you hearing what the world is trying to tell you? Or are you very much not hearing it? And at some point, is it going to have to hold you down and scream it into your ear?

Welcome to the Knowledge Project podcast. I'm your host, Shane Parrish. In a world where knowledge power, this podcast is your toolkit for mastering the best what other people have already figured out. Can you do me a quick favor? Most people who listen to the show are not subscribers. Go ahead and hit that follow button right now. Thank you. My guest today is the modern day philosopher king Ryan Holiday. His books on helping people live better and more meaningful lives have sold millions of copies. Building a meaningful life isn't just about inspiration. It's about action. And today, Ryan shares the practical ancient strategies that have helped the world-class athletes, artists, and entrepreneurs transform their lives. It's time

to listen and learn. There are too many podcasts and not enough time. What if you could skip the noise and get just the insightful moments, even from shows you didn't know existed? That's what Overlap does. Overlap is an AI-driven podcast app that uses large language models to curate the best moments from episodes. Imagine having a smart assistant who reads through every transcript, finds just the best parts, and serves them up based on whatever topic you're interested in. I use Overlap every day to research guests, explore, and learn. Give it a try and start discovering the best moments from the best podcast.

Go to joinoverlap.com. That's joinoverlap.com. How do we separate the signal from the noise? Like in a world of social media, you're getting feedback all the time. How do you distinguish what's valid and sort of helpful feedback and a whisper versus this is noise and it offers no value? Yeah, this is really hard. You can see that often to be successful as an entrepreneur, you get there by not listening. You get there by not listening to the odds, not listening to the doubts, not listening to the critics, and then you succeed.

So then you get this very wicked learning environment where, you succeeded precisely because you did not listen to the message that the world was trying to send you. But if what you generalized from that is never listen to people, you're going to be a really tough spot. So take Elon Musk, right? When Elon Musk was planning what became SpaceX, his friends held a literal AA-style intervention that said, you cannot start a rocket company. This is the worst idea that you will lose all your money. Obviously, he was correct.

And there were moments when he probably, the conventional wisdom or the data or the advice from the investors overwhelmingly was to sell Tesla or to do X, Y, and C. So what happens when, you know, it's sort of a passing fancy or, you know, an impulse consideration to buy Twitter? Some people told them it was a good idea. Some people told them it was a really, really bad idea. Some people told him most totally outside of his domain of expertise and all these things. How do you know whether to listen or not? This is like the essential question. The quote is something like a reasonable person adapts to the world

and an unreasonable man adapts the world to themselves. And so therefore all progress depends on the unreasonable man. So often this thing that makes one a groundbreaking artist, you know, a discoverer, an inventor, you know, an entrepreneur, an artist, whatever it is, the thing that makes you great is this ability to not listen to feedback. At some point, invariably, you come across feedback that you should listen to. You go past the point that you aimed for. You go past a convention that is there for a good reason.

And we only see the survivors, right? We never see the people who didn't listen and failed because they just sort of become noise, if you will, in the process. Whereas Elon gets held up as like, oh, I've done all of these things and people have told me I couldn't do them. I shouldn't do them. They can't be done. And yet I've done them. Yeah. And what we take from that is not he was right in these specific instances for these reasons. What we tend to take from that is the shorthandum, don't listen to other people or conventional wisdom is always wrong. But of course, many, many people had failed. There was a graveyard of millionaires and billionaires who'd lost their fortunes starting private space companies. I think a good part is not taking these sort of like business book headline cover story narratives from people's trajectories or from history, but actually really drilling down and getting to the actual reason as to why something worked or didn't work.

Elon Musties himself as this groundbreaking, you know, precedent-shattering entrepreneur. Or another version to look at is this guy who took massive government subsidies at critical points that allowed him to do those things. The story you tell yourself about your own experiences is really interesting. And then the story that society says about your experiences is also really interesting, too. Can you give me an example of where you missed a whisper and it's gotten louder and louder and then you're like, oh shit? I think we all have these in our personal lives, right? Like you sensed you were coming across, uh, you know, some sort of personal limitation or you sensed that you were straining a relationship, working with someone that you didn't,

you know, you didn't, you didn't quite think was right, but you ignore that. And then it becomes very clear why you should have listened to that kind of gut level instincts. I just take on too much and then I'm like, oh, okay. Like earlier this year, I rolled my ankle really bad. I had to go to the yard and they were like, you know, you got to take like six weeks off and I took, you know, like a week and a half off. I heard it again so badly like I thought when I looked down, I would see like the bone sticking out of my leg. Like it wasn't. Thankfully, I'd been given a very clear message, not just like from my own body, but from a medical professional and said like, you got to slow down and take a break.

And I didn't listen. And the irony, whenever I do this, and I've done this many times, you end up losing. losing more time than you would have if you'd just taken the prescription when it was there. It's when we rush the comeback or we rush the recovery. What I say is a lack of patience changes the outcome. And if you think about like money, that's a great area where people just try to get rich quick, whereas like the path or formula to get rich over time is pretty clear. Yes.

And almost it's available to almost anybody. But you get into trouble when you start trying to rush the timeline. Yeah, there's a Latin expression called Festina Lente, which means to make haste slowly. We often look for shortcuts and it takes longer than if we just sort of done it slow and steady. It is amazing at some level how it all can be reduced down to something in Aesop's Fables or a cliche or a little proverb. I've been amazed lately at the idea that like somebody said that for the first time. someone will invent a new word to express a concept or someone will invent a new way of thinking about things.

Oh, that's great. But a lot of these things that we take for granted, like, it's not like they're hardwired into our DNA. And so somebody who's now lost came up with that idea, the timelessness of the truth of that I just love. And that it's been true for 2,300 years or whatever. And it'll be true for 2,300 more years. Yeah, almost certainly.

I was listening to our old episode, and one thing I never asked you was, how would you define Stoicism? I've come to define it as this idea that we don't control what happens, but we control how we respond to what happens. And then when people go, what does that mean? I usually follow this idea. And then Stoic is predicated on this idea that you can respond with virtue or eritay. Annoying people, a natural disaster, extreme success, death sentence. You don't control that that happened. Maybe you controlled whether it was or wasn't going to happen, but now it is happening.

And to me, stoicism is the framework for which you orient your response. Is it harder if we caused it versus something we didn't cause? Like, is it harder to handle a situation where we messed up versus we get a cancer diagnosis? I think so, yeah, because we have guilt and shame and frustration, but it doesn't change the fact that it's now there. And I think that's part of what stoicism is, is the ability to go, okay, how I got here is separate and independent from the fact that I currently am here. I might need to, at some point, examine those causes so I can learn from it. But my impulse to dissect and blame and question what has happened is actually just a really

convenient distraction from the choice in front of me right now, which is what am I going to do about it. There's a passage of meditation's remarks realises sort of criticizing the people who are always trying to delve into what lies beneath. Like they're always like, well, what does this mean? Or what does that word mean? Or why is it this way or who's fault? What are the root causes? And again, that all matters. But usually not in the moment. In the moment, it's, well, what are you going to do? When should we look back and sort of reflect on that situation so that we can actually learn from it? Like, what is our contribution to it? Yeah, for me, it's always once the strong emotions about it have dissipated.

How do you reflect? Do you write or do you think? To me, this is Stoicism is journaling and journaling is Stoicism. Journaling is to Stoicism as meditation is to Buddhism. It is the practice of having a conversation with yourself about your thoughts and beliefs and values and actions. And that I don't think it's a coincidence that Mark Serius' sole philosophical work was entitled meditations, which the Greek title was just to himself. Almost certainly he did not give it a title. And what makes it such a remarkable work is that he didn't intend it as a work. It is a work in progress, that dialogue with the self. And so, yeah, I'm usually doing it there.

And then obviously the benefit of being a writer, and you know this, is like, you have this sort of forced self-reflection that if I was just a regular person, I think I would do a lot more journaling than I do, given that I have to wake up and think about all these things and write about them and talk about them and I get asked questions about them. So there's sort of a, there's a benefit to the profession, certainly also. You just kind of pin it around in your head. I don't think you're going to be doing it. It's because the thoughts in our head sort of makes sense in our head, but when we put them on paper, they don't. Yeah, it's like also what I'm hearing right now as I'm talking is an understanding of my

voice that when I listen to a recording of this, you see very clearly do not match up. And that's, to me, a metaphor for so much of the human experience, which is that it feels one way to us as we're feeling it or as it's coming out. And then with distance or from a different lens or a different medium, it suddenly sounds and feels and looks very different. And I think it's because it's like I'm hearing it through my own head right now, like the way the sound ways are literally going through the bones in my own head are different than when I have headphones on and it's been recorded afterwards.

