Ryan Holiday: How to Win the War with Yourself

0:00 You said before that Life is always whispering at you, and if you're not paying attention, it'll eventually scream at you. sobriety circles they talk about like two cars and 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.

0:21 And your cars. Or is a that embarrassing evening at the company Christmas party that serves to send the message.

0:32 How are you hearing what the world is trying to tell you? Or you very much not hearing it. And at some point is it gonna have to hold you down and scream it into your Here. Welcome to the Knowledge Project Podcast. I'm your host, Shane Parrish.

0:57 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 Holliday. 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.

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2:11 Give it a try and start discovering the best moments from the best podcasts. Go to join overlap.com. That's join overlap. dot com How do we separate the signal from the noise? Like in a world of social media, you're getting feedback all the time. How do you distinguish what's

2:29 valid and sort of helpful feedback and a whisper versus this is noise and it offers no value. Yeah, this is really hard. Uh 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

2:55 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 gonna be in a really tough spot. So take Elon Musk, right? When Elon Musk was planning what became SpaceX. His friends held a literal

3:16 AA style intervention. That said, you cannot start a rocket company. This is the worst idea. You will lose all your money. Obviously he was correct. And there were moments when he probably Uh the the conventional wisdom or the data or the advice from the investors overwhelmingly was to sell Tesla.

3:32 Or to do X, Y, and C. So what happens when you know it's sort of a passing Fancy or a 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 uh a reasonable person

3:58 Adapts to the world. And an unreasonable man adapts the world to themselves. And so therefore all progress depends on the unreasonable man. So often this thing that makes Wanna Groundbreaking artists.

4:13 You know, uh Discoverer. An inventor, you know, an entrepreneur, an artist, whatever it is. What w the thing that makes you great is this ability to not listen to feedback at some point invariably you come across feedback that you

4:30 Should listen to the You go past the point that you Aimed for you go. Past. A convention that is there for good reason.

4:40 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 in the process. Whereas Elon gets held up as like oh I've done all of these things and people have told me I couldn't do them, I shouldn't do them, they can't be done, and yet I've done them. Yeah, and what we take from that is not he was right in these specific instances for these reasons. What we tend to take from that is the shorthand of don't listen to other people. Or Conventional wisdom is always wrong. But of course

5:11 Many, many people had failed. There was a graveyard of millionaires and billionaires who'd lost their fortunes starting private space companies. I think the good part i is like not taking these sort of like business book. Headline. Uh Cover story

5:27 narratives from Uh People's uh trajectories or uh from history, but actually really drilling down and getting to the actual reason as to why

5:38 Elon Musk as this ground breaking You know. Precedent shattering. uh entrepreneur and another version to look at is this guy who took massive government subsidies at critical points

5:52 that allowed him to do those things. A story you tell yourself about your own experiences is really interesting. Uh and then the story that society says about your about your experiences is also really interesting too. Can you give me an example of where you missed a whisper and it's gotten louder and louder and then you're like, Oh shit. Well, I think we all have these in our personal lives, right? Like you sensed you were coming across Uh

6:16 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.

6:34 level in the state. I just take on too much. And then I'm like, Oh, okay. Like earlier this year I I rolled my ankle really bad. I had to go to the yard and they were like uh you know, you gotta take like six weeks off. And I took.

6:48 You know, like a week and a half off. 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 been given a very clear message, not just like from my own body, but from a medical professional that said, Like, you gotta slow down and take a break.

7:05 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. Then you What if if you just taken

7:17 The prescription. when it was there. It's when we rush the comeback. Or we rush the recovery. What I say is a lack of patience changes the outcome. And if you think about like money, that's a great area where people just try to get rich quick. Whereas like the the path or formula to get rich over time is pretty clear. Yes. And almost it's available to almost anybody, but you get into trouble when you start trying to rush the timeline. Yeah, there's a a Latin expression called uh fastidolente, just means to make haste slowly. We often look for shortcuts.

7:51 And it takes Longer. Than if we just sort of done it. Slow and steady. It's ca it is amazing.

8:00 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, Oh, that's great. But a lot of these things that we take for granted, like So Like they're hardwired into our DNA.

8:23 And so somebody Who's now lost. Came up with that idea. The timelessness of the truth of that I just I just love. And then it's been true for twenty three hundred years or whatever. And it'll be true for twenty three hundred more years. Yeah, almost certainly. I was listening to our old episode and one thing I never asked you was how would you define stoicism?

8:45 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 what does that mean? I usually follow with this idea and then Stoic is predicated on this idea that you can respond With virtue. Or arite.

9:00 Annoying people. A natural disaster. Extreme success. Death sentence. You don't control that that happened.

9:09 Maybe you controlled whether it was or wasn't going to happen, but now it is happening and to me stoicism is the framework. for which you orient your response. Is it harder if we caused it versus something we didn't cause? Like is it harder to handle a situation where we messed up versus we get a cancer diagnosis or yeah, because we have guilt and shame and frustration, but it doesn't change the fact that it's now There.

9:34 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.

9:47 So I can learn from it. But my impulse to Dissect. And blame. And

9:55 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 gonna

10:05 There's a passage in Meditations where Mark's really sort of criticizing the people who are always trying to delve into what lies beneath. Like they're always like, Well what does this mean? Or what does that word mean? Or why is it this way, or whose fault? What are the root causes And again, that all matters. But usually not in the moment.

10:23 In the moment it's well what are you gonna do? 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. Yeah, for me it's always once the

10:37 The ones the strong emotions of Dissipated. How do you reflect? Do you write or do you think? To me this is Stoicism.

10:46 Is journaling and journaling is stoicism. Journaling is to stoicism as meditation is to Buddhism. It is the practice of having a conversation with yourself about your thoughts. And beliefs and values and actions. And that I don't think it's a coincidence that Mark Surus's sole philosophical work was entitled Meditations, which the 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

11:13 He But 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

11:23 Obviously the benefit of being a writer and you know this is like You have this sort of forced self reflection. That If I was just a regular person I think I would do a lot more journaling than I do, given that I

11:39 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 it's sort of a There's something there's a bet there's a a benefit to the The profession certainly also. You just kinda ping it around in your head, I don't think you're

11:54 You're gonna be doing it. 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. Yeah, it's like also What I'm hearing right now is I'm talking. is an understanding of my voice that when I listen to a recording of this

12:09 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 uh

12:23 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

12:36 going through the bones in my own head are different than when I'm have headphones on and it's been recorded afterwards. Yeah, you grow up thinking your voice sounds like one thing. And then you hear it recording like oh, I'm I'm actually a very different voice. You have these thoughts about things. Yeah. feel like they make sense. Until you interrogate them.

12:56 Or ask. Is that true? Thoughts aside, like I never thought about my voice until I heard myself. Yeah. And apparently I have a very distinct voice that a lot of people don't like. It's the feedback on the audiobook. It's like Shane should not read books. Interesting. And then I 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. You just can't pinpoint where it's from. But when I listen to myself talk, I don't

13:28 I don't hear any of that. You realize in that moment just how different objective reality and perception are. How? Sometimes it's good to get external feedback and sometimes it's good to be in the A bubble because

13:44 uses this phrase that I think about a lot. Um And she catches herself to it again, so and I catch myself doing it. But it show You know, somebody does something and then you're like Well what that means or what you're say and and she always she always

13:58 Says you should preface It with this ex this phrase. What I make up about that is. What they're saying, what they're doing, it means something to them. And then You're having an interpretation of it. It is a remark, and then you are saying it's rude.

