Profound Lessons From Stoic Philosophy - Ryan Holiday

1. 0:00 – 0:28

   Intro

   1. RHRyan Holiday0:00

      If you don't know what's important to you, what kind of work you want to do, what you want your life to look like, you end up defaulting to one of two things: what pays most, or what are other people doing? You can end up very far from what you actually want, and you'll only know that when you get there. So you have to have a very clear sense of, like, where you're trying to go, or these things, these opportunities are chances to get super off track. (wind blowing)

   2. CWChris Williamson0:27

      You've got this quote

2. 0:28 – 9:53

   The Power of Sanity & Consistency

   1. CWChris Williamson0:28

      that I referenced a couple of weeks ago. "Be quiet, work hard, and stay healthy. It's not ambition or skill that is going to set you apart, but sanity."

   2. RHRyan Holiday0:36

      Yeah. (laughs)

   3. CWChris Williamson0:36

      What's that?

   4. RHRyan Holiday0:38

      Uh, well, I find, uh, as a former, like, sort of young person going places, that when I am hiring someone or I'm looking for someone, like, that could... I wanna, like, mentor or help or whatever, it's not like how talented you are or what your background is. But it... Like, the first test is like... (laughs) I just had to find this. Like, is this person fucking nuts or not? You know what I mean? Like, does this person have their shit together or not? And so I, I think we often think a lot about, like, getting better at what we do, like the craft of the thing, which is really important. But then when you look at, like, why did this person make it and this person not make it, it's usually, you know, very... some stark divergence where they started making bad decisions, they, you know, started being very egotistical, they had this shot and they blew it. You know, it's not, it's not like in sports where you're like, "This guy's just faster than that person." It's some other thing that usually sort of prevents a person from reaching everything they're capable of reaching.

   5. CWChris Williamson1:48

      Is there an element in there as well about playing a long game?

   6. RHRyan Holiday1:51

      Yeah, for sure. For sure. Definitely. I mean, one of the hard parts about having sort of potential and ambition is that it burns sort of very hot and bright. And, you know, if what you... If you wanna be established, you wanna do it for a long time, you have to figure out how, yeah, to play a long game, to not blow yourself up, to not... It's like, how do you care about it very deeply but not sweat it so much that it's like a liability?

   7. CWChris Williamson2:19

      Needs to be sustainable, man.

   8. RHRyan Holiday2:20

      Yeah.

   9. CWChris Williamson2:21

      Yeah. I, I play with this all the time, and a lot of the guys that I see that have flash-in-the-pan successes on the internet are very similar.

   10. RHRyan Holiday2:30

       Yeah. Well, look, and we live in an environment where algorithmically you can just be given a huge gift. You can just sort of blow up, right? And so that really has nothing to do with whether you deserve it or not. But then once you have it, the question is, can you maintain it? Can you do the work necessary? Can you not fuck it up, right? And I think we t- and I... When I talk to groups, I, I usually start with some version of like, you know, like, the biggest enemy in this room is not, like, what the other people are doing. It's not the economy. It's not, like, gatekeepers. Like, the person who determines, like, how this is gonna go is you, really. Like, for the most part, most failures are self-inflicted, or most big mistakes are self-inflicted, and they often come, like, right after some form of success. That's kind of the most dangerous point. That's when we overreach. That's when we go- it goes to our head. That's when we... You know, it's like, it's in that moment of success or triumph or whatever that, like, you need the most discipline. But there is the highest justification for slacking on said discipline, right?

   11. CWChris Williamson3:42

       Yes.

   12. RHRyan Holiday3:42

       So this is... That's where it happens.

   13. CWChris Williamson3:44

       There's a quote from Charlie Munger that says, "It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid instead of trying to be very intelligent."

   14. RHRyan Holiday3:55

       Yeah, that's right. Yeah. It's, it's like, uh, can I not blow this up? Like, I remember... So, like, uh, I dropped out of college when I was 19 or 20. I sort of had all these cool opportunities very early, like things that... especially with what was happening 'cause I, I was sort of left-right in the financial crisis. So all my friends are struggling, sort of watched as, you know, people my age have taken longer than you would expect to get where they wanna go. And then so I was very cognizant of the concept of, like, uh, regression to the mean, right? And so just 'cause you break out early, just 'cause you have this thing, you know, statistically, you're gonna end up like everyone else. So you have to be really cognizant of if that's what tends gonna... if, if that's what would happen sort of naturally, you better make sure you don't accelerate that process. Like, there's even less room for self-inflicted or, you know, unnecessary errors.

   15. CWChris Williamson4:47

       Mm-hmm.

   16. RHRyan Holiday4:47

       So I, I was like really in my 20s, I was thinking a lot about, like, okay, you've gotten these, like, opportunities, you have this stuff, like, the number one thing is, like, don't fuck it up.

   17. CWChris Williamson4:58

       How do you avoid being too risk-averse when that happens?

   18. RHRyan Holiday5:01

       Yeah. I, I don't know. I mean, that, that is the tension. Like, you, you, you still wanna take big swings, but, uh, it wasn't like... It wasn't like I was risk-averse in the sense of, like, I don't wanna, like. I've got this capital and I have to protect it It was more like, how do you not alienate the wrong people? How do you not, you know, take your foot off the gas at the wrong time? Like, it, it was more, like, ego, complacency-

   19. CWChris Williamson5:28

       Mm-hmm.

   20. RHRyan Holiday5:28

       ... uh, entitlement, you know, like the, uh, those kinds of...

   21. CWChris Williamson5:33

       Mm-hmm.

   22. RHRyan Holiday5:33

       You know, like, feeling like you're anointed, feeling like you're special. Like, as soon as you start thinking, like, the rules don't apply, like, I've made it, I'm good, like, that's when, you know, you're probably getting into dangerous territory.

   23. CWChris Williamson5:48

       Yes. It seems to me that ever since James Clear's book Atomic Habits this has been something everyone's thinking about, right? That your outcomes are a lagging measure of your inputs.

   24. RHRyan Holiday5:57

       Yeah.

   25. CWChris Williamson5:57

       Like, where, where you're at is just a, a lagging measure of the things that you've gone toward that... And it seems like discipline is...... pretty much exactly the same, and that's where the- I'm gonna guess the line between your future destiny is dictated by your current discipline.

   26. RHRyan Holiday6:10

       Well, I was thinking about that actually just recently, like, I- all the work that I- when I'm working on a book, so Discipline just came out, I'm working on the next one, like, all the material in those books are the result of research, writing, thinking, organizing that I did a year ago, five years ago, 10 years ago, right? And so all- all the work that you'll do in the future is, in a sense, the- dependent on the work that you're doing now and how long you continue to do it. And so, like, when I sit down, I was sitting down and writing today, the m- the material that's, uh, available is, like you said, a lagging indicator of work that I did at some unknown previous date. And so it can be really easy to be, like, consumed with what the task is in front of you and that- but if you're not simultaneously also setting up future stuff-

   27. CWChris Williamson7:06

       Mm-hmm.

   28. RHRyan Holiday7:07

       ... you're gonna wake up one day and you're not gonna have what you need. It's like you can ... And- and I think the better you are, the more momentum you have, the easier it is to coast for a long enough time that you don't even know that-

   29. CWChris Williamson7:20

       The foundation is being eroded from underneath you.

   30. RHRyan Holiday7:23

       Yes. Yes.
3. 9:53 – 14:28

   Direction Helps Discipline

   1. CWChris Williamson9:53

      thinking about discipline was the relationship between directionality or an outcome that discipline is being filtered through. It feels like you need something to direct your discipline toward.

   2. RHRyan Holiday10:03

      Sure.

   3. CWChris Williamson10:03

      Without the direction, discipline is pretty hard to deploy because what are you being disciplined in service of? What does discipline even look like? You know, as an ex-club promoter for a long time, what was discipline to me, going out until 4:00 in the morning-

   4. RHRyan Holiday10:17

      Sure.

   5. CWChris Williamson10:17

      ... may be somebody else's idea of complete destruction.