Yeah, you grow up thinking your voice sounds like one thing. And then you hear it recording, you're like, oh, I'm actually a very different voice. You have these thoughts about things that feel like they make sense until you interrogate them. Or ask, is that true? Thoughts aside, like, I never thought about my voice until I heard myself. Yeah. And apparently, I have a very distinct voice that a lot of people don't like. It's a feedback on the audio book is like, Shane should not read books.

Interesting. And then I get this thing where I'm like, I was in a hot tub in Hawaii, and this guy's like, I know your voice from somewhere. And I was like, no, all Canadians sound like this. He's like, no, it's such a distinct voice. I just can't pinpoint where it's from. But when I listen to myself talk, I don't hear any of that. You realize in that moment, just how different objective reality and perception are, how sometimes it's good to get external feedback and sometimes it's good to be in a bubble because can you do anything about your voice?

No. My therapist uses this phrase that I think about a lot. And she catches herself too again and so I catch myself doing it. But somebody does something and then you're like, well, what that means or what you're saying? And she always says you should preface it with this phrase. What I make up about that is. What they're saying, what they're doing, it means something to them. And then you're having an interpretation of it.

It is a remark. And then you are saying it's rude or it's manipulative or it's provocative or offensive or loving or not loving. You're interpreting what it is. And this is a very core idea that Stoicism, Epictetus said that, you know, it's not things that upset us. It's our opinion about things. It's the way the voice sounds to us that is the problem, not the, not the voice. And when you realize that, it doesn't magically give you the ability to not have the opinion, but it does help you realize, I'm bringing a lot to this. I'm making something up about that.

That's what an assumption is. I am assuming something. And usually those things are making. stuff harder, not easier. There's an interesting quirk, too, when you're talking with people, if you say something like, the story I'm telling myself is, and it's wrong, people have a tendency to correct you. Yes.

And so they'll actually inform you. It's like, no, that's not what's happening, but you have to be brave enough to sort of put it out there. Yeah, when thinking about how much less threatening it is to say, the story I'm telling myself about that is this, as opposed to, I don't like that what you're doing is this. because one implies judgment, and then the other implies not just a certain interpretation about that, but an interpretation plus a loosely heldness, right? But you saying what I make up about that is, or the story I tell myself about that is,

or the way that sounds to me is you are not expressing your interpretation of reality as reality, and therefore you are offering the person the opportunity to correct or other. update or contextualize that thing. A lot of people think stoicism is simply suppressing your emotions. How would you respond to that? The stoics got married. The stoics had children. The stoics went to the theater.

The stoics wrote moving works that were performed in the theater. The stoics fought in battle. The stoics participated in politics in, you know, the great causes of their time. And the idea that these people had no emotions is to me totally belied by their actual day-to-day existences that we have a lot of evidence for. And when you look at Marxian's Meditations, you're not seeing a person who is devoid of emotion. You are trying to see a person who's attempting to be less emotional in high-stakes situations

or in stressful situations. But to me, that's very different than denying or disregarding the emotions altogether. It's almost like you have a narrower band, so you don't have these big oscillations. Yeah. I mean, I make a distinction between being angry and doing something out of anger. I think that's like a pretty basic being, you know, being sad and then being in despair, again, very different. And so I think to me, stoicism is a set of. of exercises and insights and practices to help you understand those emotions, process those

emotions, and not be ruled by those emotions. But I don't think there's ever this place where you are you're able to fully transcend them. And I'm not sure you would want to. The Stoics weren't saying like, you should never laugh. You should never have fun. You should never experience pleasure. I think they were saying, hey, you know, this this thing that feels pleasurable in the moment, how do you feel after? And so let's try to have a fuller picture of that thing. And they're saying, you know, if you're wrecked every time you lose someone, life's going to be very hard because losing people is a part of life. So I think they're trying to balance both a healthy set of emotions and an unpredictable, often painful existence.

And this sort of lowercase stoicism that we have is about as far from the mark as lowercase Epicureanism is from the philosophy of Epicurus who didn't eat at fine restaurants or engage in orgies or, you know, truly give his life over to pleasure as we understand that to mean now. Can we experience like pure droids? and really high highs without really low lows?

Or do we need the lows to actually give us the variation? Yeah, I'm not sure one has to make room for the low lows in the sense that life will force that upon you. I think when the Stoics talk about joy, they are trying to remind you that if joy for you is only possible when things are going amazing, your joy or your happiness is therefore out of your hands. Like one of the sort of philosophical questions that we get from a lot of the ancients is like,

could a person be happy like on the rack? Like could you experience happiness as you're being tortured to death? And I don't think they necessarily thought you could, but it is an interesting thought experiment. The idea like if joy and happiness are dependent on external circumstances, how how good is it and therefore how fragile it is. And so the idea

to be able to experience joy and happiness in any and all situations is I think provocative and interesting. There's this woman she wrote this book called bomb shelter and I think about it all the time. With Amex Platinum, access to exclusive

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Make the most of it at Best Western. Visit bestwestern.com for complete terms and conditions. She had what she thought was a normal childhood. Her name is Mary Philpott, I think. She had what she thought was a normal childhood. And then she had what she thought was a normal childhood.

only found out later that her father, they lived outside Washington, D.C., that her father's job was to basically set up the government facilities. He was a doctor, so he would have gone in there if it happened, but to set up basically like the government in exile underground in the case of a nuclear strike on Washington. And so she's kind of thinking about what it must have been like for her father to like go to his kid's soccer games or punish them for not doing their homework or you know do anything at home with like a literal sort of domicles over him at all moments like his job was to prepare for a was to assume that it was likely that they would all be uh you know evaporated in that nuclear strike and if it's

that was to happen. Part of his job was to, like, flee and survive, you know, not with, like, it's not like the doctor got to take their family with him. So she was just talking about, like, the compartmentalization that that would require. And I think that's interesting because, one, that is actually, I think, more relatable to every parent than you think it would be. You're always thinking about stuff. Yeah, you're always thinking about stuff. And yet, you also have to listen to this ridiculous story about a video game character or something. You have to be present even though you're waiting for an email telling you that your job has been made redundant and you're about to be laid off. Or you have to have fun with your kids

at an amusement park as somebody you know is dying in a hospital or whatever. And I think when the Stokes thought about joy and happiness, they were thinking about a more resilient form of that emotion, not fun, smiling, cheerfulness, happiness, but like a happiness of a person who is surviving the blows of fate and flourishing as a human being in good situations and bad ones. There's a story about this one stoke named Agrippinus and he's exiled for running a foul of Nero. And he's told that he's been convicted and, you know, he has like, there's like an hour before the verdict comes down. And I think he exercises or something. He just like does whatever. He just goes about

his day. And then they're told, okay, you're being, you're being exiled and you can take some of your property with you. Was it going to be a penniless exile or not? He finds out he can take some of his property. And then he says to his friend, okay, we'll have our lunch on the road then. Or I forget what, it's Attica or something. He's like, we shall have our lunch in Attica. You know, he's like, basically like, we'll just get on the road. And to me, there's, that is close to the stoic idea of joy and happiness of, you just got told everything was stolen from you. You just got told you have cancer.

You just got told, you know, insert horrendous event. Does it break you or do you just go, okay, what's next? So it's not arguing with the reality or the situation as it's been given to you or the hand that you've been dealt. It's just how do I play this hand to the best of my ability? Yeah, there's no complaint about the unfairness, the capriciousness, the surprise, just what are we having for lunch? Can you train yourself to think that way, or is it something you think is more, there's people disposed to that? I know I'm not born that way. I wouldn't say that I am now that way, but I think I am further.

along in becoming that way than I was at the beginning. I think it's probably true for a lot of the decision-making and cognitive stuff that you talk about, which is like, are there people who are naturally gifted and have this sort of a computer, you know, mind? Yes. And then there are those of us that are not that way, but in the process of studying and thinking about them, can we slow that process down?

Can we be more conscious of, the things, less of a slave to the things. I would say yes. I find it easier for me to like in these moments where something has happened, like we're stuck in traffic. I love it when the kids are in the car. Because when the kids are in the car, I can be like, oh, this is a good teaching moment, right? Like there's not much we can do about it. Might as well make the best of it. Let's put some music on. Let's have a conversation. Let's do X, Y, Z. But if they're not in the car, my immediate temptation is sort of like, oh, traffic, you know. Well, we're really good. giving advice to other people and then not so good at applying it ourselves because we have that

cognitive distance you know we're able to it's our identity is less at stake or our emotions are less tied up in it with your kids you're you're able to see the impotence and the unfundness of the frustration and you also feel obligated to help them with the meta skill of that. Because of the specific instances with a kid, you're like, well, what, how is this going to matter for their life? But we're not as good as that for us. We're just thinking like, I'm mad that someone said X, Y, or Z, not, hey, how can I get

better in my life at not responding when people say X, Y, or Z? So, yeah, you learn as you teach, the Stoics say. What other misconceptions do you run into about Stoicism? Well, that it's all old rich white dudes with a lot of merit and a desire to point out the biases and sort of structural patterns of not just the ancient world, but all forms of history. Just to focus on what was obscured or what's not included, we forget just how enormous the Roman Empire was. I mean, the Roman Empire makes contact with the Han Dynasty during Marcus Aurelius' reign, and it stretches as far as England and Africa and the Middle East. And you have Epictetus who's a slave.