14:13 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, the stoicism Epictetus said that You know, it's not things that upset us, it's our opinion about things.

14:31 It's the way the voice sounds to us. That is the problem, not the not the voice. And when you realize that doesn't magically give you the ability to Not. happy 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

14:49 And Usually Those Things are making stuff harder, not easier.

14:56 There's an interesting quirk to when you're talking with people, if you say something like the story I'm telling myself is And it's wrong, people have a tendency to correct you. Yes. And so they'll actually inform you. It's like no, that's not what's happening, but you have to be brave enough to sort of put it out there. Yeah, when think 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. Yeah. Because one

15:24 implies judgment and then the other implies Not just a a certain interpretation about that, but an interpretation plus a loosely heldness. Right, but you saying Right.

15:36 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

15:53 Or contextualize. That thing. A lot of people think stoicism is simply suppressing your emotions. How would you respond to that? The Stoics got married, the Stoics had children, the Stoics went to the theater, the Stoics wrote moving works that were performed in the theater

16:13 The Stoics fought in battle, the Stoics participated in Politics and 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 existence is that we have a lot of

16:30 evidence for. And when you look at Mark Swilius'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.

16:43 In high stakes situations Or in stressful situations. But to me that's very different than Denying or disregarding the emotions altogether. It's almost like you have a narrower band, so you don't have these big oscillations. Yeah.

17:00 I mean I make a distinction between being angry And doing something out of anger. I think that's like a pretty basic Uh bien

17:08 Yeah. being sad and then Being in despair. Again, very different. And and so I think

17:16 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.

17:30 But I I don't think it 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.

17:47 How do you feel after? And so let's try to have a fuller picture of that thing and and they're saying You know, um If you're wrecked every time you lose someone Life's gonna be very hard because losing people is a part of life.

18:04 So I think they're trying to to to balance both a a healthy set of emotions and and unpredictable often. Painful.

18:14 Existence. And This sort of lower case stoicism that we have. lowercase Epicureanism is from the philosophy of Epicurus, who

18:27 didn't eat at fine restaurants or engage in orgy or You know. truly give his life over to pleasure as we understand. That to me now. Can we experience

18:39 Like pure joy and really high highs without really low lows, or do we need the lows to actually Give us the variation. Yeah, I'm not sure. one has to make room for the low lows in the sense that life will

18:56 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.

19:13 is therefore out of your hands. sort of philosophical questions that we get from a lot of the ancients is like, could a person be happy Like on the rack. Like could you experience happiness as you're being tortured to death? And I don't think they necessarily thought you could, but it is an interesting thought experiment. The idea like if joy and happiness are dependent on external circumstances

19:37 How How good is it? And therefore How fragile. It is. And so the idea to be able to experience

19:45 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.

19:55 I think about it all the time. She had what she thought was a normal childhood. Her name is M Mary Philpot, I think. She had what she thought was a normal childhood. And then she only found out later that her father They lived in outside Washington, DC, that her father's job.

20:11 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

20:22 exile underground in the case of a nuclear Strike on Washington. thinking about What it must have been like for her father. To

20:33 Like go to his kids' soccer games or punish them for not doing their homework. Or You know. Do anything at home.

20:42 With like a literal sort of Domacles 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

20:55 Uh You know. evaporated in that nuclear strike. And if s that was to happen, part of his job was to Like

21:04 Flee and survive. You know. Not with like it's not like the doctor got to take their family with them. So she was just talking about the like the compartmentalization that the that that would require. And I think that's interesting because one, That

21:17 C is actually, I think, more relatable to Every parrot than you'd think it would be. 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

21:37 Uh your job has been made redundant and you're about to be laid off. Or You have to have fun with your kids. out in a museum park. As

21:47 Somebody you know is dying in hospital. Or whatever. And I think when the Stoics thought about joy and happiness they were thinking about Аморє форма да емоці на

21:59 Fine. uh smiling, cheerfulness, happiness, but like uh happiness of a person Who is Surviving the blows of Fate.

22:09 and flourishing as a human being in good situations in bad one. There's this story about this one stoic named Agrippinus. And um He's he's exiled.

22:20 Uh for running a foul of Nero. And He's told uh that he's been convicted. And

22:31 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, um 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

23:02 Close to the stoic idea. Oh joy and happiness of uh You just Just got told everything was stolen from you. You just got told

23:14 You have cancer, you just got told. You know, insert horrendous event. Does it break you or do you just go Okay, what's next? So it's not arguing with the reality or the situation as as it's been given to you, or the hand that you've been dealt. It's just how do I play this hand to the best of my ability. Yeah, there's no complaint about the unfairness, the capriciousness, the surprise.

23:36 Just uh What are we having for lunch? Can you train yourself to think that way, or is it something you think is more There's people disposed to that. I know I'm not born that way.

23:48 I wouldn't say that I am now that way. But I think I am further along in becoming that way than I was at the beginning. I think it's probably true for a lot of the decision making and

24:02 cognitive stuff that you talk about. Which is like are there people who are naturally gifted and have just sort of a computer You know, mind you. Yes. And then there are those of us that are not that way, but in the process of studying and thinking about them.

24:17 Can we slow that process down? Can we be more conscious of the things, less of a slave to the things. I would say yes. I find it easier for me to like in in these moments where

24:33 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 XYZ. But if they're not in the car, my immediate temptation is sort of like oh Traffic, you know. 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

25:02 It's our identity as less it. Your You're able to see The impotence and the

25:16 Unfundness of the Frustration. And you also feel Obligated to help them

25:23 with the meta skill of that because of the specific instances with a kid. You're like Well what How is this gonna matter for their life.

25:33 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 XY is it So yeah, y you learn as you teach the Stoics, say.

25:48 What other misconceptions do you run into about stoicism? Um well that it's all Um Rich white dudes with a lot of merit and Uh

25:59 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 to focus on what What was obscured or

26:12 Uh What's not included. We forget just how enormous the Roman Empire was. I mean the Roman Empire makes contact with the Han Dynasty during Marcus Aurelius' reign and it stretches as far as England and Africa. And the Middle East.

26:30 And You have Epicetus who's a slave, you have Marcus Aurelius who's Uh the Emperor Zeno, the founder of Stoicism Some people uh we're convinced he is

26:45 Pack. It is described Interestingly in the some of the few descriptions we have of his physical But in the case he's like a Mediterranean merchant. And so

26:57 Just the idea that 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 Uh perfectly conformed to that cast. Just because we She're mostly of the men. Doesn't mean there weren't stoic women.

27:14 Cato's daughter, Portia, is involved in the assassination of Julius Caesar. Uh. All the stoics would have had wives and daughters. There's uh fascinating essay from Musotis Rufus, who's who's not just Epictetus' philosophy teacher, so he's teaching a slave.

27:32 But You know, he writes this essay about why women should be taught philosophy. So we know he has female students 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.

