The Learning Leader Show With Ryan Hawk - 385: Ryan Holiday - The Art Of Living (Like A Stoic)

Starting point is 00:00:01 When the journey begins is important, but I'm also as interested in how the journey evolves and how one kind of recommits to it. And it's like if you see the texts as static, then you're going to read them one time and you're going to retain whatever you retain and that's it. If you see it more as this sort of continual thing you're engaging with, the Stoics talk about how we never step in the same river twice, you see it that way, then it's this sort of almost constant. renewing thing, this expanding thing, and that's kind of more how I see the journey. Welcome to the Learning Leader Show presented by Rixie and Meyer. I am Ryan Hawk. Thank you so much for being here. Text learners to 4-4-222. In order to join tens of thousands of learning leaders from all over the world, receive my mindful Monday update when I'm reading, writing, watching, thinking about. Also give you more details about how my book, welcome to management, will help you

Starting point is 00:01:13 become a more effective leader. Text learners to 4422. Now on to tonight's featured leader. He's back. It's Ryan Holliday. Author of many New York Times bestselling books, including ego is the enemy. The obstacle is the way. Stillness is the key. He's, His latest book is titled Lives of the Stoics. A few of the topics we discussed, he shares the one maxim for every successful person. Normally, I would not speak in absolutes, but for this one case,

Starting point is 00:01:55 what he shares is absolutely true. And then the importance and value of belonging to a community. Benjamin Franklin called these, Juntos. And you'll notice towards the second part of this episode, members of my Learning Leader Academy and Learning Leader Circle joined us and asked a few questions. I loved that part. And then towards the end, Ryan shared his specific routine to ensure his productive output is very high and how yours can be too. Ladies and gentlemen, it's always good to talk with Ryan Holiday. All right, Ryan, fifth time, man. It's kind of amazing that this is the fifth time that we've recorded together.

Starting point is 00:02:50 But welcome, welcome back, man. I think you are the number one guest on the history of this show. Well, thank you. When was the first? So that's five appearances over how long? Five years. Makes sense. About one a year.

Starting point is 00:03:03 You write a lot of books. I do too. I don't think we've even. actually covered all of the books because I don't think we got one for conspiracy but we've got some of the other ones so it's good to it's good to have you man yeah of course so in speaking of that that's how I wanted to start this particular conversation because I think this is something that you adhere to and something I certainly try and that is consistency and I'll relate it to a stoic that you've written about in fact the first one in the most recent book I'm going to mispronounce

Starting point is 00:03:35 maybe every single name today. Okay. You're probably used to. Is it Zeno? It's Zeno, yes. Zeno, okay. So his work was not defined by some single epiphany or discovery, but instead by hard work. He inched his way there through years of study and training as we all must.

Starting point is 00:03:53 And Zeno said, well-being is realized by small steps, but is truly no small thing. And this is what I sense is, it feels. to me like a way that you operate, and I think a useful way for all of us to operate, is that it's not this grand, giant project or epiphany. It's the day-to-day work, which is what makes you great and prolific. Well, I appreciate that, and it certainly is at least part of my philosophy that the little things add up. George Washington's favorite expression was, many Mickles make a muckle. I don't know what that means, but I think it's the same thing, which is basically a little. like, look, you show up every day and you put in work. And at least for a writer, what happens

Starting point is 00:04:42 is if you show up every day and you work on the project, after enough days, eventually a book comes out of the other side of that. So a lot of people sort of go into a project with a lot of excitement, with a sort of a big vision. You know, I'll hear people go like, you know, okay, I'm taking the whole month of December off and I've rented a cabin in the woods and I'm going to write the book. And when I hear that, it's like, that's just not enough time. That's not how it works. Not only is that, like, even if you could work 10 hours a day, that's not enough hours. But it's also just not how great stuff is done, particularly ideas. I tend to find, like, I'm about two thirds of the way through my next book right now. And I got hit with, I got hit with an idea today that I

Starting point is 00:05:31 added back towards the interest. But that wouldn't have happened if the time hadn't elapsed in between the beginning and where I am now. So it's not just like, hey, did you work on it a little bit every day? But actually, being in the project for an extended period, it's like a team is better at the end of the season than they are at the beginning of the season, even when you take into account all the injuries and tensions and exhaustion because they now have that much experience to draw on as a as a cohesive unit. Yeah, the legendary Steve Martin said it's easy to be great every once in a while. It's kind of like a lucky hand in poker. What's hard is to be consistently good night after night after night regardless of the circumstances you find yourself in. In his case,

Starting point is 00:06:24 he's talking about doing stand-up comedy in some cases to one person in a bar. And then you see him be an overnight success 10 years later selling out arenas. And I sense that is the unsexy aspect of the work like you do. What I try to do here is that it's about doing it day after day. And then that is what leads to the, as you are now, much more prolific work over time. And I think this relates to any leader in any position. Are you willing to show up day after day after day and be consistent? No, that's right.

Starting point is 00:07:03 I had Mnuj Genoblee on my podcast recently and we were talking about. I mean, the spurs have made the playoffs since I was, I think, nine or 10 years old, maybe more every single year. Now, obviously, a handful of those seasons were much better than the other seasons. I mean, those are the seasons. they went all the way. But I think a lot of teams, a lot of organizations, a lot of people try to put themselves in a position to make one run, like the Buccaneers now.

Starting point is 00:07:35 They're trying to put together this team to be good for like maybe one, two years, right? The heat were like one to two good years. You know, the calves were a few years. The Lakers are going to be in this little window for a few years. But I'm fascinated and much more impressed by, the people were able to build an organization and a set of principles that work over the long period of time. And that's just also just a function of the writing profession. Like I let's say I live to be 70 and there's obviously no guarantees. Let's say I live to be 70. It means I got

Starting point is 00:08:08 potentially 40 more years of this. So in a weird way, I am prolific, but I'm also trying to slow down a little bit and trying to perfect the process primarily for purposes of sustainability. So it's less to do with output for me, although obviously I like the output and the output may stay the same, but I'm trying to fine tune the process and what I put into it so that what I'm putting out is living up to those standards each time. There's a stoic you write about that I think it could be helpful for us to dig into. And again, I'm going to try my best, Clenthes. Cleanthes. Sorry. Okay. So, So he was notable for his continued work. And there's a term, I believe, called philopipiponia.

