The Learning Leader Show With Ryan Hawk - 485: Ryan Holiday - The Power Of Self Control, Loving The Process, & Building Endurance (Discipline Is Destiny)

Episode Date: August 14, 2022

Text Hawk to 66866 to become part of Mindful Monday. Receive a carefully curated email each Monday morning to help you start your week off right. Full show notes at www.LearningLeader.com Twitter/IG -- @RyanHawk12    https://twitter.com/RyanHawk12 Ryan Holiday is the best selling author of 11 books including The Obstacle Is the Way, The Daily Stoic, Ego Is the Enemy, and Stillness is the Key which has sold millions of copies and been translated into thirty languages. His latest book is called Discipline is Destiny - The Power of Self Control. Notes: We must be in command of ourselves. We have to conquer ourselves before others. Self Discipline - Freedom is the opportunity for self-discipline. The trivial - The people who sustain excellence fall in love with the process. They don't cheat it. Choose to see obstacles as opportunities. Dr. Drew recommended to Ryan that he should read books about stoicism when he was 19. This was a pivotal moment. Carry The Load For Others  – General Jim Mattis. "The privilege of command is command. You don't get a bigger tent. "Being the boss is a job. Being a leader is something you earn." Seek Discomfort – Seneca was a rich man. He inherited estates from his father. He invested well. Yet every so often, for a few days, he would eat only the scantest fare and wear his coarest clothing. He would actively seek out discomfort, mimicking abject poverty and harsher life conditions.  Having a full calendar - "That doesn't seem like a rich life." Just show up — Consistency. Thomas Edison said "I've got no imagination. Thank never dream. I've created nothing." The genius hangs around his laboratory day and night." Your Why must be intrinsic. Just work - in Ancient Greece, there was a word to describe a ceaseless work ethic — philoponia  (about the author Joyce Carol Oates). She published a ton over the course of decades. Work out -- "Obviously the philosopher's life should be well prepared for physical activity." — the Stoic Gaius Musonius Rufus explained, "because often the virtues make use of this as a necessary instrument for the affairs of low." The strenuous life is the best life — exercise. You must take care of your body. And eat well. Endure - Shackelton's family motto — "Fortitude Vincimus" — "By endurance we conquer." George Washington — When he was 26, he watched a play about the Stoics and started repeating the phrase "in the calm light of mild philosophy." Focus Focus Focus — In Yogic tradition they call this Ekagrata — intense focus on a singular point. Do the hard thing first — Mark Twain - "the idea is that if we eat the frog at the beginning of the day, it will be next to impossible for the day to get any worse." Can you get back up? "Losing is not always up to us, but being a loser is. Being a quitter is." Silence is Strength — The Spartans' "laconic" style. Never use 2 words when 1 will do. Archimedes once explained at a Spartan dinner, "An expert on speaking also knows when not to do so." When Ryan speaks to NFL teams: "I try to give them one or two practical things to implement." Be Your Best - "Conquering the world is rather easy after we have fully conquered ourselves. Certainly fewer people have done the latter than the former." Taking a stand - How successful are you really if you can't be yourself?" Lou Gehrig -  "When you love the work, you don't cheat it or the demands it makes of you. You respect even the most trivial aspects of the pursuit."

Quick note before we get started, we are hosting our once per year Learning Leader Growth Summit, September 21st to September 23rd in Nashville, Tennessee. Members of my Learning Leader circles will be there. And it's built to be a small, less than 50-person workshop with a lot of interaction and group dialogue. There's a few guest speakers, a few surprises. We'll do some hard work together and we'll also have some fun. If this sounds like something you'd like to go to, email Ryan at learning leader.com. And in the subject line, write Growth Summit.

And in the body of your email, tell me why you'd like to join us. So once again, our once per year, Learning Leader Growth Summit, September 21st to September 23rd in Nashville, Tennessee. if you want to go, email Ryan at LearningLeader.com, growth summit in the subject line, and then let me know why you want to be there. All right, here we go. Welcome to The Learning Leader Show, presented by Insight Global. I am your host, Ryan Hawk.

Thank you so much for being here. Text, Hawk, to 666866 to become part of Mindful Monday. You, along with tens of thousands of other learning, leaders from all over the world will receive a carefully curated email for me each Monday morning to help you start your week off right. You'll also receive details about how my book, The Pursuit of Excellence, will help you become a more effective leader. Text, Hawk to 66866.

Now, on tonight's featured leader, the great Ryan Holiday is back, bestselling author of 11 books, including The Obstacle is the Way. ego is the enemy, stillness is the key. Those books have sold millions of copies and have been translated into 30 languages. His latest book is called Discipline is Destiny, the Power of Self Control. During this conversation, we discuss how to be more in command of yourself than the importance of loving the process of what you do, why you should move your body every morning, and how he handles a tough audience when giving a speech. I think there's some useful advice there.

Ladies and gentlemen, I know you're going to love this one. It's the great Ryan Holiday. All right, Ryan, it's the seventh time, man. That is a lot. You're number one on the list of a guest appearances on this show, and I'm so grateful, dude. So thanks so much for coming back for the seventh time. That's incredible.

That's incredible. When was the first one? What year was it? It was 2016. We did two that year. I just wrote down the dates of all of them. So we did two that year. And I've just been kind of going along every year since. So it's pretty neat, dude. All right. But since then, a lot has happened. He's written a number of books. And Discipline is Destiny is one of my favorites, the newest, the latest. And I'm really appreciative of the book. There's on page 184, you write, Conquering the World. is rather easy after we have fully conquered ourselves. Certainly fewer people have done the latter than the former. Why do you think it's so hard for us to conquer ourselves?

Yeah, Seneca said no man is fit to rule who has not first conquered himself. The stoic idea is that self-discipline or temperance or moderation, whatever the word you want to use for the idea of sort of, being in command of oneself was the first part of being, let's say, qualified to be in charge of others or qualified to be in any position of leadership. I would argue, though, that there are a lot more powerful people than there are people in their own power, right? We see this all the time, people who are extraordinarily talented or they inherit things or they build things, they get lucky at something, whatever it is.

There's lots of people who are good at what they do, but are not particularly good people and are certainly not particularly temperate people, right? They're out of control and maybe even in the thing they're actually good at, but they tend to be out of balance in some other way. And the book is really about trying to bring those things together. There's the maximum discipline equals freedom. How do you view? Because you're a very disciplined guy prior to recording.

