Ryan Holiday: How to Win the War with Yourself

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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Shane Parrish?

  You've said before that life is always whispering at you, and if you're not paying attention, it'll eventually scream at you.

• 0:06Speaker 01

  In sobriety circles, they talk about like two cars in the garage attics. 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?

• 0:53Shane Parrish?

  Welcome to the Knowledge Project Podcast. I'm your host, Shane Parrish. In a world where knowledge is power, this podcast is your toolkit for mastering the best of 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 world-class athletes, artists, and entrepreneurs transform their lives. It's time to listen and learn.

• 1:39Shane Parrish?

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• 2:22Shane Parrish?

  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?

• 2:35Speaker 01

  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 generalize from that is never listen to people, you're going to be in 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.

• 3:20Speaker 01

  This is the worst idea. 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 Z. 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 him it was a good idea. Some people told him it was a really, really bad idea. Some people told him it was 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.

• 4:04Speaker 01

  And so, therefore, all progress depends on the unreasonable man." So often, this thing that makes one a groundbreaking artist, you know, a discoverer...

• 4:17Speaker 01

  An inventor, you know, an entrepreneur, an artist, whatever it is, what 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.

• 4:40Shane Parrish?

  And we only see the survivors, right? Like, 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.

• 4:58Speaker 01

  Yeah. 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 shorthand of 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 in private space companies. I think the good part is like not taking these sort of like business book headline, uh, cover story narratives from, uh, 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 Musk sees himself as this groundbreaking,

• 5:43Speaker 01

  you know, precedent shattering entrepreneur. And 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, about your experiences is also really interesting, too.

• 6:04Shane Parrish?

  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?

• 6:10Speaker 01

  Well, 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 ER and they were like, you know, you gotta take like six weeks off. And I took, you know, like a week and a half off.

• 6:50Speaker 01

  I heard it again so badly, like I, 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 has said like, you gotta 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 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.

• 7:23Shane Parrish?

  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.

• 7:36Speaker 01

  Yes.

• 7:37Shane Parrish?

  And almost, it's available to almost anybody, but you get into trouble when you start trying to rush the timeline.

• 7:42Speaker 01

  Yeah, there's a Latin expression called fastina lente, which just 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's, it is amazing at some level how it all can be reduced down to something in Aesop's fables or a cliche or, 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. We'll go, 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.

• 8:27Speaker 01

  Came up with that idea, the timelessness of the truth of that I just, I just love. And that it's been true for 2,300 years or whatever.

• 8:35Shane Parrish?

  And it'll be true for 2,300 more years.

• 8:38Speaker 01

  Yeah, almost certainly.

• 8:39Shane Parrish?

  I was listening to our old episode and one thing I never asked you was, how would you define Stoicism?

• 8:45Speaker 01

  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, well, does that mean I usually follow this idea? And then Stoic is predicated on this idea that you can respond with virtue or erite. 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.

• 9:17Shane Parrish?

  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?

• 9:26Speaker 01

  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?

• 10:06Speaker 01

  There's a passage in Meditations where Marx realizes 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, what does that word mean? Or why is it this way or whose 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?

• 10:25Shane Parrish?

  When should we look back and, and sort of reflect on? That situation so that we can actually learn from it and like, what is our contribution to it?

• 10:35Speaker 01

  Yeah, for me, it's always once the, once the strong emotions about it have dissipated.

• 10:41Shane Parrish?

  How do you reflect? Do you write or do you think?

• 10:43Speaker 01

  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 Marcus Aurelius's 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,

• 11:27Speaker 01

  you have this sort of forced self-reflection.

• 11:33Speaker 01

  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 something, there's a, there's a benefit to the profession certainly also. You just kind of ping it around in your head. I don't think you're, you're gonna be doing it.

• 11:55Shane Parrish?

  It's because the thoughts in our head sort of make sense in our head, but when we put them on paper, they don't?

• 11:59Speaker 01

  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, you know, 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 my, the way the sound waves are literally going through the bones in my own head are different than when I'm, have headphones on and it's been recorded afterwards.

• 12:43Speaker 01

  Yeah, you grow up thinking your voice sounds like one thing. And then you hear it recorded, you're like, oh, I'm, 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?

• 12:58Shane Parrish?

  Thoughts aside, like I never thought about my voice until I heard myself.

• 13:03Speaker 01

  Yeah.

• 13:04Shane Parrish?

  And apparently I have a very distinct voice that a lot of people don't like. It's a feedback on the audiobook is like Shane should not read books.

• 13:13Speaker 01

  Interesting.

• 13:14Shane Parrish?

  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, I don't hear any of that.

• 13:29Speaker 01

  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. Like my therapist uses this phrase that I think about a lot. And she catches herself to it again. So and I catch myself doing it. But she, you know, somebody does something and then you're like, well, what that means or what you're saying. And she always, she always says you should preface it with this, 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, it is a remark and then you are

• 14:11Speaker 01

  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. 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.

• 14:52Speaker 01

  Things are making stuff harder, not easier.

• 14:56Shane Parrish?

  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.

• 15:06Speaker 01

  Yes.

• 15:07Shane Parrish?

  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.

• 15:13Speaker 01

  Yeah. And one thing 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."

• 15:22Shane Parrish?

  Yeah.

• 15:22Speaker 01

  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 update, or contextualize that thing.

• 15:56Shane Parrish?

  A lot of people think Stoicism is simply suppressing your emotions. How would you respond to that?

• 16:03Speaker 01

  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. 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 Marcus Aurelius'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

• 16:44Speaker 01

  high-stakes situations, or in stressful situations. But to me, that's very different than denying or disregarding the emotions altogether.

