The Breakfast Club - INTERVIEW: Ryan Holiday Explains How "Wisdom Takes Work", Rounding Out His Virtue Book Series + More

Episode Date: October 27, 2025

Today on The Breakfast Club, Ryan Holiday Explains How "Wisdom Takes Work", Rounding Out His Virtue Book Series. Listen For More!YouTube: https://www.youtube.com/@BreakfastClubPower1051FMSee omnystudio.com/listener for privacy information.

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Apple Podcasts, or wherever you get your podcasts. Every day I wake up, wake your ass up. You're all finished or y'all done? Morning, everybody. It's DJ NV. Charlie is Charlamagne the guy. We are the breakfast club. Long the Roses here as well. We got a special guest in the building. One of my favorite authors ever. Yeah, it's a new book. Wisdom takes work. Learn, apply, repeat. Ladies and gentlemen, Ryan Holiday. Welcome back.

Thanks for having me. How are you feeling this morning? Doing awesome. What book is this? Number what? I don't know. Is it 10? It might be 15, 16, something like that. Damn. Jesus Christ. Fifth or six time he's been up here. Yeah. Very good to me. Yeah. Now, we like having you, man. The wisdom takes Mixed work, learn, apply, repeat. And in the book, you argue that wisdom is the virtue on which all other virtues depend.

How did you arrive at that belief? So the four virtues of Stoic philosophy, which I read about are courage, discipline, justice, and wisdom. They're all separate, but they're related in that, you know, wisdom tells us when and how to apply the others. It doesn't matter, you know, how good your heart is if you don't have the wisdom, the intelligence to know how to bring it into the world or you know courage is important but you could be courageous for something real dumb so so wisdom is the sort of layer on top that we have to

apply to all our other skills and assets well it's one thing to do the research was there a specific moment in in your life that made you realize that wisdom was important yeah well you know I think we've all met some smart people that do dumb things and I think we've all done dumb things and And you look at wisdom as being the sort of the key to not just a successful life, but a good life, right? You can be really good at what you do and then you can blow it all up. Or you can be profoundly unhappy or, you know, how many smart people are lacking in self-awareness. So I just think wisdom is this sort of piece that brings it all together.

And I think one of the problems is that we assume wisdom is this thing that just happens, right? We go, sure, school is important, but, you know, experience is important. You know, wisdom comes with age. It's no guarantee. I met a lot of dumb old people, too. Absolutely. I would always talk. Smart people learn from their own mistakes, wise people learn from the mistakes of others. I completely agree that wisdom is a law start. I think you have a lot of smart people. I don't think you have a lot of wise people nowadays. Yeah, yeah. And I mean, you need this not just to be successful, as I was saying, but like, how do you not fall for demagogues or how do you not fall for scams how do you how do you rise above the noise how do you

separate fact from fiction wisdom i think is you know there's this word discernment right the art of discernment like how many people can really see the difference between good and really good you know right and almost right truth and complete nonsense that to me is the missing skill of our time we're doing guys it's over pack it up go home we're not doing yes we are no i think i think everybody eventually has something in their life that wakes them up to that, whether it's at a different, like, maybe young, might be older, but you always thought, you always thought that, like, wisdom comes with age, that saying? So you probably hate that saying, huh? Yeah, Churchill was joking about this guy he didn't like, and he said that although he

occasionally stumbled over the truth, he quickly picked himself up and carried on as if nothing had happened, right? So people are, I think life is always teaching you, right? But you don't have to hear it. And so life will sometimes whisper. Life will tell you nicely things that you need to know. And then when we ignore that, it becomes louder and louder and louder until sometimes, you know, you have to learn from some kind of catastrophic failure or catastrophe. And so, you know, your point that we can learn from the experiences of others, that's the cheap, effective, efficient way to do it. And then a lot of us go, no, no, I'd rather figure it out on my own. And that costs not just them, but the people around them.