   6. RHRyan Holiday10:21

      That's true, yeah. It- it ... What- what is the outcome? Where are you trying to get? What's it all being directed towards? That's sort of the ultimate question. Like, you know, practice without some aim is not really practice at all. It's just activity. So yeah, you have to figure out what it is that you're trying to do. Like, for me, it was, you know, okay, I want to write. That's what I want to do. So then it became clearer, like, you know, what are the composite tasks that go into being in a position to do that? Just like, if you're like, "Hey, I want to run for office," you know, okay, maybe military service would be helpful. You have to graduate from these schools, you have to cultivate this network, you have to have this ... You- there's a- there's a resume that you need to have that job, right? And you gotta know what that is. Th- that's not to say that everyone has to do it the same way, but you gotta know the sort of- the- the collection or the portfolio of assets or tools or skills that you're- that- where you want to end up. The- the Stoics have this line, they go like, um, "If you don't know what port you're sailing towards, no wind is favorable." So you have to know where you want to go. And this is- this is really true, like, even for successful people, like if you don't know w- w- what- where your stopping point is, what you want your life to look like, now all of a sudden, you know, you're in this wonderful, fortunate position where people are like, "Hey, you wanna do this? Do you wanna do this? They're offering me this." You know, "Do you want to take this amount of money to do this or more money to do this?" And, you know, if you don't know, like, w- what's important to you, what kind of work you want to do, what you want your life to look like, you end up defaulting to one of two things. Like, what pays most or what are other people doing?And those are not the worst proxies in the world. Like, it's better than no proxy. But you can end up very far from what you actually want, and you'll only know that when you get there. So you have to have a very clear sense of, like, where you're trying to go, or these things, or these opportunities are, you know, really chances to get super off track.

   7. CWChris Williamson12:32

      With that in mind, is it easier to be disciplined before success arrives?

   8. RHRyan Holiday12:37

      Well, I mean, look, it's easier to say, like, singularly focus, or it's easy, let's say, it's easier to say no to stuff when you're not getting offered a lot, right? Um, it's easy to be principled when the, you know, there's not a lot in the way of consequences, right? So all these things are easier, to a certain degree, uh, when you're dealing with sort of less volume or, like, lower stakes. Um, I mean, one of the hard parts about being disciplined early is that you're doing this thing, and the payoff may be a very-

   9. CWChris Williamson13:08

      Eating all of the shit and no reward.

   10. RHRyan Holiday13:10

       ... very far-lagging indicator.

   11. CWChris Williamson13:12

       (laughs)

   12. RHRyan Holiday13:12

       You know, so I think it, it, it's... The truth is, it's always difficult to be disciplined, right? Um, it's always difficult, and it's something you have to figure out how to do and enjoy for its own sake. Because a lot of times there's not only not rewards for it, but there can be the opposite of rewards for it, right? Like, there can be punishments for it. If you're like, "This is what I wanna do. This is the track that I'm on. This is what's important to me," and you look around, and everyone's not doing those things. And it seems like they're having a better time. It seems like they're getting ahead for it, right? The, y- you have to... I- if the only reason you're disciplined is that you think what comes on the other side of it will be worth it, not only is that gonna be hard when you're not immediately getting it, but then you find, like, "Oh, I was super disciplined until I hit the bestseller list. I was super disciplined 'cause I won a gold medal. I was super..." Then you get that thing, and even that thing itself isn't the reward that you thought it was. So if you hated the process of it, you told yourself, "It'll all be worth it when..." You know, there's a, there's a disappointment there. L- and the accomplishment is tinged with a kind of sadness.

   13. CWChris Williamson14:27

       Was there

4. 14:28 – 27:15

   Maintaining Discipline at the Top

   1. CWChris Williamson14:28

      anyone that you researched for the book that had that happen, that reached lofty heights and then their discipline fell away?

   2. RHRyan Holiday14:33

      Uh, I mean, I think it, being disciplined once you're in the Promised Land is, it's an extremely difficult thing. Um, I don't know. I- I mean, when I- when I- when I look at super disciplined people, uh, I- I, again, I'm not just making the case like, "Okay, you gotta sacrifice, then you get this, and then you don't have to do it anymore." It's more a kind of a, it's, it has to get to a kind of an intrinsic thing. I remember I was, uh, I was talking to Lance Armstrong once, and he said, uh, like, "I raced for the money, uh, but I practiced for me," some version of that. That like-

   3. CWChris Williamson15:12

      Mm-hmm.

   4. RHRyan Holiday15:13

      ... his point was like, he likes riding the bike. What they pay him for was the competition, right? And like, and look, people have obviously differing opinions about Lance Armstrong, but he's a person who clearly loved doing the thing, and you have to get to a point where you love doing the thing. That's why you do it. And like, in writing, for instance, there's writing, and there's publishing, and those are not the same thing. Um, like publishing is when it goes out into the world, and that's interacting with the publisher, and there's contracts, and there's deadlines, and there's press, and there's good stuff, but there's also a lot that's not up to you. But like, the day-to-day-ness of it is, is you. Does that make sense?

   5. CWChris Williamson15:53

      Yes, and seeing the stuff that you maybe aren't super, super enamored with as part of the price that you pay, the same as getting up on time, the same as hitting your word count.

   6. RHRyan Holiday16:04

      Yeah.

   7. CWChris Williamson16:04

      Douglas Murray says that, uh, once the book is published, that's when the real work begins. That's how he...

   8. RHRyan Holiday16:09

      It's a se- I've said it bef- it's like a second marathon, and some people are not willing to run that marathon. Um, but like I- I remember I heard this interview with a comedian once, and he was saying that like, someone asked him like, "Are you still gonna do comedy, like, once you've hit it big?" Or, you know, and his point was that like, "Yeah, of course, because if I don't, it means that like I was doing this for the wrong reasons," right? That like he was a comedian as a means to an end to do another thing, like acting or producing or, you know, having a sitcom or whatever it is. Like, I like doing the thing that I do. And then what you'll tend to find, this is why discipline is so important, as- as you get successful at something, you know, all of a sudden you're a Pro Bowl quarterback, or you're th- you know, a CEO of a company, or you write a book, well, now you have all these opportunities to do not that thing, right? Like people wanna pay you to do other stuff, endorsements. They wanna pay you to come speak here. They want you to consult on this or invest in this. And so, if you don't love that thing, you're gonna end up doing all those other things. Or worse, if you do love that thing, but you don't have the discipline to be like, "This is what I'm here for, this is, like, what m- why I did this," you'll end- the reward for your discipline and your success is that you don't have the time or bandwidth to do that thing anymore.

   9. CWChris Williamson17:33

      Yes.

   10. RHRyan Holiday17:33

       And you only have a limited window to do that thing, right? And so one of the things I tr- I try to go like, well, could other people... Like writing is a thing that only I can do. Like, only I can write the things that I have to say. So I have to figure out a, a life and a system and a practice where I'm filtering what I'm saying yes and no to, but I'm also like building systems or structures, so like I'm not spending a lot of time doing things that are prevent... And then I don't have time to do the hard thing, which is like sit down at the blank page.

   11. CWChris Williamson18:10

       That outsourcing of tasks that other people can do is an important one. One of the challenges, at least I'm seeing now, especially because Naval and his concept around leverage and, uh, uh, all of that personal accountability stuff, I think people are quite quick to outsource stuff that they probably shouldn't be. I'm seeing a lot of-

   12. RHRyan Holiday18:31

       Like what?

   13. CWChris Williamson18:31

       ... uh, so for instance, in the podcasting world would be a good example, um, the podcaster is the only person that understands the direction that they want to take the show in, but tons of shows that are smaller than the size of this one have guest bookers that look after all of the guests that come on.

   14. RHRyan Holiday18:46

       Sure.

   15. CWChris Williamson18:46

       They have researchers that read the book and tell them the questions that they should ask. They have a thumbnail and a titling guy that comes in and demonstrates how it's visib- uh, uh, visually going to look on YouTube and-

   16. RHRyan Holiday18:57

       Sure.

   17. CWChris Williamson18:57

       ... uh, and on Apple Podcasts and stuff, and you go, "Well, like, what are you now?" I have a friend who did a 330-date comedy tour over many years, basically doing the same act, and he said that after the first 50 to 70 shows, he was no longer a comedian. He was an actor, and the point being that he was no longer actually-

   18. RHRyan Holiday19:20

       It's a script, yes.

   19. CWChris Williamson19:21

       ... doing the art of comedy. He was just a mouthpiece for what had happened before, and it g- he had to take a big chunk of time off because he'd lost his love.