• 16:54Shane Parrish?

  It's almost like you have a narrower band, so you don't have these big oscillations.

• 16:59Speaker 01

  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.

• 17:09Speaker 01

  Being sad and then being in despair, again, very different. And so I think to me, Stoicism is a set 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.

• 17:52Speaker 01

  And they're saying, you know, if you're wrecked every time you lose someone, life's gonna be very hard because losing people is a part of life. So I think they're trying to, to, 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

• 18:37Speaker 01

  me now.

• 18:38Shane Parrish?

  Can we experience like pure joy and really high highs without really low lows? Or do we need the lows to actually give us the variation?

• 18:49Speaker 01

  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 the, 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.

• 19:32Speaker 01

  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.

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• 20:57Speaker 01

  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 only found out later that her father, they lived outside Washington DC, that her father's job was to basically set up the government facilities. He was a doctor, so he would have gone to, 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...

• 21:43Speaker 01

  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,

• 21:56Speaker 01

  you know, evaporated in that nuclear strike. And if that was to happen, part of his job was to like,

• 22:04Speaker 01

  flee and survive, you know, not with like, it's not like the doctor got to take their family with them. So she was 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

• 22:46Speaker 01

  as somebody you know is dying in a hospital or whatever. And I think when the Stoics thought about joy and happiness, they were thinking about a more resilient form of that emotion, not fun, smiling, cheerfulness, happiness, but like 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 this story about this one Stoic named Agrippinus and he's exiled for running afoul of Nero and

• 23:25Speaker 01

  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 gonna 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 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.

• 24:10Speaker 01

  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?

• 24:23Shane Parrish?

  So it's not arguing with the reality or the situation as, 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?

• 24:32Speaker 01

  Yeah, there's no complaint about the unfairness, the capriciousness, the surprise. Just, uh, what are we having for lunch?

• 24:40Shane Parrish?

  Can you train yourself to think that way? Or is it something you think is more, there's people disposed to that?

• 24:46Speaker 01

  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

• 25:01Speaker 01

  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.

• 25:28Shane Parrish?

  I find it easier for me to like, in, 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, ah, traffic, you know?

• 25:52Speaker 01

  Well, we're really good at giving advice to other people and then not so good at applying it ourselves because we have that cognitive distance, uh, 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

• 26:10Speaker 01

  You're able to see the impotence and the unfunniness 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 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.

• 26:48Shane Parrish?

  What other misconceptions do you run into about Stoicism?

• 26:52Speaker 01

  Um, 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's reign, and it stretches as far as England and Africa and the Middle East. And you have Epictetus, who's a slave.

• 27:35Speaker 01

  You have Marcus Aurelius, who's the emperor. Xeno, 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.

• 28:21Speaker 01

  All the Stoics would have had wives and daughters. There's a fascinating essay from Musodis Rufus, who's not just Epictetus's philosophy teacher. So he's teaching a slave, but you know, he writes this 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, you know, it's like, oh, this is a bro, 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, my audience is not male, but I also, just on a historical basis, that's not true.

• 29:04Speaker 01

  And so there, 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 Epipolis was talking about either.

• 29:26Shane Parrish?

  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.

• 29:36Speaker 01

  Chrysippus?

• 29:37Shane Parrish?

  Yes, that was the one.

• 29:39Speaker 01

  Created what? Sorry.

• 29:41Shane Parrish?

  Stoicism.

• 29:42Speaker 01

  No, Zeno was the founder of Stoicism.

• 29:43Shane Parrish?

  Okay.

• 29:44Speaker 01

  Zeno studies under this cynic philosopher named Crates. By the way, Crates is, 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 sto apo kilis, this porch in the Athenian agora. That's where Stoicism comes from. Then there's Cleentheus and then Chrysippus. But it doesn't really become a real school philosophy until later with sort of codified. But Zeno is, is considered the founder of Stoicism.

• 30:17Shane Parrish?

  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 as?

• 30:31Speaker 01

  I think so. I think, I mean, that's what sports are, is a metaphor for any kind of pursuit of excellence. It's just the most.

• 30:41Speaker 01

  Visible, you know, it's a very visible because it's a game with rules at a beginning and an end. The most observable form of excellence. Right. An entertaining form of excellence. And look, in the ancient world, they're using sports metaphors then too, because it's the same, the same process. One of the Stoics 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 does, he deals with the, the things that life throws at him, including this, this death sentence.

• 31:26Speaker 01

  There's weightlifting metaphors and racing metaphors and some of the Stoics were also athletes. So I, 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 sportsmanship and grace and coolness under pressure. You know, we 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 Stoics would have been very familiar with.

• 32:07Shane Parrish?

  Do you think anybody can be at the far right of the curve in whatever domain they're an expert or a sports or skill and be a normal sort of person?

• 32:19Speaker 01

  I think about this all the time. I would like to be both. And I think you do realize there are trade-offs. Part, it, there is something inherently unbalanced about.

• 32:34Speaker 01

  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.

• 33:00Shane Parrish?

  But if they weren't out of whack, then they wouldn't be on the right end.

• 33:06Speaker 01

  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 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 greats, you know, great, achieved 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, their family wasn't utterly

• 33:49Speaker 01

  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, I would argue, a much rarer feat. Power corrupts, absolute power corrupts, absolutely. So what I think makes Marx really such a fascinating example is here you have one of the few humans to hold absolute power as we would really define it. And

• 34:28Speaker 01

  Doesn't seem to have become deranged or grotesque is into an overwhelmingly cautionary tale. That to me is a rarer feat than if you told me he had won the

• 34:46Speaker 01

  single greatest, you know, military victory of all time. Like the greatest victory the Stoics would say would be the victory over those very impulses.