You have Marcus Aurelius, who's the emperor, Zeno, the founder of Stoicism. Some people were convinced he is black. He's described interestingly in some of the few descriptions we have of his physical form. But in the case, he's like a Mediterranean merchant. And so just the idea that it was like all people of the same social class, just because Rome was a caste society, doesn't mean that all the philosophers perfectly conformed to that caste. Just because we hear mostly of the men doesn't mean there weren't stoic women.

Cato's daughter, Portia, is involved in the assassination of Julius Caesar. All of the Stoics would have had wives and daughters. There's a fascinating essay from Musonis Rufus, who's not just Epictetus's philosophy teacher, so he's teaching a slave, but he writes his essay about why women should be taught philosophy. So we know he has female students.

We just don't know any of their names. And there's been a backlash about Stoicism. It's like, oh, this is a philosophy for bros in Silicon Valley, or this is for meatheads or, you know, this is for soldiers. Yeah, there is, I think, a connection to certain masculine worlds in Stoicism, but I mean, a huge percent of my audience is not male, but I also just on a historical basis, that's not true. And so this idea, if Stoicism is like for dudes in the army

and it's about suppressing your emotions, I get why it's not going to be attractive. But that's not what it is. Just like if you think Epicureanism is orgies and parties and retreating from the world, you're going to be like, what is this? But that's not what Epicurus was talking about either. I thought it was, not Zeno, I thought it was Sisyphus who, maybe I'm getting really confused here, who created like the first sort of Stoic. Chrysippus? Yes, that was the one.

Created what? Sorry. Stoicism. No, Zeno was the founder of Stoicism. Zeno studies under this cynic philosopher named Cretes. By the way, Cretes is an equal partner with his philosophical wife in Athens. There's always been a female influence from the beginning. But Zeno is credited as the founder of Stoicism.

He sets it up on the Stoia pockyla, this porch in the Athenian agora. That's where Stoicism comes from. Then there's Cleanthes and then Chrysippus. But it doesn't really become a real school philosophy until later, sort of codified, but Zito is, is considered the founder's doses. Is the connection with really, instead of sports and military, if we, if we sort of generalize that, is the connection just with anybody who's doing hard things? And yet we tend to hold up these professions is.

I think so. I think, I mean, that's what sports are as a metaphor for any kind of pursuit of excellence. It's just the most visible. You know, it's a very. It is because it's a game with rules at a beginning and an end, the most observable form of excellence, an entertaining form of excellence. And look, in the ancient world, they're using sports metaphors then, too, because it's the same process. One of the Stokes is talking about how he thinks that a philosopher has to be like an athlete.

He's just like a ball player. You catch the ball and throw it back, catch the ball and throw it back. And whether it's a good throw or a bad throw, you still have to catch it. He considers Socrates like the greatest athlete of all time because he deals with the things that life throws at him, including this death sentence. There's weightlifting metaphors and racing metaphors and some of the stoics were also athletes. So I think we just, there's something about sports that is the sort of unmitigated pursuit of excellence. And yet it's also not unmitigated because we expect our athletes to exhibit sports, and grace and coolness and repression.

You know, like all these traits that go into being a full, well-rounded person are at play in sports. This is, I think, why the Olympics are this sort of enduring thing. We still observe some of the same exact sports almost that, you know, the Stokes would have been very familiar with. Do you think anybody can be at the far right of the curve in whatever domain and an expert or a sports or skill and be a normal sort of person? I think about this all the time.

I would like to be both. And I think you do realize there are tradeoffs part. There is something inherently unbalanced about excellence in a singular domain because you are focusing all of your energy. on one thing. There's something dysmorphic about like the athlete's physique. And that's probably just the physical manifestation of also, if you could look at their mind and their priorities probably equally out of whack. But if they weren't out of whack, then they wouldn't be on the right end. Yeah. I mean, what I really admire and I've gotten to meet a handful of them over

the years, and I'm always reluctant to be like, well, this one is a good example of this because you don't really know what's happening in anyone's personal life. But I think it's really something special when you meet someone who has inarguably attained the heights of their profession or, you know, in some sort of all-time grades, you know, achieve the great prizes of their thing, whether it's politics, sports, business, art, and they seem reasonably well adjusted. They haven't left a trail of bodies behind them literal or otherwise. You know, their, their family wasn't utterly neglected. Their health wasn't utterly neglected. Their moral priorities weren't so, weren't grotesquely out of alignment. So when you meet someone, you're like,

oh, they did it as good as it can really be done, but they didn't have to turn themselves into a monster to do it, that's, that's a, I would argue a much rarer feat. Power corrupts, absolute power corrupts, absolutely. So I think makes Marx really such a fascinating example. Here you have one of the few humans to hold absolute power as we would really define it and doesn't seem to have become deranged or grotesque, is into an over, an over. overwhelmingly cautionary tale. That to me is a rarer feat than if you told me he had won the single greatest, you know,

military victory of all time. Like the greatest victory of the Stokes would say would be the victory over those very impulses. There's another Roman, I think it was like a Cincinnati. You know your history way better than I do. Cincinnati who like gave up power. Yeah. I tell this story. It's my son all the time.

Cincinnati is maybe not real, maybe real, but his example was certainly very real to the Greeks. Oh, I guess to the Romans, not to the Greeks. But yeah, Rome sends out its army in this big battle, and they're defeated, and the army's trapped. And so Rome had this sort of emergency, you know, smash in case of emergency button, that said you know you could make someone dictator to save the republic and so they go to

Cincinnati who had been in general and they make him dictator and he rounds up every you know straggling man and boy in Rome at this time and he marches out and he defeats he rescues the army he defeats the enemy and then he returns to Rome resigns as dictator after like 17 days. And then he returns to his farm. He just goes back to his regular civilian life. And it's this example that is told for generations and generations and generations, so much so that George Washington hears it as a young boy. And he resigns his commission repeatedly. I was just in Annapolis a couple weeks ago, and you can stand in the courthouse where he resides his military commission. and then when he resigns after two terms as president.

But King George, when he hears after the revolution, he's, you know, what is to become of George Washington, he's told that, you know, I think he intends to return to his farm to not make himself and the Washington name a, you know, a hereditary monarchy. And King George says, you know, if he can do that, he will be the greatest man on earth. And there is something about relinquishing power or walking away that takes an incredible amount of discipline and strength. And then we don't usually appreciate it in the moment.

And in fact, we tend to ridicule and mock it. Like, you know, Andrew Luck, the quarterback? Yeah. He walked away. Yeah. And we don't hear about him anymore. So he's not out there, like, fighting for his legacy, arguing about his accomplishments. He's not on TV.

So he just sort of recedes from memory. But he also made like $100 million playing football. He, as far as we know, escaped without any serious long-term, you know, brain injuries. I don't know what he does all day, but, you know, the idea is... And he walked away at the top. Yes. Yes. To be able...

Has there been any boxer in history that's walked away too early? Probably not. clearly takes more discipline to walk away early or on top than it does to go for the sixth ring or the three feet or whatever those things are extraordinarily hard but clearly if less people do this other feat it must be because it's even harder do you ever think of walking away from writing yeah why do you think it's time for me to retire no that's so I don't know saying at all. You're sort of like, you're in the middle of it, right? Yeah.

You're like, what, 12, 13, 14 books, however many. Like, the thing that for me is that's the part that I like doing. You like. And it's probably the least hard on me. Right. It'd be the other stuff that I think would, would be. Like the bookstore or YouTube? No, yeah, like YouTube or podcasts or speaking or to just be like,

no, I'm just going to do this one part. I don't know how people do podcasts once a week or more. Like, I find once every two weeks hard. How often do you do it? 26 times a year. Is that a deliberate choice? Yeah, I don't think I could remain intellectually. Like, I don't think you would be genuine if I was doing it weekly.

I'd be finding people that I could talk to, not people that I wanted to talk to. You know what I mean? Like, I'd be filling a slot versus I really want to talk to this person. Sure. Well, you also do your interviews are longer, right? So you might be the same. If somebody's doing two a week and they're an hour, that's the same as you doing. But I find all the work that goes into it.