27:51 Um 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.

28:04 True. And so there the this idea if sto if stoicism is Like For dudes in the R And it's about suppressing your emotions. I get why it's not gonna be attractive. Uh, but that's not what it is. Just like if you think Epicureanism is orgy and parties and retreating from the world, you're gonna be like, What is this?

28:24 But that's not what Epicurus was talking about. Either. Well I thought it was um Not Zeno. I th I thought it was Sisyphus who Maybe I'm getting really confused here, who created

28:35 Like the first sort of stoic. Crucippus? Yes, that was the one. uh created what? Sorry. Stoicism.

28:42 No, Zeno is the founder of Stoicism. Okay. Zeno uh studies under this Cynic philosopher named Crates. By the way, Crates is is an equator with his philosophical wife in Athens. There's always been a female inf influence from the beginning, but Um Xeno is credited as the founder of Stoicism, he sets it up on the Stoa Pochile, this porch. In the Athenian Agora, that's where stoicism comes from. Then there's Cleanthes.

29:08 And then Chris. But it doesn't really become a real school of philosophy until later with sort of codify. But Zo is Yes. Is the connection with

29:19 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 I think so. I think I mean that's what sports are is a metaphor

29:35 for any kind of pursuit of excellence. It's just The most Visible. You know, it's a very visible b because it's a game with rules and a beginning and an end the most observable form of excellence.

29:50 Right. An entertaining form of excellence. And Look, uh In the ancient world They're using sports metaphors then too because it's the same

30:01 The same process. One of the stokes is talking about how he thinks That A philosopher has to be like an athlete. He's just like a ball player. you catch the ball and throw it back, catch the ball and throw it back.

30:13 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. There's weightlifting metaphors, 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

30:45 coolness under pressure. well rounded person. Are at play in sports. This is I think why The Olympics are this sort of enduring

31:01 And we still observe some of the same exact sports almost that you know, the Stokes would have been very familiar with. Do you think anybody can be at the far right of the curve in whatever domain they're an expert or a sports or skill And be a normal sort of person? I think about this all the time. I would like to be Both. And I think she do realize there are trade offs.

31:28 Part of the It there is something inherently unbalanced. About Excellent. In a singular domain.

31:38 Because you are focusing All of your energy on One thing. There's something dysmorphic about like the athlete's physique.

31:49 And that's probably just the physical manifestation of also if you could look at their mind. And their priorities probably equally But if they weren't out of whack Then they wouldn't be

32:05 On the right end of the I mean what I really admire and I've gotten to meet a f a handful of them over the years and I'm always reluctant to be like well this one is a good example of this'cause 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

32:27 All time greats. you know, great pri uh achieve the great prizes of their thing, whether it's politics, sports Business art. And They seem reasonably well adjusted. They haven't left a trail of bodies behind them.

32:43 Um Literal or otherwise. They're Their family wasn't utterly neglected, their health wasn't utterly neglected. They're

32:53 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

33:09 That's a alm I I would argue a much rarer feat. Power corrupts, absolute power corrupts, absolutely. So what I think makes Marks really such a fascinating example is here you have one of the few humans to hold Absolute power as we would really define it.

33:25 And doesn't seem to have become deranged. Or Grotesque. Isn't uh

33:35 Huh. an overwhelming cautionary tale. That to me is A rarer feat than if you told me he had won. The

33:46 single greatest. you know, military victory of all time. Like the greatest victory the Stokes would say would be the victory over those Very impulses. There's another Roman I think it was like a Cincinnati you know your history way better than I do.

34:02 Cincinnatus who like gave up power. Yeah. I tell this story to my son all the time. Cincinnati's M maybe not real, maybe real, but his example was certainly very real. to the Greeks and the or I guess to the Romans, not to the Greeks. But yeah, Rome is uh sends out it's already in this big battle and they're

34:22 Defeated. And they are in these tracks. And so Rome had this sort of uh emergency you know, smash in in case of emergency button.

34:35 that said, you know, you could make someone dictator. To save. Uh Republic. And so they they go to Cincinnati, who had been a general

34:45 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's rescues the army, he defeats The enemy.

34:58 And that he returns to Rome. resigns as dictator after like seventeen days. And then he returns to his farm. It just goes back. to his regular civilian life.

35:11 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

35:22 He resigns his commission repeatedly. Yeah, I was just in Annapolis uh a couple weeks ago, and you can stand in the courthouse where he resides his military commission. And then when he resigns after two terms as president. But King George when he hears after the revolution, he's you know, what is to become of George Washington. Uh

35:43 He's told that you know I think he intends to return to his farm. Does not make himself And the Washington Name uh

35:52 You know, uh 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

36:06 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 market like Uh you know Andrew Luck, the quarterback. Yeah. He walked away. Yeah.

36:19 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 For memory. But he also made like a hundred million dollars playing football. He As far as we know, escaped without any serious

36:37 Long term You know, brain injuries I don't know what he does all day, but you know, the idea is And he walked away at the top. Yes.

36:49 Yes. To 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.

37:01 Early or on top. That it does. to go for The sixth ring. Or

37:09 The three P Or whatever. Those things are extraordinarily hard. But clearly Yeah. Less people do. This other feeling

37:17 It must be because It's even harder. Do you ever think of of walking away from writing? Yeah. Why didn't do you think it's time for me to retire?

37:26 No, that's not what I was saying at all. You're you're sort of like You're in the middle of it, right? Like you're like what, twelve, thirteen, fourteen books, however many. Like the thing for me is that's the part that I like doing. You like and it's probably the least hard on me. Right. It it'd be the other stuff that I think would What

37:45 B Like the bookstore or YouTube? No Yeah, like YouTube or podcasts or speaking or to just be like nah, I'm just just gonna do this one part. I don't know how people do podcasts once a week or more. I like I find once every two weeks hard. How often do you do it? Twenty six times a year. Is that a deliberate choice? Yeah, I don't think I could

38:05 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. Well you also do your interviews are longer. Right, so

38:27 You might be able to say if if somebody's doing Uh Two a week. And then an hour. That's the same as you doing it.

38:36 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 nothing. When I had my marketing company Um, one of the reasons I never wanted to hire employees was that I was

38:53 sceptical that there were enough Projects. that I would be interested in working on. to pay for Yeah. The people.

39:03 Which meant If I hired someone They would have to be a little bit more. represent a certain number of projects per year just to get back to even.

39:14 I go back and forth between whether that was a constraining kind of limiting belief or if that was actually Like a pure and Like admirable stance. And you kind of distance yourself from the work too, right? Like so if I hired somebody to do the research for the podcast, I could show up. There'd be a list of questions. But part of what I enjoy about it is actually doing all the research and the work.

39:38 The pressure to scale. Like I know a lot of people in the This kind of information. Media space. that have taken on

39:50 Like private equity investments. Like there's like the Cherdom 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

40:08 Doing it. Not having a boss and not needing to get at a s to a certain level or do a certain amount of Things. Which you

40:20 Are forgoing with you. I was talking to John Mackie about this, the whole foods guy. He sort of said I I love this analogy is like when you bring people on They're usually hitchhikers.