Like when we're late to learning lessons, that doesn't just affect us. But that affects the people that work for us. That affects our family. That affects the people who, you know, bear the consequences of that, you know, painful lesson that we chose to learn the hard way. I think wisdom has to come from age, though. Sure. Regardless.

I mean, regardless of what the person, you can meet a stupid old person. Yeah. But there is some wisdom. that comes from what they're doing, whether if they work at a plant, whether they, whatever they do at the house, there is some type of wisdom that they can continue on to give to somebody else. Well, you know, the root of the word idiot is somebody in ancient Greece who did not participate in public life. So, you know, you can read everything you want and you can read a lot and that'll make you smarter than the average person. But if you're not engaged and involved, you're going to miss

some things that you can only learn from experience. You know, Da Vinci would sign his letters a disciple of experience. You have to learn by doing, you have to put yourself out there. And that's why I say it's learn, apply, repeat. So you learn the things, you hear the lessons, you study, you go to school, then you got to go out in the world. And you find that a lot of what you learn now has to be applied or a lot of what you learned, you didn't actually understand it. And then you repeat that cycle over and over and over again, and each time that that's a positive feedback loop that's making you smarter and better. They talk about educational.

A lot of people, and I'm seeing this a lot more and more and more, that people are not necessarily wanting to go to college. Sure. They feel like the education that they get in college, they can be taught more through life experiences. And they feel like the wisdom that those professors have might be outdated. Sure. What they're teaching?

What's your thoughts on that? Well, look, I'm a proud of. college dropout. So I'm all about it. There is and always has been a difference between school and education. So I think the problem is if you don't know what you're trying to do, how do you know what the best form of schooling or education is for you? I say that all the time, by the way. I think it's stupid that we force kids to get out of high school and say go to college and pick a major immediately when they don't necessarily know what they want to do. If you know what you want to do, that's great. But there's been times where kids are like, I don't.

don't know. Like, don't make me pick a major and make me take these courses if I don't necessarily know what I want to do in life. Especially nowadays, when we live in a world where we're kind of preparing for a future that won't even exist. Yeah. Because the AI going to be having all the jobs anyway. Well, look, spending a couple hundred thousand dollars over four years is an expensive way to figure out what you want to do. Absolutely. Especially if at the end of it, you find out that what you want to do is something that didn't require college. For me, I met Robert Green, our mutual friend. And then I realized that's what I wanted to do.

And then I said, well, am I going to keep going to college or am I going to go directly learn from the person who's done it? So I'm a big believer in apprenticeships and mentorships. You've got to find your teachers. Sometimes those are college professors. Sometimes they're business executives. Sometimes they're, you know, your neighbor down the street. But you've got to find who can teach you how to do what you want to do.

And when you started off as an apprentice with Robert Green, one of the first things he put you on was 40, lot of power, right? No, I've worked on the 50th law. 50th law. Like the first thing I did was transcribe in a world before AI. I transcribed hours and hours of interviews between him and 50. And so that was part of my education, it's just listening, not just listening to it, but having to painstakingly type it all out. And so I got this master class and not just, you know, how he worked, but all the people around him. But what I was actually learning was like how you put a book together. And Robert showed me how to research a book and how to write and then how to operate in the industry, you want to find the people who are further ahead

in what you want to do and do it. Although, to be fair, like in college, I think one of the most professors are professionals in what they do. They're not just teachers. They're researchers, they're experts, they had a previous experience where they did the thing. And, you know, every week they have office hours where they have to sit there and meet with the students. And nobody comes. So I thought the crazy thing for me is like, I didn't go into the library at my college until after I dropped out and I was writing my first book because I was like, oh, wait, this is an incredible free resource that I was too busy, you know, doing the college kid thing to take advantage of. So all this stuff is there. It's just you've got to be

self-directed and self-motivated. You know, and wisdom takes work. You write that we live in an age where reaction and idle chatter are rewarded and restraint and thoughtfulness are unfashionable. And you talk to these digital decades about what you mean on that, please. Yeah, I mean, look, social media is by definition talking and not listening. That's right. Zeno, the founder of Stoicism, he said, we have two ears and one mouth for a reason. And when you're talking, what you're mostly doing is not listening. So we have this enormous sort of media culture that's about chatter and noise,