It's not like I show up. I got this one page thing, but this is like nine, ten hours. When I had my marketing company, one of the reasons I never wanted to hire employees was that I was skeptical that there were a enough projects that I would be interested in working on to pay for the people, which meant if I hired someone, they would represent a certain number of projects per year just to get back to even. I go back and forth between whether that was a constraining, kind of limiting belief or if that was actually like a pure and like admirable stance.

And you kind of distance yourself from the work too, right? Like so if I hired somebody to do the research for the podcast, I could show up. There'd be a list of questions, but part of what I enjoy about it is actually doing all the research and the work. The pressure to scale. Like I know a lot of people in the, this kind of information media space that have taken on like private equity investments like there's like the churnum group and so they'll buy like half of the business or all of the business and then the idea is like well how do we scale this into a much

larger company i've expressed no interest in doing that because like to me part of the whole joy of doing it is not having a boss and not needing to get at a certain level or do a certain amount of things, which you are foregoing when you bring on somebody else. I was talking to John Mackey about this, the Whole Foods guy, and he sort of said, and I love this analogy. He's like when you bring people on, they're usually hitchhikers. So they'll be in the car with you. And as long as you're going in the right direction, at the right speed, they'll pay for the

gas. But the minute you're like, oh, I'm really curious what's over here. they're going to be like, no, what do you do? You can't do that. And then all of a sudden, you have a boss and you have all this pressure. And, you know, they own half of your business. Yeah, it's more like you went from being the driver to being the passenger. Kind of, yeah.

The other person is like, has a, they have a break. And they have their own steering wheel and they have their own accelerator. The pressure to scale is obviously a first world problem because you're most people, and not that long ago for me, the problem was breaking through. Or breaking out. Yeah. Once you do that, because that is so rare, there's an immense amount of structural pressure,

economic pressure, cultural pressure to, you know, take a winner and turn it into a big winner, as opposed to just be like, this is nice. Even with the bookstore, every couple weeks I'll get an email being like, hey, be thought about opening another one.

And it's like, I already hit the lottery by not, failing. Do I need to start a shade of bookstores? I don't think that I do. And I don't think that would improve my life quality at all. But it's easy to be disciplined in some areas and not in other areas. So when you're successful, one of the tendencies is to start saying yes to all these other projects, start hiring a team and then your distance from the work and you can be like, you go do this, and then all of a sudden you start taking on projects just to do them. Yes. How can we use stoicism as a means to sort of focus our energy and remove distractions?

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Summer's here, and you can now get almost anything you need for your sunny days, delivered with Uber Eats. What do we mean by almost? Well, you can't get a well-groom lawn delivered, but you can get a chicken parmesan delivered. A cabana? That's a no, but a banana, that's a yes. A nice tan, sorry, nope. But a box fan, happily yes. A day of sunshine, no. A box of fine wines?

Yes. Uber Eats can definitely get you that. Get almost, almost anything delivered with Uber Eats. Order now. Alcohol and select markets. Product availability may vary by Regency app for details. Marks Frieders writes in meditation who can imagine the immense pressure and inbound that's coming at the emperor of 50 million people. He says, in everything you do and say in the thing, you have to ask yourself, is this essential?

And he says, because most of what we do in say and think is not essential. And he says, when you eliminate the essential, you get the double benefit of doing the essential things better. knowing that what you're saying yes to means saying no to other things and conversely saying no to things means saying yes to things is like the very tricky never gets easy balance that I was struggling with like even this morning my wife and I were like okay I got offered to do this and I got offered to do that what do we want to say yes to what do we want to say no to and just the you would think at some point not needing it would make it easier to say no but opportunity costs you get more opportunities yes and success tends to sow the seeds of its own destruction it'd be easy to say like oh when you're you know be disciplined while you're successful uh you know don't don't take on too much you say no to a lot of things but in sports or entertainment or art or even you know whatever it is that you do, you don't do it forever.

Do you have a narrow window? And there's going to be at some point where it dries up. And so are you going to look back and go, there was almost a bit of ego in my, in my selection process because I was assuming that I would get to do it forever. I continue to wrestle with that constantly. How do you think about opportunity cost? Is it always increasing for you or is it based sort of like on the workload right in front of you?

I was thinking about how. kind of like what seems like a lot of money to you as a kid always remains a lot of money to you. Even as your income goes up, it's hard for you, it's hard for me to pass on things because that seems like a lot, even though proportionally it no longer is. I'm trying to do work and get more clear, get more objective about like, no, hey, actually, yes, that to, to you 10 years ago, to any person on the street, That is a lot. But given what your time is actually worth at its current valuation, that's actually something you should say no to. That's hard.

Imagine if you're a billionaire, how hard that must, again, no one's throwing them a pity party. But like, that must be very disorienting and destabilizing to not have a good way to value what to say yes or no to. The problem is financial upside is always clear. opportunity costs are sometimes clear, but often not clear. If I get offered to do, I don't know, I speak and gig, that's the opportunity cost of saying no, or whatever they're offering, the opportunity cost of saying yes, is whatever creative

work I might have done had I stayed home, and then also intangibles like the rhythm. them of our households, my personal happiness, how easy things are. And so the downside is, in one sense, is very quantifiable. And the upside in the other case is very hard to quantify. And in some cases, the consequences of it are quite lagging. And so you're faced with briefcase, with cash in it, and, hey, isn't this a bit much? We're all tired. How do you balance that? My uncle taught me this thing when I was a teenager about how he used to price his business.

So he was up, he ran a plumbing company. What he did was basically the first 75% of hours were priced at 100%. So the regular rate, but 75 to 80, he would increase the rate 80 to 100. You'd increase it. And over 100% of like a normal work week, then he'd increase it even more. And he was super transparent. with people about this. Like, I'm really busy right now. I hate to give you this quote, but to do the job properly, here's what we'd have to price it at. And he's pricing it

at like 150 because he wants them to say no. He doesn't want to be the one to say no. He's like, I'll figure out how to do it for this price. And he's like, was so surprised by the number of people who said yes, in part because of his honesty. Right. But I use this. This is sort of like one of the simple principles that I use, which is like, if I'm super busy, I'm going to price it more. So I actually kind of want you to say no. Right. But if. you're going to say yes, then I'll make it work, but it's at a certain price. And so the pricing that we use is dynamic in some ways. And there's like a baseline, which is like, here's the minimum. And you need a certain amount of self-confidence and security to be able to do that. And you can

see why if you're like, if you have just an adorvis void inside you, how vulnerable that makes you. Yeah. Because you want to be wanted. You want the validation. you want the cha-ching because that feels good. But like you, like I get five speaking requests a week.

Yeah. And there's no way you can say yes to everything. So you have to have a system to sort of... Well, I think the first step is you have to have someone between you and the thing.

Oh, totally. To just eliminate three of the five that we're not serious. We're not even not serious, but we're at a number that might be tempting, but it's better for you not to see. Because you're more likely to say,

yeah. What could happen as you become successful is you can become jaded and entitled and you want to be the like you want to keep yourself as the good guy the nice guy the person who is saying yes yes so you have to set some boundaries and then task other people with enforcing them yeah i think some people go oh is it is it you know you want to pay these people commissions you just do it yourself and i think there's a danger in doing yourself which is that totally it almost it can go to your head and also kind of uh And then when it goes away, what?

Yes. I worry about this all the time, right? It's like, well, five, and I'm like saying no. You read that book, Die Was Zero? Yeah. It's a great book, but the idea is, you know, thinking about what are you trying to do all this for? You try to accumulate a large amount of money that you don't get to take with you when you die. We are borrowing money from our poorer selves to loan to our future richer self.

The example that is the book, which I think is a good one. He's talking about like a Metsuit who's like living way below their means, saving up money. they know in the future they're going to make a lot of money it's very clear how that profession works right and so they'd be more effective maybe not racking up a ton of debt but like not living as if they don't know for certain their financials they're they're not actually you know making $30,000 a year they're just temporarily making that anyways that advice is very helpful in clarifying in more predictive linear professions. But that would be bad advice to give to a rookie in the NBA

because they may only be able to do it for two years. I think it is tricky when you have a very clear element of unpredictability and a very, historically, a very clear drop-off. Like at some point you age out. At some point, you're, trend or moment goes away and maybe it come you survive long enough for it to come back but like the idea that for me as they're often that my sales are only going to go like this it's preposterously naive then it adds this layer to like okay so you're saying no because you're too busy right now yeah but

in six years you'll you'll feel like an idiot you wish for this request to come back yeah is it ever okay to lose your cool like is there strategic points where it actually makes sense to sort of sort of not be stoic and to, I wouldn't say completely lose control, but to have more variation. We had this idea that, like, crying is not manly, right? Like, being overwhelmed with your emotions is somehow a weakness. But we make an exception culturally for anger. If you went through some problematic work thing and you cried in front of your whole team, you would reasonably expect that team would be like, what's wrong with Shane, right? I'm not saying that that's right, and they just would.