40:34 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 gonna be like, No, what do you do? You can't do that. And then you all of a sudden you have a boss and you have all this pressure and You know, they own half of your you went from being the driver to being the passenger. Kind of, yeah. The other person is like has a n they have a brake and they have their own steering wheel and they have their own accelerator. The pressure to scale is

41:06 obviously a first world problem'cause you're most people and uh not that long ago for me, the Uh problem was Breaking through. Or breaking out.

41:15 Yeah, once you do that because that is so rare. There's an immense amount of structural pressure Economic pressure. Cultural pressure.

41:26 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, uh the every couple of weeks I'll get an email being like, Hey, have you thought about opening another one?

41:39 And it's like I already Hit the lottery. By it not failing. Do I need to

41:48 start a shade of bookstores? I don't think that I do. And I don't think that would improve my life quality at all. But we it's easy to be disciplined in some areas and not in other areas. So when you're successful, one of the tendencies is to start saying yes to all these other projects, start hiring a team, and then 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. Yes. How how can we use stoicism as a means to sort of focus our energy And remove distractions.

42:20 Mark Shrewd writes in Meditation to Can imagine the immense pressure And Inbound that's coming at the Emperor of fifty million people. He says And 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.

42:37 And he says when you eliminate the inessential, you get the double benefit of doing the essential things better. Knowing that what you're saying the S to means saying no. to other things and conversely saying no to things means saying yes. To technically.

42:52 Is like the Very tricky. Never gets easy. balance that I was struggling with like even this morning. My wife and I were like, okay, I got offered to do this and I got offered to do that. What do we want to say yes to, what do we want to say?

43:05 No till. And the just the You would think at some point. not needing it would make it easier. To say no, but opportunity costs. You get more opportunities. Yes. And success tends to sow the seeds of its own destruction.

43:22 You know, be disciplined. While you're successful Uh You know, don't don't take on too much.

43:31 Say no to a lot of things, but In sports or entertainment or art Or even You know, whatever it is that you do.

43:43 You don't do it for ever. Do you have a narrow window? And there's gonna be at some point where it dries up. And so Are you gonna look back and go, There was almost a bit of ego in my

43:54 In my selection process because I was assuming That I would have. Get to do it forever. I continue to wrestle with that constantly. How do you think about opportunity cost? Is it always increasing for you or is it based sort of like on the workload right in front of you or

44:11 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. 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.

44:30 I'm trying to do work and get more clear, get more objective about like No, hey, actually, yes, that To an to uh you ten years ago. to any person on the street. That is a lot.

44:43 But Given what your time is actually worth. at its current valuation. That's actually Something you should say no to.

44:52 That's hard. Imagine if you're a billionaire how hard that must Okay, no one's throwing them a uh pity party, but like That must be very disorienting. And destabilizing to not

45:04 Have a good way to value. What to say yes or no to. The problem is financial upside is always clear. Opportunity c opportunity costs.

45:17 Sometimes clear, but often not clear. If I get offered to Do I don't know, speaking again. That's the opportunity cost of saying no.

45:28 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

45:41 The rhythm of our households. My personal happiness, how easy things are. And so what is the the the downside is In one sense is very quantifiable. And the upside in the other case is very

45:56 Hard to quantify. And in in some cases the consequences of it are Quite lagging. And so You're faced with

46:06 Briefcase with cash in it. And Hey, isn't this a bit much, we're all tired. How do you balance that? My uncle taught me this thing when I was a teenager about how he used to price his business. So he was a he ran a plumbing company. What he did was basically the first seventy five percent of ours were priced at a hundred percent.

46:26 Mm-hmm. So the regular rate, but seventy five to eighty, he would increase the rate eighty to a hundred, you'd increase it and over a hundred percent of like a normal work week. They need to 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. Cause 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.

46:56 In part because of his honesty. Right. But I use this. This is sort of like the one of the simple principles that I use, which is like If I'm super busy, I'm gonna price it more'cause I actually kinda want you to say no. Right. But if you're gonna say yes, then I'll make it work. But it's at a certain price. And so the pricing that we use is dynamic in some ways. And there's like a baseline which is like here's the minimum. And you need a certain amount of self confidence and security to be able to do that. And you can see why

47:26 Yeah. You're like You have it just an enormous void inside you. how vulnerable that makes you. Yeah. Because You want to be wanted. You want

47:38 the validation you want the Chi ch Yeah. Feels good. But like you, like I get I get five speaking requests a week. Yeah.

47:47 And there's no way you can say yes to everything. So you have to have a system to sort of Well if I think the first step is you have to have someone Between you and the thing. Yeah. Three of the five. That were not serious. Or not even not serious, but

48:02 We're at a number that might be tempting, but it's better for you not to see. 'Cause you're more likely to say it. And entitled. And you wanna be the g like you wanna keep yourself as the good guy, the nice guy, the the person who is Saying yes. Yes. So you have to sets of boundaries.

48:23 And then task other people with enforcing them. Yeah. I I think some people will go, Oh, is is it You know, you don't wanna pay these people commissions, you should just do it yourself. And I think there's a danger in doing it yourself, which is that Totally. Uh And then when it goes away what? Yes.

48:40 This I worry about this all the time, right? It's like well five and I'm like saying no You read that book Die With Zero? Yeah. It's a great book, but the idea is, you know, thinking about What do you what are you trying to do all this for? You try to accumulate a large amount of money that you don't get to take with you when you die? We are borrowing money from our poorer selves to loan to our future richer self. The example it is is the book, which I think is a good one. He's talking about like a med student. who's like living way below their means, saving up money. They know in the future they're gonna make a lot of money. It's very clear how that profession works, right?

49:13 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. There's

49:25 They're not actually You know. making thirty thousand dollars a year. They're Just temporarily making that. Anyways.

49:33 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.

49:45 '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

49:57 historically a very clear drop off. Like at some point. You age out at some point. Yeah. Trend or moment.

50:08 Goes away. And maybe it come you survive long enough for it to come back. But like the idea that For me as an author that my sales are only gonna go like this. It's preposterously naive.

50:18 Then it adds this layer to like, okay. So you're saying no. 'Cause you're too busy right now. Yeah. But in six years

50:26 You'll you'll feel like an idiot. You wish for this request to come back. Yeah. Is it ever okay to lose your cool? Like, is there strategic points where it actually makes sense to sort of not be stoic and to to I wouldn't say completely lose control, but to That like crying.

50:46 Yeah. Is Not many. Right. Like being overwhelmed with your emotions is somehow a weakness.

50:54 But we make an exception culturally. For anger. If you went through some problematic work thing. And

51:03 You cried in front of your whole team. You would reasonably expect that teen 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 not you be judged for that, that might be like part of the legend of shame. Right. Which is interesting. And the stoics would point out that

51:23 Like Those are both the same process of being overwhelmed by our emotions and one is actively harmful To you And your world

51:35 And the other is not. And so it's kind of strange. So it's it's interesting. We have a couple of stories of Mark Serial's 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's gets frustrated with his secretary and he he grabs the secretary's pet and he stabs it in the man's eye.

51:55 Like this is the thing that the king could g the emperor could get away with, literally anything. And so I I do think It's interesting the allowances we make.