I asked you, I don't know how your output level with a high level of quality and consistency remains so high. And you simply said it's every day. But that's discipline though. It's almost like you've taken it for granted the amount of discipline you have for the output because it's not only the books. There's tons of articles.

There's your emails. There's your podcast. I mean, there's a lot going on. So can you talk about how that discipline is what's led to both your freedom and your output? Well, I think it's important. What we're talking about here is self-discipline, right? You can imagine an environment in which my day looks exactly the same and my output looks exactly the same, but there's like a gun to my head, right? And suddenly it's not the same thing, right?

So I'm talking about self-discipline. Of course, discipline is important. Discipline's important on a football team. It's important in the army. It's important in a prison also, right? Discipline is there and it matters. But I'm really talking about self-discipline. And there's that line, discipline equals freedom from Jocco Willing.

It's great. There's a quote from Eisenhower that's similar that I think illustrates the angle that I'm thinking about it. Eisenhower said, freedom is the opportunity for self-discipline. Right? So the idea is once you, first off, we're lucky to live in a society where we have all sorts of freedom, that most of what we, most things that we do are voluntary, right? We have choices to be and act however we want, for the most part. That's good.

But also success creates a certain kind of freedom. There's different forms of freedom. But the point is, I'm talking about what happens when you can do whatever you want, but you choose to continue to keep oneself in check or to stay disciplined. Like several books ago, I could have said, eh, you know, I'm going to take it easy from here on now. I'm not saying I don't have to work. I'm just saying the pace or the system,

the structure that I've set for myself, is not a function of like needing to eat. It's also not a function of some sort of, which is another form of slavery, I would say, I'm not trying to prove something to someone, right? Like, I'm not also like the reason I'm doing this many books is because I want to sell the most books out of anyone in the world. And that's what, you know, so I'm talking about how do you get to a place where you're doing these things voluntarily because it's who you want to be and it's what you want to do? You write about Joyce Carol Oates and this is in the section title, Just Work.

And in ancient Greece, there was this word to describe a. ceaseless work ethic called philipponia yeah close enough okay close enough and she published tons over the course is there someone like her a motivator for you to say i want to be that type of person i i'm not necessarily like hey her output like i want to publish as many books as she has published as she has published an insane amount of books and she's also gotten to do it for a very long period of time i think she's in her fifth or sixth decade as a published author, which is incredible, and I very much admire that. But I like the idea of what happens if you do the craft every day for as long as you are able to. If you trust that process, whether you get to do it for three years or 30 years, I think that

output is going to be impressive. It's also going to be the maximum that you were capable of doing. How do you relate that to somebody who's building a career for themselves within a Fortune 500 company as a mid-level manager? They're a VP of sales somewhere, and they love your stuff, but they don't necessarily fully relate to your lifestyle because they're not necessarily a published author. They may give some speeches at town halls and things like that, but they're working to build a career, support their family, and hopefully create a culture where people want to do good work. How do you relate that type of ceaseless work ethic, loving the process with that person? To me, it's about what is the craft of what you do, right? So I was talking to a baseball player yesterday on the Daily Stoke podcast,

and he was thinking about retiring. And we were talking about what he was considering doing next and how he was thinking about the transition to coaching and how baseball for him was like, hey, how many hits am I getting? How many runs am I batting in? How many games are we winning? obviously that's part of coaching, but you have to find some craft within that. So maybe it's like making people better, right?

Or raising boys or girls into adults, right? You have to figure out what the actual craft of that thing is as opposed to like what is the external metric that people tend to measure you by. And I think the ideal scenario is you fall in love with that thing. Like I, Cheryl Strait has talked about the distinction between writing and publishing. Like, I publish a lot of books, but what I do is writing, right? Like, I write books every day and or I write every day. And what tends to come out of that is published books. So if what you love is relationships, maybe what comes out of those relationships are great teams or sales or, you know,

customer, you know, bonds with the customer, whatever it is, right? But you have to figure out the craft of that thing and find out how to dedicate yourself to that. Lou Gehrig said, which you write a lot about Lou Gehrig, I love the stories. When you love the work, you don't cheat it or the demands it makes of you. You respect even the most trivial aspects of the pursuit. Again, I sense that relates to your life. It seems that discipline has been how you've been so productive in this Lou Gehrig.

quote, I think can apply to people in whatever their pursuit is of how they go after it. And I love the John Wooden story about putting on their socks. I wrote about that in my first book and the fact of these, some would say, are trivial pursuits. I'm actually working with a young quarterback right now, young kid, and I'm thinking about the most trivial aspects of what it means to be a great quarterback. It's not just having a rocket arm or a loud voice. It's all of the little things. And to me, I sense that's a big part of your career, too.

Yeah, totally. You have to love, Marks Rehost and Meditations talks about loving the discipline you know and letting it support you. I think discipline doesn't just mean like I'm stric with myself, but what is the discipline? The discipline of writing books, the discipline of being a quarterback, the discipline of sales. We refer to certain pursuits or activities as disciplines. It's loving that thing, doing that thing to the best of one's ability with all. that one has. And yeah, as you said, not cheating it, not cutting corners, not phoning it in, not going, oh, that's good enough, right? But genuinely loving and respecting that thing.

And I can feel like when I'm getting too busy or I have too much going on, I can find myself faced with the temptation or the opportunity to cheat the thing, to be like, I'm not going to spend as much. I'm just starting, the way my schedule works on these four books I'm writing, The series I'm doing is basically, as this one is coming out, I have to be well into the next one, right? And it'd be very easy for me to go, where am I going to find the time? Like, what am I going to cut, right? Am I going to cut from the writing process? Am I going to cut from family or am I going to cut from extraneous things?

And it's easy to cut from the important things because the important things are hard. The I am curious about your process now because I think you're in demand too for client work and I'm not sure how much you're doing. I am curious from a business perspective, how do you balance how because you could probably charge a lot now for the client where you can share the stuff that you do for clients. But that's some of the trading time for dollar stuff. You have a team so you have people to help you with that. That as well as the fact that you're a prolific creator. You need to be creating something pretty much every day. How do you balance between the two? Because the client stuff helps you make money. Obviously, the creator stuff does too, but the creator stuff is more delayed gratification, right? You're writing for today, you're podcasting, then that money comes later versus client stuff. It's almost immediate. Yeah, it's hard, especially for me because before I was a writer, I had a marketing company and I worked with clients and then I did ghostwriting for a long time. So I had these other things that I'm good at that I enjoy doing and that like you said, it can also be lucrative. I've had to scale that.