But if you got so angry that you punched a wall, not only might not you be judged for that, that might be like part of the legend of Shane, which is interesting. And the Stoics would point out that, like, those are both the same process of being overwhelmed by our emotions. And one is actively harmful to you and your world. and the other is not. And so it's kind of strange. So it's interesting.

We have a couple of stories of Marks Rio is crying, but we don't have any stories of him losing his temper. And I think he was chasing by the fact there's a story about Hadrian, his predecessor, who gets frustrated with his secretary,

and he grabs the secretary's pet and he stabs it in the man's eye. Like this is the thing that the king could, the emperor could get away with, literally anything. And so I do think it's interesting.

the allowances we make, particularly with men for certain kinds of emotions and not other kinds of emotions. And I'm not saying, oh, hey, we should be all with one or all with the other. It's just the idea of the stoic suppressing their tears and sadness and love and affection,

but then, you know, being a vortex of temper and rage strikes me as a contradiction that doesn't make any sense. And the idea would be to be kind of an even and keel across the board. That being said, there is a difference between being angry and doing something out of anger, and then there's a third, which is the performative element of anger.

You're a head basketball coach, and you've gotten a series of bad calls. Losing your temper, screaming at the ref, and getting ejected. Not only doesn't help your team, but it costs your team points. because you get two technicals. But if you are so even keeled that you're just allowing the refs to run over you or you're allowing a lackadaisical effort from your team to go unchastened, also probably not good. And so I am fascinated by the way that a great coach can turn up or down certain levers.

I was at a spurs game one time and I watched Greg Popovich get ejected and Tim Duncan took over and the team was down by seven or eight points and Tim Duncan coached the rest of the game and they came very narrowly

within winning like it came down in like the last two seconds and they didn't win but they almost it and somebody told me after that Pop had looked at at Duncan and said I'm going to get myself thrown out you're going to handle the rest of this game And he was just, he saw that the team needed an energy shift and that that was a tool in his toolkit. I find that very interesting.

I want to move on and talk about discipline for a second. When we think of discipline, I mean, the image that comes to mind for me and probably a lot of other people is like the Army drill sergeant. What is discipline? I'm talking about self-discipline. So the discipline of an Army sergeant is obviously important, but I don't think that's. of virtue, because it's being imposed on you. Of course, essential that an army is disciplined. How would you define self-discipline?

But the virtue of self-discipline is the discipline that you insist upon yourself. So it's what you do when no one's watching. It's what you do with the discretion that is given to you. And I think when we think of self-discipline, we shouldn't just be thinking of physical discipline. It's not just how does your uniform look and how far can you march and self-discipline is. can you keep your head about you when things are falling apart? Can you be a calm, you know, reassuring presence?

Can you keep your emotions in check? So self-discipline is sometimes rendered as the idea of temperance, which just doesn't have a good connotation in the English language. But it is, the Stokes would say, the greatest empire is command of oneself. And so whether you're the emperor or a slave, whether you're a soldier or a CEO, So it's this idea of not, like, what are you allowed to get away with?

What is being asked of you? And it's more like, what are you asking of and insisting of yourself? To me, that's what self-discipline is. Where do you struggle the most with it? Knowing one's limitations, setting reasonable bounds on things. I don't have a problem with getting up and working. I have a problem getting up from and stopping working. I mean, I have other vices, too, whether it's food or, you know,

my screen or devices or whatever. But I think for the most part, it's discipline for me is closer to balance and saying no than it is to insisting on yes. For a lot of people, it's sort of the discipline to eat healthy, the discipline to go to the gym, the discipline. And then if we miss one, we think it's like, it's over. Like we've, how do we get back on track? You told me something, though, that I've been thinking about where you said that you're,

you go to the gym every day. Yeah. As opposed to I work out three days a week. it because there's a consistency to everydayness and it's not a choice then yes it takes away the lie you can tell yourself which is i'm doing it tomorrow yeah you can you can change like duration or scope but like work out sweat every day it's like it's so life changing for me and other people who've tried it after listening to me it's been life changing for them too no it's a great way to think about i try to write every day um we're trying to do a little something every

day. And that's better for me than, okay, I'm not doing it. And then next month I'm going to start doing it. But so you use the word try. Like I try to write every day. So like how do you get back on track if you, you went two or three days, you're traveling, you're talking, you're just busy with all the stuff that goes on. You get home. The family needs you. And then all of a sudden it's three, four days. I always always have the opposite problem, which is telling myself that being five minutes late on this is not as big a deal

as it feels in the moment. I am tending to fight the compulsive side of it and so the battle for me is going, let's just have a nice weekend as opposed to I'm behind.

Right. I'm going to blow apart this nice weekend to check some arbitrary box in a race that I am preposterously ahead on and by the way,

don't even need to be doing. But if you don't push yourself, like, what's the flip side of that? What do you worry about? Are you scared? You'll just stop and be lazy? I think that's the thing about most compulsive tendencies is they're not based on anything. You have this belief that if you don't do it, things will fall apart. I'm the same way.

Like, I work every day. Yeah, it's not based on anything real. And most of the time, what you get is not even the reward for doing it. you get the relief for having not, not done it. The feeling is not, I'm proud of myself. I did a great job. This made a huge difference. The reward is, see, you're not a piece of shit.

And that is not a way to go through life. Does your workaholism sort of, I don't know, I'm using that. No, no, go for it. But does that cause issues in your relationship? Yeah, of course. I think it always has. And so what you, you oftentimes workaholism or any kind of sort of compulsive tendency to do is adapting from some sort of either childhood wound or insufficiency or it's sort of a way of soothing something that you feel. But unlike a lot of addictions or compulsions, it's somewhat productive.

It's somewhat productive and it's socially adaptive. Doing heroin or, you know, drinking all night tends not to have positive social reinforcement, but being really good at what you do and thriving on that feeling of being validated for being good at what you do is a, is nevertheless a pretty wicked feedback loop. Are you sort of like motivated, I think about this all the time, and it, like, sometimes it motivates me and sometimes I'm like, oh, it's hopeless. You know, there's like this gap between where I think I could be and where I am. And no matter where that is on a relative, like, Y axes, it's like that gap is what I focus on, which is like, how do I shrink this gap? And then, you know, like, where I think I could be is

probably growing slightly faster than where I am. And so the gap is widening. Yeah. And then it's like, I need to, there's so many things I want to do. And I have so much excitement and energy around it. Well, they do throw on top of that, like, what you hear other people are doing. Yes. It's even more hard to run your own race. Seda guys, this word euthemia, and he talks about being on the path that you're on.

This is not being distracted by the paths that crisscross yours. He says, especially the paths of those who are lost. And I think about that all the time. You don't know where someone's trying to end up. You don't know where they're going to end up. You also don't know what is propelling them. Addiction or psychological issue, What's propelling them is millions of dollars of a fortune they inherited or, you know, some dark money, you know, donor.

It could be a bazillion things. You don't know. And so I think the more indifferent and probably ignorant you are of what your peers are doing, the healthier you are and the healthier you are. And the cleaner your compass reading will be. I think of it is like swimming in your own lands and there was this video, I think it was from the Olympics post 20. I forget what year it was, but this guy is swimming and he looks over at his competitor and it ends up distracting him just enough that he loses the race. Yeah. Because he's like one, he's not worried about him and his lane and his goals and his stroke.

And he looks over just enough to distract and he lost by like milliseconds. Yeah, there's that. Although the other one that keeps me up, there was a there was like a amount. bike race in the Japan Olympics, I think. And the woman thought she was in first place, but she was actually in second place. Oh, so she let up. Because, like, it's sometimes, you know, like in swimming, you're all right next to each other. Yeah, yeah, yeah.

Like the marathon or something, the longer races, you might be, it might be two minutes. That's a closable gap, but you can't see what the other people are doing. Even if it was an insurmountable lead for her to get first, her second place time was not the best that it could be right so clearly at some level we understand that competition is healthy and motivating and yet too much competition is disorienting and ultimately is self-defeating and so that balance is tough what can we do to cultivate more discipline oh i mean look i think having a physical practice is a way to cultivate more mental and cognitive discipline Like going to the gym or running or swimming, swimming, biking.

I do endurance sports, and they help me as a writer. Like, I couldn't do what I do as a writer without those physical components. Even, like, I have a cold plunge, and there's something about, like, I'm going to get in this thing that is uncomfortable, and I'm going to decide how long I'm going to stay in it, whether or not it has any health benefits whatsoever. And I'm pretty skeptical at this point of, like, all of those claims because I've seen what nonsense like these same communities will propagate.

