Viewing Discipline as Destiny with Ryan Holiday

December 20, 2022

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Ryan Holiday is one of the world’s bestselling living philosophers. His books appear in more than 40 languages and have sold more than five million copies. In his New York Times bestselling book Courage is Calling, Holiday made the Stoic case for a bold and brave life. In the newly released second book of his Stoic Virtue series, Discipline is Destiny, Holiday celebrates the awesome power of self-discipline and those who have seized it.

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John: Welcome to another edition of the Impact Podcast. I’m John Shegerian. Thank you very much for being with us today. We’re so honored. This is our holiday edition of the Impact Podcast and no greater person than to have Ryan Holiday himself, the author of Discipline is Destiny, his new book, which is already a New York Times Best Seller. Ryan, welcome back to the Impact Podcast.

Ryan Holiday: Yeah, thank you for having me.

John: Ryan, we had a great chat the first time. But this time, we’re going to be talking about your new book. We’re going to do a very short podcast today because time is more precious than ever. I’m going to start with one of the great rules that you laid out in the book, which I think you heard from Les Snead of the Rams. The main thing is to keep the main thing the main thing.

Ryan: Yes.

John: Lay it out. Talk a little bit about that. That’s why we’re doing a really short but sweet podcast today.

Ryan: It’s easy when you don’t have much going on to decide what to do and what not to do because you don’t have that many choices. But as you become successful, as you take on more things in your life, whether that’s family or causes that you support, what happens is that you still have the same amount of time in the day, you’ll have the same amount of energy, the same amount of ability to do stuff and you have a lot of different things that you can do. Obviously, Les Snead’s the GM of the Rams. But I heard this from a performance coach in baseball as well. He said, “The major leagues, it’s all about pitch discipline or swing discipline. What pitches do you swing at? Which ones do you think are going to get you where you want to go?” And so, it becomes this difficult choice. I have here, next to my desk, I have a picture of my kids, and then I have underneath it, a sign actually that that sports psychologist gave me. It’s a picture of Oliver Sacks and behind him is just a large sign that was in his office that just says, “No.” A reminder that we have to say no. What is the important thing? What are the things that only you can do? What are the things that really move the needle for you? And then, you have to say no effectively to everything else.

John: Like I shared, this book is already a New York Times Best Seller. I’ve read it. I loved it. I’ve already shared it with many others. You were kind enough to sign some copies that we’re going to be giving away to some of our listeners. What’s your main goal that you hope that your readers or listeners on Audible take away from your new great book?

Ryan: I think it’s important that we don’t just see discipline as a means to an end. That if you eat well and exercise, you’ll be in good shape. If you work hard, you’ll succeed. But that also discipline is an end unto itself. It is a form of greatness in and of itself. Sitting down and working hard on something isn’t valuable only because it will get you to some point that you don’t have to work hard, but that by concentrating, focusing, and eliminating the inessential, by giving your absolute best to something, by learning as you do, all of the things that discipline brings out in you in that moment, which by the way, is the only guaranteed thing. The outcome is never certain. That is greatness. I want people to understand that it doesn’t all have to be professional sports, writing, or something that makes you millions of dollars. But just, again, being disciplined, committed, and in command of oneself is impressive and great by itself. The stokes are saying that look, to be in a position of leadership, you have to deserve it by being first, in command of yourself. That’s really what the book is about. It’s about being in command of yourself so that you are eligible and likely to be a good leader. But also, because, if you’re not in charge of yourself, who is?

John: Right, right. So when we look back to the greats, like Vince Lombardi, one of his great quotes was, “Chance favors the prepared mind.” Again, it’s not determinative, but it’s predictive in terms of [inaudible].

Ryan: Yes. It’s determinative, but it also is guaranteed in the sense that doing those things are good unto themselves. Again, you’re not eating well so you look good 6 months from now. You’re eating well so you feel well now. What I’m really trying to say, what the book is built around and I think this is true 2,000 years ago, but it’s definitely true now, is that look, no one is really telling you what you can and can’t do. You can do anything you want. In light of that freedom, we have the opportunity, some would say the obligation to set our own boundaries, rules, and limitations about what we do and don’t do because if we just do everything that we want, whenever we want it, we think we’re getting a great life. We’re actually getting a terrible life.

John: Got it. Phil Knight, of course, I would assume is probably one of your followers. You’ve got millions of followers now. A modern-day Phil Knight wouldn’t just come out with, “Just Do It”, he would also come out with a line of clothing that would say, “Just Don’t Do It”. His new [inaudible] [crosstalk]

Ryan: Yeah. The epigraph from the book is a quote from Epictetus, the stoic philosopher who was asked to summarize stoic philosophy as a whole and he said, “It’s two words, persist and resist. Some things you should do and you have to keep doing them and other things you have to stop doing.” That’s kind of the tension. I think what’s so interesting, even about self-discipline, is it can be taken too far and become a vice. The other way the stoics rendered this virtue was temperance or moderation. When we think about discipline, we don’t just mean always doing the hard things, but we’re also talking about rest and recovery. We’re not talking about pushing yourself harder and harder and harder, but also, are you pushing towards the right thing? And just understanding that at the core, it comes down to this very important idea of balance.

John: Ryan, one thing I loved about your book that I love about all your books, frankly, is all the storytelling that you do in it, with historical figures and modern-day figures. If you were to pick a favorite story out of this book, what would be your favorite story? I know I have one but what would be yours?

Ryan: Well, I’m very curious to hear what yours is. But as I was building the book, I didn’t just want to talk about physical discipline because although that’s easy and it’s certainly something that we need the most help with, I wanted to talk about the other domains of discipline. The first character is Lou Gehrig, who I talk about as the greatest streak in baseball. But then, the next big character I talk about is Queen Elizabeth II, who died shortly after the book went to the printers. You look at someone like Lou Gehrig, who plays 2,100 games in a row. Queen Elizabeth was on the job every day for 70 years. It wasn’t so much a physical job, although she spent lots of hours shaking hands, and standing at attention, and doing all these things, lots of travel and all that. But, you think of the restraint inherent in that position- not giving your opinion, not getting involved in politics. Even though you have unlimited wealth and unlimited access- not having affairs, not spending more than… She was the picture of temperance or moderation and mostly in the emotional and verbal sense of that idea. I found her to be a fascinating and inspiring character that I wanted to spend a good chunk of the book writing about.