• 34:56Shane Parrish?

  There's another Roman, I think it was like a Cincinnata. You know, your history way better than I do. Cincinnatus who like gave up power.

• 35:04Speaker 01

  Yeah, I tell this story to my son all the time. Cincinnatus is maybe not real, maybe real, but his example was certainly very real to the Greeks and the, oh, I guess to the Romans, not to the Greeks. But yeah, Rome is

• 35:20Speaker 01

  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 Cincinnatus who had been a 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.

• 36:05Speaker 01

  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 of weeks ago and you can stand in the courthouse where he resigns 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?

• 36:43Speaker 01

  He's told that, you know, I think he intends to return to his farm. To not make himself and the Washington name, 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 in the moment. And in fact, we tend to ridicule and mock it like, you know, Andrew Luck, the quarterback?

• 37:18Shane Parrish?

  Yeah.

• 37:18Speaker 01

  He walked away.

• 37:19Shane Parrish?

  Yeah.

• 37:19Speaker 01

  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 a hundred million dollars 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.

• 37:46Shane Parrish?

  And he walked away at the top.

• 37:48Speaker 01

  Yes, yes. To be out there, has there been any boxer in history that's walked away too early? Probably not. It clearly takes more discipline to walk away early or on top than it does to go for the sixth ring or the three P or whatever. Those things are extraordinarily hard, but clearly if less people do this other feat, it must be because it's even harder.

• 38:20Shane Parrish?

  Do you ever think of, of walking away from writing?

• 38:23Speaker 01

  Yeah. Why do you think, do you think it's sad for me to retire?

• 38:27Shane Parrish?

  No, that's not what I'm saying at all. You're, you're sort of like, you're in the middle of it, right? Like, you're like, what, 12, 13, 14 books?

• 38:34Speaker 01

  I don't remember that. Like the thing that for me is that's the part that I like doing.

• 38:37Shane Parrish?

  You like.

• 38:38Speaker 01

  And it's probably the least hard on me.

• 38:40Shane Parrish?

  Right.

• 38:41Speaker 01

  It'd be the other stuff that I think would, would.

• 38:45Shane Parrish?

  Be like the bookstore or YouTube?

• 38:47Speaker 01

  No, yeah, like YouTube or podcasts or speaking or to just be like, no, I'm just just gonna do this one part.

• 38:54Shane Parrish?

  I don't know how people do podcasts once a week or more. Like I find once every two weeks hard.

• 38:59Speaker 01

  How often do you do it?

• 39:00Shane Parrish?

  Twenty six times a year.

• 39:01Speaker 01

  Is that a deliberate choice?

• 39:03Shane Parrish?

  Yeah, I don't think I could remain intellectually like I don't think it 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 about this.

• 39:22Speaker 01

  Well, you also do your interviews are longer, right? So

• 39:27Speaker 01

  you might be the same if if somebody's doing

• 39:32Speaker 01

  two a week and they're an hour, that's the same as you doing.

• 39:36Shane Parrish?

  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, 10 hours.

• 39:43Speaker 01

  When I had my marketing company, one of the reasons I never wanted to hire employees was that I was skeptical that there were enough projects that I would be interested in working on to pay for the people, which meant if I hired someone,

• 40:08Speaker 01

  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

• 40:25Speaker 01

  admirable stance.

• 40:26Shane Parrish?

  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.

• 40:38Speaker 01

  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 churn in 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 us to a certain level or do a certain amount of things which you

• 41:20Speaker 01

  are foregoing when you bring on somebody else.

• 41:24Shane Parrish?

  I was talking to John Mackey about this, the Whole Foods guy.

• 41:27Speaker 01

  Yeah.

• 41:27Shane Parrish?

  And he sort of said, I love this analogy is 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 you're like, oh, I'm really curious what's over here. They're going to be like, no, what are you doing? 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.

• 41:53Speaker 01

  Yeah, it's more like you went from being the driver to being the passenger.

• 41:57Shane Parrish?

  Kind of, yeah.

• 41:57Speaker 01

  The other person is like has a they have a brake 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 that the problem was breaking through or breaking out.

• 42:15Shane Parrish?

  Yeah.

• 42:16Speaker 01

  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, then every couple of weeks I'll get an email being like, hey, have you thought about opening another one? And it's like, I already hit the lottery by it not failing. Do I need to start a chain of bookstores? I don't think that I do. And I don't think that would improve.

• 42:55Speaker 01

  My life quality at all. But it's easy to be disciplined in some areas and not in other areas.

• 43:01Shane Parrish?

  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 you're distanced 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.

• 43:13Speaker 01

  Yes.

• 43:13Shane Parrish?

  How can we use stoicism as a means to sort of focus our energy and remove distractions?

• 43:21Speaker 02

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• 44:20Speaker 01

  Mark Schrader writes in meditation, you 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 and think, you have to ask yourself, is this essential? And he says, because most of what we do and 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.

• 44:54Speaker 01

  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 then just the, you would think at some point not needing it would make it easier to say no, but opportunity costs.

• 45:14Shane Parrish?

  You get more opportunities.

• 45:16Speaker 01

  Yes.

• 45:16Shane Parrish?

  And success tends to sow the seeds of its own.

• 45:19Speaker 01

  Yes.

• 45:19Shane Parrish?

  Destruction.