52:07 particularly with men, for certain kinds of emotions and not other kinds of emotions. And I'm I'm not saying oh hey, we should be all with one or all with the other. It's just The idea of the the stoic suppressing their tears and sadness and love and affection. But then

52:27 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 key old. Cross the board. That being said There is a difference between

52:43 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 her temper, screaming at the ref.

52:58 And getting ejected. Not only does it 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

53:12 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

53:27 turn up or down certain levers. I was at a Spurs game one time. And I watched Uh Greg Popovich get ejected. And

53:39 Uh Tim Duncan took over. And the team it was down by seven or eight points. And Tim Duncan coached the rest of the game. And

53:49 the they came very narrowly Uh 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 at Duncan and said, I'm gonna get myself thrown out. You're gonna You're gonna handle the rest of this game. He he saw that the team needed an energy shift.

54:08 And that that was a tool in his toolkit. I I find that Very interesting. I wanna move on and talk about discipline for a second. When we think of discipline, I mean the image that comes to mind for me and probably a lot of other people is like the army drill sergeant. What is discipline? I'm talking about self discipline. So the The discipline of an army sergeant

54:31 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. How would you define self discipline? But the virtuous self discipline is the discipline.

54:45 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

55:03 Can you Keep your head about you when things are falling apart. Can you Be a calm you know. reassuring presence, can you

55:13 Keep your emotions in check. So so self discipline is sometimes rendered as the idea of temperance, which just doesn't have a good connotation in the English language, but it It is The Stokes would say the greatest empire is command of oneself. And so whether you're the emperor or a slave, whether you're a soldier or a CEO

55:32 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. Or do you struggle the most with it?

55:46 Knowing one's limitations, setting reasonable bounds on things. I don't have a problem with getting up and working. I have a problem Getting up from and stopping where 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

56:05 Mm. Discipline for me is closer to Balance. And saying no, then it is too. Insistent on yes. For a lot of people it's sort of uh 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

56:22 How do we get back on track? You told me something though that I've been thinking about where you said that your You go to the gym every day. Yeah. As opposed to I work out three days a week.

56:31 Because There's a consistency to everydayness. And It's not a choice then. Yes. It takes away

56:40 the lie you can tell yourself, which is I'm doing it tomorrow. Yeah, you can do you can change like duration or scope. But like work out sweat every day. It's like It's so life changing for me and Other people who've tried it after listening to me, it's been life changing for them too. No, it's a great way to think about it. I try to write every day. Um We'll try to do a little something every day. And that's better for me than

57:03 Okay. I'm not doing it. And then next month I'm gonna start doing it. 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.

57:21 And then all of a sudden it's three, four days. I almost always have the opposite problem. Which is Telling myself that Be it five minutes.

57:32 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 bow for me is going, Let's just have a nice weekend. As opposed to I'm behind. Right. I'm gonna blow apart this nice weekend.

57:49 To check. Some arbitrary box. in a race. That I am Preposterously ahead on.

57:58 And by the way, don't even need to be doing. But if you don't push yourself, like what's the flip side of that? What do you worry about? Are you scared you'll just Stop and be lazy or I think that's the thing about most compulsive tendencies, is they're not based on anything. You have this belief.

58:14 that if you don't do it. Things will fall apart. I'm the same way. Like I work every day. Yeah, it's not based on anything real. And most of the time what you get Is not even the reward for doing it. You get the relief. For having not not done it.

58:32 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

58:43 Not. Not a way to Go through life. Does your workaholism sort of and I'm using that term. No, no, is it but does that cause issues in your relationship? Yeah, of course. Uh, I think it always has. Um

58:56 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

59:07 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 uh

59:20 Somewhat productive. It's somewhat productive and it's socially adaptive. Do a heroin. Or you know, uh Drinking all night.

59:30 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.

59:44 Is a is nevertheless a pretty wicked feedback loop. Are you sort of like motivated? I 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 why

1:00:03 axies it's like that gap is what I focus on, which is like How do I shrink this gap? And then, you know, like where I think I could be is probably growing slightly faster than where I am. And so the gap is widening. Yeah. And then it's like I need to there's so many things I wanna do that and have so much excitement and energy around it. What did you throw on top of that? I

1:00:24 what you hear other people are doing. Yeah. It's even more Hard to Run your own race.

1:00:33 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.

1:00:46 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.

1:01:01 You know, donor, it could be a bazillion things, you don't know. And so the I think the more Indifferent and Probably ignorant you are. of what your peers are doing.

1:01:14 The healthier you are and the the clearer your compass reading will be. I think of it as like swimming in your own lands and there was this video I think it was from the Olympics. post twenty I forget what year it was, but

1:01:28 This guy is swimming and he looks over at his competitor. And it ends up distracting him just enough that he loses the rays. Yeah.'Cause he's like one he's not worried about him and his lane and his goals and his stroke and he looks over just enough to distract and he lost by like milliseconds. Yeah, there's that, although the other one that keeps me up, there was a there was like a a mountain bike race in the Japan Olympics I think. And

1:01:55 The woman thought she was in first place, but she was actually in second place. Oh, so she let up? 'Cause like it's sometimes you know like in swimming they're all like next to each other, but like The marathon or some of the longer races, you might be Might be two minutes. That's a closable gap, but you can't see what the other people are doing.

1:02:12 Even if it was an insurmountable lead for her to get. First. Her second place time was not the best that it could be. Right.

1:02:23 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. What can we do to cultivate more discipline?

1:02:40 I mін look, I think having a physicoal practice. Is a way to cultivate more mental And cognitive discipline. Like going to the gym or running. Running, swimming, biking, like I do endurance sports and they help me as a writer. Like

1:02:56 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 gonna get in this thing that is uncomfortable. And I'm gonna decide how long I'm gonna stay in it. Whether or not it has any health benefits whatsoever.

1:03:14 And I'm pretty sceptical 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 Surely. That it's hard.

1:03:28 Doing the hard thing. And how do you sort of teach your kids or instill discipline in that? It's tough. My kids are still pretty young and so I am I am hesitant to give them My somewhat unhealthy adult levels of discipline.

1:03:45 Enjoying letting them just Not be I my assumption is that they have whatever I have. And so Allowing them to enjoy not having it.

1:03:56 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. They go all in. They do they're like I need all of this. I r I read a story about Tom Brady watching his son playing video games.

1:04:10 And if some getting so upset, I'd be like throws the camera uh throws the controller at the T V or whatever and it's just like He was like Dude, I have that. And

1:04:21 Yeah. It doesn't always take you where you want it to take you. And so I I suspect that That part's there. So It can help you, but it can also get in your way.

1:04:30 Yeah. And would you wish it? On someone. Especially someone who right now is young and

1:04:40 None of these adult notions. A lot of people with dyslexia talk about how that dyslexia is shaped and It forms. The success they have and then

1:04:50 If you ask them would you want your kids to have it? They're like how you've fucking added a mind. We know like hard things and struggle and adversity. We know it's good for us. And yeah. We don't want them for our kids. We don't want it for our kids and and we also know though, like

1:05:07 If we hadn't had that. We probably just want to had something else. Yeah, I I've never met someone who had zero adversity in their life. Like sometimes people ask me, Hey Should I

1:05:16 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. Yeah, was it Dostoyevsky would like gamble all his money away so that he would write better?