John: How your book ended, one of the many great stories that you related her to and depicted was how she sat alone at her husband’s funeral.

Ryan: Yes, yes.

John: As compared to governors of maybe the fair state that I’m sitting in today and that you were born in, who were living it up at the French Laundry during the pandemic and asking the public to do one thing and living a different life himself. She basically walked the walk but talked the talk, and did it the right way.

Ryan: Yeah. You can trust that even with Boris Johnson, who is having parties at the Prime Minister’s house. She could have and would have been granted any exceptions or exemptions from the rules that she could have asked for. We can reflect on whether it was actually necessary at that point and how tragic it was that COVID even happened. All of that is secondary to the fact that she felt that as a person in a position of power and influence, as the head of this thing, that in fact, the rules applied to her the strictest. I think the lesson there for all leaders- a military officer told me this. He said, “We have this acronym in the military. RHP. Rank has privileges.” But he said, “Actually, the great leaders understand it as rank has responsibilities.” Deciding how you think about that is to me, ultimately, a matter of discipline.

John: During the pandemic, you started The Painted Porch, the bookstore in your community of Bastrop, Texas. If any one person would walk into your bookstore today and asked the clerk behind the counter, “I’d like to see Ryan because I’d like to meet him and have dinner with him tonight,” what person, who you haven’t met before, would you be immediately stoked when your clerk came up to your office?

Ryan: A living person?

John: A living person, right now.

Ryan: I’d love to have dinner with General James Mattis, who I think is a modern stoic and an all-around fascinating person who’s had a fascinating life. Yeah, if he came in, I would hurry downstairs and not pretend to be busy as I often do.

John: Ryan, one thing that I love in what you do… Martin Luther King is a hero of mine. You have him all throughout your book. One of his great quotes is over the front door of our offices here for 18 years. “Everyone can be great because everyone can serve.” But you also are very balanced in your approach to the heroes and our inspirational figures like Martin Luther King. And also, you create this Hero versus Nero in almost everybody.

Ryan: Yeah.

John: How do you reconcile the paradox that all human beings truly are when they do great things and inspire us to continue doing great things-JFK, MLK, and Winston Churchill? But also, they have a little bit of Nero in them and in some of them, the little bit of Nero sometimes unravels them, and sometimes, they actually overcome that.

Ryan: Yeah, yeah. That’s a great question. King himself talked about this. He said that inside all of us is a civil war. He said there’s the north of our soul and the south of our soul. I think, perhaps, the reason that he was able to empathize and not write anyone off as being totally this or totally that, was he understood that even in himself he was complicated. Lincoln does this also. He says, “We are just what they would be in our position,” realizing that people are complicated. People are a product of their environment. People are not fully good or bad. I do try to celebrate what’s great in people, but I think one of the problems if you only celebrate what’s great in people is that you make it sound like they’re saints, that they’re perfect, that they came out of the womb better than you and I did. That’s why we’re not capable of doing the kinds of things that you’re doing and realizing that these are very flawed human beings. But that also, it was through self-discipline, courage, justice, or wisdom- the virtues that I’m talking about in this series- that they made themselves into the person we now admire. This goes all the way back to Aristotle. He says, “Look, if you want to be a generous person, start doing generous things. If you want to be a disciplined person, start acting with discipline.” It’s not this magical state that you arrive in. It’s a thing that you do. You’re a product of these actions. I think if you look at someone like Martin Luther King, did he have flaws? Did he make mistakes? Did he do some things that were shameful and embarrassing? Yes. But, if you’re looking at the totality of his actions, the vast majority of the time, he does the right thing. Sometimes, does the wrong thing. If that’s the ratio that we aspire to, we’re going to get closer to those kinds of heights and further away from the lows or the south inside all of us.

John: One last question, Ryan.

Ryan: Yeah.

John: Planning is everything. You and I would rather be the founders of Facebook than MySpace.

Ryan: Sure.

John: It seems as though, I know you had planned out this series of topics in books long ago because you said in our last podcast when we were talking about courage. It seems like this book on discipline is almost- the timing is perfect. It seems like there’s been a massive rise in these discipline gurus when you look at the guardians of the world, in the Jocko Willinks and the Rich Rolls of the world. And we’ve had a slide in society and culturally speaking, in terms of the icons that we’re so used to believing, in business icons- just look at what’s happening with FTX, political icons, January 6th, and even media, is your book perfectly on time? Is your timing that good and is it just perfectly on time for really what we need right now in society?

Ryan: I mean, I think you’re always a product of what’s happening in the world, and you try to tap into what’s happening, I got some really good advice from Robert Greene who was my mentor early on. He said the key to a great book is to be both timely and timeless at the same time or to find the timelessness in what is timely. So as I’m writing this book over the last 2 years, I’m obviously influenced by what’s happening in the world. I’m a product of what’s happening in the world but I’m also trying to root what we’re dealing with thinking about going through in ideas or people and places and things that are going to continue to be relevant and have historically always been relevant. So, I think for me it’s always about striking that balance. If you are only thinking about what’s cool, popular or trendy right now, if you’re trying to ride that wave, you’re going to miss the bigger, timeless, more important ones that are coming down in the future. I don’t know how perfectly timed it is. Certainly, it has been working lately which I’ll take. But if you ask me to choose do I want the book to be popular right now or continue to be popular for a long period of time, I would always choose the latter. I try to focus on that more than I focus on timing in the sense that you are talking about.

John: Ryan, thank you for your time today. I want to be very, very cognizant of the time you spent.

Ryan: Well, thank you.

John: I love this coin.

Ryan: It seems amazing.

John: This coin is on my desk. This is my office here where I’m taping this from and this reminds me of what’s really most important every day.

Ryan: I have a ring version that I’m wearing.

John: Nice. Is that new or is that…?

Ryan: Yeah, it’s just coming out.

John: Awesome. Well, that’s a great holiday gift. This coin is a great holiday gift. For our listeners and viewers, Discipline Is Destiny. This is a great holiday gift to find Ryan, you can find them at, listen to his podcast, and read his daily ponderings at Also, Ryan, you’re on Instagram and your YouTube viewership is off the charts. So, for our listeners and viewers out there, or go down to The Painted Porch and buy a case of these books and give them out at the holidays like I’m doing. Ryan Holiday, I thank you for everything you’ve done. You have made me a better person in the last 5 years since I’ve been following you, and you’re the reason why we’ve enjoyed having you on the Impact Podcast. Thanks, John. I’ll talk to you soon.