   20. RHRyan Holiday19:29

       Yeah, yeah. There, you have to maintain the authenticity of the, the craft or the thing, and yeah, you, you, you do outsource, and you, you find leverage points. But it's usually about the trivial things that don't matter-

   21. CWChris Williamson19:42

       Yes.

   22. RHRyan Holiday19:42

       ... to free you up to spend the most time on the things that do matter. So when you're saying no to stuff, it has to be clear that that is part of a process of saying yes, 1,000% yes, to, like, the things that really do matter. So yeah, when I outsource, if I have an assistant or if someone mows my lawn or w- or I've- I'm sort of taking tasks off, that's not so I can just dick around, right? That's so I really do have the time to, like, sweat the details of the stuff that I make, right? Um, I tell a story in the book. There's this exchange, um, Coretta Scott King, Martin Luther King's wife, is, is called by the actor, uh, Harry Belafonte, uh, and, you know, she's e- I think Martin Luther King had just gotten arrested or was, you know, sort of away doing this, uh, march or something, and as they're talking on the phone, uh, he can tell, like s- she keeps having to put the phone down. She gets interrupted. Kids are- need something. She has to take food out of the oven. She's, like, just busy while they're on the phone, and, and Belafonte goes like, "I ha- this is a personal question, but I have to ask, like, are, are y- do you have, like, any staff? Like, are you doing... Are you totally by yourself right now?" And she goes, "Yes, yes, of course." Uh, and he says, "Why don't you have any help?" And she goes, "Well, you know, like, my husband's a minister." She, he thinks the optics are bad. You know, "I don't know if we can afford it." It, it, it was just this sort of combination of this block that they had, and, and Belafonte goes, like, "That's ridiculous, and it ends now." He's like, "I'm... I will pay for you to have staff." And he realizes that, like, he's like, they're doing... They're running this massive organization. They're the head of this movement that has the potential to change the world. Like, uh, Martin Luther King can't be worried about whether there's milk in the fridge or not, and his wife can't be, you know, worried, you know, about this or that. Like, th- there has to... You have to have the ability to, to delegate and build, like, a system or a structure around you. And th- and I think that can be really hard for people, especially if you came to what you did from a very sort of scrappy, like, uh, uh, passionate thing where you loved doing it, one, but two, like, you didn't think anyone could do it as well as you.

   23. CWChris Williamson21:59

       Yes.

   24. RHRyan Holiday21:59

       And, and it takes a certain amount of discipline to, to, to find out wha- to separate the essential from the inessential, to delegate or eliminate the inessential, and then that leaves you with the essential. Uh, in meditations, Marcus Aurelius, so you can imagine, he's the emperor of Rome. He's having to think about this exact thing, and he says, you know, "The question you have to ask yourself in every moment is, is this essential?" And he said, um, "Because most of what we do and say is not essential." And he says, "The, the thing is, when you, when you eliminate the inessential, you get the double benefit of doing the essential better." And so, this, this isn't, you know, this sort of hoity-toity, like, first-world problem. It's a, it's an, uh, a critical dilem- a, a critical juncture point as you get better at what you do. How do you find the way to professionalize and systematize and scale the stuff so you can spend more time on the things that matter and less time on the things that don't matter? Or you can bring in other people who are better than you at certain things that allow you to take what you do to another level.

   25. CWChris Williamson23:01

       It's such a common, uh, dynamic that I see, especially coming from the North East of England, right? Spit and sword and salt of the earth people-

   26. RHRyan Holiday23:09

       Yeah.

   27. CWChris Williamson23:09

       ... who are that person that you said, scrappy, they've come up from the bottom up. They've done all of the things themselves. They were HR and marketing and finance and accounts and all that, everything.

   28. RHRyan Holiday23:20

       Yeah.

   29. CWChris Williamson23:20

       And they get to the stage where you go, "Look, man, like, you are now bouncing off the rev limiter in first gear. The only way that you're gonna be able to do this is to relinquish some of this control," and it's a combination of fear or of perfectionism, of, uh, a lot of-

   30. RHRyan Holiday23:32

       Yeah.
5. 27:15 – 38:08

   Lessons from Marcus Aurelius

   1. CWChris Williamson27:15

      So that would be somebody, not with excess discipline, but with, um, discipline that is heavily focused perhaps in a suboptimal direction or perhaps behind them almost. It's focus on tasks that they should have let go of a little while ago.

   2. RHRyan Holiday27:28

      Yes.

   3. CWChris Williamson27:28

      What about someone on the other side of that? What about somebody that achieves the accolades and gets to that stage and then everything falls away? I think you had, uh, was it Robert Mos- Moses-

   4. RHRyan Holiday27:39

      Yeah.

   5. CWChris Williamson27:39

      ... was somebody that was like that, and you could compare him with, like, a George Washington who, or, um... Who was the guy that was in charge in 1944 when America was in the war?

   6. RHRyan Holiday27:48

      Uh, George Marshall?

   7. CWChris Williamson27:49

      George Marshall. Yeah, him. Uh, that would be a big difference, right? You have someone that's basically in charge of, what was it you said, about 70 million human lives were in d-

   8. RHRyan Holiday27:58

      Oh, Eisenhower. Yeah, I was gonna say Eisenhower.

   9. CWChris Williamson27:59

      Eisenhower, sorry. Yeah.

   10. RHRyan Holiday28:00

       Yeah, E- Eisenhower is basically, i- this sort of brief moment after the Second World War, the most powerful man in the world. He leads this enormous army. You know, he's the head of the nuclear arsenal. You know, he is a conqueror of conquerors, the head of th- you know, the most powerful nation in the world for this sort of brief moment. And he has this line that I think a lot about. He says, you know, "Freedom is better defined as the opportunity for self-discipline." And so, you know, we think of discipline as this thing you need to achieve a kind of success, right? And you do. You have to be disciplined on the way up. Uh, but also, like, people make you disciplined on the way up because you have fewer options. There is no other way, right? You, you have to be disciplined about your money 'cause you don't have any (laughs) , right? You have to be disciplined about your work ethic, etcetera because, like, you're in this competition with all these people, and it's sort of a forcing function. But then you get there, you get to the top, and now the rules that previously bound you or the things you needed to prove, that's not there. And so if you're not self-driven, if you're not, you know, enforcing that discipline on yourself, it all falls apart, right? And I think deep down the reason a lot of people are ambitious and wanna be successful is they, they have, they wanna be the president or they wanna be the CEO or they wanna start their own company. What they think is at the end of that rainbow is an exemption from all the rules that they don't like, and in fact, it's those people have to be stricter on themselves. The Stoics would say, "No one is fit to rule who is not first master of themselves." And so the idea is that discipline is, is not this thing that is enforced on you, like, when you're in school, "You can't go to the bathroom at this time. You gotta be here at this..." You know, as you work your way up, a lot of those things not only, th- not only fall away, but actually life says, "Well, what time do you wanna be here?" Right? Like, "What do you want from us? What do you need from us," right? Suddenly-... people are accommodating to you, and so, or, you know, they're building you up, they're telling you how great you... If you don't have this sort of strong internal compass, the strong sense of what you're okay with, what you're not okay with, what you need to do, what you shouldn't do, then the success is gonna be deeply unmooring, right? And deeply disconcerting and, and l- liable not to last because you've... It's like you ran past all the barriers and now you're just there. And so, uh, yeah, discipline has to be this kind of internal thing that you cultivate that stays with you, whether the circumstances are really good or really bad.

   11. CWChris Williamson30:57

       Do you not think that this is where Commodus would have probably played a stark contrast to his father's role?

   12. RHRyan Holiday31:04

       Yeah. I mean, what's so interesting about Antoninus, Marcus Aurelius, and then Marcus Aurelius's son, Commodus, you have sort of a great emperor, a greater emperor, and you have one of the worst emperors. And why, why is that? Um, I don't... I, I mean, there's so much we don't know, right? We don't know what their relationship was like. We don't know what happened. It could be that Marcus Aurelius was the greatest father in the world and his son was a psychopath, right? Um, we know there's a, there's a, just a tragedy... The whole thing is tinged in tragedy in the sense that, you know, Marcus Aurelius had 12 or 13 children and every one of his sons dies. Commodus is the only one. Um, we have some sense that Marcus, for instance... The first thing Marcus Aurelius does with absolute power, this, this incredible moment in human history, he's named emperor and he anoints his brother, his stepbrother, co-emperor. The first thing he does with his power is he shares it, right? Uh, which is a nod to the old Roman system which had two consuls, like had two presidents who would serve, like co-presidents who would serve these one-year terms. Then Rome becomes an empire and, uh, and, and this changes, but Marcus says, thinks that there needs to be this kind of check on power, and so he and his brother serve as co-equals. We get the sense that he s- he was setting up some system where two of his sons or his son and his co-emperor's stepbrother's son-

   13. CWChris Williamson32:38

       Oh.