1:05:33 I don't know if we needed. How would you define character? Mm. I just heard something. Someone said like character Like your reputation is what other people think of you and

1:05:45 characters like what you do and There's like an element of Right and wrong embedded in this. Who sort of defines what's right and wrong. That's the hard part. I so I just I'm been doing this series on the Cardinal Virtues, so I did courage and Discipline.

1:06:00 Than justice. And on one level, yeah, I would go, How do we know what's right and wrong? Is it the Ten Commandments? Is there some You know scientific basis or utilitarian argument for what's okay about And then

1:06:14 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

1:06:28 You know, do this or that. Culture. religious tradition and philosophical school has formulated some conception of the golden rule. And all the philosophers that Yeah.

1:06:41 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. It makes them so complicated as to Make them almost worthless. Like how do you know what's right and wrong?

1:06:58 What about this? What like we it's like we almost focus on the edge cases as a way of There's such a middle ground that we can all agree on. Yeah, that's like ninety five percent. You know, we're like should You know A Nazi's banging on your door. They want to know.

1:07:14 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 con's categorical imperative. You know, a trolley is racing out of track. And it's gonna kill.

1:07:27 five people, but if you pull this lever, it'll go here and kill one person. What would you do? It's a way of abstracting Away from the fact that we have morally charged decisions in front of us all the time. And we Don't think about it.

1:07:44 And don't do anything about it. And that that that middle ground, if everyone just did a little bit better on this middle ground, the whole world would 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 totally.

1:08:02 How do you live up to the best version of yourself? We think of virtue as this thing that you Have or don't have. Think of it as a noun. When it'd be far better to think of virtue as a verb.

1:08:15 Aristotle says like how do you get better at playing the flute? It's by playing the flu. How do you become a more generous person? It's by doing more generous actions. virtue to any other craft.

1:08:31 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

1:08:44 Perhaps you will find yourself In some decision of enormous moral consequence upon which The fate of the world will depend. And then let's hope that you draw from this ethical framework.

1:08:57 That you read about in a book. And we'll Make everyone proud. But in fact it's like a series of small daily decisions. Just like any other

1:09:07 discipline. And that's why these virtues are so related. Like there's a discipline to justice. I keep my word. I Help people. I

1:09:19 think about the consequences of my actions on other people. I Don't do insert X, Y, or Z thing that might be legal. But not right. And so if you think about it as a practice.

1:09:35 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 gonna happen. some random ass person and put the fate of the world on their shoulders. You have to be Involved.

1:09:49 In the thick of things, making Decisions of consequence. To ever find yourself in a position Of Decisions of consequence.

1:10:02 your slip up in character, which we all make. Yes. 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. You know the Profumo scandal in uh London in the sixties? There was this Uh 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

1:10:27 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 won but

1:10:36 I forget which government, but It brings about the Uh Prime Minister vouches for him. And then uh

1:10:45 has to apologize and ends up resigning and as a result. And I tell the story of Perfu because I think he's so interesting. So he Destroys his political career. And you know, today we would say he was canceled. And what would happen today is that this person would be

1:11:02 Basically shunned by One Half of society. And then perversely like embraced by another

1:11:10 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

1:11:23 get rid of all of his political beliefs from before, embrace a different set of political beliefs. And kinda 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. Um

1:11:39 It was like a Like a Salvation Army style. Charity House. And he shows up one day and asks if they need any help. And they put him to work in the kitchen.

1:11:50 Like he's washing dishes. And he volunteers there every day for like the next forty years. And he becomes its like chief fundraiser. And its main leader. He just quietly goes about his life doing

1:12:04 And eventually there is an arc of redemption to it, the You can't do Good every day for Decades without it. Inevitably being noticed. Did he get his political career back? No.

1:12:16 Did everyone forgive him? No. Is his name still Inextricably linked with a certain scandal, sure. But On that. Most people Look back and go

1:12:28 Probably overreacted. We certainly made judgments about this person. Based on a singular Set of decisions.

1:12:36 That His subsequent actions revealed to be Uh More complicated. Aber aber sort of care. Exactly. And and I think

1:12:47 Uh 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. It it you're you're right. The Internet makes

1:12:58 The internet is not a place where grace is commonplace and uh where things can be retch out of context and all of that. Yeah. Actual danger is that in All of that scandal and attention and negativity.

1:13:14 Does it Change who you are. Like I am fascinated by People who are Fascinated by it, impressed by the people who have

1:13:25 Messed up. had scandals been the subjects of Cancel culture or mobs or whatever. And then they emerged from it.

1:13:34 Not caricatures of them. That it's not a good thing. It actually wasn't this life defining, formative.

1:13:43 Like the stoves talk about look, 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.

1:13:55 That is The thing you have. But oftentimes that's the first thing to go. Because we're angry. Or we feel mistreated.

1:14:03 Or because our willpower collapses or whatever. So so like can you not turn into a radicalized asshole? Is to me the interesting question. There's another sort of subset to this that w we sort of sometimes will behave better than we want to because we know we're being recorded, we know we're being watched, and then it's it's not Character anymore'cause if character's sort of like what you do and nobody's watching.

1:14:28 Debate that question too, like Is it good if you're doing good? 'Cause you want a reward or because you're following It should just be enough to do good because you're doing good. Yeah. But if I had to choose You know, like people are today are like Oh, it's all this virtue signal in, you know? It's like

1:14:45 Certainly better than the alternative. You know. Totally. I'm not sure this sort of Import like This the cruelty is the point.

1:14:53 Vice signalling. is preferable. Even if it's more honest. I would love people to be signaling birth. The they say uh what um

1:15:03 Uh Hypocrisy is the uh Is the credit that Vice plays to virtue. Never though.

1:15:11 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 Signal in Than not than the nihilism of

1:15:22 Titan. Lol nothing matters. Where in life do you have the highest standards? Professionally because it's easiest. And it's the most measurable.

1:15:35 And You'll 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

1:15:47 We naturally Or unbalanced. Like I don't work as hard at being a parent as I do at being a great writer. But at the end, which is which am I gonna think is

1:16:01 More meaningful. But one so much more measurable. More people care about the other one. 'Cause it affects more people, at least in the Short term.

1:16:09 Yeah. What do you feel like you have the highest standards? Oh, I hold myself to these like unrealistic expectations in every domain. I wanna be the best father. I also want to be super successful at what I do at work.

1:16:26 And trying to pursue those two things. I want to be a great son to my parents. I wanna be you know, I wanna 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 I I can't balance being great at work and being a great father. And so sometimes I'm like It's gonna be busy for the next couple of months. I'm traveling a lot.

1:16:51 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. Right. And then it'll come back. And it'll restore and there'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 Yeah, it's not coming at the expense of being a great father or a great parent or a present parent. And then when I fail at these things, like the parenting thing, man, like I've

1:17:29 Going 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 kinda beat yourself up, but you're holding yourself to this expectation. It is interesting how this is like basically every woman's experience. Up until Very recently.