John: Welcome to another edition of the impact podcast. My name is John Shegerian, and I’m so honored to have with us today, Ryan Holiday. He is one of the best-selling authors that we have today in the United States. This is his 12th book. We’re going to be talking about today, Courage Is Calling. Ryan, welcome to the Impact Podcast.

Ryan: Yeah. Thank you for having me.

John: You know, I’m not only a huge fan. I read your Daily Stoic and you already have, at 34 years old, a huge body of work behind you. The Obstacles Is The Way, Ego Is The Enemy, The Daily Stoic, Stillness Is The Key. I mean, 4 million plus copies, New York Times bestseller. Before we get talking about Courage is Calling, where did you grow up and how did you even get on this journey of being this prolific writer?

Ryan: I grew up in beautiful Sacramento, California. Not a child of writers or really anyone involved in anything sort of like this. My dad is a police officer. My mom is a school principal. Sort of ordinary civil servant kind of family. I fell in love with books. I knew I wanted to do something around books. I wasn’t sure if I could be a writer. I just knew that I loved reading and I wanted to do something very different than how my parents’ lives were. I didn’t want to go to an office. I didn’t want to have a job and ended up here through a variety of strange twists and turns. I wrote my first book when I was 24 I think so I do have a body of work behind it, but I also got started earlier than most. So it’s a somewhat unfair advantage.

John: Right. What informed you, what made you such a bibliophile growing up, and what books informed you to say this is maybe a path I’m interested in taking?

Ryan: Yeah. I really loved books and I loved reading, but I didn’t really get turned on to the kinds of books that I like now until much later, probably 18 or 19 years old. I just was a prolific reader of anything. The Hardy Boys books and then my sister would have Nancy Drew and I’d read that too. I read literally anything that was between two covers. So I think I started just loving the printed word. I loved the experience of reading. It wasn’t until a little bit later on that I really got sort of exposed to philosophy and even this sort of genre of self-help. I remember when I graduated from high school, my aunt gave me a copy of Man’s Search For Meaning, which was probably the first book in this kind of genre that I guess I’m in now that sort of exposed me to, that a book could be more than entertainment. That a book could really not just teach you about a specific thing like a book about gardening or a book about how to use a computer, but a book about how to sort of actualize as a human being. That was probably the book that sort of opened my eyes to most, or at least at first.

John: And you wrote your first book when you were how old?

Ryan: 24. I wrote an expose of the marketing industry which I had been in for several years after college. I started writing when I was 24. I think it came out right after I turned 25.

John: Got it. You have all these books behind you. You’re a New York Times bestselling author, and you’re also seen as one of the top philosophers out there right now. I enjoy your Daily Stoic, and for those who want to find you there, they can go to, sign up, and get Ryan’s daily newsletter. It’s so informative and actually really inspirational to get that every day. But what prompted you then to now go into this what is going to be, I believe, the series that you’re going to be writing the 4 cardinal virtues? You started with Courage Is Calling. What then prompted you to take on these 4 virtues now and start with Courage?

Ryan: My first book of philosophy was this book I wrote called The Obstacle Is The Way which I didn’t really have much in the way of plans for. I thought I wanted to talk about this sort of very specific way of thinking about stoic philosophy aimed at a very specific thing which is sort of the obstacles that life rolls in our path. It was my sort of first, I might say, my breakthrough book. I followed it shortly thereafter with another book which I’ve been thinking about before Obstacle came out, but ended up becoming more of a sequel to Obstacle than I had intended, or at least that I had planned for. So, 1 book became 2 books and then the 3rd book in that trilogy, which came out in 2019, was called Stillness Is The Key. So I sort of backed in unintentionally to this 3-book series, although none of it was planned as far as what follows each book. So they are sort of 3 independent but related books. So, as I was thinking about what I wanted to do next, I was thinking about doing a book on courage, I was interested in the topic. Then the fact that courage is the first of the 4 cardinal virtues really excited me not just because that goes to the core of what stoic philosophy is about, but I like the challenge of having to try to do a series. Obviously, philosophically, very interested in the sort of the idea of courage and its relation to the other virtues. As a writer, I was also excited by the challenge of tackling something as complex as a 4-book series.

John: So when you were going into this, you took on Courage first because you believe it’s central to the stoic of virtues?

Ryan: The cardinal virtues are the cardinal virtues of both stoicism and Christianity. It goes sort of way back, thousands of years- courage, temperance, justice, and wisdom. Cardinal comes from the Latin kardos, which just means hinge. So these are sort of pivotal virtues. I’ve written about them many times before. I just had never written a book about them. Could you do one book on all 4 virtues like a 4-part book on all 4 virtues, or would you decide to tackle it as 4 distinct books? I was excited about doing that. Then I started with courage. What it tends to be what is listed first like when you list them- we move the order around but typically, courage comes first. I think it’s the most essential of all the virtues in that you cannot have temperance, justice, or wisdom without courage. You really can’t have any of the virtues without each other. But I think courage is sort of the buy-in on all of the virtues. So it just felt like the right place to start. A lot of this stuff is kind of an intuition. Like when someone says, oh, why did you decide to write a book about this? You just sort of learn as an artist to trust what is interesting to you, what you’re thinking about, what you can’t not think about. That’s really what it is. I mean, honestly, my first book came from the fact that I kept talking about it and I finally thought I’m just going to write a book about this and then I won’t have to talk about it anymore, which is never really how it works. But you’re just motivated by this itch that you can’t seem to not scratch.

John: When you decided you’re going to do this series, before you started writing a word on Courage, did you already have in your mind which book you thought- you haven’t done them all yet- that was going to be the more difficult challenge to write?