Starting point is 00:09:03 I don't know how to pronounce any of the things either. I've never heard them said out loud. We talked about this last time. There's so many of these words where we only seen them in print. But anyways, the reason why I like this is because this is what the ancients used to describe a love of work. Yes. I feel very lucky to love the work I do. I think you do as well. And I've, I've sensed that the only way to be truly excellent over a sustained period of time is to have this philipponia, this love of work. And Cleanthes is one of those examples of someone who did that. And again, I sense this is I'm relating it to your life because I think that's what's most interesting is how the Stoics relate to you and then how that relates to. us. And to me, I feel like that is a critical component to doing, to having sustainable,

Starting point is 00:09:56 excellent work. Curious to you. Of course, you could almost pity someone who's extremely talented, but, you know, hates baseball. It's like you have this thing and it feels stupid to not, you know, make a go of it, but, and you still have to do most of the work, but, but, but, you're not going to go as far as you could and you're not going to enjoy how far you do end up going because really what you want to be doing is something else. And so, you know, for me, what I really, like, I've started to realize that, like, I don't actually like publishing books. Like, I have this book coming out and, and obviously, like, you know, we're doing this

Starting point is 00:10:36 interview and this wonderful about this conversation. But all the stuff that goes into putting out a book, like, you know, the printer delays. And then there was this conversation. And then there's how much time do you clear on the schedule? And then, you know, it's like putting out a book in a middle of a pandemic is like a crazy thing in and of itself. It's like if you told me that I didn't have to do any of it and I could just go, I could just be focused on the book that I'm working on now. I'd be happier because primarily what I love is making books. Like I love the thing.

Starting point is 00:11:07 And in a weird way, publishing is the tax that you pay for the gift of getting to do it. Now, I'm a little bit different than I actually also do love marketing. I love the challenge of it. and I've really enjoyed that in other phases of my career. And I'm in a position where I don't have to focus as much on the marketing now because I have an audience for my work. But the point is, like, you've got to ask yourself, do you love the outcome or do you love the process?

Starting point is 00:11:37 And if you're in a position where the process is more pleasurable to you than the outcome, that's vastly preferable place to be. The book we're talking about is called Lives of the Stoics, the art of living from Zeno to Marcus Aurelius. And I think a natural question is, so this, this as I've dug into it, is really, it's the history of some of the most famous and most well-known Stoics in history. Yeah. And you get deep into the lives of each of those from Zeno to Marcus Aurelius.

Starting point is 00:12:11 And I'm curious, what was it about wanting to go deep into each of these leaders, these philosophers, because in your other books, you're focusing on, you'll tell a story about Sean Green and how he uses stillness or the obstacle away. You're bringing in different type of metaphors. This is really showing the history of specific people without much relation to stories of today other than how it could be applied to today. So what made you want to do it this way? So in the other books, I feel like what I'm doing is I'm illustrating the ideas, specific ideas from the philosophy to teach sort of very specific lessons. And that's like what I'm working on now in my next book. But in lives, what I wanted to do was sort of answer this question of like,

Starting point is 00:13:00 well, who are the people that came up with the ideas in the first place? And, you know, I think it would be problematic, for instance, if they were enormous hypocrites or just overall crappy people, or if they were totally theoretical, you know, abstract thinkers who were never put in any position to test the ideas that they were talking about. So the premise of lives is, and Plutarch, one of the great biographers of history talks about this. He's saying, you know, like, biography is one thing. He's like, but lives are different. Lives is like that you can learn more from an anecdote or from a quip or. or from a single response and a single stressful situation.

Starting point is 00:13:48 You can learn more from that than you can from biography. So literally it's a series of biographies, but I'm focused. There's so much stuff that's not in the book. And there were even figures in Stoicism that I didn't include because they just weren't particularly interesting and there wasn't, there weren't events in their life that taught anything.

Starting point is 00:14:10 And so, yeah, the premise of the book is like, well, Zeno, the founder of Stoicism, well, like, how did he come to do it? And is there anything about the shipwreck that he underwent that put him on the path to awakening that created the philosophy that we can learn from? And then, you know, obviously we conclude with Marcus Aurelius, like, well, this guy was a philosopher, sure, but he was also the emperor of Rome. And so what did he do day to day in that job? Did he live up to the ideas? Where did he fall short? you know, how did the philosophy actually help him become the sort of profoundly respected leader that he was even in his own time?

Starting point is 00:14:53 I think what it does is it goes from theory to practice. And as David Epstein has said, or he may have quoted others, we are who we are in practice, not in theory. The actual behaviors, what we actually do on a daily basis makes up us, what a company does, what a business does, their actions are their calls? culture, not what they say. And so to me, that's, that's what this is about is, is, is as if you take this and relate it to the, the person who may be watching or listening, Ryan, who is leading within a business and say, what could I take from lives of the Stoics to actually implement and

Starting point is 00:15:31 execute upon within my team to build a better culture, to overperform, right, to do the things that you're supposed to do when you have a business? What are some of the key takeaways you, you could, you could grab. Well, I think the meta, meta lesson here is, and this is a thing that the Stoics talk about from day one, you know, Marcus Aurelius says, he says, you know, don't talk, he says, waste no more time arguing what a good man is like B1 and Epictetus says, don't talk about your philosophy, embody it. So one of the things that leaders do is they read leadership books, they, they create brilliant leadership decks, you know, they come up with the company culture, and they think that this is a thing that you talk about. Do you know what I mean? Like I'm seeing this now. I'm very disappointed, for instance, in, you know, college athletics, you know, all this talk about, you know, doing the right thing. These are student athletes. It's more important who you are as a person, blah, blah, blah. And then they're like, I know you guys could all die of COVID, but, you know, it'd be really bad for the university if we hit pause on the season. Do you know what I mean?

Starting point is 00:16:38 I think you're watching, and this isn't just in athletics. I mean, there's, I think, six universities in the country right now that have had more than a thousand COVID-19 cases. We are watching across the board at the federal level, the national level, the collegiate level, the administrative, whatever it is. We are watching leaders violate all the things that they've ever talked about. Do you know what I mean? Like they are not putting people first. You know, they are not doing the right thing, even when it costs you. We are watching, and I realize there are difficult decisions.