and it's not about thoughts and reflection. I mean, even how much of what we listen to and talk about is what's happening right now. now, not the historical context or the, you know, the bigger picture. And I think not that there's anything wrong with news or podcasts or social media, but if you don't have like the historical basis, the larger context, you're not going to know what any of it means. Truman's famous line was there's nothing new in the world but the history you don't know. And so most of what's happening now has happened before. But if it's the first time you're hearing about it or experiencing, you're going to have the wrong read on it because you think it's like somehow

unprecedented, but in fact, it's very precedented. Some of this is unprecedented, though. A lot of what we're seeing right now. You think so? At least in America. I guess you mean, I guess if you can rely on historical context. That's what I mean. Okay, got you. Yeah, I mean, this archetype, you want to look at a Donald Trump, Donald Trump exists in half a dozen Shakespearean plays. He exists in Greek tragedies. There are historical precedent after historical precedent for guys like that. I mean, one of the interesting lines in Marx Surrealis' meditations, he says that he thanks his philosophy teacher for for teaching him not to fall for every smooth talker. So like the idea of the demagogue, the idea of the strong man,

the idea of the con man is as old a thing as there has ever been. And part of the reason I think people have trouble spotting it or seeing it for what it is, is that they don't know that this has happened again and again and again. And therefore, they don't know how badly this ends. Is he a smooth talker? I wouldn't consider him a smooth talk. I mean, he's not smooth in the sense that, you know, he's particularly good at it, like he's this soaring order.

But he's really good at telling aggrieved people what they want to hear. And that's what demagogues have always done and always do. They point to the other and they say, your problems are not your fault. They're these people's fault. I'm going to be your weapon of vengeance against them. That's as old as, you know, political strong men have ever been. What's the second brain? Second brain?

So, and I learned this from Robert Green, the writer, is like, you have to be recording and synthesizing the knowledge that you get. So it's not enough to have a mentor. It's not enough to read books. It's not enough to listen to podcasts or watch documentaries. how are you collecting and organizing this information so like I'm I'm reading the book right now and I'm I'm taking notes on my pen's fine ever I'm taking notes right it's a it's a big one this is a Jill Lapoor history of the United States all it's great book and I'm going to record

this stuff I'm going to read it I'm going to take my time with it and then I'm going to break this down into note cards which I organize and then that's what I use in my writing in my videos and my talks so I think if you're not keeping a journal, if you're not recording the information that you're consuming or learning, where is it going? It's just going in a black hole somewhere. So that's what they call the second brain. What's an information diet? Oh, well, what do you, just like they say garbage in, garbage out, right? What are you eating? What are you consuming? We understand that what we eat affects our health, affects our mood, affects, you know, our happiness. And yet people just consume

straight garbage directly in their ears, directly in their eyes all day. And I think, you know, you definitely see this on the right, this just sort of depraved garbage information diet of like the worst slop and nonsense, whether it's coming from podcasts or Twitter, like, like, if you're not protecting what's going in your brain, you're going to destroy your brain. And I think we see this happening. Like, no one should watch as much cable news or spend as much time on social media as Donald Trump does. And so you're watching it to great. I think the most telling example of this is like, at one point in his life, Elon Musk was reading Soviet rocket manuals to figure out physics and space and the aeronautics industry. And now he just spends all his time on Twitter,

you know, mainlining memes. And he's insane, right? He broke his brain. And that's, That's why your information diet matters. It's not just the quality, but it's also, like, if you consume too much, your brain will break. You've got to have some discipline and boundaries, too. But if it's like, if it's habitual, right, like, how do you manage the diet after you already broke your brain? Yeah. I remember growing up as a kid and my friend's parents watched so much Fox News.

It was literally burned in the corner of the TV. And that's not healthy. Like, that's just not healthy. You got to say, hey, this is when I get my news. This is when I get my information. This is who I trust to give me my information. And I think people consume way too much real-time information and don't go back far enough. I think books are better.