Ryan: Certainly. I mean, I thought Courage would probably be the easiest. Courage is right down the middle as far as what it is, how you illustrate it, and why people care about it. There’s no society on earth, past or present that does not hold up courage as an admirable thing. There’s no society, the ancient culture of X that celebrated its cowards. That doesn’t exist. Courage felt like the reddest meat of all of them. I’m in the middle of the self-discipline book right now or temperance, which is proven to be trickier than I thought but it also is sort of straight down the middle. I think justice will probably be the hardest book, one because it veers the closest to politics. It’s the most clearly based on a sense of right and wrong, which obviously, there’s a lot of disagreement about. So that’s probably the book that I am most intimidated by. Then the one that I have the most reservations about is the wisdom book. In that writing a book about wisdom- all the books have this, but writing a book about wisdom, it still feels a tad presumptuous to be writing about that topic. So the wisdom book has its perils for different reasons.

John: In your book, and again, for our listeners and viewers out there, Courage Is Calling: Fortune Favors The Brave. Ryan Holiday, he’s with us today. This is going to be actually our Thanksgiving edition of the Impact Podcast because I think this is really a real special call to action. And Ryan, you’ve really written, as you can tell, a book that I’ve enjoyed tremendously and gotten a lot out of after my 59 years, a lot that I never even learned or even understood before. You’ve explained it simply and really clearly here with illustrative stories. In the book, you mentioned that we prize courage maybe the most, but courage is in absolute short supply. What’s your definition of courage and what do you want your readers and listeners to come away with from this great book?

Ryan: The definition that I have in the book, first stipulating that we tend to see there being two types of courage, what we call moral courage and physical courage. Physical courage, pretty obvious, that’s the courage of a soldier or a fireman or something. Moral courage is more the courage of a whistleblower, a scientist, or a groundbreaking artist or something. But I think what both those forms of courage share is willingness to put one’s self on the line for something or someone. So I think that the core of courage is obviously the idea of risk. If there is no risk, if the outcome is guaranteed, courage is obviously not in play. Risk is courage. It’s predicated on there being some form of danger, reputationally to your actual health, whatever it is. If the company is guaranteed to succeed, it’s not courageous to go start it.

John: Right. One of my favorite things that you did in the book is you gave all these illustrative examples of courage and you mentioned and quoted so many great people. I made a little game of it. I started writing down just like my list of everyone that you gave some great stories and quotes from. One of my favorite stories that I relate to the times that we’re living in right now, is you brilliantly explained the Kitty Genovese story. Kitty Genovese, as you explained it, and the neighbor that came to her rescue, put herself on the line when no one else was doing anything. It’s so relatable to what we just went through in 2020 with George Floyd and just a few weeks back on that train in Philadelphia with the woman who was brutally attacked. Unfortunately, as you pointed out, history will repeat itself unless we learn from those mistakes. When you hear about or read or watch the news about those kinds of recent things, do you just shake your head? When people see something, say something, why not see something, do something?

Ryan: Sure. Yeah. I think as it pertains to that expression, the idea of saying something is doing something. I think it’s interesting when you look at the Kitty Genovese story, it is this sort of shameful story that we’ve told ourselves about the indifference of neighbors, particularly in the modern city, which it was in some ways. And then, in other ways, she was held by a neighbor as she died. A neighbor who she knew quite well, who had left her apartment and her small child inside to go answer these screams and finds her dying neighbor there, and then asks for zero credit or recognition for this experience even as she is implicated for a generation as being part of this horrible tale of indifference and inhumanity. I don’t know why that happens. I mean, you think about the girl who won the Pulitzer Prize for taking the video of George Floyd. I mean, it wasn’t just that she took the video. She stood there filming the police who clearly were not wonderful human beings or they wouldn’t have been in the middle of murdering this man. As you said, it’s more than just seeing something but doing something about it, trying to take some active step towards solving a problem. I think what’s interesting about the George Floyd thing is the woman filming who obviously sees something wrong. But you have the two other officers just standing there or kneeling there as their boss does this horrible thing right in front of them. There’s a line from Marcus Aurelius where he says, “You can commit Injustice by doing nothing also.” It’s of course easy to say this isn’t my problem, this isn’t my fight, this isn’t up to me, I don’t care about this, but you are complicit in the outcome of what happens.

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John: What makes it worse to me is in that situation, in the recent Philadelphia train attack situation, is back in the Kitty Genovese days, people could have said well, I didn’t hear her, I wasn’t at home that night. This is now a world of we all become sort of

democratized reporting and all people have cell phones. We know people were there and people were watching. They were filming it. So that to me decompounds the complicity, like you said, of an action.

Ryan: Yeah. I think that’s right. Maybe that should remind you that, hey, people are always watching and that one ought to go through the world acting as if someone is watching. So you mentioned the Daily Stoic email, the email today that we sent out to the list. Obviously, I write them in advance, but the point of today’s email was talking about how your children and your grandchildren are going to ask you about what you did and what the pandemic was like. And so, just in the same way that I ask my grandfather about D-Day and I asked my grandmother about the depression, they’re going to ask you about this historical event. And what are you going to be able to say? Are you going to say, well, I posted a lot of misinformation on Facebook about it, or are you going to say, hey, I volunteered in a vaccine clinic or we did X, Y, or Z. We kept you guys home. What are you going to be able to say? When your kids ask you and you start to describe your experiences in this time, are you going to seem like you were part of the problem or you’re going to seem like you’re part of the solution, or you’re going to seem sort of wildly out of touch? There’s a famous exchange with John F. Kennedy, where John F. Kennedy sort of admits that he’d learned about the Great Depression in Harvard. He was rich and his life was so sheltered that he missed the Great Depression. He wasn’t 5. He was 15 during the Great Depression. So you’re like, oh wow, okay. So this person, they weren’t part of the problem, but they were also part of the problem. This is exactly the kind of out-of-touchness that probably caused the Great Depression to begin with. So as we kind of think about how history is going to judge us, both the larger scale of history, but just also your future self. What are you going to think about yourself in 10 years? Hopefully, society will have progressed in 10 years. Hopefully, we’ll be kinder and gentler and more equitable, all these things. And when you look back at where you were, you’re going to be like, oh, you know what I mean? I didn’t do everything that I could.

John: You talk about in the book, you give some great examples, and of course, you mentioned one of my heroes, Pat Tillman, and how we’re all going to be called, different times in our lives. But we have to be ready to answer that calling, and the calling could be, as you pointed out, and you gave so many brilliant examples throughout the book. One of the great examples was the 6-second example with our brave troops that prevented many more people from dying over in the other side of the planet. But with Pat Tillman, he answered his calling and he said you know when you get called. You can feel it. Can you explain to our listeners and readers what do you mean by that, and how can we get better in tune with ourselves? Someone we know we have to exhibit courage. We could actually get over our fear and over ourselves.