So to me, the benefit is purely that it's hard. That it's hard and that I am doing the hard thing. And how do you sort of teach your kids or instill discipline in that? It's tough. My kids are still pretty young and so I am I am hesitant to give them my somewhat unhealthy adult levels of discipline. Part of me is just like letting them enjoying letting them just not be. My assumption is that they have whatever I have. And so allowing them to enjoy not having it is part of how I think about it.

Because I watch, as they get into things, they don't just, like, kind of get into things. They go all in? They're like, I need all of this. I read a story about Tom Brady watching his son playing video games and his son getting so upset. And he, like, throws the controller at the TV or whatever. And he's just like, he was like, dude, I have that. And it doesn't always take you where you want it to take you. And so I suspect that that part's there.

So it can help you, but it can also get in your way. Yeah. And would you wish it on someone, especially someone who right now is young and pure and has no, none of these adult notions? A lot of people with dyslexia talk about how that dyslexia is shaped in. informed the success that they have, then if you ask them, would you want your kids to have it? They're like, are you fucking out of your mind? We know like hard things and struggle and adversity. We know it's good for us. And yet, we don't want them for our kids. We don't

want it for our kids. And we also know, though, like, if we hadn't had that, we probably just would have had something else. I've never met someone who had zero adversity. Like, sometimes as people ask me, hey, should I create adversity in my kids' lives? Or do I need to seek out obstacles? And I'm of two butts. I think like having a physical practice, it's obviously a way of creating adversity at the same time. You know, was it Dostoyeski would like gamble all his buddy away so that he would write better? I don't know if you needed to do that. How would you define character? I just heard something. Someone said like character, like your reputation is what other people think of you and characters like what you do and people don't see.

There's like an element of right and wrong embedded in this, but who sort of defines what's right and wrong? That's the hard part. So I just, I've been doing this series of the Cardinal Virtues, so I did courage and discipline and then justice. And on one level, yeah, we go, how do we know what's right and wrong? Is it the Ten Commandments? Is there some, you know, scientific basis or utilitarian argument for what's okay about? And then it is remarkable how much societies and cultures all agree on some fundamental level as to what, yeah, there's disagreement.

Some countries burn their dead, some bury their dead, some, you know, do this or that. Pretty much every culture, religious tradition, and philosophical school has formulated some conception of the golden rule. And all the philosophers have, you know, come to some love. level of like, well, what would happen if everyone did that? One of the things I don't like about philosophy is the way that it looks at these moral questions and it makes them so complicated as to make them almost worthless. Like, how do you know what's right and wrong? What about this?

It's like we almost focus on the edge cases as a way of... There's such a middle ground that we can all agree on. Yeah, that's like 95%. You know, we're like, should, you know, a Nazis banging on your door? They want to know if you have a Jew in your basement. Should you lie to them or should you tell the truth? You know, like this is a cons categorical imperative. You know, a trolley is racing down a track and it's going to kill five people.

But if you pull this lever, it'll go here and kill one person. What would you do? It's a way of abstracting away from the fact that we have morally charged decisions in front of us all the time. and we don't think about it and don't do anything about it. And that that middle ground, if everyone just did a little bit better on this middle ground, the whole world would be immensely better. We've all sort of had moments where we didn't act to the person.

We didn't choose the action to the person that were capable of being. Totally. How do you live up to the best version of yourself? We think of virtue as this thing that you have or don't have. Think of it as a noun. when it'd be far better to think of virtue as a verb. Aristotle says, like, how do you get better at playing the flute? It's by playing the flute.

How do you become a more generous person? It's by doing more generous actions. He sort of compares virtue to any other craft that, you know, a carpenter builds stuff, and that's how they become a carpenter. So a good person does good things, not the way we sometimes think about it, which is like, go through your regular life, and then perhaps you will find yourself in some decision of enormous moral consequence

upon which the fate of the world will depend, and then let's hope that you draw from this ethical framework that you read about in a book and will make everyone proud. But in fact, it's like a series of small daily decisions, just like any other discipline. And that's why these virtues are so related. Like, there's a discipline to justice. I keep my word.

I help people. I think about the consequences of my actions on other people. I don't do insert X, Y, or Z thing that might be legal, but not right. And so if you think about it as a practice, you can get yourself, not only can you get yourself to a place where you're capable of doing it, but by doing it. But by nature of doing the practice, it's never going to happen that we're just going to pick some random-ass person and put the fate of the world on their shoulders. You have to be involved in the thick of things, making decisions of consequence to ever find yourself in a position of decisions of consequence. We live in a world where your slip-up in character, which we all make, can now become viral on the internet. It's like you yell at somebody.

You weren't generous when you could have been generous. You did something stupid. Somebody had their phone out. And now you can't recover from this. You know the Profumo scandal in London in the 60s? There was this cabinet officer in the British government who has this affair. So he's cheating on his wife. He's cheating on his wife with a prostitute that turns out to be a Russian spy.

And then he lies about it. And it ends up bringing about the fall of, I forget which government, but it brings about the prime minister vouches for him and then has to apologize and ends up resigning as a result. And I tell the story of Perfewan because I think he's so interesting. So he destroys his political career

and today we would say he was canceled. And what would happen today is that this person would be basically shunned by one half of society and then perversely, like, embraced by another darker side of society that doesn't like those people, right? And you would see him get radicalized and fight against cancel culture. You know, we almost know exactly how that scandal would go. He would, like, get rid of all of his political beliefs from before, embrace a different set of political beliefs, and kind of become almost like a, they become almost like these Joker-like figures. And instead, he just quietly shows up one day at this charity.

I'm forgetting the name of it. It was like a Salvation Army style charity house. And he shows up one day and asks if they need any help. And they put him to work in the kitchen. Like he's washing dishes. And he volunteers there every day for like the next 40 years. And he becomes its chief fundraiser and its main leader. And he just quietly goes about his life doing good work.

And eventually there is an arc of redemption to it that you can't do good every day for decades without inevitably being noticed. Did he get his political career back? No. Did everyone forgive him? No. Is his name still inextricably linked with a certain scandal? Sure.

But on net, most people look back and go, probably overreacted. We certainly made judgments about this person based on a singular. set of decisions that his subsequent actions revealed to be more complicated. An aberration of sort of character. Exactly. And I think to me, that's the danger in today's world. It's not so much that you'll make a mistake and people will judge and criticize you for it. Because I think that's always been true. You're right. The internet makes, the internet is not a place where grace is commonplace and where things can be wretched out of context and all of that and yet actual danger is

that in all of that scandal and attention and negativity does it change who you are like i am fascinated by the people who are fascinated by and impressed by the people who have messed up had scandals and the subjects of cancel culture or moms or whatever, and then they emerged from it, not caricatures of themselves, that it actually wasn't this life-defining, formative change. Like, the Stokes talk about, like, look, people can come and take all your stuff from you

and you can be treated profoundly unjustly, but, like, no one can affect your character. That is the thing you have. But oftentimes that's the first thing to go because we're angry or we feel mistreated or because our willpower collapses or whatever. So like can you not turn into a radicalized asshole is to me the interesting question. There's another sort of subset to this that we sort of sometimes will behave better than we want to because we know we're being recorded.

We know we're being watched and then it's it's not character anymore because if character is sort of like what you do and nobody's watching. And, yeah, look, philosophers can debate that question, too, like, is it good if you're doing good because you want a reward or because you're following? It should just be enough to do good because you're doing good. Yeah, but if I had to choose, you know, like people today are like, oh, it's all this virtue signal in, you know? It's like, certainly better than the alternative, you know? Yeah, totally. I'm not sure this sort of, like, the cruelty is the point.

vice signaling is preferable, even if it's more honest. I would like people to be signaling. They say what hypocrisy is the credit that Vice plays to virtue. Never heard that. Like you're at least saying that you think it's important, even if you can't live up to it. You know, I would rather have virtue signaling than not. than the nihilism of, like, lull, nothing matters. Where in life do you have the highest standards?

The easy answer would be professionally because it's easiest, and it's the most measurable, and you get the most feedback. Is there something a little shameful and sad about that, probably? I don't know anyone that's like, I suck at work, but I'm great at all. So we naturally, or unbalanced. Like, I don't work as hard at being a parent as I do at being a great writer, but at the end,

which is, which am I going to think is more meaningful? But one's so much more measurable, more people care about the other one, because it affects more people, at least in the short term, without you. What do you feel like you have the highest standards? I hold myself to these, like, unrealistic expectations in every domain. And I want to be the best father. I also want to be super successful at what I do at work and trying to pursue those two things. I want to be a great son to my parents.