I've had to scale that back, like almost to nothing at, you know, not a small cost, right? And it's been tough in the sense that I would like to do all of it, but I can't do all of it, right? And so what do you say no to is really important? I have a – I may have already told you the story, but I have a picture on my – I have a – right behind my computer. I have a picture of my youngest and a picture of my oldest, and then in between it, I have a picture of a sign that says no, which is to me a reminder is – when I'm saying yes to stuff, I'm also saying no to other things. And conversely, when I'm saying no to things, I'm saying yes to things. And so, yeah, you have to choose what's important.

And for me, the test is usually, if I don't do this, will someone else do it? Right. And if someone else can do it, then it's probably not like what I'm really need to do, what I was put here to do. And it's probably to go back to the idea of the gift. And I know this can sound a little pretentious. But like, if you have a gift, you're good at something. something. You're also pretty good at this other stuff. You have to make this hard choice of

prioritizing the thing you were really put here to do and the other things which can be lucrative. Now, it's a balance and at different points of my career when I had, let's say, more energy or more time where I needed, you know, I needed to create a financial base of freedom. There's different tradeouts. But at this point in my career, I much more think, like, is this what I was put here to do? What were you put here to do? I was put here to write books about like ancient philosophy, to take ancient wisdom and make it accessible in the modern world. That's what I really feel called to do. And I feel like, even if I wasn't called to do it, I feel like it's my comparative advantage, something I'm better at

than most other people. So can I ghost write the hell out of this book for this athlete? Sure. is there also a school bus of reporters who could do that book too? Yes, so I'll let them do that. How much of that do you think you were born with versus skills you developed to become great at writing books? Well, I think it's both. You know, Robert Green talks about this idea of a life's task. Obviously, I think there is something for whatever reason, your circumstances, your DNA, your upbringing, that points you towards something, you bump into this thing and it touches something in you.

And then, of course, you can choose to ignore, not cultivate that task, not develop those skills. And a lot of people do that. But when you do develop, you cultivate those skills, you now possess something that is satisfying and fulfilling that's also unique. And so it kind of is this reinforcing thing. And anyway, that's what I feel. This may be something we edit out, but I feel like I read at one point that you have made a shift in your life from being an atheist to more agnostic. Is that true?

Is that something you're comfortable talking about? Yeah. I talked about this in stillness is the key. The idea of like, how do you feel at peace? and I have a chapter in the book about a higher power. When I think about what that means, I think about it more in the sense that they talk about in 12-step groups, the idea of like,

you are not the center of the universe, you are not the one pulling the strings. Someone or something is, I think it's a little presumptuous to say with certainty that one knows what that is, and that happens to be whatever the affinity, of your, it almost always happens to be whatever the affinity your parents had was, right? Like, I, I, I, if we start to get an discussion of organized religion, that's where my doubts

and questions come in. But the idea that one does have a life's task and it might come from something or some force that you cannot even comprehend, or that, that one's choices in life have meaning or significance, that we have obligations, that we're not just, you know, this sort of evolved species that's made to reproduce and nothing else. That's where the philosophical side of me starts to go, eh, I think they're taking it too far. Yeah. One of the things I love that you write about is the ability to endure. And you talk about Shackleton and his family motto. Again, every time I read your books, I mispronounce and butcher these words because I've never said him aloud. Well, you should hear me doing the audio books of them because I've never pronounced them either.

I find myself with like going to YouTube and saying how do you pronounce such and such as I'm recording the audiobook. I feel like that happened 50 times last time. You probably had it even more. But this fortitude vinsimus by endurance we conquer. And I think this is another element of discipline, another element of production, another element of excellence is the ability to endure, the ability to keep going. This way we conquer because we're able to push past the tougher things. Can you talk more about endurance and shackleton and how that impacts you as a, again, prolific producer of content? Well, to take it back to writing, I think people think that books are this strike of inspiration, right? Or that it's this sort of beautiful, idyllic,

creative process. I mean, a book is a work of manual labor, right? And then on top of the manual labor, there are many dark nights of the soul where you can't see your way out. You don't know what you're supposed to do next. You don't think it's going to come together. I mean, this book had had that for sure. There was a number of moments where I almost, not canceled it, but decided to push it because I wasn't sure it was going to come together. So you have to cultivate this ability, not just to endure, not just to sit with the uncertainty or the doubts of it. It's like walking a long, dark hallway, right? And you, you may be there's light at the end, but you're not really sure how much closer you're getting and it's playing tricks on you all the time. And so you have to cultivate this

ability to really just, what do I have to do today? Like what, what, what am I supposed to get through today? And you know that, and you know this having done it enough times. That is one of the benefits of being prolific or sticking with something is that like, let's say Tom Brady's second season, he'd only been through it one time. So we really had very little context for like, you know, the ups and downs of it, right? Now, 15 seasons in, you have a sense of the rhythms and you know, not just the rhythms, you have the sense of the rhythms before it starts and the middle and the end. And you know, like, hey, there's going to be moments like this, right?

I've been through things like this before. You want to cultivate that ability. And so one of the things about endurance is that it makes you. you more able to endure things. This is also why I think is important. Have a physical practice. Why to have hobbies is that you want to cultivate this experience where you regularly feel like all is lost or that you've bitten off more than you can chew or that's not

going to work and that you persevere anyway and then you do get through it. I think we're very aligned on this, the element of an early morning physical practice. Yeah. Morning routines have become almost overplayed, but for good reason, I think. And to me, and I think you're aligned because you run and you swim and you take your kids on walks, I know, and that's a part of every single day. And for me, it is too. And you write about this a lot, the importance. And I think sometimes I talk with senior leaders that have the back-to-back-to-back-to-back calendars.