Ryan: Everyone gets the call, but almost everyone refuses to call. If you’re familiar with the idea of The Hero’s Journey which Joseph Campbell puts forth, one of the steps in the hero’s journey is the refusal of the call. So this is part of it. We have this sense or we hear this voice or we see this inspiration that calls us to do something and almost invariably, we come up with reasons why we can’t do it or we can’t do it right now. Steven Pressfield calls this the resistance. We don’t say I’m never going to do it, we say I’ll start tomorrow. Understanding that this sort of tension, if it was obvious, everyone would do it. It’s not obvious, it’s hard and we wrestle with it. For me, when I dropped out of college to become a writer, when I decided to go from writing marketing books to philosophy books, these were not easy or obvious decisions. I went back and forth about them. I had a lot of doubts about them, but you sort of have to go toward that scarier thing. So the call is there. The call is usually- we’re coming up on Halloween here- the call is coming from inside the house but you have to answer it. You have to decide to act on it because what would a world look like without the Pat Tillmans, the Florence Nightingales, the Winston Churchills, or the Martin Luther Kings? Martin Luther King is just an ordinary pastor in Montgomery. He doesn’t have to get involved. There were other black preachers in major black churches that didn’t step forward. And there were some that just step forward but not as far as King did. I think he’s 25 years old. You think of Thomas Jefferson or George Washington as old men, but they were in their early 20s and 30s when this happened. They weren’t certain about it, it was scary as hell, but they proceeded anyway. They answered the call.

John: Answered the call. You talked in the book about your own fear. And as you just pointed out, switching from the marketing guy to a philosopher, dropping out of college- I dropped out of law school. It wasn’t an easy decision. Of course, the abyss is always scarier than where you are today. What do you want? There are so many amazing quotes in this in this book, and as you can see, I’ve marked it up. But anyone who can quote both Martin Luther King and Frank Serpico in a book is someone that I’m a huge fan of. I took out so many quotes and I wrote down so many. What would be your favorite 2 or 3 quotes in the whole book that you want people to sear in their brain and keep in front of their brain every day as they work through their journey?

Ryan: One of the ones I love, it’s often attributed to Andrew Jackson although he probably didn’t actually say it. It’s this idea that one person with courage makes a majority. The whole world depends on people who stood alone on a certain issue and brought other people around. Again, to go to Martin Luther King. Martin Luther King was I think at a 60 or so percent disapproval, disfavourable opinion at the time of his death. Not even a majority of African Americans were a fan of Martin Luther King. But this is what happens when you are ahead of your time is that you often upset people or your hard to wrap your head around so the idea that it’s going to require standing alone. It’s not always as high-stakes as civil rights. It might just be, hey, this is the direction that I think my industry is going to go in and everyone on your team might be convinced you are completely wrong and that may be why you have to break out on your own or why you have to put in more of your own money on it or whatever it is. But the point is being okay standing alone, having the courage to do that, and the perseverance to understand that this is how change happens from a person who takes a position and convinces other people to come along with them. One of my favorite ones though, and I think we’re in the middle of this right now, is although courage is rare even amongst people who think they understand courage, we have trouble understanding what it’s about. So there’s a quote from the poet Lord Byron that I have towards the end of the book. It says, “Tis the cause makes all that hallows or degrades courage in its fall.” Is it courageous that Kyrie Irving is willing to risk $400,000 a game to not get vaccinated because he’s protesting vaccine mandates or whatever? I mean, it’s certainly risky. It’s certainly a scary thing to do. You’re betting millions of dollars on a thing you believe. The problem is when we’re talking about courage as a virtue, it has to be in the pursuit of what the stoics would call the right. To courageously protect your right to be a vector of a deadly virus is not what we’re talking about when we’re talking about courage. Was it courageous for Robert E. Lee to break with the country that he had served honorably for years to side with the state of Virginia? Was he courageous under fire many times? Of course, but we also understand and this is why we’re having this debate now about these statues, that there’s something empty and hollow, not hallow, hollow about this courage because it was in the pursuit of a monstrous injustice, a monstrously incorrect cause. So, when we think about the virtues, we have to understand that they’re related to each other. Not only does courage have to be balanced by justice, it also has to be balanced by wisdom. So if you’ve courageously decided to jump off a cliff that everyone told you you’re going to die when you hit the ground, this is where wisdom comes in. The wisdom to accept information and integrate it is really, really important. Yes, you can courageously resist vaccines as much as you want, but if the reason you’re doing that is because you’re also, again to go to Kyrie Irving, a person who believes the world is flat, you’re an idiot. You’re not brave. That’s an important decision.

John: The book and on the Kyrie Irving story to me is Muhammad Ali. He was a hero because he had the courage to push back against the war that he didn’t believe in. It turned out that history was on his side and he lost a lot of his career because of that.

Ryan: Yes. And look, even if he was wrong, there were conscientious objectors in the Second World War. I think we go like, look, the cause itself was not bad but we understand there’s a sincere religious conviction behind the resistance. So, even if Vietnam was not a travesty or a tragedy, in Muhammad Ali there is a sincere religious conviction that is motivating the decision that he’s making. It’s just important to say that courage is truth-telling, but if you’re just rudely telling truths to hurt people’s feelings, that’s not what we’re talking about.

John: Right. Again, we’ve got Ryan Holiday with us. This is the Thanksgiving Special. We all should give thanks for Ryan and his new book, Courage Is Calling: Fortune Favors The Brave. We could all use wisdom on how to be more courageous in our lives, every one of us. You know, Ryan, one of the things I love about the book is you talk a lot about the stoics, obviously, which you’re a philosopher. What do you think if the stoics were here today, they came down for just 2 days here on this planet and saw everything that was going on, what would they be intrigued about and be fascinated by, and what would they be totally turned off about what’s going on right now?