I think conversations with real human beings are better. You're just, there's this recency bias. And so much of what's happening right now is ephemeral and trivial. and and or developing you know what I mean like you shouldn't be watching the news as it's happening unless you are a hedge fund trader or you hold elected office like wait for them to figure it out then check in and get that information and check it against your larger historical sense of what things mean and how the world works it just always feels like things are moving so fast sometimes and for a person like me when you talk about like how you download information

If I'm watching the news when things are happening, I retain it way better than if I have to go back and, like, sit with it sometimes because I feel like it's a lived experience. You think so? That, I mean, that, it's just kind of what I've been experiencing and working in news. Like, I literally remember January 6th when they went into the Capitol because CNN was on and I watched it. So when I was able to talk about it, I watched it. Like, I mean, I talked about it from me watching it in real time. Yeah. Versus when I go back and read things.

I don't know. It's just different. No, I get that. I think sports is a great example. Like, you could watch Stephen A. Smith all week. That's not going to change what's going to happen on Sunday. Like, what's going to happen on Sunday is what's going to happen on Sunday. And so we sometimes conflate, like, speculating about what's going to happen, debating about what happened, you know.

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Can wisdom protect you from being influenced? Because I do agree with you with the information diet, but I can look at a whole bunch of stuff throughout the week and not be influenced by it. I think it's the influence of it that I think is, you know, worse than just consuming it. Yeah, and look, I think part of this comes down to media literacy, technological literacy. I mean, like, look, something like 20% of Americans think that chocolate milk comes from brown cows. like no if that's where your starting point is you're going to you're going to have trouble like when you are reading a complicated news story telling you why something happened or what it means so so yeah you have to have a certain amount of intelligence and savvy to be able to separate you know what and

I do think that's why it's such a battle for attention is that you know some people are up for grabs and some people aren't and I think you want to be one of the people that's not up for grabs because you sort of know what's what. To me, that's like a good working definition of wisdom. Like, I know what's what. I know what humans are. I know how humanity works. I know history.

I know enough about the world that I can, look, we can all be made fools and suckers. But the bigger basis, you know, protects you against, you know, the day-to-day barrage, for sure. You really know people that think chocolate milk come from a blood. black cow brown that is that is a that is a statistical fact is nuts that is like is that 20 it's like 20 percent it's a lot of the same number what book was that Ryan what was that that's crazy it is crazy but but but you you realize that not everyone's working with the same toolkit yeah and and that that that makes it hard to go through life how do you attack what book you're going write about like you know this was about wisdom takes work how do you know you know I'm going to

go this way on this book and next next time it's about this one so how did you pick this book and what stood out about this that made you want to write about wisdom taking words it's seven percent two seven percent seven percent it should be zero percent yeah that is true who's drinking milk either but uh look it's uh I've been doing the series I did courage discipline justice and wisdom those are the four virtues so I I knew that was the the the the the That's what Stoicism is based on. Correct. But I wanted to save wisdom for last because it strikes me as the hardest, and it strikes

me as the thing in exactly what we're talking about this world, not just of lots of noise and information, but also AI, like the most essential. I think that's the interesting thing about AI is people are acting like it's going to be this magical thing that solves every problem or can teach you anything. But in fact, what you need, not just to be able to take advantage of AI, because it requires you to prompt it, which means you have to be able to ask it smart questions. But like, if you're not,

if you don't have some sense of wisdom, some sense of knowledge, you're going to be vulnerable to a thing that, that by the way, hallucinates a significant percentage of the time. That's wrong all the time. So you're going to, like, this idea of needing wisdom,

needing a good bullshit filter is like more important than ever. Because A.S. It is going to eat you a lot. live if you don't have, if you don't have a sense of reality. People don't. I agree. Another claim you make in the book, you say cultivating wisdom requires mental struggle.

And there's no shortcut for that. So what does mental struggle look like from a practical sense? Well, look, like books are basically free. You know, you can get them from the library. The amount of wisdom in a book is incredibly cheap. but it still takes work. You got to wrestle with the book. You got to read it.

