Stoic Success Strategy - Focus on good character, intentions, and actions for true success, not just external achievements. - Build a meaningful life by being a good person, earning trust, and inspiring others. Transcript: Ryan Holiday People want to be successful. They look for an edge. They look at what successful people have done throughout history, and then they try to reverse engineer those strategies. They look for models. And it makes sense then that people would look to Stoicism for help with this. Many of the Stoics were successful. Seneca was. Marcus Rillus was the most powerful man in the world. And in the centuries since, the philosophy has been part of the toolkit of artists and athletes and entrepreneurs and actors on the world stage. The problem, though, is that people miss the real stoic success strategy. Good fortune, Marcus Aurelius writes in meditations, is that which you make for yourself. But he didn’t mean that in the way that business people and gurus claim that we make our own luck and destiny. He was referring, in fact, to good character, good intentions, and good actions. This is something we talked about in the course that I did with Masterclass. It’s four episodes about how we use ancient virtue ethics, how we use these philosophical strategies to be more resilient and communicate better and have more meaningful connections. It was about creating growth as a person, as opposed to growth as a professional. Scott Galloway actually talked about this when we asked him what advice he tends to give his students. We talked about this when he was on the Daily Stoic podcast. He didn’t talk about killing the competition or disruptive ideas. No, he spoke of the importance of being a good person, being a good friend, being kind, being generous with your time and thoughts and emotions. What I tell people, he said, is if you want to be successful, if you want to be wealthy, be a good person. We have to remember success isn’t simply about titles and accolades and outdoing others. It’s about who you are along the way. So the real stoic success strategy, as Mark’s realist and countless others have shown, is rooted in character, cultivating integrity and kindness and purpose in what you do. And it happens that when you focus on being a good person, someone that others trust and admire and want to support, you’re not just building a career or reputation, you’re building A meaningful life.

Stoic Success Strategy - To achieve true success, prioritize being a good person. - Focus on kindness, generosity, and integrity. - True success isn’t just about titles and accolades, but about your character and actions along the way. - This advice comes from Scott Galloway, shared during his appearance on the Daily Stoic podcast. Transcript: Ryan Holiday Scott Galloway actually talked about this when we asked him what advice he tends to give his students. We talked about this when he was on the Daily Stoic podcast. He didn’t talk about killing the competition or disruptive ideas. No, he spoke of the importance of being a good person, being a good friend, being kind, being generous with your time and thoughts and emotions. What I tell people, he said, is if you want to be successful, if you want to be wealthy, be a good person.

Stoic Success Strategy - Focus on being a good person: kind, generous, and someone others admire. - True success isn’t just about titles and accolades, but about character and integrity along the way. - Building a meaningful life and fostering trust leads to a fulfilling career and reputation. Transcript: Ryan Holiday Scott Galloway actually talked about this when we asked him what advice he tends to give his students. We talked about this when he was on the Daily Stoic podcast. He didn’t talk about killing the competition or disruptive ideas. No, he spoke of the importance of being a good person, being a good friend, being kind, being generous with your time and thoughts and emotions. What I tell people, he said, is if you want to be successful, if you want to be wealthy, be a good person. We have to remember success isn’t simply about titles and accolades and outdoing others. It’s about who you are along the way. So the real stoic success strategy, as Mark’s realist and countless others have shown, is rooted in character, cultivating integrity and kindness and purpose in what you do. And it happens that when you focus on being a good person, someone that

Focus on Your Response - Focus on what you can control, which is your response to events, not the events themselves. - Don’t dwell on whose fault it is or if it’s fair; focus on your next action. Transcript: Ryan Holiday This one’s basic, but it’s one of the hardest things to do in the world. My kids struggle with it. I struggle with it. Heads of state struggle with it. But Epictetus says that it’s essentially our first task in life to find out what’s in our control and what’s not in our control. Basically, stoic philosophy is centered around this idea that we don’t control what happens. We don’t control what other people do. We don’t control what life does. We don’t control when we were born, how we were born, what our circumstances are, but we control how we respond to all that. We don’t control what happens. We control how we respond to what happens. So the advice is really simple for a young person. Focus on what you’re going to do about it. Focus on what you’re going to do next. Focus on your part, whose fault it was, why it happened, whether it’s fair, whether you like it. You got to get better at putting all of that aside, not thinking about it, and focus on what you’re going to do about it.