Starting point is 00:17:18 So I'm not being glib about this. But I have seen very few people in institutions make the right harder choice as opposed to the easier expedient choice. And then these same people are going to harp on, you know, some 19 year old freshman athlete for not, you know, for some minor rule infraction. And it's like, why would they listen to you? I'm going to get back to some of the stories of the from the book, Cricypice. Is that right?

Starting point is 00:17:55 I say Cricypice, but I don't think he's around to object. He was introduced to running. And it changed his life. you are either walking or running daily. How has running and physical exertion made you better at your craft? You know, I was talking to Eric Burns about this the other day that, and I think a difficult crisis like the one we're in now, you know, I'm seeing people say stuff like, well, how much longer can this go on or we can't do this forever?

Starting point is 00:18:30 I think one of the things you learn about in, you know, endurance sports is like, all of that is irrelevant. Like, a marathon doesn't care that you're tired at 20 miles. Like, you got six miles to go. You can quit or you can keep going, but no amount of arguing is going to shorten the race, right? Like, it's either a marathon or it's not, right? The time to beat is either a minute flat or it's not. no pre-existing condition, no argument, no special exemption allows you to change that. And I think one of the things you learn training, whether it's running or swimming or, you know, weightlifting, is that your mind wants to quit much earlier than your body physically has to. And so you have to learn how to push past that.

Starting point is 00:19:23 Obviously within reason, there's certainly, you know, recklessness and and, and, and, and, burnout is real and dangers and all of that. But you have to understand that just because you feel like you're done doesn't mean that you're done. And the more you cultivate the muscle, you know, David Goggins talks about this. He's like, when you think you're done, you're at like 40%. And that's an idea that you can understand intellectually, but unless you've really pushed yourself in some sort of competitive context or, you know, unless you've really cultivated that willpower and seen that that's true in your experience, you don't really understand that idea. How does this make you better in non-physical work?

Starting point is 00:20:11 Well, I mean, speaking. Sure. Sure. Like, so a book is a marathon and a sprint and it requires so much more of you than you want to have to give. Like you would like it to, you submit, I'm sure you went through this with your. your book, you're like, you killed yourself to do it. And you're like, this is the bet. There's a story about Henry Kissinger where like an aide came to him with like a briefing he'd asked for. And he grabs it and he,

Starting point is 00:20:37 you know, he looks at it. And he goes, this is garbage. Go redo it. And then they bring it back. And then he calls him back. This is garbage. Go redo it. Then a third time, this is garbage. Go redo it. Then they bring it a fourth time. And he says, now I'm ready to read it. He had an actually. actually looked at it the first four times. The first three times. And the point being, we think that we've done our best, but reality, we've been holding something back. And so, you know, you go through this with books. You're like, this is the best I can do. And then somebody looks at it, and they go, well, what about this, this, this, this, this, this, this, this, this, this, and this. And you have to, that, that's a choice, right? You have to say, like, no, no, no, I'm done.

Starting point is 00:21:17 I can't do that. Or you have to say, actually, I do have the ability to answer all these questions. And the book becomes 4% better for that process. And that that is, that is the way that work is done. I mean, you think you made it all the way. You gave everything. And then, oh, shit, the game is tied at, you know, when the clock is zero. And then there's another quarter. Like, that's just how it works. And so it's not just a physical thing, but it's, I think in all, almost everything requires more of you than you would like it to have required. required. When you look at, let's, let's pick the obstacle is the way. Yeah. There's been some time, some time has passed since you published that. You are a better writer today than you were when

Starting point is 00:22:04 you turn that book in. Yes, definitely. Do you have moments where you look at it and you're really mad at yourself or you're upset because you're like, God, that is not like you pull a paragraph or a page or even a chapter. It's like, oh, I could have done so much better. Or do you, are you just like, you know what, that was then, it's done, and I've got to move forward and not look back. It's a little of both. I'm having a weird experience right now. My son asked me to read them to him, and they seem to work very well at putting him to sleep. And so, like, when I read him, like, so like last night, we read Curious George, but when I'm reading Curious George, he wants to pay attention and he wants to look at the pictures. It's like, it's a fun thing to do. And so as soon as I

Starting point is 00:22:50 close, curious George, and I open the obstacles the way, you know, he's asleep, you know, like that because he doesn't have any idea what's happening and it's much more boring than I'd probably like to admit. But I've had the weird experience over the last few months, rereading both, I haven't done stillness, but I've reread obstacle and ego. And the last time I'd read those two books was when I recorded the audiobook for them. So I think I definitely see things that I, you know, I feel like I was a little bit too glib about or that, you know, I talk about Ulysses S. Grant somewhat negatively and ego is the enemy. And as I've studied him more, I've come around and maybe I'd have nuanced that chapter a little bit, for instance.

Starting point is 00:23:36 So there's definitely things you see where like, I don't know if I totally agree with that as much anymore. Maybe I'd change this or that. But one of the things I'm thinking about this now as I'm writing my book, as I've got, as I've become a better writer, I've also become more informed and more aware of what's possible with each sentence. So on the one hand, that that improves the quality. But when I read obstacle, like, ego is probably 15% longer than obstacle and stillness is probably 15% longer than ego. And so when I read obstacle, there's a quickness and authenticity to it and sort of an, I don't want to say unpretentiousness, because that's not really the word,

Starting point is 00:24:25 but there's a, there's a looseness to it that I appreciate. And the way that, like, you listen to a band's first album, it just tends to be quicker and less self-conscious. And so I'm trying to think about that more like, not how do I go back to it, but, you know, it was would be if every one of your books got longer and heavier and more deliberate, at a certain point, that's not sustainable either. I want to talk about community. Okay. It's partially why we're doing this today with friends along in Rome.

Starting point is 00:25:05 Pinesius, Gauss. We'll call him Panateas. That's what I call. I looked it up on Google. And that's how they did it. So this is a fun exercise in trying to properly pronounce names. Anyway, there were three people. One of them was one of the Rome's great generals.