• 45:20Speaker 01

  It'd be easy to say like, oh, when you're, you know, be disciplined while you're successful. You know, don't, don't take on too much. You say no to a lot of things, but

• 45:35Speaker 01

  in sports or entertainment or art or even, you know, whatever it is that you do, you don't do it forever. 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.

• 46:03Shane Parrish?

  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?

• 46:10Speaker 01

  Or? I was thinking about how kind of like what seemed like a lot of money to you as a kid always remains a lot of money to you. Even as your income goes up,

• 46:22Speaker 01

  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 clarity, 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

• 47:04Speaker 01

  have a good way to value what to say yes or no to. The problem is financial upside is always clear.

• 47:13Speaker 01

  Opportunity opportunity costs are sometimes clear, but often not clear. If I get offered to do, I don't know, a speaking 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 of our households, my personal happiness, how easy things are. And so one is the downside is in one sense is very quantifiable. And the upside in the other case is very hard to quantify.

• 47:58Speaker 01

  And in some cases, the consequences of it are quite lagging. And so you're faced with a briefcase with cash in it. And hey, isn't this a bit much? We're all tired.

• 48:13Shane Parrish?

  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 a, 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, he'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.

• 48:58Speaker 01

  Right.

• 48:59Shane Parrish?

  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 because I actually kind of want you to say no. 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.

• 49:19Speaker 01

  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 adoramus void inside you, how vulnerable that makes you.

• 49:33Shane Parrish?

  Yeah.

• 49:33Speaker 01

  Because.

• 49:35Speaker 01

  You want to be wanted. You want the validation. You want the cha-ching. Because that feels good.

• 49:43Shane Parrish?

  But like you, like I get, I get five speaking requests a week.

• 49:47Speaker 01

  Yeah.

• 49:48Shane Parrish?

  And there's no way you can say yes to everything. So you have to have a system to sort of.

• 49:53Speaker 01

  Well, if I think the first step is you have to have someone between you and the thing.

• 49:56Shane Parrish?

  Oh, totally.

• 49:57Speaker 01

  To just eliminate three of the five that were not serious or not even not serious, but we're at a number that might be tempting. But it's better for you not to see.

• 50:06Shane Parrish?

  Cause you're more likely to say, yeah.

• 50:08Speaker 01

  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, the person who is.

• 50:18Shane Parrish?

  Saying yes.

• 50:18Speaker 01

  Yes. So you have to set some boundaries and then task other people with enforcing them.

• 50:25Shane Parrish?

  Yeah.

• 50:26Speaker 01

  I think some people go, oh, is it, you know, you don't want to pay these people commissions? You just do it yourself. And I think there's a danger in doing it yourself, which is that.

• 50:34Shane Parrish?

  Totally.

• 50:34Speaker 01

  It almost, it can go to your head and also kind of.

• 50:39Shane Parrish?

  And then when it goes away, what?

• 50:40Speaker 01

  Yes.

• 50:41Shane Parrish?

  This, I worry about this all the time, right? It's like, well, five and I'm like saying no.

• 50:45Speaker 01

  Have you read that book, Die With Zero?

• 50:46Shane Parrish?

  Yeah.

• 50:47Speaker 01

  It's a great book, but the idea is, you know, thinking about.

• 50:52Speaker 01

  What are you, what are you trying to do all this for? You're trying 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 he uses in the book, which I think is a good one, he's talking about like a Mets student 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.

• 51:31Speaker 01

  Anyways, that advice is very helpful and clarifying in more predictive linear professions. But that would be bad advice to give to a rookie in the NBA. Cause 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.

• 51:58Speaker 01

  Historically, a very clear drop off. Like, at some point, you age out. At some point, your trend or moment goes away. And maybe you survive long enough for it to come back. But like, the idea that, for me, as an author, 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.

• 52:24Shane Parrish?

  Yeah.

• 52:24Speaker 01

  But in six years, you'll feel like an idiot.

• 52:27Shane Parrish?

  You'll wish for this request to come back.

• 52:29Speaker 01

  Exactly.

• 52:30Shane Parrish?

  Is it ever okay to lose your cool? Like, is there strategic points where it actually makes sense to sort of not be stoic? And to, I wouldn't say completely lose control, but to have more variation?

• 52:43Speaker 01

  We have this idea that 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, they just would. But if you got so angry that you punched a wall, not only might you be judged for that, that might be like part of the legend of Shane.

• 53:19Shane Parrish?

  Right.

• 53:20Speaker 01

  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 Mark's real crying. But we don't have any stories of him losing his temper. And I think he was chastened 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, the emperor could get away with, literally anything.

• 54:00Speaker 01

  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.

• 54:21Speaker 01

  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 keel across the board. That being said, there is a difference between

• 54:43Speaker 01

  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

• 55:27Speaker 01

  turn up or down certain levers. I was at a Spurs game one time and I watched Greg Popovich get ejected. And

• 55:41Speaker 01

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

• 56:13Shane Parrish?

  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?

• 56:25Speaker 01

  I'm talking about self-discipline. So the, the discipline of an army sergeant is obviously important, but I don't think that's a virtue because it's being imposed on you. Of course, essential that an army is disciplined.

• 56:41Shane Parrish?

  How would you define self-discipline?

• 56:43Speaker 01

  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 initial language. But it is, the Stoics would say, the greatest empire is command of oneself.

• 57:27Speaker 01

  And so whether you're the emperor or a slave, whether you're a soldier or a CEO, 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.

• 57:44Shane Parrish?

  Where do you struggle the most with it?

• 57:47Speaker 01

  Knowing one's limitations, setting reasonable bounds on things. I don't have a problem 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.

• 58:12Shane Parrish?

  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?