And part of what gets cut out is like working out, taking care of their body. me I always say hey man you have one body one sure and if it fails if your health goes away if it fails all of this other stuff doesn't matter doesn't matter so one on one end it's it's literally about taking care of your body on the other end I think the physical is what leads to being great from a mental perspective like to me I think it's more mental than physical of all of the morning early morning workout seven days a week can you talk more about why this should become part of, if you're able, right, this should become part of a leader's practice.

I mean, I have a bunch of thoughts there. Specifically on the calendar thing, I think I look at some people that I know is calendar and I go, that doesn't seem like a rich life, right? Like, you know, you go like, wow, you're very powerful and yet like you have no control over what your day looks like. Your day is entirely owned by other people. to me that doesn't that doesn't sound great at all. So to me, like a great day is a day with a lot of white space and specifically space in the morning to do things the way that I want to do them, which to me is usually I end up waking up early.

That's part of what gives you that space, right? If you wake up at 10.30, like you're behind the eight ball. If you wake up at 5.30 or 6.30, you know, also, of course, depending on what time's zone you're in, you're ahead of people. So that space is yours. And then what is the first decision that you make when you wake up, right? I was talking to someone the other day and they were like, you know, I wake up early, get out of bed. I check my email to see if there's any fires, right? And I was like, well, that's it right there.

Like you consciously in the beginning of the day go looking for trouble. Of course you find it. You always are going to find something to be upset about, something to take up some of your time, something to distract you. I think you've got to protect that space in the morning. And it's usually in the morning. I mean, obviously, very few people are actually morning people, right? They're so excited to be up. It's not sunny yet.

But you usually have more willpower than at the beginning of the day. So like if you get up at six and you work out at 630, I think you're going to do more, have more energy and then get it done than if you wait until 630 in the evening when you may or may not. have a million excuses, plus you're tired, you know, plus you've eaten poorly, et cetera. So I try to just own that morning. And I know that if I'm, if I get up at a good time, I get outside, I get some exercise, I don't get sucked in the phone. And maybe I do a little bit of work, like a little bit of writing. Like, it could be 1030. And like, I've already won, you know, most of the day. I mean, there's still a lot more to do. And there's things that can determine whether it's a super great day or a, you know, a pretty good day. But it's not going to be

a terribly unproductive, unpleasant day if I start things off right. Well begun as half done is is a great expression that I like. And longer term, too, it's just the benefit of taking care of yourself. I just, it's so it just, to me, it's the priority number one. It has to be because like I'm not going to be a husband or a dad if I fall apart. And so I can't predict the things that could happen to me health-wise. But this is what I'm really happening. Both my mom and my dad are really good about this. They're like, we can't predict it as we get older.

But what we can do is we can work out every day. We can watch what we eat, right? We can party in moderation, still have fun, right? And I think that's the thing that's inspiring to me is like we can't control everything. But the thing that we can control, we're going. going to. And I think that's the mentality that great leaders, people who sustain excellence seem to have. Yeah, you don't control if you get prostate cancer at 56, but you do control at 56, for the most part, whether you can walk up a flight of stairs without, you know, breathing heavily, right?

Or whether you can pick up your grandkids or whether you can swim in a pool or you control those things. And you control those things by the decisions you're making long before that, you know, the decision to go for a walk, to eat decently, yeah, to not get addicted to certain things, to practice, you know, habits in moderation, right? And that's what temperance is about. I think living a strenuous life in the sense of you're active, you're engaged, you're in control of your body is a form of discipline that carries over to the other places of your life. I talk about this in the book, too. I mean, also, like, if your office is a mess, I think your work is going to be a mess, right?

If your body is a mess, if you feel terrible, are you going to be as good controlling your temper? Probably not, right? Because you feel like garbage, right? And so you treat yourself and other people like garbage. So these things are all very related. it. Yeah. In line with leadership, we've talked about General Mattis before, and I love when he talked about carrying the load for others, and the privilege of command is command. And he says, you don't get a bigger tent. Being the boss is a job. Being a leader is something you earn, right? Being a boss is a job. Being a leader is something you earn. Can you share more about carrying the load and what you've learned from Mattis when it comes to the fact that the privilege of command is command.

Well, so when we think about this self-discipline, it's not just for ourselves. We're cultivating strength and fortitude and regulation. Ideally, so not just we inspire people by our example, but also so we can help other people. There's the famous story about Mattis. Some general pulls up to the Marine headquarters. And like, it's Christmas Day. And Mattis is working the guard booth at the entrance to the base. And he's like, what are you doing here?

It's like a four-star general. And he goes, look, the guy who is supposed to do it has kids. I'm not married. I don't have kids. I'll do it. Right. And the idea that you're strong enough to carry the load for other people is to me a big part of it. Like I think obviously a leader can't do everything in the organization and there is such a problem as as not delegating and micromanaging, but you also have to be in a place where when things get tough, when things get difficult, people can turn to you and you can be like, yeah, sure, I'll carry that for you.

The idea is you have a surplus of discipline and strength so that one might be of service to others. and how does this relate in your personal life as a husband and a dad of carrying the load of being a provider I'm curious how you look to this when it comes to leading your family yeah sure it's attention right also you can't do everything for your kids uh you're also not helping anyone by burning yourself out but the idea that like um you know you're you're the uh I'm not the sole provider in my family, but the idea that like you're a provider that these people depend on you should give you strength and remind you why you are doing this stuff. I think there's a tension though.

I think oftentimes that can be very seductive, if not outright misleading to people. Like people go, you know, I'm doing this for my kids. And it's like, that's not why you're in Vegas at a conference, right? Like, you know, what your kids want is you. And you have said, oh, no, for you, I'm on the road 280 nights a year or whatever, right? You have to be disciplined about being disciplined. You have to be disciplined about your drive. You have to be disciplined about being a provider.