You got to put the time in. You know, I think it's not just the struggle to, you know, make the time to do the work, to read, to go to class, whatever, but then it's also wrestling with big questions. Like if you think life is black and white, if you think it's easy, if you think everyone is trying to tell you the truth all the time, I think, again, you're going to find yourself pretty vulnerable. So it is struggle. It's a battle.

It's a battle against ignorance. It's a battle against misinformation. It's a battle against your own biases. I think one of the things the Stoics remind us is that like your mind is not always your friend. We all have prejudices. We all have biases. We all have mental shortcuts that we do that prevent ego being another one that gets in the way of us learning and seeing what we need to see. So you've got to struggle against yourself too.

Absolutely. And I like the subtitle, too, learn, apply, repeat. Yeah, like you're saying it has to be a cycle, not a one time of it. Yeah, like you become a student when you're young, that's all sort of forced upon us. But to me, the essential question is, how long do you stay a student? There's a story about Marxian's Reli's, philosopher king, is the wisest man in Rome, the most powerful man in Rome. And he's seen leaving the palace. And a friend stops him, and he says, you know, sir, where are you going?

He says, I'm off to see sexist, the philosopher, to learn that way. which I do not yet know. The man says, this is amazing. Here we have the philosopher king still taking up his tablets and going to school. But that's why he was a philosopher king. And I like that he was going to the teacher

instead of sending the teacher to him. So there is something about staying hungry, but also staying humble. Like, you know, if you're a know-it-all, you're right. Because if you're a know-it-all, you know all that it is possible for you to know. But if you focus on what you don't know,

If you focus on how much there is left to know, then you're always going to get better. And that, you know, think about what the Socratic method is, it's asking questions. So Archie's doesn't go around Athens, you know, lecturing people. He goes around asking them questions, trying to find things out. And so this decision to become a student is part one, but part two is staying a student and remaining a student all of your life. I was going to ask, with your books, it seems like your, you're, um, your target. your goal is to allow people to think freely but have an educated base that they're pulling from?

Yeah. How hard does it be coming for you to go around teaching all of this in this time with this administration? I saw the thing that happened with you at the naval base and canceling your lecture that you do. Yeah, I've been doing a series of lectures at the Naval Academy on the Cardinal Virtues for the last four years. And the last one was canceled. I was supposed to lecture about wisdom. And I was going to talk about Admiral James Stockdale as a famous graduate there who famously took a course on Marxism at Stanford before he was shot down in Vietnam and sent to a Marxist prison. And the idea is,

like, you want to learn from the enemy. You want to understand what they think, or else you're vulnerable to brainwashing and propaganda. Actually, Seneca, the Stoke philosopher, said this. He said, we want to study like a spy in the enemy's camp. So I was supposed to give this lecture, and like a couple weeks before I went, they started removing books from the library at orders of the Secretary of Defense and the President because they were too woke or pro-D-E-I. And I own a bookstore. I can't get up to give a lecture about wisdom

as they're literally removing books from a library. So I was going to mention it. And they found out. And they said, look, you've got to remove those slides or you can't come talk here. Damn. And this is one of the elite universities in this country. These are people who someday are going to be pilot

fighter jets or aircraft carriers or nuclear submarines like these are these cannot be sensitive little snowflakes or we're in big trouble these are people who are going to not just have to make highly complex technical decisions but profoundly ethical and moral questions and and yet here we are protecting them not just from from you know protect the potentially political books but maya angelou's memoirs was one of the books that they that they removed probably because no one in higses's offices has read it, knows anything about it. He probably chat GPT told him it was a woke book, so he wanted to remove it. So I felt I couldn't do that.

And that's, by the way, where all the virtues are interrelated, because it's not just knowing that book banning is stupid and reckless and dangerous. But then I have to decide, you know, do I want to preserve my access or do I want to say what I think is true? And also, do you want the, you know, Secretary of Defense to be mad at you? That's where courage comes in. but then also justice. Like, hey, it's the right thing, so you do the right thing.