• 58:24Speaker 01

  You told me something though, that I've been thinking about where you said that you're, you go to the gym every day.

• 58:28Shane Parrish?

  Yeah.

• 58:29Speaker 01

  As opposed to I work out three days a week.

• 58:31Shane Parrish?

  Yeah.

• 58:32Speaker 01

  Because there's a consistency to everydiness and.

• 58:37Shane Parrish?

  It's not a choice then.

• 58:38Speaker 01

  Yes, it takes away the lie you can tell yourself, which is I'm doing it tomorrow.

• 58:43Shane Parrish?

  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.

• 58:51Speaker 01

  Yeah.

• 58:51Shane Parrish?

  Other people who've tried it after listening to me, it's been life-changing for them too.

• 58:56Speaker 01

  No, it's a great way to think about it. 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.

• 59:08Shane Parrish?

  But see 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.

• 59:24Speaker 01

  I almost 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.

• 59:46Shane Parrish?

  Right.

• 59:46Speaker 01

  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.

• 1:00:00Shane Parrish?

  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 or?

• 1:00:08Speaker 01

  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.

• 1:00:18Shane Parrish?

  I'm the same way. Like I work every day.

• 1:00:19Speaker 01

  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

• 1:00:30Speaker 01

  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, not a way to go through life.

• 1:00:46Shane Parrish?

  Does your workaholism sort of, I don't know, I'm using that term.

• 1:00:49Speaker 01

  No, no, go for it.

• 1:00:50Shane Parrish?

  But does that cause issues in your relationship?

• 1:00:52Speaker 01

  Yeah, of course. Uh, I think it always has. Um, 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, it's sort of a way of soothing something that you feel. But unlike a lot of addictions or compulsions. It's

• 1:01:20Shane Parrish?

  somewhat productive.

• 1:01:21Speaker 01

  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.

• 1:01:48Shane Parrish?

  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 axis, 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.

• 1:02:15Speaker 01

  Yeah.

• 1:02:16Shane Parrish?

  And then it's like, I need to, there's so many things I want to do and have so much excitement and energy around it.

• 1:02:21Speaker 01

  Well, then you throw on top of that, like what you hear other people are doing.

• 1:02:26Shane Parrish?

  Yes.

• 1:02:27Speaker 01

  It's even more hard to run your own race. Sadek has this word euthymia and he talks about being on the path that you're on. This is not being distracted by the paths that crisscross yours. 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.

• 1:03:05Speaker 01

  And so I think the more indifferent and probably ignorant you are of what your peers are doing, the healthier you are and the

• 1:03:17Speaker 01

  Cleater your compass reading will be.

• 1:03:20Shane Parrish?

  I think of it as like swimming in your own lanes. 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.

• 1:03:36Speaker 01

  Yeah.

• 1:03:37Shane Parrish?

  Cause he's like one, he's not worried about him and his lane and his goals and his stroke and

• 1:03:42Speaker 01

  Yeah.

• 1:03:42Shane Parrish?

  He looks over just enough to distract and he lost by like milliseconds.

• 1:03:46Speaker 01

  Yeah, there's that. Although the other one that keeps me up, there was a, there was like a mountain bike race in the Japan Olympics, I think.

• 1:03:55Speaker 01

  And the woman thought she was in first place, but she was actually in second place.

• 1:03:59Shane Parrish?

  Oh, so she let up.

• 1:04:00Speaker 01

  Cause like it's sometimes, you know, like in swimming, you're all right next to each other.

• 1:04:04Shane Parrish?

  Yeah.

• 1:04:04Speaker 01

  Like the marathon or some of 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.

• 1:04:22Shane Parrish?

  Right.

• 1:04:23Speaker 01

  So clearly at some level, we understand that competition is healthy. And motivating and yet too much competition is disorienting and ultimately self defeating. And so that balance is tough.

• 1:04:37Shane Parrish?

  What can we do to cultivate more discipline?

• 1:04:40Speaker 01

  Ooh, I mean, look, I think having a physical practice is a way to cultivate more mental and cognitive discipline.

• 1:04:50Shane Parrish?

  Like going to the gym or running.

• 1:04:52Speaker 01

  Running, swimming, biking, like I do it during sports and they help me as a writer, like I couldn't do what I do as a writer without those physical components. Uh, 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.

• 1:05:12Speaker 01

  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 is purely.

• 1:05:25Shane Parrish?

  That it's hard.

• 1:05:26Speaker 01

  That it's hard and that I am doing the hard thing.

• 1:05:29Shane Parrish?

  And how do you sort of teach your kids or instill discipline in them?

• 1:05:33Speaker 01

  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. Cause I watch as they get into things. They don't just like kind of get into things.

• 1:06:03Shane Parrish?

  They go all in?

• 1:06:04Speaker 01

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

• 1:06:28Shane Parrish?

  It can help you, but it can also get in your way.

• 1:06:31Speaker 01

  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 has shaped and informed the success that they have. And 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.

• 1:07:01Speaker 01

  And yet.

• 1:07:02Shane Parrish?

  We don't want them for our kids.

• 1:07:04Speaker 01

  We don't want it for our kids. And, and we also know though, like if we hadn't had that, we probably just would have had something else. Yeah, I've never met someone who had zero adversity in their life. Like sometimes 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 is obviously a way of creating adversity. At the same time, you know, was it Dostoevsky would like gamble all his money away so that he would write better? I don't know if he needed to.

• 1:07:35Shane Parrish?

  Yeah.

• 1:07:36Speaker 01

  How would you define character?

• 1:07:39Shane Parrish?

  Ooh.