Starting point is 00:25:26 And they formed kind of a philosophical club. And this is also similar to what Benjamin Franklin did with his junto, where they would meet, they'd discuss and debate the stoic philosophy they all pursued. And to me, I have found one of the greatest. benefits in my work is regularly meeting with small groups or leadership circles to have these conversations to go deep on a specific topic to get a variety of point of views from a variety of places in the world and to hear and to learn through dialogue and I feel like this is something that is is a powerful thing that I wish everybody I know you go on a trip with some of the

Starting point is 00:26:10 best writers in the world you guys go off to a house and do physical things outside together. And that's part of like your version of Agento. I think this is a critical component to progressing, to learning, to improving. I'd love to hear your philosophy on it. And maybe share a little of the story

Starting point is 00:26:28 too from ancient Rome. Yeah, so it was called, and I'm actually writing this down because you gave me an idea. Sorry. It was called the Sipionic Circle. And the Sipionic Circle was a collection of the sort of greatest philosophical and political minds of its time, and they would get together

Starting point is 00:26:47 and talk. And it's a, you know, we tend to think of the Stoics as these kind of solitary, lone, joy-hating, introverted figures, and that's just the opposite of what they were. I mean, Cato, who famously, you know, takes his own life in protest of Julius Caesar, his last meal was a big philosophical discussion with all his friends. And that was a tradition he'd absorb. all of his life. He worked constantly. So the only real time he had for friends was over dinner. But it wasn't just like, hey, let's gossip. It was like, let's talk and debate the big questions of life. And this goes back really to the founding of stoicism. For people, it's like, what is stoicism? You know, most philosophies were named after the person who founded it, right? So stoicism is not called xenoism. Stoicism is called Stoicism because Stoia is the

Starting point is 00:27:44 Greek word for porch, which is where the Stoic, they started on what's called the painted porch in Athens. And I just love even the image of the cemetery of the idea of stoicism being named after a porch, which is a, you know, an open air structure. It's where, you know, there's no doors on it. you know, it's facing the city, it's facing people, anyone can come up on it. And it's, so it's like this idea of like, well, what is your stoa? Like, where, who's on it and where is it? Where are you having these discussions? Yeah, I'm a big fan of like mastermind groups.

Starting point is 00:28:24 I'm a big fan of, you know, I'm on a couple different, I don't know if you had this, but like text threads with different people in different professions. And it just allows people to kind of dip in and dip out and benefit from it, you know, different people's perspectives, but most of all, you want to be benefiting from other people's experiences. And so what these groups really let you do is you go, hey, I'm trying to find someone to redesign my website. Has anyone gone through this? Or, you know, on some of my books, there's been some issues with the printers, like the printers are overloaded. And so, you know, I'm in a text this group today and be like, hey, is anyone else that other publishers having this

Starting point is 00:29:02 problem? And how did you solve it? And so I think just, the ability to share and benefit from other people's wisdom is really, really important. What's it like when you go do one of your trips? I've talked to James a little bit about this, James Clear, and I've had some of the other guys that go on this trip. What are those off-site retreat-like events like for you guys? Well, James deserves all the credit because he's the one that put it together and he just invited a bunch of folks and it seemed like fun the first time. I didn't really know what to expect. But, you know, writing is a strange profession in that, you know, you're competitors, but you're not really competitors. And even though you are competitors,

Starting point is 00:29:47 you probably all benefit from sharing more than you do from stockpiling. I spoke at a couple, a couple years ago in Austin. I got invited by an AD. I won't say from what's cool. But the athletic director at a big school. It was like, hey, we're getting a bunch of other AEDs together. And I, you know, I went to this house. It was like the house of one of the donors for the program. Anyways, the point was, there I was. And there were the, there were the ADs from like 10 schools that all are constantly trying to destroy each other and beat the crap out of each other on the football field, steal, like, you know, their coaches are trying to recruit athletes away from each other. They're fighting over ostensibly a finite amount of advertising dollars and television rights and whatever.

Starting point is 00:30:39 And yet for like 20 years, these coaches have gotten together and shared with, and not coaches, ADs have gotten together and shared with each other what they're learning, what's working, what's not working. You know, one of them gets fired and the other ones help them get a job somewhere else. It was just really interesting to see. So I think the more you, the more you sort of get up. close and personal with elite performers, whether it's in sports or the management of sports or business or the armed forces, you find that there's a lot more sharing than you might expect.

Starting point is 00:31:15 And I think that's what allows them to continue to grow and improve. It reminds me of the word, I'm going to spell it, you can pronounce it, O-I-K-E-I-O-S-I-S, that we share something and our interests are naturally connected to those of our fellow humans. This is, it was pressing in the ancient world, and it certainly is today. And I feel like that is, is something that I wanted to bring up and talk about and have you expand on and pronounce it properly for me. Because I actually don't, don't remember how to pronounce it. But, but it translates to like a mutual affinity, that we have a mutual, a natural affinity, a natural almost altruism. And then what happens is we lose it.

Starting point is 00:32:02 We beat it out of each other, we pressure it out of each other. And it's the root of so much pain and unnecessary difficulty. I think people, I mean, look, I think, I think that's been one of the saddest parts of the pandemic is like people, it's like you can't seem to get people to care about other people. Do you know what I mean?

Starting point is 00:32:26 Like, we don't even have to get into the mask thing. but you'll hear people say things like, you know, those 200,000 people would have died anyway, or they go, you know, a huge percentage of them had pre-existing conditions. And it's like, do you not hear how horrible you sound right now? Like, I mean, not only is it not true, but like, what? It's just heinous. Do you know what I mean? It's just heinous that we've gotten to a place where we're so callous and we're so self-interested

Starting point is 00:33:04 that we can't even understand why it's bad that these people have died. And the weirdest part is you can make a very strong self, and this is what the Stoics do, a very strong self-interested case. I mean, we've lost doctors, we've lost artists, we've lost, you know, people's grandparents, We've lost caregivers. There's going to be orphans from this, right? And that has a profound cost that ripples through society. And that's something that Stokes talk about over and over again,

Starting point is 00:33:38 that we're all part of this large organism. And that to harm one person is to harm all people, to cheat is to cheat yourself. And that you just have to care. Like you just have to care. And if you don't care, then you have to work to make yourself care. And that's been the hardest part for me to grapple with is just people that I know are, either I believe we're good people or I know deep down are good people, just expressing like abhorrently callous indifference to the suffering and loss