Nobody Knows Anything - Nobody can predict what will truly work or fail, even experts. - Trust yourself, be humble, and don’t be dissuaded by naysayers because ’nobody knows’. Transcript: Ryan Holiday That is your first and your most important job in life. This is an old and essential one that’s been proven time and time again in my own experience, but it comes from the screenwriter William Goldman. He says, nobody knows. Nobody knows anything. Nobody knows anything about what’s going to work. People have an idea. They’re really quick and firm with what they tell you obviously isn’t a good idea, what’s obviously going to fail, but they don’t know. When I went to my publisher with an idea to write a book about an obscure school of ancient philosophy, they were not that excited. They were just hoping I would get it out of my system. They offered me half what I got for my first book for this second book that I did about Stoic philosophy. And then it went on to sell millions of copies and reach millions of people all over the world. They’re happy to take credit for it afterwards, but nobody knows. I didn’t even really know. You want to trust yourself, but you want to have some humility. You want to have confidence. You want to listen to the feedback, the wisdom out in the world, but also not take it too seriously. Almost nothing that ultimately succeeds was a sure thing at the time. In fact, a lot of people thought it was crazy. A lot of people thought it was a bad idea. You got to understand that nobody really knows. Steve Jobs talked about how all the rules, all the assumptions, these were just made up by people at some point. Nobody knows. That includes you. You don’t know, right? So don’t be certain that you know better than everyone else. But understand, ultimately, nobody knows. And there is a first time for so many things. And you can’t be intimidated by or dissuaded by the people who are simply pretending to know.

Youthful Intensity - Youth often brings a lack of perspective and an intensity of feelings. - It’s easy to get worked up and take things too seriously when you’re young because of a perceived lack of experience. - This can be detrimental. Try to calm down and step back, realizing that most things aren’t as critical as they feel in the moment. Transcript: Ryan Holiday You’ve been through stuff like this before, so you don’t get too worked up. When I look back on my 20s or even before that the intensity the of everything that i felt some good but some not so good right i was worried about stuff i was stressed about stuff i thought If i don’t do this thing and i don’t do it amazingly well i’ll never get a chance like this again it was just too intense i took everything too seriously taylor swift is right you you need To calm down you need to

Calm Down - Gain perspective by realizing that intense feelings are temporary. - Calm down and consider how you’ll feel about this in the future. Transcript: Ryan Holiday One of the hallmarks of youth is a lack of perspective. By definition, you don’t know. You haven’t been through this thing a million times. You don’t have years and years of experience. But what comes with years and years of experience is a kind of turning down of the volume on things. You’ve been through stuff like this before, so you don’t get too worked up. When I look back on my 20s or even before that the intensity the of everything that i felt some good but some not so good right i was worried about stuff i was stressed about stuff i thought If i don’t do this thing and i don’t do it amazingly well i’ll never get a chance like this again it was just too intense i took everything too seriously taylor swift is right you you need To calm down you need to step back. You need to look at the history of this space, this thing, even in your own life. Yes, the breakup feels devastating right now. The missed opportunity feels very acute right now. The humiliation or the pain you feel for having been criticized or fired or reprimanded, it feels like a lot. In the big scheme of your life will feel very differently. Someone told me once like this moment is not your life. This is simply a moment in your life. But when you haven’t had that many moments, it’s hard to understand how to feel about this thing. So you need to zoom out, take the big picture, calm down. As Mark really says, you don’t have to turn this into something. You can let it be what it is. See it in the big scheme of things. Calm down. Get the benefit. Try to fast forward to how you’re going to feel about this in one year, five years, 10 years, 20 years. And almost certainly you will not feel as intensely as you feel about it right now.

Trust the Process - Trust the process, even if beginnings are small. - Everything starts at zero, so be patient and follow the process for growth. Transcript: Ryan Holiday Everything starts at zero. I remember once when I was at American Apparel, we were looking at these stores that the company had just opened and one wasn’t doing well. And I said, look, this store is not doing well. And Dev Charny looked at me and he said, all run rates start at zero. What he had the benefit of understanding, having watched stores open and then succeed, was that not everything gets off to a roaring start, but that if you follow the process, if you Do the right things, eventually you get where it needs to go. This idea that all run rates start at zero is something I’ve applied in so much of my life. Like every book starts with a sentence, starts with a page. Everything starts on page one, right? Everything starts, my books start with a single note card. It’s easier to trust the process when you have been through the process. And that’s one of the hard things to do as a kid, as a young person, is trust the process that you haven’t been through. But other people have been through that process. The process is tried and tested and true. Everything starts at zero. The beginnings of things are small, Cicero says, but they can turn into very big things. They can turn into a platform. They can turn into a career. It can turn into a relationship, which can turn into a marriage, which can turn into one of the pillars of your life. These things, they start small and you have to appreciate that and understand that and respect it.