• 1:07:39Speaker 01

  I just heard something. Someone said like, character, like your reputation is what other people think of you. And character is like what you do when people don't see.

• 1:07:48Shane Parrish?

  There's like an element of right and wrong embedded in this, but who, who sort of defines what's right and wrong?

• 1:07:55Speaker 01

  That's the hard part. I, so I just, I've been doing this series of the cardinal virtues. So I did courage and discipline, then justice. And on one level, yeah, we go, how do we know what's right and wrong? Is it the 10 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 people, 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.

• 1:08:39Speaker 01

  And all the philosophers that, you know, come to some 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? What, like, we, it's like, we almost focus on the edge cases as a way of.

• 1:09:03Shane Parrish?

  There's such a middle ground that we can all agree on.

• 1:09:06Speaker 01

  Yeah, that's like 95%, you know, we're like, should, you know, a Nazi's 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? Because, you know, like, this is a Kant's 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.

• 1:09:35Speaker 01

  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.

• 1:09:53Shane Parrish?

  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 we're capable of being.

• 1:10:01Speaker 01

  Totally.

• 1:10:02Shane Parrish?

  How do you live up to the best version of yourself?

• 1:10:04Speaker 01

  We think of virtue as this thing that you have or don't have. Think of it as a noun. Wouldn't it 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

• 1:10:48Speaker 01

  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 the 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 illegal, but not right.

• 1:11:31Speaker 01

  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 do, by nature of doing the practice, it's never going to happen.

• 1:11:42Shane Parrish?

  It's like a muscle.

• 1:11:42Speaker 01

  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 think of things, making decisions of consequence to ever find yourself in a position of.

• 1:11:58Speaker 01

  Decisions of consequence.

• 1:12:00Shane Parrish?

  We live in a world where your slip up in character, which we all make.

• 1:12:04Speaker 01

  Yes.

• 1:12:05Shane Parrish?

  Can now become viral on the internet. It's like you yelled 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.

• 1:12:15Speaker 01

  You know that Profumo scandal in London in the sixties? 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, a prime minister vouches for him and then has to apologize and ends up resigning as a result. And I tell the story of Profumo because I think he's so interesting. So he destroys his political career and today we would say he was cancelled.

• 1:12:58Speaker 01

  And what would happen today is that this person would be basically shunned by one half of society and then perversely 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, you would, you, 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.

• 1:13:39Speaker 01

  It was like a, like a Salvation Army style charity house. And he shows up one day and asks if they needed 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, it's like chief fundraiser and it's 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 it 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.

• 1:14:22Speaker 01

  But on net, most people look back and go.

• 1:14:28Speaker 01

  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.

• 1:14:42Shane Parrish?

  An aberration of sort of character.

• 1:14:43Speaker 01

  Yes, 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 is not a place where grace is commonplace and where things can be wrenched 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 people who are fascinated by and impressed by the

• 1:15:24Speaker 01

  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 Stoics 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?

• 1:16:10Speaker 01

  Is, to me, the interesting question.

• 1:16:12Shane Parrish?

  There's another sort of subset to this, that we sort of, sometimes we'll behave better than we want to because we know we're being recorded, we know we're being watched, and then it's not character anymore. Because if character is sort of like what you do when nobody's watching.

• 1:16:26Speaker 01

  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?

• 1:16:35Shane Parrish?

  It should just be enough to do good because you're doing good.

• 1:16:38Speaker 01

  Yeah, but if I had to choose, you know, like people are today are like, ah, it's all this virtue signaling. You know, it's like certainly better than the alternative, you know?

• 1:16:48Shane Parrish?

  Totally.

• 1:16:49Speaker 01

  I'm not sure this sort of like this, the cruelty is the point vice signaling is preferable. Even if it's more honest, I would like people to be signaling virtue. They say what hypocrisy is the is the credit that vice plays to virtue.

• 1:17:10Shane Parrish?

  Never heard that.

• 1:17:11Speaker 01

  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

• 1:17:20Shane Parrish?

  than not.

• 1:17:21Speaker 01

  than the nihilism of like, lol, nothing matters.

• 1:17:25Shane Parrish?

  Where in life do you have the highest standards?

• 1:17:27Speaker 01

  The easy answer would be professionally because it's easiest and it's the most measurable.

• 1:17:35Speaker 01

  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, we, we naturally

• 1:17:51Speaker 01

  are 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.

• 1:18:12Speaker 01

  What do you feel like you have the highest standards?

• 1:18:14Shane Parrish?

  Oh, I hold myself to these like unrealistic expectations in every domain. 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, you know, I want to be the best at whatever it is that I'm doing. And I go through these oscillations where I think of it as harmony, not balance, 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 of months. I'm traveling a lot and we're gonna, you know, my kids are teenagers now. So it's a little easier, but like, we're gonna figure this out together.

• 1:18:56Speaker 01

  Right.

• 1:18:57Shane Parrish?

  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 gotta work out. And so my work day is really short. And then when I don't have them, I'm like, okay, I gotta make up for this lost time because

• 1:19:19Speaker 01

  Yeah.

• 1:19:19Shane Parrish?

  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.

• 1:19:39Speaker 01

  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. We're dealing with a set of expectations and a set of responsibilities for which there is not

• 1:19:59Speaker 01

  centuries of cultural experience and lessons and examples to draw on.

• 1:20:05Shane Parrish?

  Yeah.

• 1:20:05Speaker 01

  You know what I mean? Um, like, your dad wasn't ever doing that. And your grandfather certainly wasn't ever doing that. And then you go back a couple of generations and they're like, probably 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, 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?