Starting point is 00:34:13 that we're still probably not even halfway through. Yeah. You wrote a piece, I'm with you, you wrote a piece titled The Maximum, for every successful person. And I think it flows well with what I believe in here. And that's that's that's to always stay a student. To always put yourself in the position of being a learner. And my favorite leaders in history, my favorite leaders I've worked directly with are those who are, they always have this strong belief that they will be better tomorrow than they are today because of, or at least they'll be better when they go to bed at night than they were when they were when they

Starting point is 00:34:54 woke up because of their intentional, purposeful action towards learning, towards growing, towards improving. And there's some misconceptions even about like Genghis Khan who, that maybe this wasn't him, but you've written about the fact that he was one of the greatest learners in history. And I'd love for you to share that story because it could be misconstrued by people who haven't studied enough about why one, that's the maximum for every successful person, maybe specifically about him. Yeah, that's a chapter in ego as the enemy. And really, the argument that I'm making against ego is, is not that it's, you know, unattractive or unappealing or whatever. It's that it, it makes you vulnerable. It ossifies you. There's a great line from Seneca, or sorry, from Epictetus, who's one of the stoics. He says, it's impossible to learn that which you think you already know. So great leaders are humble and students because they realize that it's a self, it's a self, it's a,

Starting point is 00:35:53 a self-fulfilling prophecy. If you think that there's more left for you to learn, you will keep learning. If you told yourself that you've figured it all out, you've certainly figured all that it is possible for you to figure out. And so, look, the Socratic method is about, you know, asking questions and Socrates was considered wise because of, you know, he knew what he didn't know. The scientific method is about a guess that you then go see. if it's true. Like you say, here's what I think, but that's not the end of it. Then you have to go conduct experiments that you're really trying fundamentally to disprove what you think. And so, yeah, great leaders are focused on learning. There's a great story about Marcus Aurelius. I think it's in

Starting point is 00:36:41 lives. If it wasn't, it's only because I didn't have room for it. But he's an old man at this point. And one of his friends finds him leaving his palace and walking on foot, which is very unusual for the emperor at that time. And he says, where are you going? And Marcus says, I am off to the house of Sextus, the philosopher, to learn that which I do not yet know. And so, and the man supposedly explains like, this is the most powerful man in the world

Starting point is 00:37:12 and he's going to learn at the feet of an old philosopher. And to me, that's what leadership looks like. And I mean, the really crazy weird story is Sextus was Plutarch, who I mentioned, earlier was Plutarch's grandson. But Marcus, and Marcus thanks, sextus at the beginning of meditations for all that he learned from him. And so, you know, this relentless focus on learning and finding out what you don't yet know is the key to greatness, I think. Love it. Ryan, I'm going to open up to some questions here. We got some big fans first.

Starting point is 00:37:45 Happy early birthday to Joe Nykirk. His wife Emily texted me and said this would be really cool if you could get Joe to talk directly to Ryan. he's read pretty much every word you've ever written. So Joe, how about you take it away, man? Appreciate it. Thanks. Thanks, Ryan. Thanks, Ryan as well. My wife just told me that on the way up here. We're on a family trip. And she's right, though. I appreciate it. I read all your books, get the Daily Stoic, read the Daily Stoic every day and Daily Dad. So thanks for all you do and all your work. Appreciate it, man. Yeah. And I mean, I think close to the topic that we were just talking about,

Starting point is 00:38:23 with that word we couldn't pronounce, but, you know, with courage, justice, wisdom, and temperance being, you know, the four stoic values, especially in this day and age with how divisive, I feel like the environments are today with just everything, you know, racial injustices and the pandemic, how have you found ways or what methods do you have to balance, especially temperance and justice? I feel like, you know, fighting for what is right, but also letting things kind of go and and maybe not get into arguments. You don't want to, how do you balance those things?

Starting point is 00:39:00 Yeah, no, it's really difficult, right? It's like you could spend your whole day, you know, just angrily tweeting about things. And that might make you feel good, but what is it accomplishing? And how quickly do you end up sort of losing hope if that's the strategy you do? So, yeah, it's a balance. Like, how do you sort of maintain your sanity? your moral compass, you know, amidst a world that feels maybe a little bit like it's tearing itself to pieces. And then at the same time, not give up and not just sort of tolerate the status quo.

Starting point is 00:39:32 I think that's the struggle that a lot of us are in right now, myself included. I think, you know, first off, it's, you know, how do we start just by, you know, being better ourselves as people? how do we start, you know, we can have the most impact at home with our own children, for instance. So I think that's good. Obviously, you know, as a writer, you know, how do I use my platform to make a difference? But then just as a citizen, like, where do you draw the line? Where do you say, like, that's not okay with me. I'm not going to be complicit in that.

Starting point is 00:40:07 Particularly, and I think this is the struggle that a lot of people are having, particularly when it's not in your interest to do so, right? So like, you know, there's a joke, like it's only a principle if it costs you money. You know, I think people are, people are, you know, I see people that are like, hey, you know, social distancing, you know, you shouldn't wear a mask, blah, blah, blah. And then as soon as soon as that sort of limitation impacts their career in some way, it goes like right out the window. So, you know, sort of what are you, what do you, what do you,

Starting point is 00:40:41 willing to sacrifice or pay to insist on the formula or the standard by which you believe? And I think that's where we can start. If each person just didn't do things that violated what they believed to be their conscience, that would exert an immense amount of pressure systemically. But we have trouble doing that. I think everyone just thinks like, oh, we have to solve this like on the national level, on the international level. But really, I think if we focused on like, well, what am I, where am I drawing the line?

Starting point is 00:41:16 What am I okay to do, not okay to do? And I'm going to enforce those boundaries and ethics in my own personal life, like, whether it's like, hey, look, I have people would be better if I had them come work in my office. But I don't feel good about that. I don't feel good about asking someone to do that. So I'm not going to do it. Right. And so, like, I think that's a good place to start.