I want to be the best of whatever it is that I'm doing. And I go through these oscillations where I think of it as harmony, not balanced, because I can't balance being great at work and being a great father. And so sometimes I'm like, it's going to be busy for the next couple. months. I'm traveling a lot. And we're going to, you know, my kids are teenagers now. So it's a little easier, but like we're going to figure this out together. Right. And then it'll come back and it'll restore and they'll sort of be a different balance. But I also like, it's caused me to do these crazy things where it's like, I am home every day when the kids get home from school. My work day when I have the kids is basically like nine to three. And in that period, I got to work out. And so my work day is

really short. And then when I don't have them, I'm like, okay, I got to make up for this lost time because Yeah. It's not coming at the expense of being a great father or a great parent or a present parent. And then when I fail at these things, like the parenting thing, man, like I've gone to bed crying, you know, just being like, man, I lost my cool in the kids, you know, I wasn't a good dad today. And then you kind of beat yourself up, but you're holding yourself to this expectation. It is interesting how this is like basically every woman's experience up until very recently and almost no men were thinking about these things were. dealing with a set of expectations and a set of responsibilities for which there is not centuries of cultural experience and lessons and examples to draw on.

You know what I mean? Like your dad wasn't ever doing that and your grandfather certainly wasn't ever doing that. And then you go back a couple generations and they're like, I didn't even know all their kids' names. It has changed. way for the better, but yeah, I think about that too. You go, okay, I try to, I'm, I'm either dropping my kids off or picking them up or sometimes both every day, uh, that I'm in town. I'm not always in town, but when I'm home, I'm doing that. And so yeah, very quickly, your day is super circumscribed.

And then there is this challenge or tension of like, can you be great at what you do? working not even bankers hours but like stay-at-home mom hours or something you know it pushes me they go to bed so they're like i gotta log in i got to do work you know we used to travel in the summers and we go away for kind of like a month and we just pick a random place and we'd live there and i would be present with them all day and then as soon as they went to bed i'm like oh god i got to work right and now it's easier because they sleep in so i get a full work day and before when they get out of bed. Yeah, Tony Morrison talked about how she wanted to do all her writing before she

heard the work mom. And so she would have to get up at like four in the morning. And she'd write until six or something. I'm not quite on that schedule. But I do, yeah, I try to, like my day is circumscribed by their day. And I also go, how the fuck are other people doing it? This is crazy. I can pick my own schedule.

I could stop working if I wanted to. But like, how can you expect society to function? And you're in Canada, so you have some social safety net. But, like, how could you expect your average American parent to drop their kid off at school sometime between nine or seven and nine and then pick them up between two and four if you've got, and then also, let's say, you're two different kids at two different schools or more. Yeah. It's insane. No one, no society can't function this way. We're expecting, rightfully so, for parents to spend a lot of time with their children.

but the world is not conducive to that in all unless you've retired or you're not working. I think about this all the time, right? Like I have an eight minute commute to work in the morning and I'm like, I don't know how people would do 30 minutes. You know, like that's an extra, almost an hour a day you're going to lose just on commuting.

And then I think about family and the role of like, I'm so blessed to have my parents close by who are an active part of my life and my kid's life. And there's a lot of people who don't have any family support in the city that they live in. And I wonder, like, how they do it all the time. Crazy. And then I get text from people going, like, oh, God, I just had the kids alone for a weekend. I don't know how you do this all the time.

And I'm like, okay, maybe I'm not that bad. But also just think about the fact that, like, for basically up until, let's say, 20 years ago. And that might be generous. And we're not all on different scales. But, like, only one parent was thinking about these things, really at all. And so just the immense cognitive load, and only one of the genders is aware of it in any way, is insane in retrospect. Sad, unfair, and then still doesn't change the fact that it's now different, and not a lot has gone into helping people manage that. I have a lot of respect for the parents out there.

Yeah. whether single parents are together, it's a lot going on. You've said that writing helps clarify your thinking. Can you double click on that a little bit? I actually have a chapter about this in the book that I'm doing now. You know, Amazon has this culture where they, you're not allowed to call a meeting unless you've written a memo about what's going to be discussed at the meeting.

And multiple people have to edit that memo before you can sit down and do it. And why is that? It's not because memos are fun or anyone likes reading memos. It's that the act of having to put your thoughts and the agenda and the purpose of the meaning on paper is essential. There's this story about Eisenhower at the outbreak of the Second World War. Marshall is chief staff of the U.S. Army, and he's bet Eisenhower before he sees sub-promise of the town officer. And he calls him in and he says, you know, it looks like World War II is about to break out. Japan's on the March.

What do you do? And it's a job interview. And Eisenhower could have just pulled an answer off the top of his head and riffed. And he says, can I have a desk in two hours? And Arsha says, I'm sure. And he goes, he gets a typewriter. He sits down and he basically types out a memo. Everything he has studied and learned and thought about this exact problem,

his whole military career. He's been in the Philippines. He's been in South America. He's been, you know, he's done a lot. But he gets it on paper, and I think there's something about getting it on paper instead of spouting it off. The answer I just gave you is not as good as the answer or the analysis of that problem that I wrote in the book that I'm doing right now. That's how my mind works. And I think that's how most minds work.

They are the process of really stopping to think and clarifying and going over. Joan Didion said that writing is a hostile act. because you're having to convince someone to see things the way that you see them or think the way that you think. And that's like it takes an immense amount of skill to do that. Very few people can do that off the top of their head. Kind of have to meet people where they are and then take them where you want them to go. Yeah, you zoom out, you zoom in.

Yeah. You know Thomas Merton, the Catholic monk? He becomes this monk and he's a trappist monk, which they didn't technically take a vow of silence, but they are supposed to spend their lives in contemplation. But he becomes this prolific writer, and a lot of people are upset because it's somehow a violation of the vow. And he was saying,

no, like writing is contemplation. I'm thinking about what I think. And for people who are not writers, maybe that doesn't make sense. To me, writing my impulse to write comes from my inability or the insufficiency of what I can come up with off the top of my head.

my belief in my ability if I sit down and have an uninterrupted bit of focus and concentration that I can get it. I can do that hostile act of change in mere thinking. As a writer, how do you see the impact of AI? I haven't seen it do anything that even a pretty good writer can do. but it can do things a lot better than people who are bad at writing. We clearly have problems in our society with people who are extremely credulous and susceptible to misinformation and disinformation and conspiracy theories and nonsense. I don't know about you, but when you interact with AI about something you really know about,

you realize it's not very good and it's very prone to telling you what it thinks you want it to hear. And so one of the things I'm nervous about is people's inability to handle that. Like one of the things you learn as a project manager, like if you're working with someone who has technical expertise is you have to know enough and they have to know that you know enough that they can't bullshit you. Like they can't say, no, that's not possible. Right. Or that's going to take six months or that's going to cost this amount of money. You have to have enough technical domain expertise that you can push back and get to the truth of things. And when I've worked with AI and I'm needing it to track something down, that maybe I'm

like, hey, didn't so-and-so say something about this? And they go, oh, yeah, they said this. And then I go, wait, or was it actually so-and-so? And they go, yeah, yeah, it was that. And what it's doing is it's telling me what I wanted to hear it. The same way that people, Google stuff or see some on social media and they go that feels true that's it if what human beings are good at is using tools and using and cooperating with other people what we're going to have to have in this age of AI is a strong sense for bullshit and an ability to know when to push back and to examine and when to verify because a lot of what it's going to spit out is not true or is only partially true

and if you're just defaulting to it you're going to be embarrassed do you use it for any writing or any purpose? I mean I use it when I do presentations I have it do like I want a picture of

insert a thing that's never been painted by a Renaissance painter before when I'm trying to visualize things I use it and sometimes we'll use it in videos and we're like you know show mark is really like in a suit of armor show marks realists like so i use it for things like that like track stuff

down but then i i i verify i have to i have to get a second opinion i have to have it in some way because i'm that skepticism keeps me up because it the the costs the reputational costs are bored it's like trusting wikipedia you know it's good if it's right the reputational hit is felt by you alone totally do you use it yeah we use it all the time and home, the kids like will write their essay. The way that I I encourage it at home is like you're growing up at this world. Like you need to use it. But here's the appropriate use. The appropriate use isn't like I need to write an essay on the Civil War that's 2,500 words go. The appropriate use is you write something reasonably good. Yes. And I want to see your full history. So yeah,

like I always keep the kids full history. But you submit it and you're like, you're a grade nine teacher. What would you say other weak points in my argument? So it's like almost like a personal tutor and then I'll submit like here's a draft chapter like what did I miss what do you think and sometimes it's pretty insightful I've used it with my kids we'll have fun like they'll be like draw this or make that they get increasingly excited about making it do more absurd things and the idea of seeing it as a as a tool as opposed to a replacement for something I think is really important I want them to be familiarized with the inherent limitations of it yeah right so it's like you say draw you know it i had to do i was doing a slide and i was like

draw this the socrates doing x y right z and then one of the characters in the back had glasses on and i was like this doesn't make any sense they didn't have glasses so like get rid of the glasses and then it's like they redid it and then now more people have glasses you know what like yeah and it's also its inability to to iterate like it's not very good at this I want this, but five percent different. It starts from scratch, you know? And so again, yeah, I think the more you learn the limitations of it and the logic of it. And if you can get good at prompting, like prompting as a skill, I want my kids to have that.