   14. RHRyan Holiday32:38

       ... would rule together.

   15. CWChris Williamson32:39

       Okay, so do you think that maybe Marcus was trying to future-proof any one tyrant from being in too much control 'cause you would always have this other person, and by doing it at the moment that he was given power, it set... It was the, the, the highest cost that he could pay?

   16. RHRyan Holiday32:56

       Yes.

   17. CWChris Williamson32:56

       Yes.

   18. RHRyan Holiday32:56

       Like, one of the most beautiful passages in Meditations, again, it's his pri-... You have the private journal of the emperor of Rome and, and he's saying, "Be careful not to be Caesarified. You can easily be dyed purple," he says. The, the, the Roman emperor wears a purple cloak and he, he's saying, "You, you can't be dyed purple. You can't be stained or changed by this position you're in," right? We, we have Lord Acton's rule of, like, absolute power corrupts absolutely. He was saying, like, he, he was consciously talking to himself about trying to prevent that from happening, and I think obviously the decision at the very beginning to share power is, like, uh, you know, a, a, a very big sort of step. Like, it, it's preemptively trying to prevent that from happening, and we, we believe that his succession plan for his son was to set up some sort of system or tradition where that happened again. The other quirk is Marcus is the only emperor of five emperors in a row to have a male heir. So Marcus, hi- Marcus's father is not Antoninus. Marcus... A- Antoninus is his adopted father, just as, uh, Antoninus's adopted father is Hadrian and Hadrian's adopted father is Trajan. It... There's this period, there's this process. So Marcus isn't able to do that, right? He's not able to choose an heir 'cause he has a male son, uh, but we get the sense that he wanted to have two... Maybe one his son, one of his brother's son, or two of his sons rule together, um, but you know, the best-laid plans, they all die, and so Commodus is the only one left, and you know, we don't know what Marcus thinks of Commodus. We can imagine every father is blind to a certain degree to the flaws of their children and trapped by, you know, insaneness of this system, uh, but certainly something goes wrong, and it's, uh, a tragedy of, uh, and in some ways an indictment of Marcus, right? Like, if you're the most disciplined, you know, decent human being but somehow you're not able to pass that along to your family, I mean, what does it say? It, it, it raised a lot of questions for sure.

   19. CWChris Williamson35:15

       That is interesting, the fact that you have this emperor, philosopher, god king thing going on. Incredibly giving, very benevolent, very caring, you know, was... Equality, like ideas that were-

   20. RHRyan Holiday35:28

       Yes.

   21. CWChris Williamson35:29

       ... literally millennia before their time.

   22. RHRyan Holiday35:30

       Yeah.

   23. CWChris Williamson35:31

       And yet one of the few roles that every father has-

   24. RHRyan Holiday35:35

       Yeah.

   25. CWChris Williamson35:35

       ... that they need to fulfill somehow happened, but then everybody is so idiosyncratic and unique an individual, you don't know... I mean, we all know about the rebellious rich kid that happens to be a dick-

   26. RHRyan Holiday35:47

       Yeah.

   27. CWChris Williamson35:47

       ... who d- smashes up the father's car and has parties in the house when the parents are away and all that stuff, so...

   28. RHRyan Holiday35:53

       Yeah.

   29. CWChris Williamson35:53

       And the... I suppose the open loop here that may never, is most likely to never be closed unless we discover some more hidden something-

   30. RHRyan Holiday36:00

       Yeah.
6. 38:08 – 44:30

   How Principles Can Aid Focus

   1. RHRyan Holiday38:08

   2. CWChris Williamson38:08

      That's the interesting element about the life cycle that discipline has, especially as you progress as a human. That in the beginning, it's about working hard, it's about, uh, l- leaning in. As you start to develop more and more, it's actually perhaps a little bit more about leaning away. It's about restricting the options that you have. It's about leaning in a little bit less, and that what got you here won't get you there mentality-

   3. RHRyan Holiday38:34

      Yeah.

   4. CWChris Williamson38:34

      ... has never been seen more for me than l- watching that kind of transition at least begin to happen in- in my life as well where I'm like, "Look, I have more things that I need to say no to than things to say yes to." And I was a, uh, pathological yes-er. Um, so I'm like, "Okay, well, what do I, what do I do now?" I- I can't people please anymore.

   5. RHRyan Holiday38:53

      Sure.

   6. CWChris Williamson38:53

      Uh, I- if I take my eye off the ball on the main thing, the main thing is the podcast, that needs to happen. I need to prepare. I need to choose guests that I'm interested in. I need to make sure that I am on my game as much as possible. That's the- the single ordinating function. Two examples actually that I keep on using, uh, and I don't know whether you came across them. So apparently when he was at Amazon, Jeff Bezos filtered every decision through one heuristic, and it was, does this make the customer experience better? And apparently, uh, Elon Musk has got the same, and it's, does this get us closer to Mars? And I don't know if it's true, but...

   7. RHRyan Holiday39:27

      It certainly doesn't look like he's following said rubric.

   8. CWChris Williamson39:30

      That's up for debate.

   9. RHRyan Holiday39:31

      Yeah.

   10. CWChris Williamson39:31

       Uh, my point being, even if it isn't, the idea, you can see how much more simple everybody's life would become if you had a single ordinating principle.

   11. RHRyan Holiday39:40

       Yeah.

   12. CWChris Williamson39:40

       It's like does this make the people of Rome, uh, uh, their- their existence better?

   13. RHRyan Holiday39:45

       Yeah.

   14. CWChris Williamson39:46

       Everything from do I have wine tonight, to what time do I get up tomorrow, to who do I have meetings with, and this is where the multiplicity of options that people have in the modern world creates a difficulty for discipline, I think, because the- the- the amount of distractions that are there.

   15. RHRyan Holiday40:01

       Well, that's the idea. If you- if you don't know what port you're sailing towards, no wind is favorable. How do you judge whether you should do X or Y, whether you should do it now or later, right? Whether you should say yes or no. Y- how much you should charge, how long it should take. You don't know any of the things unless you know where you're trying to go. Like for me, I- I don't have like a- a question where I'm like, "Hey," like, "is this helping me become the most of this or the most of that?" I kind of think about it 'cause the reality is we have multiple things, right? So if- if Marcus Aurelius is I gotta be the, the, "Is this good for Rome?" Well, you know-

   16. CWChris Williamson40:38

       What about your son?

   17. RHRyan Holiday40:39

       ... is this good for my son? Right.

   18. CWChris Williamson40:40

       Yeah.

   19. RHRyan Holiday40:40

       So, I think about it in terms of like, I wanna be very good at my professional life. I wanna be a great writer, I wanna be a great husband, and I wanna be a great father. And those three things are related, but also in tension with each other. But the nice part about the tension is it prevents you from going too far in one direction. And I think it- it sort of forces a kind of discipline. 'Cause there's things I could do that would make me more successful as a writer, but would come at the cost of my marriage. Or there's things, uh, like that my wife and I could do that would make our marriage better, but then, you know, we're personally happier, but we're gone all the time or whatever, right? Like you have to think about how these things matter to each other or balance with each other. And, uh, my friend Austin Kleon, uh, said to me once, he said, um, actually right when I moved to Austin, he said, uh, "Work, family, scene. Pick two." So the point was, you can be good at your work, you can have a family, but like partying, being cool, ex- like the fun experiences, the perks of the job, you know, you gotta say no to that. Conversely, you can be great at your job and party it up, but like, you're probably not gonna find that person, or your kids are gonna be like, "Where's Dad?" Right? So you- you can't have all those things, and- and when you know, okay, well the important things to me are work and family, or the important things are family and having a good time, okay, well, you're gonna leave some potential, some your- whatever your magnum opus is, it's not gonna happen, right? And so knowing that, okay, here's what I want and then here's will- what I'm willing to trade or give up to that- to get that thing, you know, like that clarity is super, super important.