1:17:45 And almost no men were thinking about these things. Well Dealing with A set of expectations And

1:17:53 A set of Responsibilities for which there is not centuries of cultural experience and lessons and examples to draw on. Yeah. You know what I mean? Um Like

1:18:07 Your dad wasn't ever doing that. And your grandfather certainly wasn't ever doing that. And then you go back. couple generations and they're like I didn't even know all their kids' names.

1:18:17 It has Changed. Way for the better. But Yeah, I I think about that too. You go, Okay I try to

1:18:25 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.

1:18:35 And so yeah, very quickly your day is super circumscribed. And then there is this challenge or tension of like can you be great at what you do. working not even bankers hours, but like Stay at home mom hours or something. You know? Well pushes me. They go to bed, so all the like, I gotta log in and I gotta do work, you know? We used to travel in the summers and we'd go away for

1:18:59 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 and now it's easier'cause they sleep in. So I get a a full work day in before they get out of bed. Yeah, uh Tony 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 ride until six or something.

1:19:24 I'm not quite on that schedule, but I do yeah, I try to I like my day is Circumscribed by their day. And I also go How the fuck are other people doing it? This is crazy. I could 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

1:19:44 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

1:19:57 two and four. If you've got and then also let's say you're two different kids at two different schools or more, yeah. It's insane. No one uh no society can't function this way. We're expecting Rightfully so to for parents to spend a lot of time with their children. But the world is not conducive to that and Oh unless you've

1:20:16 retired. Or you're not working. I think about this all the time, right? Like I have a eight minute commute to work in the morning and I'm like, I don't know how people would do thirty 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 active.

1:20:39 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 I wonder like how they do it all the time. 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, I'm maybe I'm not that bad. But also just think about the fact that like for basically up until let's say twenty years ago.

1:21:04 And that might be generous and 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. And only

1:21:18 one of the genders is aware of it in any way. Insane in retrospect. Sad. Unfair. And then

1:21:28 Still doesn't Change the fact that it's now. different and not a lot has gone into helping people manage that. I have a lot of respect for the parents out there. Yeah. Whether single parents or together, it's it's a lot going on. You've said that writing helps clarify your thinking.

1:21:45 Can you double click on that a little bit? I actually have a chapter about this in the book that I'm doing now. Um 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 gonna be discussed at the meeting. And Multiple people have to edit that memo before you can sit down and do it.

1:22:03 And why is that? It's not'cause memos are 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

1:22:15 Story about uh Eisenhower at the outbreak of the Second World War Marshal is chief of staff of the U S Army And he he's he's bet Isawer before he sees uh sub promise of this young officer.

1:22:30 And he says uh You know. It looks like World War Two is about to break out. Japan's on the march.

1:22:39 What do you do? And it's a job interview. And Eisenhower could have just, you know, pulled an answer. Can I have a desk in two hours? And I and Marsha says, Um, sure.

1:22:52 And he goes, he gets a typewriter, he sits down and he basically types out a memo. Everything he has studied and learned and thought about this exact problem. his whole military career he's been in the Philippines, he's been in South America, he's been Uh You know.

1:23:06 He's done a lot. But it gets it on paper. And I think there's something about getting it on paper. Instead of spouting off. Whenever my ans like the answer I just gave you.

1:23:18 It's 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're the process of really stopping to think and clarifying and going over Joe Diddy said that writing is a hostile act. Because you're having to convince someone to see

1:23:40 things the way that you see them or think the way that you think that and that's why it takes an immense amount Oh. skill to do that. Very few people can do that off the top of their head. kinda have to meet people where they are and then take them where you want them to go. Yeah, you zoom out, you zoom in. Yeah

1:23:56 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.

1:24:08 But he becomes this prolific writer. And a lot of people were upset. 'Cause it's somehow a violation of the vow. And he was saying no, like writing is contemplation of thinking about Well I think. And for people who are not writers, maybe that doesn't make sense. To me, writing my impulse to write comes from

1:24:28 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. But I can get it.

1:24:42 I can I can do that hostile act of Change in your thinking. As a writer, how do you see the impact of AI? I haven't seen

1:24:53 it do anything That Even a pretty good writer. Can do. But it can do things a lot better than people who are bad at writing.

1:25:08 problems in our society. With people who are extremely credulous. and susceptible to misinformation and disinformation and conspiracy theories and nonsense.

1:25:22 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.

1:25:35 nervous about. Is people's inability to handle that. Like One of the things you learn as a project manager Like if you're working with someone

1:25:46 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 us a amount of money. You have to have enough technical domain expertise.

1:26:03 That You can push back. And get to the truth on things. And when I've worked with AI and I I'm needing it to track something down.

1:26:13 that maybe I'm I'm like, Hey, didn't so and so say something about this? And they go, Oh yeah, they said this And then I go Wait, or was it Actually so and so. And they go, Yeah, yeah, it was that. And

1:26:24 And what it's doing is it's telling me what I wanted to Here, in 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

1:26:43 a strong Sense for bullshit. And an ability to No. When

1:26:51 To push back. And to Examine And when to verify. Because a lot of what it's gonna spit out.

1:26:59 Is not true or is only partially true. And if you're just defaulting to it. You're gonna be embarrassed. Do you use it for any writing or any purpose? I mean I use it when I do presentations, I have it do.

1:27:13 Uh huh. I want a picture of insert a thing that's never been painted by a Renaissance painter before. visualize things, I use it. And sometimes we'll use it in videos and we're like, you know, show Marcus Aurelius like

1:27:30 in a suit of armor show Mark's realistic like so I use it for things like that Like track stuff down. But then I I I have to f I have to get a second opinion. I have to have it verified in some way because I'm That skepticism.

1:27:46 ' 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. Totally. Do you use it? Yeah, we use it all the time at home. The kids like will write their essay. The way that I

1:28:03 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 twenty five hundred words. Go. The appropriate use is you write Something reasonably good. Yes. And I wanna 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.

1:28:26 What would you say are the weak points in my so it's like almost like a personal tutor. Yeah. And then I'll submit like here's a draft chapter. Like what did I miss? What what do you think? And sometimes it it's pretty insightful. I've used it with my kids, we'll have fun, like They'll be like, draw this or make that they get increasingly excited about making it do more absurd things. And the idea of seeing it as a as a tool as opposed to a replacement for something I think is really important. I want them to be familiarized with

1:28:57 the inherent limitations of it. Yeah. Right. So it's like you say Draw You know, it I had to do I was doing a slide and I was like ha draw this The Socrates doing X, Y, Z. And then s one of the characters in the back had glasses on.

1:29:12 And I was like, This doesn't make any sense. They didn't have glasses, so like get rid of the glasses. And then it's like they redid it. And then Now more people have glasses. You know what like and it it's also its inability to To iterate.

1:29:27 Like it's not very good at This I want this but five percent different. it starts from scratch, you know. And so again, yeah, I think the more you learn the limitations of it And The logic of it.

1:29:39 And if you can get good at Prompting, like prompting as a skill. Um I want my kids to have that. So here's the like interest I actually get it to write its own prompts. I am going to prompt AI. I want a s a summary of this podcast, and then it'll give me like a five Wow.