Read Widely - Reading is crucial for wisdom; it’s like conversing with the dead. - Ask people you admire for book recommendations and read them. Transcript: Ryan Holiday It’s crazy, but it’s true. It’s true for most people. Most people leave a superpower on the table or on the shelf. A young future philosopher named Zeno visits the Oracle of Delphi as a young man, and he gets this prophecy. The prophecy says you will become wise when you begin to have conversations with the dead. It’s only years later that Zeno realizes that the Oracle is talking about reading, that reading is a way to talk to the dead. And yet most people don’t do this. Most people could commune with the wisest, smartest, most accomplished people who have ever lived, and they refuse to do that. It’s like that quote about how there is no difference between someone who can’t read and someone who doesn’t read. The great General Mattis, whose life was shaped by stoic philosophy, becomes a four-star general in the Marines, secretary of defense. He says that if you haven’t read, and if you haven’t read a lot, he says you are functionally illiterate, right? You are turning away. You are ignorant of all the wisdom that’s out there. Experience is essential. You’ve got to learn by experience in life. But if you are not learning by the experiences of others, you are leaving incredibly valuable things on the table, on the shelf. You must be a reader. Mark Surrealeus’ life is changed by a book recommendation from his philosophy teacher, Rusticus. But it’s not the recommendation that counted. Those are commonplace. It’s that he read the book. He did the work. Go around, ask the people you admire, the people you respect, ask them for book recommendations. What’s a book that changed your life? And then read the book that changed their life. My life was changed because someone turned me on to the Stoics also. There are amazing books out there full of hard won experience and wisdom. And to not avail yourself of that is not just stupid.

Live an Interesting Life - Live an interesting life full of experiences to inform your work. - Don’t just study; be a doer, like Cato, whose life was his philosophy. Transcript: Ryan Holiday Someone looked at me and said, writers live interesting lives. They were saying that I shouldn’t go just try to master the craft, really figure out how to string sentences together, but I should go do stuff. Should meet people, go places, have a life worth writing about. My first book was a memoir of this sane experiences of my 20s working in the sort of dark underbelly of public relations. My books today are informed by the personalities, the characters, the stressful situations that I got in the lawsuits that I saw, the enormous success and what it did to people that Failures, what it did to people, why those failures happened. My writing is informed not by my deep study of philosophy, although I feel like I’ve done that work. My writing is informed by my experiences in the world, which allowed me to understand what the philosophy was talking about. The Stoics had no interest in the pen and ink philosophers. They wanted to be doers. They admired the doers. Cato is the greatest of the Roman philosophers. He doesn’t write anything down. His life was the philosophy. That was his magnum opus. If you want to be a writer, if you want to be an entrepreneur, if you want to be a comedian, if you want to be a leader, if you want to be anything, live an interesting life that will shape and Inform and inspire what you’re able to go on and do.

Prioritize Learning - When you’re young, prioritize learning in your decision-making. - Instead of focusing solely on money or social status, ask yourself what opportunities will provide the most learning experiences. - Seek out situations that expose you to new things and expand your knowledge. - Consider jobs or experiences that pay you to learn, like internships or research positions. Transcript: Ryan Holiday One of my rules when I was young, when I was deciding between things was always, which of these things am I going to learn more doing? So if you’re making all your decisions when you’re young about what’s going to pay more, what’s more socially acceptable, what seems more exciting, you know, that can work out. But you’re missing the real opportunity. What you really want to do is learn. You should be like a vacuum that’s just soaking up everything that’s possible. So I was always like, is this going to teach me something I don’t know? Is this going to get me in rooms where I can see and experience things I otherwise wouldn’t? I was really excited, always looking