   20. CWChris Williamson42:19

       What was that word?A- akrasia? Akrasia?

   21. RHRyan Holiday42:23

       Yeah. The- the idea that there's sort of a higher self and a lower self, and these-... it's sort of, for the ancients, there was this sort of perennial battle between the higher self and the lower self. And, you know, discipline, to me, is the deciding factor, right?

   22. CWChris Williamson42:41

       To mediate them.

   23. RHRyan Holiday42:42

       W- which wins, right? You know, w- w- what side are you just gonna win out here? And, you know, it takes a- a- a sort of a strength of will. The- the story I, uh... that goes to the beginnings of Stoicism, uh, is the, it's called The Choice of Hercules. Hercules is walking through the hills of Greece, and he comes to this crossroads, and basically, there's two goddesses. One is the goddess of vice, and the other is the goddess of virtue. You know, basically one is the lower self and the higher self, the easy way and the hard way, and he has to choose, you know? He has to choose. Do you get, you know... Do you get everything you want, and it's easy? Are you willing to work for it? Are you willing to sacrifice, you know, virtue or vice? That choice of Hercules was at the essence of, you know, Stoicism. Are you, are you, are you choosing the disciplined way or the ill-disciplined way, uh, you know? And that choice, we- we face that choice not just like this one big pivotal moment in our lives, where you choose between, "Am I gonna go for it or not go for it?" But like you said, you- you- you also choose it every day. "Am I gonna eat this or that? Am I gonna get up at this time or this time? Am I gonna push through when it's hard, or am I gonna wait for it to be easy?" Like, that choice happens over and over and over again. And the Stoics would say that, you know, if you wanna be beautiful, if you wanna be great, you have to make beautiful or great choices. It comes down to, over and over again, we have this choice of Hercules, and do we make it often enough? I don't, I don't know if you have to make it always, but more often than not, you have to make that right, beautiful, great choice, and that is what determines whether you will be those things.

   24. CWChris Williamson44:29

       Do you think there's a

7. 44:30 – 53:37

   The Downside of High Standards

   1. CWChris Williamson44:30

      risk of attaching a sense of self-worth to your ability to be disciplined? It seems to me that a lot of the friends that I have who are superbly disciplined spend more time lambasting themselves for missing out by one to 5%-

   2. RHRyan Holiday44:46

      Yeah.

   3. CWChris Williamson44:46

      ... on the- the perfect game for each day-

   4. RHRyan Holiday44:49

      Yeah.

   5. CWChris Williamson44:49

      ... because their- their meditation was good, and they did it, but maybe they thought about work for a minute of their 15-minute meditation. Do you know what I mean?

   6. RHRyan Holiday44:56

      Yeah.

   7. CWChris Williamson44:56

      It makes you fragile.

   8. RHRyan Holiday44:57

      Well, the- the paradox of- of having high standards is that it makes you more likely to reach great heights, but also almost constitutionally unable to enjoy or appreciate or even recognize that that's where you are, right? Like, the person who goes, "Oh, that was the greatest game in the world. I crushed it," is, you know, not going to see all the things they could've done better, right? The person who goes, "Oh, but I messed up this, this, this, and this," that person is tends gonna be the one... Is- is going to tend to be the one that's improving and growing, and- and- and that's good, but it's also not a recipe for happiness, for contentment, for sustainability. Seneca is writing this letter to his friend, Lucilius, and- and they're talking about Stoicism, this idea that, you know, you try to get better every day, hold yourself to these high standards, you know? And at this point, he's probably in his 60s or 70s. He's been doing this a long time. And he goes, "How do I know..." he's sort of rhetorically, but maybe Lucilius had asked him, like, "H- how do you know you're doing it right," right? And he goes, "How do I know that I'm doing it right, that I'm getting better?" And he says, "I- each day, I become a better friend to myself. That's how I know I'm making progress." And I think what he means is that discipline or Stoicism is not this constant whipping of oneself, this constant feeling of falling short, of not being good enough, being like, "You piece of shit. I hate you." Like, "Look at... You coulda done all these things better." But it's a sense of like, "You did your best. Good job. I love you. I respect you. Uh, there's still room to grow, but there's nothing that you have to feel guilty or terrible about." And I think it's, if- if you wanna do this well, you wanna do it sustainably, uh, you have to understand that discipline is not a form of self-flagellation. It should not be hurtful. Uh, you should love it. Like, in Meditations, Marcus Aurelius says, "Love the discipline you know and let it support you." And I think he- he means that discipline in both senses. He means the philosophical discipline, but he also means like the practice of it. And I- I think that love and support are two, like, operative but also, uh, underrated words there, right? Like, it- it... If you feel bad about yourself, and that's what you think discipline is, I think you're getting it wrong.

   9. CWChris Williamson47:28

      It's a motivating factor though, right?

   10. RHRyan Holiday47:29

       Sure, yeah.

   11. CWChris Williamson47:29

       That's why people do it. They- they need to have both carrot and stick, and for the most part, a lot of the people I think that are seduced by heavy discipline, they're stick people.

   12. RHRyan Holiday47:39

       Yeah.

   13. CWChris Williamson47:39

       A good example of this, so Andy Frisella, who, uh, reached out a couple of months ago, he did that 75 Hard thing. He was the guy that made 75 Hard. Have you heard of this?

   14. RHRyan Holiday47:47

       No.

   15. CWChris Williamson47:48

       Okay, so it's a- a challenge for 75 days in a row, and you have to do two 45-minute workouts, read 10 pages of a non-fiction book, m- m- meditate, uh, drink a gallon of water, do something else, and don't break your diet.

   16. RHRyan Holiday48:04

       Okay.

   17. CWChris Williamson48:04

       Something like that. It's like a list of- of things.

   18. RHRyan Holiday48:06

       Yeah.

   19. CWChris Williamson48:06

       Kind of basic but pretty intense. And if you miss any one thing on any one day of the 75, you go back to the start-

   20. RHRyan Holiday48:15

       Mm-hmm.

   21. CWChris Williamson48:15

       ... and you start again. And from the outside, I loved the idea... I haven't done it, but I love the idea of something that created a framework for people to build discipline around. However, I haven't got a single friend that's done 75 Hard and not snapped afterward.... and not gone to a, a period of, um, a decrease in discipline. Even if you smeared it across 150 days-

   22. RHRyan Holiday48:39

       Yeah.

   23. CWChris Williamson48:39

       ... their discipline overall is lower. One of the guys didn't train for half a year after he did it. One of the guys didn't meditate. Another one of the dudes couldn't bear to go into work and do a bunch of other stuff because they just myopically nailed themselves to this goal and sustainable perseverance, commitment over time. Like, these are the sort of words I think that being introduced into a more holistic view of discipline would be interesting.

   24. RHRyan Holiday49:01

       The magic words for me are "more often than not." Like, more often than not, are you doing what you're supposed to be doing? Are you, uh, holding yourself to high standards? Are you taking the, you know, the, the hard choice over the easy choice, putting in the extra? More often than not, are you doing it, right? If you, if you try to hold yourself to this perfect or impossible standard, um, not only are you liable to sort of not do it, uh, and then feel terrible afterwards, but I think it can so often come at the expense of other things that are important. Or it become- you become so terribly out of balance that it's almost an excuse, right? You're like, so, uh, y- you do some challenge for 30 days or 75 days or whatever, it's like, they don't throw you a parade at the end, you know? I mean, look, I, I, I appreciate the idea of challenging ourself, pushing ourselves. And to a certain degree, all discipline is arbitrary. But like, I'm not trying to just win made-up competitions or check arbitrary, you know, things off the list. I, I want to, I want to do this consistently over a long period of time. So I, I run. And so one of the things that happens when people, when y- people find out you're a runner, they go, "Oh, are you running a marathon? Are you training to do an Ironman?" I'm not trying to win at my hobbies, you know? Like, the, to me, the doing the thing is the reason I'm doing it. It's good for me for a variety of reasons. If I... But, but it could very easily become an unhealthy, unproductive thing that comes at the expense of the other things that are important to me. So, I think sometimes people can get caught up with seeing it, again, as this kind of a means to an end when it, it should be a sort of an integrated practice into your life.