You have to have a sense of what is enough also. So there's a tension in all of these things. Me, I tend to have more of that problem, right? The problem of I could work 40. eight hours straight and I have to go that's not healthy that's not reasonable I'm gonna I want to do a more balanced sustainable approach and to me I want to be disciplined enough in my day-to-day routines and habits that I can be home in time for dinner and be home in time for dinner and have energy to play and to do stuff like that's that's kind of how I try to think about it what made you want to live on a farm

with a bunch of animals to take care of well my wife really wanted a farm and it sounded fun to me but it was thinking about, you know, where are you happiest and what does your ideal life look like? I think a lot of people, you know, they get a job, and then the job says, we need you to move to Charlotte, and we need you to move to Anchorage, or we need you to move to Midland, Texas. And that's why they live where they live, even though they hate it, right? And it makes their family miserable, but it's well-paying or it's their job, you know, deciding, hey, where are you at your best, you know, what are you doing all of this for? These are important questions you have to ask. And obviously, my line of work has certain freedoms, but it also has certain obligations. I mean,

I would probably make more money. My books maybe would sell better if I lived in New York or L.A. and I had more a direct connection to those industries. Maybe I'd have to travel less and things like that. But the payoffs, the lifestyle that comes from where we've chosen to live, I think, has contributed overall to a happier and more balanced family life. And I find that not being around a lot of people who do what I do allows me just to focus on what I do and not spend so much time comparing myself to other people or trying to compete with or beat other people. How frequently are you on the road speaking?

Well, I mean, the pandemic was incredible because I realized I spent like 500 consecutive nights, not at home exactly because we took road trips and stuff, but 500 consecutive nights with my family, which I probably never had before and never will have again. But for like, let's say almost two years, there was very little in the way of travel, which was quite nice. And I very much realized not just how much better that made me at home, but actually better at my job.

Like this is the first September and August and September tend to be very big speaking months, because people book like back to, I don't know why. It seems like a weird time, but the fall is the speaking, speaking, like, zone. And so this is the first September and August where I'm like packed, back to how it was before. And like, I'm already realizing, oh, man, this is going to cost me. So it'll be lucrative in some ways, but it'll cost me in a lot of ways because I'm going to be not just away from my family, about my routine and the structure and the mornings that I do my work are going to be different. So I don't have a good answer to that question right now because it hasn't been normal for

so long that I don't feel comfortable going like, this is how often I'm gone. But I try to be home a lot more often than I am gone. I was recently in Tahoe at a house with a number of NFL players. And I asked them, you know, how is it when you're, coach or your general manager brings in a guest speaker. Yeah. And man, they were like, oh God, that's the worst. Like we hate those things.

Yeah. Like those guys don't have a chance with us. So it seems like the hardest audience ever. And this is an audience that you have, quote, performed for. You've spoken for many times. How is it for you in that type? Because what I'm getting at is like performing in front of a tough crowd, a tough audience.

I think it's good learnings, probably. Life for all. What's it been like for you? So I've done a number of sports teams. The weirdest one I ever did was I spoke at the NFL owners meeting like three years ago, which four years ago, I forget exactly, but it was all the, all the owners of the NFL teams and spouses, all the head coaches in the NFL and spouses and all the GMs and spouses. Target rich environment for more gigs though. Yes, certainly, but but you go, okay, there's a minimum of 30 billionaires.

you know, then everyone else is someone you've seen on TV many times and then all the other people run billion-dollar franchises. Speaking to coaches and GMs is often an easier environment because they really are specifically looking for something. When I talk to athletes, which I do all the time, I'm supposed to do an NFL team next month, what I try to think is okay these people they didn't none of the players asked for me to come right

all they do in the off season in these sort of training camps is practice and sit in on meetings so they're already burned out and so I just try to think like what are one or two very practical things that they can take from my work that might apply to their work so I I don't I don't try to inspire them. I don't try to like do a sermon or something. Like I very much scale it back and I just go like here's like five things that I know work and I'll just hit you with those things. And if you want to have a conversation after, let's do that. But I think a lot of people get in there and their ego comes into play and they want they they're imagining some situation where they give a talk. And then when the teams being interviewed the weekend before the Super Bowl, they're like, everything

changed when so and so came in and talked to it. And when you strip that away and you're just like, I just want to give you something. I'm not going to blow smoke up your ass. I'm not going to, I'm not going to perform. I'm just going to try to hit you with something that I think works, that I believe in myself. And then you kind of leave it there. when you're in front of 30 billionaires and GMs and all those people, do you have imposter syndrome? I mean a little bit. So when I spoke at that one, it was, it was, the NFL had hired Ted, the conference to have like four speakers come and give miniature TED talks on what they were experts about.

So I had, I think, 12 minutes to talk, which was, as you know, a short talk is often harder than a long talk. Way hard. So I had 12 minutes. They had to approve it beforehand, which was, so you had to practice, like you had to do, you couldn't just like get up there and give a talk. You had to perform a thing, which made it harder. The trickiest part of that one where I do find there can be a little imposter syndrome as they go, okay, so I was the last of four or five speakers and they were like all the speakers,

I was going last, and they were like, and then all the speakers will sit here. You'll go, the one will speak, give the clicker to the other one. one right after another. And I was like, you got to be out of your mind if you think I'm going to sit here for 50 minutes watching other people give talks. To then, I was like, I need to be pacing in the back like a crazy person, which is what I ended up doing. And I knew a few of the coaches and they were all just sort of looking at me and laughing.

But for me, it's not, it's not like imposter syndrome because I, in that situation, am I the most qualified person in that room to give a talk about stoicism? yes, right? And so, so like I feel, I feel confident in my ability to do it. I also think, like, yeah, like, who am I talking to? These are not people that have Yale degrees in philosophy that are going to pin, you know, that are going to try to find errors in what I'm doing. They're just actually going to try to listen. So I try to sort of think about it that way. For me, it's more the trying to not get in my own head. So like ordinarily, if I was choosing the environment, I would have gone for a run. I would have, you know, sort of gone through my ritual and then gotten there and sort of gone straight

into the thing. So it's more about like the nerves and the energy as opposed to like, I don't think I can do this. It's about getting in the right headspace. When you think about those handful of actionable takeaways you try to deliver to these guys who don't necessarily have not signed up to see you speak. I'm transitioning to the player one. What are a few of those, we're shifting to the actionable, implementable things that people could do? Like, what are a few of those things that off the top of your head that you think you would normally share in those settings? Yeah, I think my talk to Alabama is on YouTube and I think my talk to the Browns is on YouTube. But if I'm remembering what I usually start with what the core exercise of stoicism is,

is it called us the dichotomy of control, what's in your control, what's outside your control, which of course is a thing that athletes have heard a bazillion times. But I try to, I'm trying to take something I know, in that case, I'm trying to take something I know they already probably agree with. And I want to explain what its roots are and why it matters and what it looks like, how you can take the philosophical precept and apply it more directly to sport. So I might start with something like that. I might talk about the idea of the obstacle is the way that how we can choose to see obstacles as opportunities, right? This, which relates to the idea that we don't control what happened, but we control how we respond to it. Usually I'll talk about ego