Be Realistic - Be realistic about the world’s imperfections; don’t expect fairness. - Understand how the world truly is before trying to change it. Transcript: Ryan Holiday It would be wonderful if life was fair and everyone was kind and decent, if cause always led to the right effect, if karma was real. But it’s not. That’s not how life is, man. Life is unfair. Life is heartbreaking. Life is cruel. And your youthful idealism is important, but it can’t be naivete. Don’t go expecting Plato’s Republic, Mark Sevelius writes in Meditations. Cicero said something similar about Cato. He said Cato’s problem was that he believed he lived in Plato’s Republic and not, he said, in the dregs of Romulus, where he actually resided. You got to be realistic. You got to have both eyes open. One of the novels I read in my 20s was All the King’s Men. There’s this quote from Jack Stanton that I remember underlining. And when I reread it recently, it was there. And I go, oh, I’m so glad I learned this then. Jack Burden is talking about Adam Stanton. And he says, you know, because he is a romantic, and he has a picture of the world in his head. And when the world doesn’t conform with respect to the picture, he wants to throw the world away. If you have these illusions, these ideals that are not based on reality, you’re going to painfully lose them at some point. So you got to go into the world with your eyes wide open. You got to be pragmatic. You got to be savvy. You got to be smart. This isn’t to say you can’t want to change things, you absolutely should want to change things. But to be able to change things, you first have to understand how and what they are. And the study of history does that, mentors help us do that, real world experience does that. Your picture in your head or what’s in the books, it’s you got to know how the world really is.

Maintain Idealism - It’s good to be open-hearted and idealistic when you’re young. - Don’t let the world steal your values and principles. - Don’t give in to nihilism or become cynical with age. - Actively cultivate openness, caring, compassion, and empathy. - Look for the good in the world and protect your worldview from negativity. Transcript: Ryan Holiday It’s good that you’re open-hearted and idealistic, that you have values and principles. Don’t let the world steal those from you. Don’t give in to nihilism. Gandhi was once asked, you know, what worries him the most? And he said, hardness of heart of the educated. You have to keep that openness and that goodness inside you. Have to carry the fire, as Cormac McCarthy talks about in The Road. Don’t let the assholes bring you down. Don’t let the assholes turn you into an asshole. Don’t let crazy times make you crazy. Life is gonna be dark. There’s gonna be dark people, dark experiences, but you can’t let that ruin your worldview. You can’t let that harden your heart. I’m proud of the fact that I think as I’ve gotten older, I feel more open, more caring, more compassionate, more empathetic. That didn’t happen naturally. That was a lot of work. That took a certain stubbornness and a commitment.

Keep the Fire - Maintain your idealism and values as you age; don’t become cynical. - Do the work to stay open, caring, and compassionate despite life’s darkness. Transcript: Ryan Holiday But then that leads us to the next one. I remember as a young man, my dad said something to me. He said, you know, if you’re not liberal when you’re young, you have no heart. And he said, if you’re not conservative when you’re older, you have no brain. And look, the broad strokes of that message make sense in that, you know, your idealism when you’re young can not be based on anything real. And it’s as you get older, you experience things, you can become a little cynical. You have to become a bit more pragmatic and realistic. But as it happens, this quote, which was popular in sort of talk radio circles in the 90s, actually dates back to the 1800s. There’s also something terribly, terribly sad about it, something I think you want to be careful about when you’re young. It’s good that you’re open-hearted and idealistic, that you have values and principles. Don’t let the world steal those from you. Don’t give in to nihilism. Gandhi was once asked, you know, what worries him the most? And he said, hardness of heart of the educated. You have to keep that openness and that goodness inside you. Have to carry the fire, as Cormac McCarthy talks about in The Road. Don’t let the assholes bring you down. Don’t let the assholes turn you into an asshole. Don’t let crazy times make you crazy. Life is gonna be dark. There’s gonna be dark people, dark experiences, but you can’t let that ruin your worldview. You can’t let that harden your heart. I’m proud of the fact that I think as I’ve gotten older, I feel more open, more caring, more compassionate, more empathetic. That didn’t happen naturally. That was a lot of work. That took a certain stubbornness and a commitment. That took actively looking for the good, right? And you have to do that work and you have to do that work every day because the last thing you want to end up is old and bitter and resentful and cynical.