Ryan: Let’s say you dropped Marcus Aurelius into 2020. Here you have a guy who is head of state during the beginning of the decline of the Roman Empire, who’s also the majority of his reign is made up of what we now refer to as the Antonine Plague. So, I feel like he’d have looked around and accepted some of the technology, being like, “This is very familiar to me.” He would understand. Actually, that’s one of my favorite quotes and meditations and it certainly became more so over time, but he talks about how during a plague he says there are two types of plagues. He says there’s the pestilence that destroys your life and he said there’s another that affects your character. And I think we’ve seen this also during the pandemic where people who whether they got CoVid or not, also got some sort of character infection that made them sort of deeply selfish or susceptible to conspiracies. When you watch a video of some lady screaming at a supermarket clerk who asked them to put on a mask, you’re like, you might not have CoVid but I’m pretty sure you got something worse. You caught something. So, that Marcus was familiar with that 2000 years ago I find to be really interesting. I said accepting the technology. I do think they would be appalled by our dependency on these devices. That our inability to focus for 5 minutes on the simplest of tasks, I think they would struggle to comprehend that. I mean, obviously, human beings have always struggled with attention and focus and whatever, but I think they’d look at our dependency on these devices and ask why we’re doing this to ourselves.

John: Got it. You know, one of the things I loved about your journey- and you’re only 34. You know, my 2 children are above me here with this and this was up on my walls for years before this pandemic ever hit, but it turned out to be a nice background for all my Zoom calls. My daughter’s 34 and she’s a lawyer and I’m so proud of her. She’s 35 and I’m thinking, oh my gosh. I mean, at such a young age, you’ve done so much and now during the pandemic, you are called again. When all of retail shut down or virtually all of retail, you decide to go counter to the absolute trends that are existing in 2020 which was literally a silence that I’ve never seen in my 59 years in the United States and around the world. And you opened up a bookstore called The Painted Porch in your hometown now, where you live in Bastrop Texas. Explain where that calling came from, why you decided that 2020 during the pandemic was the right time to answer the call, and how has it gone since you launched this. I’ve been online. I’ve seen the books and all the photos, and it looks just gorgeous and beautiful and something out of a Norman, Rockwell painting. Why?

Ryan: Well, to be fair, I started before the pandemic. I just decided not to quit during the pandemic. I didn’t decide in March that opening a bookstore would be a good idea.

John: Okay, fair enough.

Ryan: But I did stand in the empty bookstore in March and go, I can’t believe we have to do this now. It was a long journey. It was an exhausting, expensive and terrifying journey in many ways, but it was a really good experience. I love books. You can see books behind me. I love physical books most of all. That’s how I read. But now even as an author, something like 60% of my book sales are digital, either ebooks or audiobooks. Obviously, I’m very grateful for that, but something about the physical experience really means something to me. As we were looking for some office space for our company, we sort of came up with this hybrid idea of office space plus there was a storefront involved. So it worked out somewhat accidentally as an opportunity to do both and it’s turned out to be very cool and fun. It was harder and took longer than expected, but it’s been a really cool experience and there’s something about being part of a community and doing something in the real world. I could hear right now like little kids running around excited. There’s just something I love about that.

John: Hey listen, I love it. I grew up in New York City and one of my favorite places of peace and enjoyment was Fifth Avenue and 18th Street, the big Barnes & Noble, their flagship store. So opening up a bookstore sounds wonderful. Just during a pandemic, maybe not so much, but how [inaudible] [crosstalk]

Ryan: It was not the best business decision, but it’s been a fun personal experience, to say the least.

John: Talking about personal experiences, you’re married with two boys, and I know you take that seriously. I’ve read what you’ve written about fatherhood and being a husband. I know you really lean into it. How do you find time given how busy you are, how much you loved to read, and also you’re writing? You’re already writing the second of this 4 series, the book on temperance. Where do you find time to get into your flow and actually still continue to be at the peak of your abilities?

Ryan: I mean, it’s kind of an unfair profession. I mean, if I was a professional baseball player, I would be away a lot more. One of the benefits and probably why I chose it, but your sort of a lone wolf as a writer as far as doing your actual thing and so you’re able to kind of squeeze it in into different pockets but I’m a big creature of habit. Part of the reason we did the bookstore, part of the reason we live where we live was kind of setting up a system to optimize for those things that allowed all of them to be possible. If I had a fire at a 90-minute commute or something, obviously, that would eat up large chunks of the time in the day. So I’ve tried to sort of design my life around the things that are important to me. But it also means saying no to sort of stuff that maybe would ordinarily be perks of the profession to a single writer my age or something. I’m not experiencing but that hasn’t been something I’ve particularly missed.

John: Right. One of my favorite quotes in your book is, “The world is a narrow bridge and the important thing is not to be afraid.” Explain why you put that in the book and what that means to you or why that was so important to put that in your book.

Ryan: Yeah. It’s a little Hebrew prayer. There’s actually a great novel called The World Is A Narrow Bridge by a guy named Aaron Thier, which I love as well. But to me, the wisdom of that prayer is it’s like when you’re walking… Have you ever been on a narrow rope bridge or something over like some Canyon? Just keep walking, don’t look down,

don’t look over the edge, don’t stop, don’t look behind you, just get across the bridge. And any of those other things, as tempting as they might be, are very dangerous because you slow down, you lose your heart to continue, and suddenly you get really nervous. You just got to get across.

John: Got it. In a lot of your writings that I’ve read before, before he even Courage Is Calling, you talk about the stoics’ virtue of controlling their response, and how we can all learn to be better at controlling our response. What do you want people to learn when you write about controlling their response and how the stoics held that in high esteem and how we can all get better at practicing that and actually exhibiting that kind of behavior?

Ryan: Well, I think, look, at the core of Stoicism is the idea that we don’t control what happens, we control how we respond. That’s life, right? So I think if you think about it just as a resource allocation issue, are you going to spend time on the things you don’t control, or are you going to put all that energy towards the parts of it that you do control? So I think the stoic just tries to say what part of this is up to me, what can I do, where can I move the ball forward? I’m not saying I’m perfect at it. On the contrary, I just know that sometimes you get all worked up at something then you’re like, what am I really saying here? And what you’re really saying is I wish that it hadn’t happened this way, but it did. And so are you going to spend time litigating that or you’re going to focus on what comes after?

John: Yeah. You made a point in the book where you said or in your book or somewhere else when I read one of your passages, you said, “Really, do you ever feel excited or do you look back favorably on a time where you got mad or got it exploded at somebody or something?” It’s not fun to look back at those moments.