because that seems to connect to sports. And then usually I end with something about momentum more, the sort of practice of the shortness of life. So I kind of, it's not that I have a greatest hits, but I go like, these are the things that the stoics themselves were talking about over and over and over again. And so how do I reduce them down to their essence? So someone who is not interested in philosophy in any way can go, oh, I see how that would pertain to a shitty ref or bad weather or a coach that's being unfair. Like, I see how that works in my life. What do you think your life would be like if Dr. Drew didn't talk to you about or recommend you read a book on stoicism? You know, we should always have a,

a certain amount of humility and gratitude that our life ends up the way that it does. Like a certain chance encounter can set you down an entirely different path. You know, I get this book recommendation at 19 that opens up this whole world to me. Is it likely that I probably would have been introduced to Stoicism anyway, given the people that I knew and the things I was reading about? Probably. And that's probably what primed me to jump on that recommendation when I got it. But we can be very hard on people who are not successful or don't know certain things or their life has turned out a certain way.

And we discount how much a single interaction or a single chance encounter can just totally change the direction of somebody's life. So I think about it less like how different would my life be. And I think about it more in terms of like how do I pay that forward? How do I have a similar impact on other people because I know, I feel very grateful that that happened to me. I'm curious about your views on friendship. Maybe it may seem odd, but to me, I think about how to be a great friend. And that includes with your partner, first and foremost. But when you're thinking about friendship, what are the qualities, what are the makeups of a great friend?

I'm thinking about this now, is the third book in the series I'm doing is about. about justice. And I would put friendship and love and marriage, those under the virtue of justice. How does one treat other people? What does one owe other people? You know, I think it comes down in many ways to the Golden Rule, which is this beautiful thing

that is expressed in almost every philosophical school and every religious tradition. You know, how do you treat people? And usually I would say, you want to treat people kindly, patiently, generously. I think we tend to think of stoicism as this individualistic philosophy, this thing about controlling your emotions, about being tough, about enduring, about having a schedule like we're talking about. And that is a part of it. But I think some of the most beautiful stories in stoicism are about friendship, they're about

loyalty. They're about what we do for each other, which I do find to be rather lacking these days. What do you mean? Well, I think people often turn to stoicism for, you know, an excuse to be a better sociopath, right? Or they, I think you obviously saw this during the pandemic. People are like, I'm going to do what's good for me, right? And the idea that it's not that simple. Like the actions we take, the decisions we make, they have, they have implications. for other people, right? And not only do we have an obligation to do this, but it's also good business to think about, like you think about the companies that treated their employees poorly during the pandemic, those are the companies that are having trouble hiring people. The companies

that have treated people well, that are generous, that are supportive, that are aligned with what their employees care about and like, who don't accept, you know, abusive, bosses, et cetera, those are the companies that retain people that get buy-in from their people. And so when we think about friendship, think about relationships, I think it's worth noting that it's not just this moral thing to do. It also benefits you, right? There's a self-interested case to be made for it as well. Controversy. I'm curious. You, from the outsider's perspective, have taken stands on some thing. Speaking of the pandemic, your, your bookstore, you guys wore mask a lot longer than

you needed, like at least in the state said that you had to. You've paid to take statues down. I think just recently there was a book reading in your store that people, there's a news article or a TV show, a news came and covered. And you have not shied away from these things. I know it's cost you fans. It's cost you readers. And I'm curious, you're over. You're over. overall philosophy and mentality on taking a stand, doing what you think is right, even though it costs you. The opposite kind of of the Mike would Jordan, will the Republicans buy shoes too type of mindset? Yeah. You know, it's funny because when you do stuff like that, some people are mad. Some people are like it. And then some people accuse you of doing it cynically because they think you're doing it because people will like it, even though objectively it's quite expensive.

It's strange. But the way I think about it first and foremost is, like, as a writer, people say, well, why are you talking about that? Don't you realize you're going to upset some people? And I think about it in terms of what is the point of being a writer and having a platform if I then don't say what I think for fear of offending certain people or fear of costing myself? is it how how successful are you really if your success is so precarious that you cannot be yourself or worse you cannot do or say the right thing because you're concerned about losing customers or supporters or whatever like i didn't open an independent bookstore in rural texas to get rich right

like uh so knowing that and being very clear about that from the beginning like with myself and with my wife who opened the store with me, it makes it very easy and clear about whether we should or shouldn't do certain things because like money has not been part of the calculus from like the beginning. If it was, if we were thinking like, okay, this is how much money we have to make or this is how we optimize because we want to turn it into franchises or whatever, then these these decisions would be more fraught. When I'm opening a bookstore because I want to have the books. store that I want to have and I want to do certain things with it, then if I think something is right or we think something's right, it's much more clear cut. Does that make sense? Yeah. And also

that, you know, like the people that work there, like to go to the mass thing, and I know it's like a controversial discussion, but I think about it very simply. In the early days of the pandemic, I did not want to get sick and I did not want my family to get sick. And I did not want people in my community to get sick. And then when, you know, vaccines became available and there's drugs, etc., we sat down and had a conversation with the employees. And we said, do you guys, the mask thing is not coming from us anymore. Do you want to continue wearing masks and do you want to have the customers wear masks? And they said, yeah, COVID sucks. It sucked getting COVID. I don't want to get it again. And so he said, all right, then issue settled, right? So the decision there is not

motivated by what I want or some statement I'm trying to make. It's actually much simpler, which is if I was a cashier at a bookstore, would I want people breathing in my face all day? And the answer is no. And so I asked them and they said, no, we don't want that either. And so the issue is settled. Does that make sense? It does.

It does. And I think owning a bookstore seems like it would be a really cool thing, although I imagine and it's really hard. I'm curious, what do you like best and least about owning a bookstore? You know, I really like the physicality of it. Like, I've always loved physical books. It's beautiful space, I mean, from what I've seen. Yeah, you've got to come.

We'll do something if you ever come. But for me, like this podcast, you're reaching millions of people remote. That's super cool. Probably 50, 60% of your book sales are digital, either in audio or ebook. also really cool, right? Social media, enormous reach, really cool. So to have something that's physical and real, and I can be like, what am I going to put in the window today?