• 1:20:46Speaker 01

  Working not even banker's hours, but like,

• 1:20:50Speaker 01

  Stay at home mom hours or something, you know?

• 1:20:52Shane Parrish?

  Well, it pushes me. They go to bed, so I'll be like, I gotta log in, I gotta do work, you know? We used to travel in the summers and we'd go away for kinda like a month and we'd 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 gotta work, right? And now it's easier because they sleep in. So I get a full work day and before they get out of bed.

• 1:21:13Speaker 01

  Yeah, Toni Morrison talked about how she wanted to do all her writing before she heard the word 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?

• 1:21:58Speaker 01

  If you've got, and then also, let's say you're two different kids at two different schools or more.

• 1:22:03Shane Parrish?

  Yeah.

• 1:22:03Speaker 01

  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 at all unless you've retired or you're not working.

• 1:22:20Shane Parrish?

  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 gonna 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 kids' 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.

• 1:22:50Speaker 01

  Crazy.

• 1:22:50Shane Parrish?

  And then I get texts 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.

• 1:22:58Speaker 01

  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 the, just the immense cognitive load.

• 1:23:17Speaker 01

  And only one of the genders is aware of it in any way.

• 1:23:21Shane Parrish?

  Yeah.

• 1:23:21Speaker 01

  Is insane in retrospect.

• 1:23:24Shane Parrish?

  Yeah.

• 1:23:24Speaker 01

  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.

• 1:23:35Shane Parrish?

  I have a lot of respect for the parents out there.

• 1:23:38Speaker 01

  Yeah.

• 1:23:38Shane Parrish?

  Whether single parents or together, it's, it's a lot going on. You've said that writing helps clarify your thinking. Can you double click on that a little bit?

• 1:23:47Speaker 01

  I actually have a chapter about this in the book that I'm doing now. You know, Amazon has this culture where they, uh, 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 could 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 meeting on paper is essential. There's this story about Eisenhower at the outbreak of the Second World War. Marshall is chief of staff of the US Army and he, he's, he's bet Eisenhower before he sees sub promise to this town officer.

• 1:24:29Speaker 01

  And he calls him in and he says, uh, you know, it looks like World War Two 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, you know, pulled an answer off the top of his head and riffed and he says, can I have a desk in two hours? And I, and Marshall says, um, sure. And he goes, he gets a typewriter and 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, uh, 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.

• 1:25:15Speaker 01

  Spouting off. Whatever my, like, 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

• 1:25:30Speaker 01

  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.

• 1:25:50Shane Parrish?

  Kind of have to meet people where they are and then take them where you want them to go.

• 1:25:54Speaker 01

  Yeah, you zoom out, you zoom in.

• 1:25:56Shane Parrish?

  Yeah.

• 1:25:56Speaker 01

  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 were upset because it's somehow a violation of the vow. And he was saying, no, like, writing is contemplation. I'm thinking about

• 1:26:19Speaker 01

  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, I can do that hostile act of changing your thinking.

• 1:26:47Shane Parrish?

  As a writer, how do you see the impact of AI?

• 1:26:52Speaker 01

  I haven't seen it do anything that even a pretty good writer

• 1:27:02Speaker 01

  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 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.

• 1:27:40Speaker 01

  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 gonna take six months, or that's gonna 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, I'm needing it to track something down, that maybe I'm being, 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.

• 1:28:24Speaker 01

  And, and, and what it's doing is it's telling me what I wanted to hear. The same way that people Google stuff or see stuff 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 gonna 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 gonna spit out is not true or is only partially true. And if you're just defaulting to it, you're gonna be embarrassed.

• 1:29:08Speaker 01

  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. So, you know, like, when I'm trying to visualize things, I use it. And sometimes we'll use it in videos. I want like, you know, show Marcus really is like in a suit of armor, show Marcus, like, so I use it for things like that, like, track stuff down, but then I, I Verify. I have to, I have to get a second opinion. I have to have it verified in some way because I'm that skepticism.

• 1:29:46Speaker 01

  Keeps me up at night because it, the, the costs, the reputational costs are borne by, it's like trusting Wikipedia, you know? It's good if it's right. The reputational hit is felt by you alone.

• 1:29:57Shane Parrish?

  Totally.

• 1:29:57Speaker 01

  Do you use it?

• 1:29:58Shane Parrish?

  Yeah, we use it all the time at home. The kids like will write their essay. The way that I, I encourage it at home is like, you're growing up in 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.

• 1:30:19Speaker 01

  Yes.

• 1:30:20Shane Parrish?

  And I want to see your full history. So 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 are the weak points in my, so it's like, almost like a personal tutor.

• 1:30:31Speaker 01

  Yeah.

• 1:30:31Shane Parrish?

  And then I'll submit like, here's a draft chapter. Like, what did I miss? What, what do you think? And sometimes it's pretty insightful.

• 1:30:38Speaker 01

  I've used it with my kids. We'll have fun. Like they'll be like, draw this or make this. 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.

• 1:30:59Shane Parrish?

  Yeah.

• 1:31:00Speaker 01

  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, Socrates doing X, Y, 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 had glasses, you know, like, and it's also its inability to, to iterate. Like it's not very good at this. I want this, but 5% 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.

• 1:31:44Speaker 01

  I want my kids to have that.

• 1:31:46Shane Parrish?

  So here's the like interesting, I actually get it to write 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 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.

• 1:32:09Speaker 01

  Yeah, much, much better.

• 1:32:10Shane Parrish?

  And so it's going to get exponentially better over the next decade or 20 years. And it'll 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 draft. And now that 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.