But yeah, we are in a dangerous moment. Do you know the word cacistocracy? So like oligarchy, democracy, different types of governmental system. Cacistocracy is government by the stupidest. And that's what we are facing in this moment. People who are not just not smart, but actively afraid of and angry at and resentful of people who have competence and knowledge because they're fundamentally threatened by it. Are they? Hmm. So we have to replace the term idiocracy then. Yeah. I mean,

idiocry, it's a similar way to say the same thing. Okay, okay. But I mean, I don't think the American people are that stupid. I think we are in a moment where we have elected a number of officials who are actively stupid and deliberately ignorant. And what you said is, interest because you said they're resentful of people who are smart. And to me, I'm like, I don't think they don't, I don't think they believe anybody's actually smarter than them. There's a hilarious list of all the people that Trump has said he is smarter than. And it's like basically everyone that's ever existed. That's what I'm saying. Yeah. But it's this idea that like my feelings are more true or stronger than your expertise. So it's this, it's this antipathy towards expertise,

credentialism. And look, like, the experts are wrong all the time. I'm not saying they're flawless. But, but, like, you don't want to be driving the smartest, most qualified, most experienced people out of the armed forces, out of the government, out of business. And that's the sort of bent that we're on. It's going to end very, very badly. Oh, listen, I want to ask you about that, listen, if, do you think the political climate made them feel that way? Because for the last 10 years, all the political pundits and the strategists. They've just been wrong. They have been wrong. Like, and that, so it's like, do you know this idea of negative capability? Negative capability is the idea, can you, can you hold two opposing

ideas in your head? So on the one hand, the experts are wrong a lot. On the other hand, expertise is still really important. So you can't throw the baby out with the bathurst. So you got to go, hey, why were the experts wrong about this, that, or the other? What biases or tendencies? do they have that you've got to protect against. And at the same time, you've got to elect qualified people. You don't go, hey, that guy talks about the military on Fox News on the weekends. Let's put him in charge of the most powerful military in the world. I mean, he's not even qualified to be the spokesperson for the Pentagon, let alone running the Pentagon.

And so you got to go, hey, here's what I believe, here's what I think is important, and then still respect, you know, wisdom, intelligence, credentials, experience. I want to ask you, what role is listening more than talking, play when you're in like a culturally diverse setting or when you're sitting with somebody with a different ideology and you're listening to them? Yeah. But at some point you might be like, well, that's wrong with some bullshit. Do you just keep listening to you in a jacket?

But that is that idea of negative capability is like realizing, for instance, I have to think about this in my case. kids are never wrong about their feelings because they're their feelings. Now, I might feel differently. It might not change, hey, you got to go to school. You got to do X, Y, or Z. But like, your opinion is your opinion. And so I think what strong people are able to do, resilient people are able to do, wise people are able to do is understand that people feel differently about different things, have different opinions about different things. And to, be interested and curious about that without necessarily changing your mind all of the time.

So I think diversity is strength in the sense that you want to bring as many different opinions and viewpoints and worldviews into the equation. But at the end of the day, you do have to decide what you think, what you feel, what you're going to do, especially in a position of leadership. The leader ultimately has to listen to everyone and then make and own the decision. But it's based on what their opinions are based off, meaning your opinion or how you feeling could be a certain way. Yeah. But if it's based off of some bullshit, that's not true. Yes. Then your feeling is kind of wrong. And I think that's our problem with expertise is people are like, well, but I don't want that to be true. And it's like, okay, that's great. And I respect

that you don't like it, but it is what it is. Right. Wow. Yeah. Well, Ryan Holiday, ladies and gentlemen. New book, Wisdom takes work. Learn apply, apply, repeat. It's available right now. And thank you for joining us. Always a pleasure when you pull up, Ryan. You're the best. Thank you guys. Next time, bring some chocolate milk from a brown cow. I do have a brown cow. It does not make chocolate milk. It's the breakfast club. Good morning.

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