Right? It's really cool. Like, come out. Like I was saying, come see the space. The physicality of it is really cool. And I've really enjoyed that. And then it's actually helped the, like, the idea originally was like bookstore downstairs,

office upstairs and COVID and like every for everyone else like now the hybrid work is a reality. And so we kind of just have a rule with the employees that's like I ask the employees and obviously it'll fluctuate depending on what happens with COVID. But I said you have to average two days a week in the office. So if you want to come six, you know, eight days in a row and then not come in for three weeks, that's cool. If you want to come, you know, every Monday and Thursday. That's cool, too. But the idea is there's just always people that work for the company like in and out. So there's like bump in sort of serendipity and like people have lunch together or we talk about stuff. You know, conversation happens instead of 46 emails about it.

That physicality of it has been really great for someone whose work was always remote well before the pandemic. And all these people were contractors or remote employees. That's been really helpful too. It seems like you've invested a lot in content creation videos, social media. I read that you shifted your marketing budget from buying like Facebook ads or other things to just content creation. I sent you a message a while ago. I'm like, dude, your social has really gotten good. The video specifically and you said I had to hire it in-house, man, because I was like, where can I find that? How can I get that going on you? I hired her in a house. So can you share a little bit more about that philosophy and content creation and getting more out to the masses as well as maybe

even the business elements of hiring people to build up that team. Well, it's funny because I was just saying how much I love the physical element of it. I love books. I love text. That's how I consume information or ideas and having to come to terms with the fact that like lots more people consume via podcast, consume via Instagram, consume via YouTube, consume, via TikTok and going, if your ideas matter to you and you think they matter to the world, you have to figure out how to translate them that message into the formats of these different mediums. And so that took a lot of experimenting and a lot of work and some significant investment, but not more than I might ordinarily be spending on, yeah, Facebook ads or whatever. It was

the decision to say like, hey, instead of doing this other stuff that doesn't really mean anything, let's just make stuff that we're proud of and get fluent in the different mediums. Like TikTok is not something I consume, but figuring out, okay, here's how you would take an idea that I might have spent two years writing about in a book. How can I distill that down into 46 seconds straight to camera? And then going like, wow, that thing was consumed by more people than have read my book, right? And so I've just spent a lot of time trying to translate the stuff into different mediums. But what I have found is that when something works in one medium, if you do take the time,

it almost certainly will work in another medium. So, you know, a blog post is an idea. And that idea could be expanded into a book. It could also be distilled down into a tweet. It could be translated into a YouTube video. or let's say translate it into a TikTok, which can also be an Instagram reel. And then a collection of Instagram reels about those ideas can be a YouTube video, right? Or a podcast episode.

And so I just try to think about making it work in these different mediums. Speaking of the distillation process, and this isn't exactly a line, but I wanted to touch on it before we go, silence is strength. The Spartans quote, I think it's laconic style. Leconic. is me yeah that means that the spartans were the lacedamians or the lacedomians and so they were known for their witty one-liners like uh have you seen the movie 300 right like we shall fight in the shade that that's what leconic means okay okay so basically never use two words when one will do uh when i've had robert on robert green on a number of times we've talked a lot about this say less

than necessary don't speak unless you can approve upon the silence right and and and i think Archimedes once explained at a Spartan dinner, an expert on speaking also knows when not to do so. I think this is, whether it's from power with Robert Green or others, this is what people get wrong a lot. I've certainly messed this up. But when thinking of a leader of, like, sometimes I'll go to a meeting and not talk for two hours. And you see other people around the table, like just, you know, have an opinion on every single thing. And I'm like, well, I don't really know. So I'm not going to say anything. And sometimes it looks bad. I'm not going to lie. Like, this actually happened to me recently where I was quiet for a very extended period of time because I had no idea

what they're talking about. And I think though that, but I think of this a lot of like, don't speak unless I can improve upon the silence. And so many others are speaking and not improving upon the silence. Can you share more about like why this is an important thought for people to think about? Well, I think you're right to point out that that requires an immense amount of self-discipline, right? To be quiet. It's easy just to pull something out of your ass. It's easy just to agree. It's easy. When I talk to athletes, I talk about this too. Like, almost never is you expressing your opinion about one of your teammates or about the organization or about another player going to benefit you positively. So just don't send the tweet, right? Like, just don't send it.

It's going to cause more problems than it solves. But like, you find, incredibly powerful people. The most recent president of the United States could not not say things that popped into his head, right? And so it's a superpower to have something to say and to not say it takes a lot of strength. Also, I think to say what you're saying clearly and succinctly takes a certain amount of self-discipline too. Like the guy who spoke before Lincoln at Gettysburg spoke for two and a half hours, you know, 13 or 14,000 words, some incredibly long speech. And Lincoln gave a speech of 230 words. You know, which one spoke the loudest, which one had the biggest difference. And so often it's not just not speaking, although that's important,

because you can't regret what you, well, you can't regret what you didn't say, but more often than not, you regret what you said, not what you didn't say. But also, to say, hey, how can I say this in the fewest words possible? When I go back and edit my books, that's what I'm doing. I'm deleting things. I'm getting rid of things and realizing I've already made this point, less is more. That's why the best stand-up comedians, right? They are carving every possible word to get it to the minimum number to tell that joke.

And it looks like they're wandering around just talking, but the best of the best, they are not doing that. They are refining constantly to get to the essence and share that message in the fewest number of words. And I think all of us, whether you're a keynote speaker, you're giving town hall speeches, you have Monday morning meetings with your team, whatever may be. Like that should be the mentality. The problem is it takes a lot of extra work. It takes a lot of time to edit your books. It takes a lot of time to carve a speech down or to carve a joke to a shortest number of words. and people, I guess, are lazy or they're not willing to put in the time to get it down to its essence?

I think that's right. No, it's easier to just riff, right? Right. Just go on and on and on and on. And you have to cultivate the ability to stop yourself. Or if you can't do that, you have to cultivate people around you who can go, all right, let's go, you know, who can wind that down. I always love when you watch someone talking and you can tell they're about to stop and then they almost interrupt themselves and with a tangent and now you're like, oh man, it's going to be another 30 minutes. So the ability to sort of keep it brief and wind it down is, yeah, the most important thing. When you think about it, I've actually before, but I'm going to ask again because we're going to, we talk at least once a year. The people who have, which I love as you know, the people who have sustained excellence, right?