Prioritize Learning - Prioritize learning when making decisions, especially when young. - Seek opportunities that offer valuable experiences and lessons. Transcript: Ryan Holiday One of my rules when I was young, when I was deciding between things was always, which of these things am I going to learn more doing? So if you’re making all your decisions when you’re young about what’s going to pay more, what’s more socially acceptable, what seems more exciting, you know, that can work out. But you’re missing the real opportunity. What you really want to do is learn. You should be like a vacuum that’s just soaking up everything that’s possible. So I was always like, is this going to teach me something I don’t know? Is this going to get me in rooms where I can see and experience things I otherwise wouldn’t? I was really excited, always looking for opportunities where I was getting paid to learn. One of the reasons I dropped out of college was to get a job at a talent agency and then to be the research assistant to Robert Greene. I went from paying to learn. That’s what, you know, higher education is very expensive to being paid to learn. I wasn’t getting paid a lot, but I was getting paid enough. I was getting paid so much in experience and lessons. I remember Robert Greene would have to remind me to invoice him. I was like, I’m getting the better end of this deal, man. So you got to go towards what’s going to teach you more, not what your parents want, not what seems like the natural, mature, responsible thing. But what is the thing that’s going to pay? What’s the thing that’s going to pay you most in education and lessons and insights and experience? Go towards what will teach you the most.

Prioritize Learning - When deciding between options, prioritize learning opportunities. - Focus on experiences that expose you to new things and different perspectives. - Seek opportunities where you’re paid to learn, gaining valuable experience and lessons. - Prioritize acquiring knowledge over immediate financial gains or social status. Transcript: Ryan Holiday So I was always like, is this going to teach me something I don’t know? Is this going to get me in rooms where I can see and experience things I otherwise wouldn’t? I was really excited, always looking for opportunities where I was getting paid to learn. One of the reasons I dropped out of college was to get a job at a talent agency and then to be the research assistant to Robert Greene. I went from paying to learn. That’s what, you know, higher education is very expensive to being paid to learn. I wasn’t getting paid a lot, but I was getting paid enough. I was getting paid so much in experience and lessons. I remember Robert Greene would have to remind me to invoice him. I was like, I’m getting the better end of this deal, man. So you got to go towards what’s going to teach you more, not what your parents want, not what seems like the natural, mature, responsible thing. But what is the thing that’s going to pay? What’s the thing that’s going to pay you most in education and lessons and insights and experience? Go towards what will teach you the most. Gary Vaynerchuk has this thing, you know, people will come up to him and he’ll ask him how old they are. They’re worried about this or that. He goes, you’ve got so much time. He’s like, you’ve got time. The point is, a lot of us, even when we’re young, we think it’s too late for us to do stuff. That we’ve already made the decision, the die is already cast, the choice is already made. No, you’ve got time. It’s not too late.

Time’s Paradox - Recognize that you have time but also that life is short. - Don’t delay; start pursuing your goals now. Transcript: Ryan Holiday Gary Vaynerchuk has this thing, you know, people will come up to him and he’ll ask him how old they are. They’re worried about this or that. He goes, you’ve got so much time. He’s like, you’ve got time. The point is, a lot of us, even when we’re young, we think it’s too late for us to do stuff. That we’ve already made the decision, the die is already cast, the choice is already made. No, you’ve got time. It’s not too late. One of my favorite books is by Nell Painter, and it’s just called Old in Art School. She was this famous, well-known historian who like in her 70s goes back to get an MFA in art. It’s not too late. You have time, right? You are still so young. The things I was worried about when I was a kid, oh, it’s too late. I remember when I was thinking about dropping out of college, my mentor said, if this doesn’t work out, man, you’ll just go back to school. He’s like, you’re so young. You have time. And at the same time, this is the tough part. This is the paradox. Life is complicated. Be ready for that. You don’t have that much time. Life is short. You don’t know how much time you have. You don’t know how long you’re going to live for. Mark Schmieler says, you could be good today. Instead, you choose tomorrow. Don’t put stuff off. The one thing all fools have in common, Seneca says, they’re always delaying getting ready to start. That was one of the reasons I decided to drop out. I was like, I want to do this now. I don’t want to wait a year to get started on this thing. I want to do it now. Seneca says it’s important that we realize death isn’t this thing in the future that happens once. Death is happening now. If you’re 20, yeah, maybe you have 50, 60 years left. That’s a long time. But you’ve also already died, Seneca says, 20 years. You have two decades that are dead and gone, never to be returned. Time is our most precious resource. Our youth goes by like that. Don’t waste it. Don’t take it for granted. Don’t assume you have forever. When we say you have time, we mean it’s not too late for you to do the thing right now. Don’t wait any longer. Do it now. Memento more. You could leave life right now. Let that determine what you do and say and think. That is the most critical stoic lesson for young people.