Starting point is 00:41:34 It's just what are you going to do with your own personal behavior? Thank you. Love it. Thanks, man. Liam, are you good to go next, man? Thank you for the opportunity. So something in my company, but I've noticed it's just been an aspect of my whole life, has been trying to figure out, you know, you started a very young age of what do you want

Starting point is 00:41:58 to be when you grow up, who are you going to be when you grow up? But now in the business that I'm part of, we think a lot about how to get people in the right roles and what do they want to do with their careers and what do they want to go on to be even after our company. and I had the opportunity to visit with my grandfather, who's 97 and very fortunately still lucid, and we were talking a little bit about his career. He had this kind of weird career path kind of going from the Marine Corps to a machine shop and then ultimately to selling records.

Starting point is 00:42:27 And I asked him, I said, you know, what kind of made you choose that career path? And in the way my grandfather does, it was just sort of, well, I had to eat and they had a job. So that's why I did it. And it kind of got me thinking that we're to the point now where, this, we have this incredible luxury of thinking about what we're going to do with our careers. But from, from your perspective or the Stoic tradition, have we almost put too much weight on that of exactly what it is you're going to become and thought less about the day to day and really how you're living your life day to day?

Starting point is 00:42:58 No, that's a, I think that's a great question. Yeah, you do find people are sort of, they can be sort of paralyzed like, this isn't my dream job. This isn't exactly what I want. and, you know, if they just sort of chose and committed to it, they might be able to make it into that thing. And so a lot of sort of millennials I know have kind of bounced from thing to thing and sort of never really found their footing. At the same time, like I do, I do, to go to your other point, I do find with my employees, it's like, if, look, it's like we both know you're not

Starting point is 00:43:32 going to work here for the rest of your life. So if you can be much clear with me about what you want, to do, like where you see yourself going or what kind of life you want to have, this is going to be a much more fruitful relationship for both of us because I can help you, right? It's like, I can only pay you what I can pay you, but I can give you all sorts of advice and guidance and send opportunities your way that are going to be worth a lot more than what I'm paying me, but I can only do that if you help me get a sense of what that is for you. And so I think a lot of people struggle with thinking about that and then communicating it.

Starting point is 00:44:15 And then it's sort of a suboptimal relationship for everyone involved. It's like if I have a research assistant who is like, I want to become a writer someday, that's so much better for me than a research assistant who's just sort of like, well, I don't know, you know, maybe I want, you know, it's like if I can, if I'm specifically training you for a thing, that's much better than if this is just like, you know, a transactional relationship. You know what I mean? So I think it's like all things, probably a mix of both. Good stuff. Thanks, man. Yeah, I found that I know you're friends with Kyle as well, Newport and his kind of be so good.

Starting point is 00:44:59 They can't ignore you. Yeah. Especially, I think when you're getting started, to me, it was really helpful just to be kind of grateful that somebody gave me a job, even though it was making 80, cold calls a day. And it wasn't that fun. But the desire to get good at something that I had never done before has now helped me in everything else I've ever done. Like learning how to sell as a critical skill and a component that I'm so grateful for, even though there are a lot of parts of that job that were awful, but were very rewarding and potentially lucrative if you did well, like

Starting point is 00:45:36 one of those tiny base salary, high variable compensation jobs. So not. only that. And so I think you can learn some skills through saying, this isn't like my dream job, but I'm going to work to be excellent at whatever job I'm lucky to have. Yeah, that's, that's right. Hey, you know, this isn't my dream job, but what I want to learn from this, you know, two years I'm here is X, Y, and Z. And that becomes, you know, just a much more straightforward transaction than the, well, I don't want you to, you know, like, just when people are clear about their intentions, I think just everyone's better off. Yeah, agreed. Okay, Nikki, you good to go? Yes. All right. Hi. Hey, Ryan. Hello. So as a student of Stoicism, thanks to Joe, I am a huge fan of your work.

Starting point is 00:46:29 I'm excited to ask you. So what was your personal turning point or moment where you began this sort of stoic journey. Yeah, I don't know. I mean, you could go to when I was first introduced to stoicism when I was in my, I think I was 19 or 20 years old, and I just asked someone for a book recommendation and that's how I got turned into stoicism, which ironically is sort of how Zeno is introduced to stoicism, which I talk about in the book. But, you know, what's been interesting for me is how the books have evolved over

Starting point is 00:47:07 time. So, you know, I was talking about sextus, the philosopher earlier. I've probably read Marcus's little section on him like 30 times. And it was only recently that one, I even made the connection between him and Plutarchin and that there was a passage that really struck me that I've been trying to apply in my life. The point being that when the journey begins is important, but I'm also as interested in how the journey evolves and how one kind of recommits to it. it. And it's like if you see the texts as static, you're, you know, then you're going to read them one time and you're going to retain whatever you retain and that's the it. That's it. If you see it more as this sort of continual thing you're engaging with, the Stoaks talk about how we, we never step

Starting point is 00:47:54 in the same river twice, you see it that way. Then it's this sort of almost constantly renewing thing, this expanding thing. And that's kind of more how I see the journey. Love it. Good. Good. stuff. Thank you, Nikki. Tom, you good to go? I am. Can everybody hear me? Yeah. All right. Great. Well, thank you. Thanks, Ryan, for being the prolific writer that you are. So I just recently finished reading deep work. It's interesting that you mentioned Cal Newport just a few minutes ago, but a lot of the strategies did resonate with me. And I'm just wondering if you could share some of your best practices, you know, routines, what have you for getting into that creative and productive mode, you know, with every, with us. Yeah, for, for me, it's, it's all about the

Starting point is 00:48:52 morning. So, like, this morning, I got up at, like, six. That's when my kids woke up. First thing we did was we went for a long walk together. I didn't check my phone, probably, let's say I got up at six, I probably touched my phone for the first time at like 8.15, you know, didn't check my email, email until I was, you know, at the office. And then the first thing I did was go sort of right into the work and worked probably from, you know, eight to 11 or 12 o'clock. So like for me, I mean, I have a bunch of crap on my to do list I have to do today. But it's all extra like administrative creative stuff that if it gets pushed until tomorrow or the next day so be it but like the main writing thing I had to do the primary creative like thinking task it's already done and it was done almost you know

Starting point is 00:49:46 before you know the mid-morning had passed and so so for me my deep work stuff is just like get up early you know go right into it and then do it in an in as uninterrupted and continuous form possible. Good stuff. Thank you, Tom. Ryan, one of the commonalities between you and all the Stoics is that at least most of them were prolific writers. And I've been pushing this lately because of what I learned through the process

Starting point is 00:50:22 of turning in a book on time and getting the edits and then rewriting. And just I think I fully realized how much I learned. learned through the process of having to write every single day. And I feel like that is a, that is a skill and an exercise that every leader who wants to influence teams to outcomes should do. It's worth it. What, what would, what advice do you give to people in leadership positions as to, and I don't want to put words in your mouth, but at least I believe they should write. I would assume you do. Leaders seem to, to be able to get their words out in a, cogent way to move people.