   25. CWChris Williamson50:49

       I think that this becomes very prevalent when you grow up a little bit. That my ability to view broader time horizons has only really kicked in in the last couple... I'm 34. It's only kicked in in the last few years. That you presume the thing you're doing now is going to be the way that life's going to be forever, and the training plan that you do now, even if there's a 10%, 20% risk of injury over the next six months doesn't matter because you want to be jacked to go away on summer holiday or whatever. And then after a while you realize, no, my goal is in 20 or 30 years to be significantly more capable than I am now.

   26. RHRyan Holiday51:24

       Yeah.

   27. CWChris Williamson51:25

       What is the route between me now and me there? And the fear and the, um, degree of neuroticism around it being, "Well, it's, it's not fast enough, it doesn't happen quick enough," that dissolves quite nicely.

   28. RHRyan Holiday51:38

       I was talking to the Olympian, uh, Kate Courtney. She's this amazing, uh, mountain bike racer, and she was telling me, you know, like her, her coach would give her a workout. She'd be like, you know, "Ride 20 miles." She'd ride 25 miles. Or, you know, "Do it in two hours," and she'd do it in 90 minutes. And I think a lot of successful driven people understand that impulse. Like, you're like, "I want to win everything," right? Even practice. And he said to her once, uh, and, and when I signed, uh, her copy of Discipline Is Destiny, I, I wrote this in it 'cause I think about it all the time. Uh, he said, "Do you want to be fast now or do you want to be fast later?" Right? The purpose of training, the purpose of practice is to peak in the race, in the moment that it matters. Um, life is a little bit different than the Olympics 'cause there is no sort of one moment. But if you have this idea that, you know, your big moment is in the future, that it's a marathon and not a sprint, the idea of sort of forcing it now, peaking early is actually something you should be quite worried about. So you have to be disciplined about your discipline. You have to curb that impulse-

   29. CWChris Williamson52:46

       Mm-hmm.

   30. RHRyan Holiday52:47

       ... to do, in some ways, the easier thing now, which is like, "I want to go all out. I want push everything into the center of the table. I want to go now." But now might not be the moment, and the ability to step back, to restrain yourself, to, to, to, to focus on sustainability and endurance and all that, you know, it, it's... may well be the harder thing. And so it's like, do you want to be great now or do you want to be ready when like a truly great opportunity is there? Do you want to do your best work at 22 or the only work at 22, or do you still want to be doing this when you're 82 because you love it? Because you'll have more experiences and wisdom and all that stuff now, and those are the kind of questions I think people at a really elite level are thinking about.

8. 53:37 – 58:19

   The Tragedies of Lou Gehrig & Babe Ruth

   1. RHRyan Holiday53:37

   2. CWChris Williamson53:37

      What was that comparison between Lou Gehrig's career and Babe Ruth's career and how their trajectories went?

   3. RHRyan Holiday53:44

      Well, I mean, clearly, Lou Gehrig and Babe Ruth are two of the greatest baseball players of all time. Uh, both achieve incredible athletic feats. But when you look at Lou Geh- or when you look at Babe Ruth, you're sort of like, "How?" Like, "How did you even..." Like, he doesn't look like an athlete, and so in some ways he's very impressive that he could hit all these home runs. But you, you definitely get the sense, and, and the more I think you study, uh, you know, sort of elite performance throughout history, sometimes you're just amazed and saddened at the greatness of someone because you're like, "How did you do it and what could you have been capable of if you weren't your own worst enemy?" So both Lou Gehrig and Babe Ruth's careers are cut short, right? Uh, Lou Gehrig from Lou Gehrig's disease or ALS, and then Babe Ruth, I mean, this wasn't a guy who took care of himself. He burned through millions of dollars. He treated his body like a garbage can. You know, he sort of has this precipitous decline at the end and, you know-He was not Tom Brady, right? Like, uh, in peak, uh, athletic conditioning at the end of his career. He was a obese, you know, uh, drunk old man, right? And I thi- that's so tragic to me, right? And- and th- to me, the idea is, like, if you respect the craft, if you really love the thing you're doing, you owe it to that craft to- to take the responsibilities of it seriously, right? And I think, um, I- I- I wanted to show that contrast because we so often just assume, oh, this person accomplished all these things, therefore it's good. But what else could they have done had they had more discipline? And I think one of the small consolations of someone like Lou Gehrig is you go, he left it all in the jersey. Like, there was nothing that he could have done in his career that he didn't do. The only thing that, uh, the only tragedy was that, for reasons that were not his fault, he didn't get to do it as long as he could have done it, right? But the games that he played, he showed up for, and he played them. And I think about that, you know, every day when I wrap up. I'm like, "Did I leave it all there? Or did I phone it in today? You know, did I, uh, make excuses today? Did I not bring my best self to this thing?" And again, more often than not, you want the good answer to that question.

   4. CWChris Williamson56:16

      I like the idea of the more often than not because it means that an individual repetition that is suboptimal, today I- I just didn't quite work, it seems like it would give you a little bit more detachment from it-

   5. RHRyan Holiday56:29

      Yeah.

   6. CWChris Williamson56:29

      ... and I think that that's very important.

   7. RHRyan Holiday56:31

      Yeah, you, Marcus Aurelius in Meditations goes, "You got to pick yourself up when you fall, but also celebrate that you're a human being, that none of us are perfect, that we're gonna mess up, we're gonna screw up." But if you have this sort of baseline that you- you know what you're capable of, you know what you should do, you know that you're not always going to be able to do it, but you know what to come back to, to me is more important than having these impossible perfect standards that are almost in their own way paralyzing or impossible or discouraging. And- and so I think cultivating a kind of, r- like a rhythm, that there's, like, this thing, and sometimes you, sometimes you fall off the rhythm, but you know how to come back to it. That, to me is a- a more sustainable, conscious, kinder way-

   8. CWChris Williamson57:21

      Yes.

   9. RHRyan Holiday57:21

      ... to be c- committed to something.

   10. CWChris Williamson57:24

       I think that, again, that's something that you learn through experience. I was locked into, perennially locked into a work so hard that I can't take it anymore, burnout, sp- spend three days in bed-

   11. RHRyan Holiday57:39

       Yeah.

   12. CWChris Williamson57:39

       ... work so hard. That was me.

   13. RHRyan Holiday57:40

       Sure.

   14. CWChris Williamson57:40

       That was, that was the cycle of how I worked pretty much for most of my 20s. One of the advantages of doing that was that now I know some of the warning signs when I start to get close to that-

   15. RHRyan Holiday57:50

       Yeah.

   16. CWChris Williamson57:51

       ... and I can just-

   17. RHRyan Holiday57:52

       You wobble a little bit.

   18. CWChris Williamson57:52

       Yeah.

   19. RHRyan Holiday57:52

       Mm-hmm.

   20. CWChris Williamson57:52

       And I can just about fly underneath that a little and go, "Okay, how long can I hold this for?" And-

   21. RHRyan Holiday57:57

       Yeah.

   22. CWChris Williamson57:57

       ... I'll back off a little bit more. But it's less of this.

   23. RHRyan Holiday58:00

       Yeah.

   24. CWChris Williamson58:01

       Uh, apart from the fact that it's less efficient because three days of doing nothing is a lot worse than a couple of days of doing 50% of something.

   25. RHRyan Holiday58:08

       Yeah.

   26. CWChris Williamson58:09

       But it's just s- (laughs) suffering. The difference in terms of suffering is- is pretty drastic. And I think another interesting example, so you're talking now about two

9. 58:19 – 1:08:02

   Can You Achieve Extreme Results in a Balanced Life?

   1. CWChris Williamson58:19

      different types of athletes, one of whom left everything on the table, another one who didn't, and, you know-

   2. RHRyan Holiday58:24

      Yeah.

   3. CWChris Williamson58:24

      ... took it in a way. Michael Jordan seems to be someone that was almost tyrannical in the way that he went about his game and left it all on the table but did it in a way that sacrificed everything else, pretty much everything else. Do you think that it's possible for people to get extreme results in life whilst still having that balance? It seems like you're trying to- to do that, and that was the two out of three, uh, example.