So here's the like interest. I actually get it to read its own prompts. I am going to prompt AI. I want a summary of this podcast. And then it'll give me like a five sentence thing that I could basically just submit. it back to itself and tweak a few things here and there. But it gives me a much better prompt than I would give it. This is the worst it's ever probably going to be.

Yeah, right, much, much better. And so it's going to get exponentially better over the next decade or 20 years. And it would be interesting to see how we use it. And I find it interesting because the schools are like, don't use it. And I'm like, you can use it. I need the chat history because I want to go in if I have to argue with your teacher. I want to say, here's what you submitted. Here's your first drive.

And now they've done this thing where they make them write a draft in the school and they take a picture of it. And so your final submission can't differ too much from the original submission. Well, so I do this thing. So when I read a book, I often type up the passages that I liked in the book. Yeah. And sometimes, because I'm just sending it to myself to print back to the office or whatever, I'll do it in Gmail. And Gmail has always had this kind of predictive AI in it where it's guessing the end of what you're saying. Yeah.

And I always found it really interesting as a writer. So I'm typing some sentence from Hemingway. So this is a sentence that has been written before. Unlike, you know, my average sentence, I'm making it up. This is a sentence that exists. So it's not that there's a right answer, but there is an answer. And we're largely in agreement that Hemingway did a good job, right? Because he's considered one of the great writers.

So it's like you're doing this simulation of a pattern. that someone actually flew, never is the AI able to predict the next couple words in that sentence. I've always found that very interesting. And it's a reminder to me that still the act of creative genius of doing not any sentence, but like the right sentence, the right way with the right words. Like Twain said that, you know, that's the difference between lightning and lightning bug. You do get a sense of the limitations of AI when you can see. how insufficient it is compared to really great stuff. Tyler Cowen wrote this book like 10 years ago called Average is Over.

And I think that kind of defines my philosophy of life, which is a lot, these technologies aren't eliminating, they're going to be eliminating large chunks of the people who are able to do that thing. But the people who could do that thing at an elite or an excellent level will probably, it's leverage, will be better at it and be more highly compensated and the importance of it will be higher. And so you have to figure out what is the thing that you're going to be excellent at. And then you have to be, as we were saying, somewhat dis-unbalanced in the pursuit of that excellence. But it's like the cost of being mediocre get higher and higher.

One thing I have noticed is like the length of emails and the grammatical perfection in emails has increased quite a bit. And I'm like, I know you. There's no way you wrote 16 sentences without making your grammatical error, spelling error. People are just putting, you know, their point form and be like generate a non-violent email to send to this person, put this in non-violent communication. Then you get it and you're like, this is half a page. It should be like two sentences. Well, just like social media is bots talking to bots. Like a lot of our life is going to be like AI talking to AI. Like if I open an email and I don't know the person, it's more than like five sentences now. I'm just delete, right? I don't even get it. Well, you're going to have to get

better. Just like you're going to have to get good at spotting bullshit, you're going to have to be good at spotting AI versus non-AI. Yeah. Because the cost to generate an AI email is zero, at least before you had to type something in or copy, paste. You've gotten those emails. It's like, dear Joe, and you're like, wait, my name's Ryan. What are you reading right now that's challenging your thinking? I just, I've read these three huge books on LinkedIn. So I've been doing a huge deep dive into Lincoln for the book that I'm writing now. And I think that's like, you know, maybe earlier in my writing career, I would have read one book and called it.

And now I'm like, now I'm going to read another and another and another. And so I'm just going deeper and deeper and stuff. I'm reading this book now about the founding of Australia that I'm finding a real interesting called The Fatal Shore about like why, why did they start a penal colony on the other side of the earth? What's, what's the? Well, the argument was that London had extremely strict legal system, an abysmal for-profit prison system.

and a belief that like there was essentially a race of people that were criminals as opposed to crimes being an act of opportunity or desperation and that reform was possible. Then America rebelled and the ability to send colonists or the undesirables across the Atlantic to America evaporated and they had to find some new place to do it. That's crazy. It's fascinating.

Do you read many business books? Like, what are the best business biographies you've read? Best business biographies? I don't read that many business biographies. I like, my dream book is like a 900-page biography of someone I know nothing about or someone that I know a lot about. Because you want the detail and then you want. I'm looking for illustrative stories or insights into how that person operated or solved. problems. So, like, you know, I read a book about Lincoln specifically as a politician. I read a book,

you know, specifically about Lincoln's cabinet. I read a book specifically about, you know, Lincoln and literary inclination. You know, like, I want to go really deep in a specific thing. And, and then I'm finding stuff that didn't appear in one, but appears in the other. And that's how I'm building out the chapter that I'm writing. And do you do that without having this story in mind? You're like, oh, this story is representative of X, Y, Z, tag it. Sometimes I'm just reading generally about something, like I'm not writing anything about Australia. I'm just was there, and now I'm interested in it,

and I have some basis of knowledge I'm building on. And then it'll help me understand the 1700s, the 1800s, and often it's, I'm chasing something down that I think I know is down this whole way. How do you define success today, and how has it changed? Do you remember what I said the other times? No. I still think my definition of success,

is autonomy. Like I've been saying recently, like, success is how much you see your kids and power is how much control you have over your schedule. My son's school called and he was sick and I was like, all right, I'll be right there. You know, I like that. To me, that's that's both success and power. I didn't have to ask anyone's permission. I didn't need to worry about the cost of missing a day's work or whatever. I just could handle it. Turns out it wasn't actually sick, you know, he just had a cough or something. And so we just hung out all day. And then I had a talk that afternoon and he came with me. How is that changed from like a decade ago when you would define success when you were younger? I think success was often more predicated on like either

very specific things or relative to other people and their accomplishments. And I think I've gotten closer and closer to just not really care. And part of that is, living where I live, how my life is set up, just valuing different things. The relative thing is fascinating because if you compare yourself to people who are relatively not pursuing the same goals, maybe not as successful as you are, you sort of feel good about yourself, like maybe you're not reaching your potential because you can sort of coast a little bit. And if you compare yourself to people who are better or more successful, then you're perpetually sort of like not where you want to be and it can sort of like

destroy your satisfaction. I try to remind myself that I write about an obscure school of ancient philosophy, that there's a floor and a ceiling to that. Look, if where you compare ourselves to James Clear, we're all failures. Yeah. And far as book sales. But if you compare yourself to the millions of people who would kill to even have a meeting with an editor, it's a huge success.

Sometimes it can be helpful to really think about how bodice you would have previously defined success. Oh, totally. And then there's there's also like a relative or sort of like a relative success and absolute success, which is, you know, if you sell, I think I don't know what the actual number. I heard it was like 50,000 books. Yeah. You're in the top 1% of books ever published in the history of humanity. So like there's always a different way to change your perspective on where you're at and sort of. And what a friend of mine used to say this, like if we threw everybody's shoes in a big pile and you picked out the shoes and you got all the problems with it, you probably pick your own shoes. Like a whole. world basically you know you could pick anybody's problem you're most of the time you're going to pick yours there's a lot of people who would try to pick our problems when i feel jealousy i try to remind myself that you can't pick and choose like if you want what someone has you have to trade your whole life and in that case you almost would never take it or maybe not even your whole life but let's just

say like oh why did they get this opportunity i should have got this but it's no no no you have to swap your whole career for theirs would you do it and it becomes more complicated It's, it's, it's, it's, we want, yeah, we want to be a little from here, a little from here, a little from here. But that's not a possible combination because every decision, every goal inherently is making things not goals. There's tradeoffs. Yeah. And yeah, you can't be like, I want to be classical musician and then compare yourself to Taylor Swift. They're just, they're different genres of music that have different floors and ceilings.

So, like, you know, it might be easier to break out as a classical musician. I'm not saying it's easy. But, like, you know, there's a set audience and there's also a ceiling. You're never going to be the number one album in the country. But by going for the number one album in the country, you might get nothing. And just understanding that you made certain choices and that you can't. Strategy is by definition choosing certain objectives and not choosing other objectives. And if you try to straddle two strategies, you'll destroy yourself.

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