Ryan: Yeah. I mean, I don’t think I’ve ever lost my temper and then been proud of myself after. Are there certain moments where I’m glad I stood up for myself? Yeah. But even in those moments, I say I wish I’d done that without saying X, Y, or Z, .

John: You get to meet a lot of people like you said because of the over 4 million copies you’ve sold, Ryan. You’re a New York Times bestseller. Many times over, athletes, entertainers, and so many military leaders around the world read your books. So you have great access to so many people. What I’d love to know is if tonight and tomorrow night, you had two chances at dinner. One, tonight with someone who’s still living- not a family member- go to dinner with somebody, and tomorrow night with someone who’s passed, anyone who’s passed, who would be your 2 favorite people to have dinner with, past and still alive?

Ryan: Yeah. I mean, I’d love to meet General Mattis. I’m a big fan of and I know a little bit but we’ve never met in person. So if I had to pick a living, maybe I’d go there. And then, I feel like I would lose my stoic credentials if I didn’t choose Marcus Aurelius, but if I had to pick, let’s say you’re limiting it to an American, I think Lincoln, probably Lincoln.

John: It could be anyone. No, no, [inaudible]

Ryan: No, I’m just saying, just so I could choose 2, I’d say Marcus Aurelius is number 1.

John: You got a bonus one in there. I see what you did.

Ryan: Yes, exactly.

John: You self-limited it.

Ryan: Yes.

John: I got it. Again, Courage Is Calling. You can buy this book not only at The Painted Porch but at Barnes & Noble, Amazon, and every other place you can buy great books. This is just really one of the favorite books that I’ve read in 10 years. You can see how much I’ve marked it up. You know, you talked about David Brooks in the book. You talked about The Second Mountain. Can you share a little bit about what you mean about what Brooks meant by The Second Mountain?

Ryan:: Yeah. The Second Mountain is sort of once you climbed the top of the first mountain, that’s your career success. What is the second mountain for you? Giving back, what is the other thing that you’re doing? It is a great book. [inaudible] by that title. Look, it’s up there? Anyways, I’m going to talk about that more probably in the Justice book. The bookstore was part of the second mountain. It was like, hey, I’ve had this success. This is the thing I’m good at. What is a cool thing I could do in a place that I live? What’s another project to tackle that might not be as financially lucrative, but might be richer in meaning or purpose, and it’s certainly been that. So I think The Second Mountain is sort of what is it that you are doing after you have achieved the thing that you wanted most in the world.

John: Got it. Well, first of all, you share some stories that I’ve never heard. I mean, I love the story that you shared- and if you want to just hit the high notes on it, I think it would be fun for our listeners and viewers- on the relationship between Martin Luther King and Richard Nixon, which I had never read that or heard that anywhere, and the relationship between JFK and Martin Luther King, and how 2 phone calls could have probably turned that whole election.

Ryan: Yeah. So Nixon and King were actually friends because Nixon was in charge of Eisenhower’s civil rights platform so they met each other many many times. And then, Kennedy did not really know King until the 1960 election. King is arrested in Georgia on these sorts of trumped-up charges and there’s a real concern that he’s either going to do a long prison sentence or he’s going to mysteriously disappear while in police custody. It’s going to be murderer Lynch. And so Coretta Scott King who’s pregnant I think with their third child at the time, calls both campaigns and says, “You guys got to do something, you can’t let my husband die.” Both parties had some civil rights plans in their campaign. Nixon decides not to get involved. He doesn’t want to be seen as grandstanding. He wants to wait until after the election. He also doesn’t want to lose some of the southern votes. It’s sort of razor-thin there anyway. He doesn’t want to lose the southern vote. So he doesn’t get involved. Kennedy on the other hand, decides mostly at the prompting of his brother-in-law, Sargent Shriver, to place a phone call, one to Coretta Scott King and then he and his brother both called the judge in Georgia, and they ultimately sort of applied enough pressure that King is released. Martin Luther King, when he gets out of jail, he’s like stunned. He would have sworn that it would have been Nixon who would have helped him, not Kennedy who’s a Democrat, who is more dependent on Southern Democratic support. So, he just puts out there what happened. He’d been planning to vote for Nixon and he changes his mind. I think Kennedy goes on to win the presidential election by like 30,000 votes across 3 states. Almost entirely people think due to the swing in the black vote due to these 2 phone calls that he makes. I think it’s an important example of how a single but 30-second burst of courage can change one’s life, and conversely, that a momentary lapse of courage, a moment of cowardice can change your life for the negative as well. Nixon doesn’t get involved because he doesn’t want to hurt his re-election prospects and ends up costing himself the election. So, when we have these moments, when our conscience is telling us what to do, when we feel that pit in our stomach, you just got to do it.

John: You got to answer the call.

Ryan: Yes.

John: You’re very self-reflective, Ryan. I really enjoyed the afterword. I have to tell you, the afterword was really interesting to me. I never heard that story, never read all that, I had just seen the business side of that story, never understood the underpinnings. It’s the American Apparel, you’re involvement with American Apparel, and as you said, you’ve already pointed out during this interview and other places, complicity is just as bad as [inaudible].

Ryan: Sure.

John: But I love when you write about yourself like 34 Mistakes on the Way to 34 Years Old. Do you enjoy the process of being so self-reflective and on varnish? Is it a cathartic experience for you, or do you find it informative to the platform that you’ve created, or is it a duality of both?

Ryan: I think it’s both. I mean, I do think as far as counter-programming goes, most people celebrate their successes and show a very selected picture of who they are and how things are going. I certainly understand this for branding purposes, but it’s also kind of boring because everything’s positive, everything’s going well, nothing feels particularly real. So I do try to consciously make an effort to show how things actually are and I think people appreciate that. But I also feel like it’s just really easy to buy into your own crap. So I try to sort of consciously look at things like I did in this story. I could have told some sort of narrative that presented myself as a particularly courageous person or I could have shown all the things, but I don’t know. It just didn’t feel right. I talked earlier about intuition. There’s just a part of me that said, the best way to wrap up this book would be with a story of cowardice or a failure of courage as opposed to somehow trying to ride on the coattails of these people whose stories you’ve just told. So it just felt and I certainly benefited from the experience of reflecting on it as well. But part of it also, it just felt like the honest thing to do.