1:29:58 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 gonna be. Yeah, right. And so it's gonna get exponentially better over the next decade or twenty 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 wanna say here's what you submitted. Here's your first draft and now they they've done this thing where they make them write a draft in the school and they take a picture of it.

1:30:35 Oh and so your final submission can't differ too much from the original submission? Well so I do this thing, so when I read a book, I often type up the passages that I liked in the book. Yeah. And sometimes'cause 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 it's guessing the end of what you're saying. Yeah. And I always found it really interesting as a writer, so I'm typing some sentence from heavenweight. So this is a sentence that has been written before. Unlike

1:31:06 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 Odd answer. And were largely in agreement that Hemingway did a good job.

1:31:20 Right. Um considered one of the great writers. So it it's like It's like your your doing a simulation of a path that someone actually flew. Never.

1:31:31 Is the AI able to predict the next couple words in that sentence. I've always found that very interesting. And it's a reminder to me that Still the cr the act of creative genius of

1:31:42 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

1:31:57 can see how insufficient it is compared to really great stock. Tyler Cowan wrote this book like Ten years ago called Average is over. And I think that can defines my philosophy of life, which is a a lot These technologies aren't eliminating

1:32:12 They're gonna 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 Yeah. It's leverage. be more highly compensated and the importance of it will be higher.

1:32:28 And so you you have to figure out what is the thing that you're gonna be excellent at. And then you have to be, as we were saying, somewhat dis unbalanced in the pursuit of that excellence. But It's like the cost of being mediocre. get higher and higher. One thing I have noticed is like the length of emails and the grammatical

1:32:46 uh perfection in emails has increased quite a bit. And I'm like I know you. There's no way you wrote sixteen sentences without making a grammatical error or spelling error. People are just putting, you know, their point form and being like generate a nonviolent res you know email to send to this person. Put this in nonviolent communication. Then you get it and you're like this is half a page. It should be like two sentences. Well just like social media is bots talking to bots. Like a lot of our life is gonna be like AI, talking to AI. Like if I open an email and I don't know the person is more than like five sentences now, I'm just delete, right? I don't even know you're gonna have to get better just like good at spotting bullshit, you're gonna have to be Good at spotted. AI versus non AI. Yeah.'Cause the cost to generate an AI email is zero. At least before you had to type something in or copy paste. Yeah, like you've gotten those emails. It's like dear Joe and you're like, Wait, my name's Ryan.

1:33:40 Uh what are you reading right now that's challenging your thinking? I've read these three huge books on LinkedIn. So I've been doing a huge deep dive into Lincoln for the book that I'm writing now. Um and I think that's like You know, maybe earlier in my

1:33:55 Right in career, I would have read one book and Called it. And now I'm like I'm gonna read another and another and another. And so I'm just going deeper and deeper in stuff. Um

1:34:05 Read 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? Well the argument was that Uh London had.

1:34:20 Extremely strict legal system. uh an abysmal for profit prison system. and a belief that like there was essentially a race of people that were criminals. As opposed to

1:34:35 crimes being an act of opportunity or desperation. And that reform was possible. That America rebelled. And the ability to send colonists. Or the undesirables

1:34:48 across the Atlantic to America. evaporated. Some new place to do it. That's crazy. It's fascinating. Do you read many business books? Like what are the best business biographies you've read. Best business biographies? I don't read that many business biographies.

1:35:04 Uh I like My dream book is like A nine hundred page biography. Of someone I know nothing about. Or someone

1:35:13 That I know a lot about. 'Cause you want the detail and the nuance. I'm looking for Illustrative stories or insights into

1:35:24 how that person operated or solved problems. So like, you know, I read a book about Lincoln specifically as a politician. I read a book, you know, specifically about Lincoln's cabinet. I read a book specifically about You know, Lincoln and literary inclination. You know, like I want to go really deep in a specific thing. And and then I'm finding stuff that didn't appear in one, but appears in the other, and that's how I'm building out the chapter that I'm writing.

1:35:51 And do you do that without having the story in mind? You're like, Oh, this story is representative of XYZ, tag it. Sometimes I'm just reading generally about something I like I'm not writing anything about Australia. I'm just was there and now I'm interested in it. And I have a some basis of knowledge that I'm building on. And then it'll help me understand. The seventeen hundreds, and the eighteen hundreds, and Often it's I'm I'm chasing something down that I think I know is

1:36:16 Down this hallway. How do you define success today and how has it changed? Do you remember what I said the other times? No. I still think my definition of success is autonomy. Like I've been saying recently, like success is How much you see your kids. And power is how much control you have over your schedule.

1:36:34 My son's school called and he was sick. And I was like All right, I'll be right there. Yeah. I like that. To me that's

1:36:41 That's both success and power. I didn't have to ask anyone's permission. I didn't need to worry about the cost of missing A day's work or whatever, I just could handle it. Turns out it wasn't actually sick. You know, it was just

1:36:56 had a cough or something and so we Just hung out all day. And then I had a talk that afternoon and he came with me. How has that changed from like a decade ago when you would define success when you were younger? I think success. was often more predicated on Like either very specific things.

1:37:14 Or relative to other People and their accomplishments. And I think I've gotten closer and closer to Just not really care. And part of that is living where I live. The relative thing is fascinating because if if you compare yourself to people who are

1:37:33 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 than you're perpetually sort of like not where you want to be and it can sort of like destroy your your satisfaction. I try to remind myself that I write about an obscure school of ancient philosophy. that there's a floor and a ceiling to that. Look, if we compare ourselves to James Clear, we're all failures. Yeah. And for our book sales. But if you compare yourself to

1:38:09 the millions of people who were killed even have a meeting with an editor It's a huge success. Sometimes it can be helpful to really think about how bodice you would have previously defined success. Oh total. And then there's there's also like a rel or sort of like a relative success and absolute success, which is

1:38:27 You know, if you sell I think I don't know what the actual number I heard of is like fifty thousand books. Yeah. You're in the top one percent of books ever published in the history of humanity. So like there's always a different way to change your perspective on where you're at and sort of And what A friend of mine used to say this like if we threw everybody's shoes in a big pile And you picked out the shoes and you got all the problems with it, you probably pick your own shoes. Like the whole world basically, you know, you could pick anybody's problem. You're Most of the time you're gonna pick yours. There's a lot of people who would try to pick our problems. When I feel jealousy, I try to remind myself that you can't pick and choose.

1:39:03 Like if you want what someone has You have to trade your whole life. And in that case you almost would never take it. Or maybe not even your whole way, but let's just say like Oh, why did they get this opportunity? I should have got this, but it's

1:39:16 No, no, you have to swap your whole career for theirs. Would you do it? And it becomes more complicated. It's it's we want Yeah, we wanna 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.

1:39:31 inherently is making things not goals. There's trade offs. Yeah. And Yeah, you can't be like I wanna be Classical musician. And then

1:39:44 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

1:40:02 There's also a ceiling. You're never gonna be the number one album in the country. But By going for the number one album in the country. You make it nothing.

1:40:13 And just understanding that You made certain choices. And that you can't. Strategy is by definition choosing certain objectives and

1:40:25 Not choosing other objectives. And If you try to straddle two strategies, you'll Destroy yourself. Thanks for listening and learning with us. For a complete list of episodes, show notes

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