   4. RHRyan Holiday58:49

      (laughs) To me, that- that's the challenge. Like, it's almost easier to be great than it is to be good. And I- I don't mean to contrast good and great in that sense. I mean that, like, like, to say, "I don't care about anything but succeeding in this thing," is almost taking yourself off the hook to a certain degree. There was a- a- a writer once, she said, like, "I don't want to have kids. I don't want to get married. I want to be an art monster." Right? And I get that, right? I think anyone who's like, loves what they do, there's a certain, like, "I want to be the center of everything. I only want this thing to matter." But that's almost the easier path, right? Like, to- to- to be like, "Well, why is this person an asshole?" And they're like, "Well, they're great." You know? Like, that, it's- it's, I think sometimes people think that their innate talent, or their success, or their commitment to a path or a goal is, like, an exemption from the rules of human behavior, right? Um, I don't have to care about other people. I don't have to keep my word. I, you know? There's a- there's a story about this writer. I'm forgetting her name, but she was at this party. She had a young daughter, and, uh, she's a poet, and she's at this party and Jack Kerouac is there. And she, you know, it's one of those famous parties, and she's there, and- and, uh, she gets up to leave. She goes, "You know, I- I, um, I promised the babysitter I'd be home by 10:00." She has, like, a young daughter, had to leave. And Jack Kerouac, you know, sort of a different model of a kind of writer, says, "You know, if you don't forget about that babysitter, you'll never be a great writer." And she gets up and she leaves anyway, and- and she says later, "I knew in that moment that if I didn't keep that promise to the babysitter, I wouldn't be a great writer." And her point was that, like, having some talent, some calling doesn't exempt you from keeping your word. And that, in fact, if you tell the babysitter you're gonna be home at 10:00 and then you blow that off, you're also the kinda person that says, "I'm gonna be at my desk writing by 9:00."... and you break that promise also, right? And so actually, I think cultivating a practice or a set of standards that are more than just, like, how good are you professionally, makes you a more well-rounded and better professional. And the people that I really admire are people who have, you know, gotten to the commanding heights of their profession, but are still good neighbors, and citizens, and activists, and fathers, or daughters, or wives. Like, I- I just... There's something, to me, hollow and, and kind of a cop-out about being great at one thing at the expense of all the other things, when, especially at the end of your life, you don't get to take that thing with you, you know? Um, you don't get to take it with you. So, what does it matter that you made more money or you wrote one extra book? Like, you're gonna sit back and go, "I really fucked it up."

   5. CWChris Williamson1:02:01

      That's why it's so important to start with the end in mind, I think.

   6. RHRyan Holiday1:02:03

      Yeah.

   7. CWChris Williamson1:02:03

      Why am I doing this?

   8. RHRyan Holiday1:02:04

      Yes.

   9. CWChris Williamson1:02:04

      What are the ordinating principles that I have-

   10. RHRyan Holiday1:02:07

       Yes.

   11. CWChris Williamson1:02:07

       ... that I'm working toward?

   12. RHRyan Holiday1:02:08

       Yes.

   13. CWChris Williamson1:02:08

       Because, yeah, you could spend a very, very long time climbing up a ladder to find out that it's up against the wrong wall.

   14. RHRyan Holiday1:02:14

       Yeah, I mean, and how many people, they're on the medal stand, you know, they're accepting the Nobel Prize or, you know, they've- they get to that number they told themselves, like, "I wanna make th-" and then, f- like, "This is it?"

   15. CWChris Williamson1:02:27

       What was that thing about- about beyond mountains, there's more mountains?

   16. RHRyan Holiday1:02:31

       Yeah, it's a Haitian proverb, behin- beyond mountains, there are more mountains. But I think it's more, it's more like you think that this thing is going to fix it, "It's gonna make me feel good, it's gonna make my parents proud of me, it's gonna make me part of a club." We think that these external things are gonna address this internal lacking or need or emptiness that we have. And I- I've done a lot, I've read a lot, I've talked to a lot of people, I've yet to find someone that got it. It just- it's a, it's a mirage. It- it- it's a phantom. You get there, and it moves. And, uh, in one sense, that's a tragedy. In the other sense, it's a great gift, right? The first time you do that thing and you get it, the thing you've been working for, and then it isn't what you thought it would be. If, in that moment, you can accept the gift you've been given, which is a decoupling from external success and internal contentment, happiness, enough-ness, if you can make that break in that moment, you're free and empowered forever. Because now, you can still do the things that you're good at, you can still want them, but you, you are no longer at the whims of this lie or this delusion.

   17. CWChris Williamson1:03:57

       Yes.

   18. RHRyan Holiday1:03:58

       Uh, but what most people do in that moment is tell themselves a second lie, which is, "Oh, it's- I have to prove I can win an NBA championship on my own. I have to show that this wasn't a fluke. Oh, it's not $10 million. Actually, it's $100 million," right? Or it's- it's not number two that's enough. It's, "I gotta be number one." Um, if that's what you do, I think you have- i- i- you have made a bargain or told yourself a lie that is now almost impossible for you to get free of.

   19. CWChris Williamson1:04:37

       I think the people need to see that for themselves.

   20. RHRyan Holiday1:04:40

       Yes. Yes.

   21. CWChris Williamson1:04:41

       I've been told this lesson a million times.

   22. RHRyan Holiday1:04:45

       Yeah.

   23. CWChris Williamson1:04:45

       And I- each time that something good happens that feels like a success, it helps me to prove that same rule to myself-

   24. RHRyan Holiday1:04:54

       Yes.

   25. CWChris Williamson1:04:55

       ... a little bit more.

   26. RHRyan Holiday1:04:56

       Yes.

   27. CWChris Williamson1:04:56

       Uh, Robert Wright's Why Buddhism is True, in that he talks about, um, life is suffering, said by the Buddha.

   28. RHRyan Holiday1:05:02

       Yeah.

   29. CWChris Williamson1:05:02

       And the word Dukkha, D-U-K-K-H-A, contested by some scholars as not meaning suffering, but unsatisfactoriness. Life is unsatisfactoriness. And given that, uh, Robert is a evolutionary psychologist now writing about Buddhism-

   30. RHRyan Holiday1:05:17

       Yeah.
10. 1:08:02 – 1:15:13

    What Ryan Learned from Queen Elizabeth

    1. CWChris Williamson1:08:02

       You mentioned Queen Elizabeth-

    2. RHRyan Holiday1:08:04

       Yeah.

    3. CWChris Williamson1:08:04

       ... earlier on. What did you learn about her?

    4. RHRyan Holiday1:08:07

       Well, I think she's this remarkable person. I mean, when you look at someone, you don't wanna talk about sustainability, you have this job for 70 years. And, you know, the, as I was saying, the idea of Marcus Aurelius is given these privileges, this immense power, platform, et cetera. And he proves himself worthy of it. I mean, look at the outpouring of support for this woman when she died, even from people who have sort of an ideological disagreement with the monarchy. Uh, to me, that's very high praise, when people who disagree with what you do still find the way that you did it to be admirable and impressive. And, you know, she was a remarkable picture of restraint and dignity and poise. Tradition, but also flexibility and innovation. And I, I just, you know, discipline is not just how far can you run, you know, how hard can you work? It's also, you know, are you in control of yourself? Like, you're ta- you wanna talk about someone who was in command of themselves, this is a woman who over 70 years never lets the mask slip, never has the outbursts, never has the, you know, dropping of the... For 70 years, she's like on point for a thing that she didn't choose, for a thing that, you know, only because of a quirk of history even was in a position to take.

    5. CWChris Williamson1:09:36

       Tell people that story, in case they're not familiar.

    6. RHRyan Holiday1:09:38

       So, uh, her uncle was the King of England. Uh, he abdicates in this sort of fit of passion as he's in love with this terrible woman, basically (laughs) . Uh, and suddenly Queen Elizabeth's father becomes king. You know, you, he would've been expected to rule for 20, 30, 40 years. Instead sort of dies I think after like 20, 25 years. The, d- uh, uh, uh, her father dies unexpectedly young of lung cancer. And then in her, what, late 20s, early 30s, is I think, yeah, early 20s, is suddenly the queen of, of this enormous empire. Uh, and what is her job? You know, her job is better defined by all the things she's not allowed to do as opposed to the things that she can do. It's this symbolic role. And, you know, I wanted to illustrate the idea of discipline. Again, it's not just grr, but it's also when you feel like grr and not doing it, right? The restraint and poise, uh, the, the ability to, to want to do something, to very understandably want to do something and then to not do it, because it's not the right thing to do. That-

    7. CWChris Williamson1:10:53

       Becoming-

    8. RHRyan Holiday1:10:53

       Yeah.