Starting point is 00:51:06 What are your thoughts on that? Yeah, I mean, writing as a practice is a deeply sort of meditative experience. It forces you to clarify your thinking. It forces you to marshal the evidence for your thinking. Forces you to communicate distinctly and directly. There's a reason, like at Amazon, they don't want you to give like PowerPoint presentations about, you know, this initiative or that project. Do you have to write it in a like a long?

Starting point is 00:51:32 long form memo letter kind of a thing. You have to make your case. And so I feel like a lot of leaders are just sort of, you know, they're just kind of like shooting from the hip. They're like, well, I got to do this phone call, so I'll say this. And, you know, like I much prefer, like I actually love email as a medium because it's like, no, I'm going to lay my thoughts out here. And I'm going to put it down in a way that the facts are there. When we're doing this on the phone, what's, you know, somebody doesn't want to hurt somebody else's feelings or, you know, somebody, the perception is breaking up or whatever. I think writing as a practice is really important and as a way of clarifying one, even if it, even if the writing is never seen, the purpose of clarifying our own thinking is

Starting point is 00:52:19 beneficial in and of itself. Yeah, Ryan, one more question before we come to the end here. I completely agree and I would urge everyone, even though it's painful and it hurts and especially like I regularly work with an editor because for me at least, even if I don't publish the words I'm having edited, it creates positive momentum to see my words and my thoughts look better. That may be weird, but that to me, getting that critical feedback sent back to me and then I say, oh, my stuff actually isn't that bad. Like it's, it's, and I, so I think if that's a good practice to get into for anybody who cares to be an excellent leader because I'm a firm. believer to be an excellent leader, you have to be able to communicate your ideas in a compelling

Starting point is 00:53:07 way in both the written and spoken word. So you wrote a post, I don't remember when it was published, but it's called advice to a young man hoping to go somewhere or get something from someone successful. So it starts with when you dropped out of school at 19 to start your first job in Hollywood, there are, I've, I've, as I've asked this question to a lot of people, Ryan, I've noticed that the advice that people give to a 19-year-old or a 24-year-old who's a new college graduate is usually useful for all of us. And so given your career and you're still young, you probably get just bombarded with advice from people who are younger.

Starting point is 00:53:46 What are some of the general life principles slash pieces of advice you share when you're posed with that question? You know, honestly, I don't remember what's in the article. But I'll tell you to that I've been thinking about recently that I get a lot of. And so people go like, you know, people think mentorship's important. So they'll ask someone like, hey, will you be my mentor? Or they go like, I want a relationship with this person. So they're like, hey, you know, I've following your stuff.

Starting point is 00:54:17 Like, can we get on the phone and maybe talk or like the one I get the most is, or that drives me the nuts the most is people go, hey, blah, blah, blah, blah, blah. can I ask you a question? And what I've never understood about this and what's, because I've never seen that work is like, why don't you just ask the question, right? Like, you wouldn't walk up to a pretty stranger in a bar and say, hey, can I, can I talk to you for a while?

Starting point is 00:54:47 They'd be like, what are you talking about, right? You would, you would, that's not how conversations start, right? Like, the way you start a relationship with someone who's your mentor is with an exchange of an idea of ideas. So it would be like, send them a link to an article or ask them a very quick question. Like, you know, like that was how I got introduced to stoicism. I asked somebody like what their favorite book was. And so, so like the way you start these relationships, the way you learn, the way you get access to, you know, a busy person's time is not asking them for a 20-minute coffee, it's asking them a two-second question that then can begin the germ of a relationship.

Starting point is 00:55:32 And so, you know, it's like I always respond, you know, when people, like, when they go, hey, can I ask you a question? I'm like, you just asked me a question. Like, you wasted your question by asking if you could ask a question. If you got me to open this email and you're, you now want me to reply. So then you could send me enough. other email. That's twice as inefficient. Right. And so I think that the main thing I think about is like, the way you start relationships is by starting relationships. It's not by asking for a relationship. Right. And so I think people miss that. And be direct. And I think it's helpful to to have done something that, to create a reason for somebody to potentially be interested in you. I think being a great writer,

Starting point is 00:56:17 having a good podcast, putting putting your work out there publicly, open. the door to potential new friends that you want to talk to. Yes. You've shown an ability to add value to the world. That is a great networking tool to gather and build real relationships because it's like, hey, I dig what you do. Oh, I dig what you do. I think is Jordan was, yeah, Jordan's still on the call.

Starting point is 00:56:42 You know, he's, he is assistant coach with the Brooklyn Nets. And yesterday, all of a sudden, Steve Nash gets hired. And I'm thinking, oh, my God, Jordan, what's going on? And we're texting about, about what you're working with Jacques Vaughn and now how is that going to work. It's because he has a job of significance that I'm curious. And he originally reached out to me because of the podcast. And now we formed a relationship over a mutual respect. And I think that's another key aspect.

Starting point is 00:57:08 If you want to build those relationships, do something worthy of it. And that's a way that I found that has been one of the coolest parts of doing this. No, totally. Cheryl Sandberg has talked about that. She says, people think like find a mentor and you will do well. She's like, do well and a mentor will find you. It's like if you do interesting things, if you're showing promise, you will have no shortage of potential relationships.