John: Before I let you go today, Ryan, I want to talk about 2 fascinating shows that really hit it big during this pandemic. One was The Last Dance with Michael Jordan, the 10-part series. I believe it was episode 8, the last part of it, the last 4 or 5 minutes was the only time he got emotional during the whole interview. He had a quote and this is when he literally started breaking. I’ve never seen him break. He said at the end of episode 8, “Leadership has a price and winning has a price.” If we replace the words leadership and winning with the words courage, do you find that analogy is absolutely spot-on?

Ryan: Yeah. When you look at whistleblowers, I had- what’s-his-name? Who was the whistleblower? Oh, I had Lieutenant Colonel Vindman on my podcast, the White House whistleblower. You look at what that decision cost that guy. It cost not only him, his military career, but it cost his brother his career as well. So these things don’t come for free. They come at a cost. I think that’s right. But that’s what makes it so impressive. Again, if it was free, if it was easy, everyone would do it and there’d be a lot more Michael Jordans and thus, there’d be no Michael Jordans.

John: Especially during this pandemic, Moderna became one of the great brands now that we all know about because they had a breakthrough technology with Pfizer to come up with the great vaccination, but we all look back then to Jonas Salk and you mentioned Jonas Salk in the book. Now, I always knew him for, of course, creating the polio vaccine. I never knew until I read your book that he didn’t patent it and he didn’t, again, personally take advantage of that great breakthrough.

Ryan: There’s another woman, her name is Dr. Katalin Kariko, and she had been working on mRNA research for 30 years. She came to America as an immigrant from Hungary with $900 in her pocket. She never made more than $60,000 a year. She constantly had to fight for funding. She was constantly having to fight for her job. Everyone thought this was this sort of scientific dead end. And then lo and behold 2020 comes around and suddenly it’s the ticket and it’s the invention of a lifetime or the breakthrough of a lifetime. That wasn’t easy for her, right? I’m sure it took a lot out of her, and I’m sure it took a lot out of her family, but we need people like that. Where would we be without people like that? It’s almost unfathomable.

John: My last question for today and then I’m going to leave you of course because you’ve been so generous, is about the new hero of the world, Ted Lasso.

Ryan: Yes.

John: So, Jason Sudeikis, he was being interviewed the other day and they said, listen,

how did you come up with such an amazing idea to execute this series when your life was sort of falling apart? You and your wife had split, you were separated from your children and stuff. He talked about it. He said, listen, you have a choice, and you talk about this choice in the book. He said you have a choice. You could either- become when the world crushes you and it’s going to crush you, all of us are going to somewhere somehow get knocked down or beat up or crushed. He goes, “You can become a pile of 206 bones and broken bones, which means,” he goes, “All your bones are broken. If we all have 206 bones,” he goes, “That means you’re a pile of 400-plus bones, or you can put yourself back together, get up, and move forward every day and if you do it right, the bones come together and heal even stronger than when you started.” You talked about the Japanese art called kintsugi, I think. It’s K-I-N-T-S-U-G-I. Can you talk a little bit about how all of us in some way, shape, or form are broken and how we can either decide that death is the option or we’re going to come back stronger and smarter?

Ryan: What I love about Ted Lasso as a show and I’d start to talk about this a little bit in the book is I loved his earnestness. It’s a positive show. He actually sincerely tries to be a decent human being instead of this sort of action hero or antihero or whatever you want. And I love that. I think hope is probably the most courageous thing that there is or just earnestly trying because it’s one of the most courageous things you can do in this life. So I love that. The art form you’re talking about, it’s a Japanese form of art where let’s say a piece of pottery breaks. Instead of gluing it back together, they attach it either via gold or silver. So the thin becomes not just more valuable as a result, but it becomes more beautiful as a result. It’s a fascinating form of art. And I think it’s a good metaphor for the human experience. You can break and become stronger as you heal in the broken places, or you can become weaker and more vulnerable in those places, but that’s your choice. And I think, look, the last year has been really hard. The last year and a half has been really hard. Some of us are going to emerge from this better and some of us are going to emerge from this broken shells of a human being. Again, you look at some of the ways that people [inaudible] now. The things they say, you understand where it comes from. It’s been a rough year and a half. But the choice is are we going to be better, kinder, more loving, more connected, more appreciative, more generous, as a result of what’s happened, or are we going to become bitter and angry and aggressive and anti-social as a result of what’s happened? That’s ultimately to go back to the question about what do you control. That choice is on you. You didn’t choose what happened the last year and a half. No one would have chosen it. If they did but it did happen, and so what are you going to emerge looking like? That’s the question.

John: Got it. That’s why you’re here with us today on this Thanksgiving special. We want people to emerge better with more courage. Ryan, my lifelong friend since I’m 5 years old, so that’s 54, 55 years now, Greg Saffer first told me about you and he’s still of course my good friend, and he told me about your coins.

Ryan: Oh, lovely.

John: And this coin sits underneath my speaker here. So when I do all these interviews at my business desk, I’m always able to remember. But can you just share with our listeners why Memento Mori, and, “You could leave life right now,” means so much as something that we all should keep in mind as we move through this journey?

Ryan: Well, I think the point about the pandemic stands. It put in stark relief how fragile life is, how you really can’t take anything for granted, and how things can change in an instant. And the stoics wanted us never to lose sight of that. To remember that we’re mortal, to remember that we’re not in control, to remember that life has a definite end. Every single person who’s born will die. When that is is an open question but it could be 5 minutes from now, it could be 50 years from now. But how are you going to spend that time, who were you going to be, and what decisions are you going to make while you’re still in control, again, those are the important questions.

John: For our listeners and viewers who want to buy these coins, they can go to, and sign up for Ryan’s newsletter to buy this book. You can buy it of course at The Painted Porch, or you can buy it on Amazon, Barnes & Noble, and all great bookstores, both physical bookstores and online in the United States and around the world. Courage Is Calling: Fortune Favors The Brave. Ryan was kind enough to sign a bunch of copies for us. We’re going to be giving them out during our Thanksgiving special. Thank you, Ryan Holiday. You are making a huge impact on this planet. You also made a huge impact on me and my family. Thank you for this time. We’re really grateful for all that you’re doing.

Ryan: John, thank you so much.

John: Thanks, Ryan.

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