    9. CWChris Williamson1:10:54

       ... the queenly...

    10. RHRyan Holiday1:10:55

        That, that, that is a kind of discipline and grace that I think we need to see more of. You know, when you think about, you know, like, "Why is this person tweeting this? Why are they saying this? Why are they doing this?" And you're like, "Well, they can." You know? Not 'cause it's the right thing to do, not 'cause it's important, not 'cause it's gonna accomplish X, Y, and Z, but this kind of lack of self-control, I think. She is a, she is a inspiring picture of what self-control can look like. And not, not self-control in the masculine sense, which is what we, I think we so often tend to stereotype it as.

    11. CWChris Williamson1:11:31

        How would it be feminine?

    12. RHRyan Holiday1:11:33

        Well, I just mean like, she's, she's not... This isn't a physical thing. This is a, a spiritual and emotional and a mental thing.

    13. CWChris Williamson1:11:41

        Yeah. As you're getting news headlines written about you that are claiming you think a thing or did a thing or were part of a thing, and you don't have the compulsion to write a response to.

    14. RHRyan Holiday1:11:51

        Well, and it, like, she's a, she was a little old lady, you know?

    15. CWChris Williamson1:11:54

        Mm-hmm.

    16. RHRyan Holiday1:11:54

        And that i- it, she's not this big, hulking thing. She's a little old lady. And yet, you know, was more restrained and disciplined than these ambitious prime ministers, male or female, right? Like, she, she had a, a sort of a different path to power. And in a world where everyone says everything that they think and is constantly fighting for their recognition, for their chance in the spotlight, I think she's a really powerful example, or was a really powerful example that the opposite of those things is often more impressive or a better path.

    17. CWChris Williamson1:12:33

        Didn't Martin Luther King get punched by a Nazi or something, and it was, that's kind of a similar situation?

    18. RHRyan Holiday1:12:40

        Yeah. Uh, yeah, again, uh, we tend to think of discipline as strength, force. Um, there's a, a moment, uh, in Martin Luther King's career. He's obviously a committed proponent of non-violence. And it's, it's one thing to be like, "Strategically, we are marching from here to there. The police are gonna attack us, we just need to keep going." You know, he's, he's on stage and a, and a, and a Nazi, uh, walks on stage and just-... starts punching him in the face, in front of everyone that he knows. And what people said they found... So he's, so he's attacked, so first, uh, you know, he's hit. And, uh, the natural human thing when you're hit would be to protect yourself, which he does, instinctively hits himself. And people said the shocking sound, like, the, the auditorium goes dead silent. You could just hear, you know, flesh on flesh. And then there's this moment, so he's, you know, he's being tested at the highest levels. He says, "I am a practitioner of non-violence. Um, that doesn't mean I don't just not engage in violence, but, like, what do you do when you are violently attacked?" And in this split second as he protects himself, he catches himself, and they said he drops his hands, and it was like this, you know, it's a, a, this is more than self-discipline. This is some higher, almost saint-like place that he's managed to reach where, you know, again, he's not just protecting himself, not defend- like, not actively defending himself. But he is, for philosophical and spiritual reasons, that the discipline is to actually allow yourself to be attacked in this moment, which he does. Um, and, you know, it was this shocking moment that sort of fundamentally... It teaches the power of non-violence, and that, that tr- that his commitment to the message, more than any other thing that you could've possibly done. Um, and, and then, you know, obviously the man is swarmed, and the first words out of Martin Luther King's mouth are, like, "Don't, uh, don't hurt him. Don't hurt him." And again, it's easy to say these things, but then what do you do in that moment of being tested? And that, to me, it, that's more impressive than, you know, any Olympic gold medalist or, you know, feat of athletic strength, that he's able to conquer his, like, almost innately human need to protect yourself. He's able to stop that in the moment. That, that to me is, you know, discipline at some sort of transcendent, heroic level.

    19. CWChris Williamson1:15:12

        What about perseverance?

11. 1:15:13 – 1:27:08

    The Virtue of Persevering Through Trials

    1. CWChris Williamson1:15:13

       What did you learn about people who coped when things got really difficult? It seems to me that discipline, even in the modern world, you know, no matter how hard it is that you're working toward a thing, and how difficult the pursuit is, it's still quite a bourgeois, sort of luxurious position to be in. You know, we, I e- I know that you recently got a cold tub.

    2. RHRyan Holiday1:15:33

       Yeah.

    3. CWChris Williamson1:15:33

       We've got one in, got one in the house as well. Uh, let's not get that wrong. We are LARPing at discomfort.

    4. RHRyan Holiday1:15:38

       Sure.

    5. CWChris Williamson1:15:39

       We're, we're electing to go into discomfort because w- the world has become so nerfed and so comfortable around us that we need to buy pieces of kit that we can get into that force us to feel cold. What about times... Where, where do you stand? Where can people find that's firm for them to stand when they're doing the discipline and the world just continues to punch them in the face?

    6. RHRyan Holiday1:15:59

       Yeah, I mean, I, I wouldn't, I wouldn't be so quick to dismiss the difficulties of life, right? Like, uh, I think it's good to have practices, physical practices that push us. But, like, life is fucking hard, and it breaks your heart. The, there's Murphy's Law, right? What can go wrong, will. There's also another law that says, like, it always takes longer than you expect, even when you take this law into account, right? Like, it's hard. Like, people go, "I wanna start a podcast." How long it took you before you even started to see rewards or it pay off. I can be... Even just now, you're probably early in it, right? It takes longer than you think. It's fucking hard, and it breaks your heart, you know? Um, is that, is it certainly preferable to, like, starving to get, to death on some, you know, desert plain? Of course, right? Um, it's better than, it's better h- you know, here in this moment than anywhere in history probably anywhere in the world, of course. But, like, if you don't have a sort of a fort- what the Stoics call an inner citadel, kind of a s- a, a fortress that you can retreat into, uh, that, that, that you can rely on, I just, I don't think you're gonna make it. Maybe, maybe algorithmically you get lucky, and it always goes your way, maybe. But to count on that or to let alone expect that, you know, I think is to, is to set yourself up to be crushed by what is inevitably a heartbreaking, difficult, you know, soul-testing process. Paul Graham talks about after the rush of the excitement of an idea, he calls it, like, the TechCrunch bump, right? You get your first bit of attention as a... Then you enter the Trough of Despair, right? And the Trough of Despair is fucking real. Like, every book I start it, it starts off exciting, it's fun, here's what I'm gonna do, and then shh right into the Trough of Despair. And you might not come out of that for months. Like, and by the time you're out of it, you don't even, it, it, uh, catch- oh, I'm on the downhill side of this. Like, I'm... You don't even realize that you're out of it until you're so far out of it that, that you're almost surprised by it. So you have to have this ability to endure, to show up, fucking, every day, even though it's hard, even though it doesn't feel like you're making progress. Even though not doing it would be way easier. You, you have to cultivate that strength, and it doesn't matter if it's, you know, you're trying to become a massage therapist or you're writing a, you know, some, some, like, you know, the, the great American novel. Like, it's fucking hard. Or you're starting some movement, you know, you're trying to build this movement off the ground, uh, from nothing to change the world. Like, it's gonna take a long time. Things are gonna constantly go wrong. It's gonna be way harder than you think. And it might not test you in the sense, in, in the way that, like, starving tests you, but it's gonna challenge you in every conceivable way, and you have to have, you have to have what it takes to get through, and you have to have a really strong why too, or you're not gonna get through it.

    7. CWChris Williamson1:19:02

       One of the other elements that gets laid on top is, I think, shame and guilt around it not being as bad as it could be.

    8. RHRyan Holiday1:19:10

       Yeah.

    9. CWChris Williamson1:19:10

       You know, the fact that...... a lot of the people that do deal with discomfort, it's them choosing to go after a pursuit that they care about. You're choosing to write these books. No one is holding a gun to your head, other than your own existential conscience, but you have to go and write these books. So, okay, well, what, what, what does that mean? How do I ameliorate the fact that I'm, I'm choosing to do a thing, I'm electing to do it, but it's causing me suffering, but I also... The suffering from that, I derive meaning, and on the... it's, uh, it's sort of all this big mess, I think.

Episode duration: 1:37:47