Starting point is 00:57:32 It's like you won't need to go ask people for things because, you know, these things will naturally ensue from this sort of incoming, I might call it deal flow that you're experiencing. And so, yeah, do it. And when we talked about jobs earlier, like when people are thinking about, should I do this opportunity or this opportunity, I go like, well, what's the one that's going to, you know, be the most interesting that's going to teach you the most. It's going to get you the access to the most things. And so I think people underestimate the value. They're thinking about where they want to go to college. It's like, look, do you want to go to a college, you know, in New York City where you're going to be exposed to all these things? Or do you want to go to a college in the, you know, in the middle of Iowa where you're not going to have any access to anyone. doing anything. You know, so I think thinking about what's going to give you proximity is, is a great, you know, a great tool for this as well. Love it, Ryan. Thanks so much, man. It flew by number five. Already looking forward to number six. Where would you send people to

Starting point is 00:58:37 learn more about you online? Ryanholiday.net. And then I do a daily stoicism inspired email at daily stoic.com. Most recent books titled Lives of the Stoics, the Art of Living from Zeno to Marcus Aurelius. Are you talking about your next one yet? Or is it still a secret? Oh, yeah. No, I sold the next four,

Starting point is 00:59:01 and I am about two-thirds of way done with the first one. The next four? Is it another series like... Yeah. Are you going to share a little more? I can't tell you. I'd have to kill you. All right.

Starting point is 00:59:14 We'll talk about it next time. I'm sure. Thanks so much for being here. It's great to talk to you again. See you. Yeah. Thanks, everybody. I hope you enjoyed that wide-ranging conversation with Ryan Holiday.

Starting point is 00:59:29 I'm going to answer another question that I recently received. I actually did a group session with some fantastic leaders from a company called VM, where they took the Learning Leader Academy and, throughout their sessions, I would have Zoom calls with them and answer questions and further reinforce some of the key learnings. And one of the questions that I want to answer for this episode on The Learning Leader Show came from Joe DiPasquale, another fantastic leader from VMware. He said, what was the catalyst that led you to leaving corporate America and working on the learning leader full time. In other words, what gave you the motivation slash security to work for yourself? It's great question, Joe, and I spoke with him about this, but I wanted to share with all of you

Starting point is 01:00:29 because I get asked this a lot. So there's a number of points. One, if you remember how I started this show more than five years ago, initially began out of me following my, genuine curiosity. I had just completed my MBA. I had considered going back to school to get my PhD. However, when going through that process of applying and analyzing the course load to earn my PhD, I found that I was only curious about a quarter of that material. And at the same time that I was going through this process to apply, I had a dinner set up with Todd Wagner. Todd Wagner is Mark Cuban's business partner. And through the course of that dinner, Todd shared the thought process and framework behind creating broadcast.com with Mark and to eventually he was in the room with

Starting point is 01:01:37 the leaders of Yahoo, back when Yahoo was like Google, and sold broadcast.com for more than $5 billion, making him and mark both billionaires. And I was fascinated by the combination of his storytelling ability, his humility, his ability to share the intricate details to deconstruct the process of how they were able to do it. And I thought, could I create my own form of a leadership PhD program. Instead of going back to school, let me create my own school and have the guts and willingness to share it publicly so that others could learn along with me. And that's how the Learning Leader Show was born. I titled it Learning Leader because my favorite leaders, the leaders I look up to the most, are the ones who have always been constantly striving to

Starting point is 01:02:32 improve, to grow, to get better, and then share with it. they've learned with others, the best bosses and coaches and leaders I've had the great fortune to be around. That's how they operate. And so that's what happened. Well, I never anticipated leaving my job. I never anticipated leaving corporate America. I was happy with what I was doing. But fast forward a bit. I'm starting to get asked to consult with companies, to advise with leadership teams, to do one-on-one work, to give keynote speeches. to write a book. I'm getting asked to do a lot of these things that actually,

Starting point is 01:03:11 if you start listening to what the market is telling you, I was being told that there is a business. And at the same time that all of that's happening, a great visionary leader by the name of Doug Meyer from Bricksey and Meyer, owner, shareholder, CEO of the firm, came to me and said he had an idea for me to join him and the firm to run and create the leadership advisory practice is what we called it at the firm

Starting point is 01:03:41 and what we do call it at the firm full time run the learning leader full time the podcast speaking consulting advising build out new products like the learning leader academy do more grow the business focus 100% of your time on it and so for me my my thought process was certainly it's a risk as Miranda, my wife and I discussed on the episode with her, that it would be taking an initial hit financially, but the thought of getting to do what I love on a daily basis and wake up and be excited about my work, going to bed, being excited about what I've done that day,

Starting point is 01:04:21 I thought it was too good of an opportunity to pass up. And I believe in my ability, if I ever had to, I guess I could go get a job. I have no intention of that. I don't want to do that. But if I had to and we had to make money in order to do it and this thing didn't work out, my thought was, well, I could probably do that. Well, now, fast forward to three years of doing this.

Starting point is 01:04:45 And despite the fact that a big portion of revenue that I earned comes from in-person keynote speaking, we still have grown the business to be a very profitable endeavor for me and for Doug and for the entire Bricksey and Meyer firm. And so what gave me the motivational and or security was Joe's question. What gave me that motivation was I just feel, one, a sense of responsibility to people who have supported me, who have supported the show, who have listened and shared it and have given me, afforded me the opportunity to do this. I feel responsibility to lean into that, to work harder at that. And by doing so, it could help even more people in a broader scope. I am one who loves to prove my supporters right. And I am super lucky to have the support of my family,

Starting point is 01:05:37 to have the support of the firm, Bricksey and Meyer and Doug specifically, and most notably to have the support of an incredible spouse. My wife Miranda has always, from the day I've met her, believed in me and supported me and has been my number one fan in everything I've chased. after, including this work to follow my genuine curiosity with obsession and great rigor. And so that is what has given me the motivation.

Starting point is 01:06:09 And what continues to give me more motivation is hearing from you, the fantastic, loyal, hardworking, intelligent leaders who listen to this show regularly fuel me, give me the juice to want to keep doing it day after day to never miss on a Sunday night, to never miss on a Monday morning at 9 Eastern for Mindful Monday. And to be able to do that for hundreds and hundreds of weeks in a row is because of that support, because of you, because of your belief in this mission, in this work and becoming a learning leader. And so that would be my answer to Joe's question. and if you like to be a part of a future episode, email me, Ryan at learningleader.com.

Starting point is 01:06:58 Thanks again for listening. Talk with you soon. Can't wait.

The Learning Leader Show With Ryan Hawk - 385: Ryan Holiday - The Art Of Living (Like A Stoic)

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