• 1:32:41Speaker 01

  Well, so I do this thing. So when I read a book, I often type up the passages that I liked in the book.

• 1:32:46Shane Parrish?

  Yeah.

• 1:32:47Speaker 01

  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.

• 1:32:58Shane Parrish?

  Yeah.

• 1:32:58Speaker 01

  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, it's like you're, you're doing a simulation of a path that someone actually flew. Never is the AI able to predict the next couple of words in that sentence. I've always found that very interesting.

• 1:33:37Speaker 01

  And it's a reminder to me that still the act of creative genius of, 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.

• 1:33:57Speaker 01

  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.

• 1:34:20Shane Parrish?

  Yeah.

• 1:34:21Speaker 01

  Will probably.

• 1:34:22Shane Parrish?

  It's leverage.

• 1:34:23Speaker 01

  Will be better at it and be more highly compensated and the importance of it will be higher. And so you, 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 disunbalanced in the pursuit of that excellence. But it's like the cost of being mediocre get higher and higher.

• 1:34:42Shane Parrish?

  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 being like, generate a nonviolent, you know, email to send to this person. Put this in nonviolent communication and then you get it and you're like, this is half a page. It should be like two sentences.

• 1:35:08Speaker 01

  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.

• 1:35:14Shane Parrish?

  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.

• 1:35:19Speaker 01

  Yeah. Well, you're going to have to get better, just like you have to get good at spotting motion. You're going to have to be good at spotting AI versus non-AI.

• 1:35:26Shane Parrish?

  Yeah. Cause the cost to generate an AI email is zero, at least before you had to type something in or copy paste. You know, like you've gotten those emails. It's like, Dear Joe, and you're like, wait, my name's Ryan. Like, uh, what are you reading right now that's challenging your thinking?

• 1:35:43Speaker 01

  I just have read these three huge books on Lincoln. So I've been doing a huge deep dive into Lincoln for the book that I write now. Um, 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 in stuff. Um, I'm reading this book now about the founding of Australia that I'm finding really interesting called The Fatal Shore. About like, why, why did they start a penal colony on the other side of the earth?

• 1:36:15Shane Parrish?

  What's, what's?

• 1:36:16Speaker 01

  Well, the argument was that, uh, London had extremely strict legal system.

• 1:36:24Speaker 01

  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.

• 1:36:54Shane Parrish?

  That's crazy.

• 1:36:55Speaker 01

  It's fascinating.

• 1:36:56Shane Parrish?

  Do you read many business books? Like, what are the best business biographies you've read?

• 1:37:00Speaker 01

  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.

• 1:37:14Shane Parrish?

  Because you want the detail and then you want...

• 1:37:17Speaker 01

  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 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.

• 1:37:51Shane Parrish?

  And do you do that without having the story in mind? You're like, oh, this story is representative of XYZ, tag it.

• 1:37:58Speaker 01

  Sometimes I'm just reading generally about something and 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 hallway.

• 1:38:19Shane Parrish?

  How do you define success today? And how has it changed?

• 1:38:21Speaker 01

  Do you remember what I said the other times?

• 1:38:23Shane Parrish?

  No.

• 1:38:23Speaker 01

  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

• 1:38:50Shane Parrish?

  Yeah.

• 1:38:50Speaker 01

  missing a day's work or whatever. I just could handle it. Turns out he wasn't actually sick. You know, he was 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.

• 1:39:02Shane Parrish?

  How has that changed from like a decade ago? When you would define success when you were younger?

• 1:39:07Speaker 01

  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 caring. And part of that is living where I live, how my life is set up, just valuing different things.

• 1:39:29Shane Parrish?

  The relative thing is fascinating because if you compare yourself to people who are relatively, you know, not pursuing the same goals, not maybe not as successful as you are. You sort of feel good about yourself, but 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, your satisfaction.

• 1:39:55Speaker 01

  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 we compare ourselves to James Clear, we're all failures.

• 1:40:05Shane Parrish?

  Yeah.

• 1:40:05Speaker 01

  And for ours, book sales. But if you compare yourself to

• 1:40:10Speaker 01

  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 bodacious you would have previously defined success.

• 1:40:20Shane Parrish?

  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.

• 1:40:32Speaker 01

  Yeah.

• 1:40:33Shane Parrish?

  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'd probably pick your own shoes. Like the 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.

• 1:40:58Speaker 01

  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, y'all else 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, you have to swap your whole career for theirs. Would you do it? And it becomes more complicated. 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 trade offs.

• 1:41:36Shane Parrish?

  Yeah.

• 1:41:37Speaker 01

  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, 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.

• 1:42:20Speaker 01

  Strategy is by definition, choosing certain objectives and not choosing other objectives. And if you try to straddle two strategies, you'll destroy yourself.

• 1:42:40Shane Parrish?

  Thanks for listening and learning with us. For a complete list of episodes, show notes, transcripts, and more, go to fs.blog/podcast or just Google The Knowledge Project. Recently, I've started to record my reflections and thoughts about the interview after the interview. I sit down, highlight the key moments that stood out for me, and I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out. This is available to supporting members of The Knowledge Project. You can go to fs.blog/membership, check out the show notes for a link, and you can sign up today. And my reflections will just be available in your private podcast feed. You'll also skip all the ads at the front of the episode.

• 1:43:26Shane Parrish?

  The Farnham Street Blog is also where you can learn more about my new book, Clear Thinking: Turning Ordinary Moments Into Extraordinary Results. It's a transformative guide that hands you the tools to master your fate, sharpen your decision-making, and set yourself up for unparalleled success. Learn more at fs.blog/clear. Until next time.