Over time, as you continue to update your answer to this one, I'm curious, what have you found to be some of the virtues the behaviors, the thought processes, the routines, the actions of the people who have sustained excellence over an extended period of time. Yeah, that's a good question. I just did an interview the other day where someone had asked me the same question like three or four years apart. And I gave the exact same answer, which I was very, I didn't know this, but they showed me after. I was like, oh, wow, I guess I actually mean this. I wasn't just pulling it out of my ass. But when I think about sort of sustained success, obviously, standards are important. Obviously, sort of drive is important, hunger is important. But I would say the big thing is like a process or a system, right? Like this is what I do. Right. So the ability to not have to think about the external results, but think about that process allows you, I think, to get lost in it and to endure the ups and downs. Like you're going to have good seasons and bad seasons. But if you, what you love is the game.

game, you can endure that. If you need everything to be going your way, you know, you're going to have trouble with those those bad years, right? So to me, it's about systems. Like, again, to go back to writing, if your system is, you know, I'm trying to prove something to someone, you know, I write when I'm inspired, or I write with my back to the wall or whatever, I don't think that's sustainable. But if you have a process that you follow and you're just always following that process, like Joyce Carol Oates, I think published work comes out of the other side of that. It's it's you probably get this with writing and podcasting and other things, but frequently someone says like will you help me launch a podcast like share with me all the stuff that goes into it?

I'm like sure, but I have one question before we we get into all of that. Why are you doing it? Sure. And if they say something like well, it'll help me get more speaking gigs then I'll say no like it's yeah it's too hard. It's too hard to do it well where you're going to prepare and read a full book, right, and take diligent notes to ask thoughtful questions of the, if you're going to do a show like this one. It's too hard if you have this goal of one you get speaking gigs. The why, I think at least, could be wrong. The why I think is you have to love the act of preparing and actually having the conversations and the recordings itself.

And whatever comes from it, comes from it. But if you don't love that aspect of it, you won't sustain. it. It won't happen. And this happens nearly 100% of the time. If it's because of the speaking gigs or maybe I get a book deal or whatever, they'll do it for a little bit and they'll be excited. Don't get me wrong. And then what do you think happens? They quit. Now, you're right. The why is the why is hugely important and the why can't be, and what the Stokes would say, external. So the why can't, like if your why is I want to get rich, that is a why. Right? That's better than I don't know, everyone else is doing it.

But it's it or I want to be accepted by this group. The why has to be something you control, which is I love expressing myself. I have something I want to say, right? The why has to be sort of intrinsic. And yeah, you have to genuinely love the process of the thing. Like for me that like what I do is very simple. It's the daily email. You know, I write, you know, I try to write the books,

or collections of stories and then I do the podcast. The thing is very simple. And I could show you what camera equipment I use to do the TikToks. And I could show you, you could poach all my people from me. But almost certainly, one, because luck and timing plays a big part in why it's work. But almost certainly you will not recreate what I have because you won't actually do. Like someone just hired me a couple months ago and we went over it. And at the end of the day, it was like, well, where is it?

the stuff. Like I showed you all this how to do it all and I gave you all the resources to do it, but you didn't make the stuff that plugs into the pipeline. And at the end of the day, the stuff is the only thing that matters. The daily aspect of your work, that seems almost overwhelming. Like do you ever get that sense of like, wait, maybe I should scale this thing back? Daily is kind of a lot. Daily is a lot, but it's not actually daily for me. So the output is daily, but the creative and the creative process is daily, but it's not one to one. Like my friend Casey Nystad did did this daily vlog for like two years and it almost killed him because he would make a vlog about yesterday every day, which is insane, right?

I do a daily email, but at any time I'm 25 to 30 emails ahead. So I make stuff when I feel like making it, I record, like I'm always. doing it because I always feel like it. And if for whatever reason I lost heart, the system would eventually come off the tracks. But I'm just making stuff on a regular basis that plugs in. And I have people that put it out. But I'm not like one to one. I have to write an email for today. That would be a grind that I don't think would be sustainable. The book's called Discipline is Destiny. And I absolutely plowed through this one. We probably cover like 15% of it today. So there's so much more.

to get. I'm really grateful for you, man, for sending it to me early so I could take a look. I read all your stuff, cover to cover, articles, books, whatever it may be. So thank you for doing it. Thank you of putting this out. And it's obviously impacted my life in a big way. And I know millions of other people. So I really appreciate it, man. Discipline is destiny. I highly recommend people pick this book up. Oh, thank you. And as always, certainly love to continue our dialogue as we both progress, ma'am. Let's do it. All right, ma'am. I wouldn't have somebody on my podcast seven times over the past seven years if I didn't love their work and the manner in which they did it. And Ryan Holiday certainly fits the bill. I admire his production, how prolific he is, and constantly

publishing work that is useful and makes my life better. That's why I always enjoy speaking with him. I hope you found this conversation beneficial for your life. A few takeaways from my notes, the Lou Gehrig quote, When you love the work, you don't cheat it or the demands it makes of you. You respect even the most trivial aspects of the pursuit. That to me embodies how we should go about our work. We can't cheat it. It helps to love it.

And if so, the results just happen. And as my friend Brooke Cups might say, you need to surrender the outcome and fall in love of the process. And then be your best. Conquering the world is rather easy after we have fully conquered ourselves. Certainly fewer people have done the latter than the former. It's tough to conquer ourselves. It's a never-ending process. We need to spend regular time in reflection and understanding what we're,

we're doing, why we're doing it, and the impact it's having on people. And then carry the load for others. General Jim Mattis said the privilege of command is command. You don't get a bigger tent. Being the boss is a job. Being a leader is something you earn. I think if you're listening to this podcast, that's something you're working to earn every day. Once again, I want to say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with Ryan Holiday. I think he'll help you become a more effective leader. And because you continue to do that and you continue to write reviews and rate the show, hopefully five stars on Apple Podcasts, you are giving me the opportunity to do what I love on a daily basis.

And for that, I will forever be grateful. so, so much. Talk to you soon. Can't wait.