Get Your Shit Together - Deal with your personal issues and keep your private life private. - Avoid oversharing on social media or at work. - Professional maturity and responsibility are often valued over raw talent, especially when trust and resources are involved. Transcript: Ryan Holiday You got to get your shit together. I mean, you got to deal with your issues from your childhood, your issues with your parents. You got to keep the crazy at home. That’s what I tell young people who work for me. Like your private life is your private life. Don’t vomit it out at the office. Don’t overshare it on social media. You got to figure out how to rein it in.

Managing Anxiety - Settle down and calm your nerves. - Work through anxiety; don’t let it control your life or ruin opportunities. - Ryan Holiday shared that anxiety was his most expensive habit when he was young, making him fragile and hindering his ability to enjoy his experiences. Transcript: Ryan Holiday You got to settle down, calm those nerves, work through that anxiety. Don’t let it ruin your life or your opportunities. Ego is the enemy. I have it tattooed on my arm. I knew that as a kid who’d gotten a lot of crazy, awesome shots very early, that I wasn’t going to be destroyed by anything but myself. If this went to my head, it would ruin me. If I got complacent, it would ruin me.

Get Your Act Together - Address personal issues and maintain composure in professional settings. - Show maturity, responsibility, and trustworthiness. Transcript: Ryan Holiday You got to get your shit together. I mean, you got to deal with your issues from your childhood, your issues with your parents. You got to keep the crazy at home. That’s what I tell young people who work for me. Like your private life is your private life. Don’t vomit it out at the office. Don’t overshare it on social media. You got to figure out how to rein it in. Keep it together. If I’m looking at hiring two young people, I will take someone who seems like they are mature and responsible and have their shit together over someone who’s incredibly talented, but A hot mess. Because I’m trusting them with things that are valuable and expensive. There are only so many opportunities to go around. You want to show that you are worth putting time and energy into, that you are worth investing in, that you can be trusted, that you’re not going to blow things up, that you’re yourself Not going to blow up and spin off the planet.

Make Your Boss Look Good - When you’re young, focus on making your boss look good. - See your job as providing them with the tools and information they need to succeed. - Discover, learn, and share things that will benefit them. - Forget about taking credit; focus on being a team player and contributing to their success. Transcript: Ryan Holiday A lot of times when you’re young, your job, your key to success is to make your boss look good. I always saw as my job is to make Robert Greene or the executives I worked for was to give them canvases to paint on, to set them up to succeed. Right. That’s your job. It’s not about you. It’s about them. Your job is to discover things, learn things, bring things back them that’s going to make

Make Your Boss Look Good - Focus on making your boss look good and contributing to the team. - Forget about credit; focus on learning and proving your worth. Transcript: Ryan Holiday Got to get your shit together. A lot of times when you’re young, your job, your key to success is to make your boss look good. I always saw as my job is to make Robert Greene or the executives I worked for was to give them canvases to paint on, to set them up to succeed. Right. That’s your job. It’s not about you. It’s about them. Your job is to discover things, learn things, bring things back them that’s going to make them look good. You got it when you’re young. Just forget about credit. It’s not about credit, right? It’s about being a team player. It’s about contributing. It’s about being someone who brings things in, who proves their worth. And if you can’t cultivate that, you’re not going to last long in an organization, in a company, or with the opportunity you’ve been given.

Manage Anxiety - Manage your anxiety; don’t let it control your life and ruin opportunities. - Enjoy the process and don’t overthink or be too sensitive. Transcript: Ryan Holiday Look, I had a very expensive habit when I was young. Wasn’t drugs, wasn’t partying. It wasn’t fancy stuff. It was anxiety. I was just worried all the time. I picked that up in my childhood probably. And I was ignoring that critical stoic lesson about like, is this in your control or is it not? And so I just sweated things more than I needed to. I stressed more than I needed to. I got places way earlier than I needed to. I took feedback way harder than I was just too sensitive, too worried to what about this and this and this and this. I was extrapolating out too often. And that made me really fragile. It made me hard to be in a relationship with, my wife tells me. It sucked a lot of the fun and enjoyment out of this period that I should have had more fun doing. This is something you talk to a lot of athletes or people who had short careers because what they’re able to do, you can’t do it that long. They look back and they go, I wish I’d enjoyed it more. And that can be hard to understand when you’re a kid, but it’s true. Don’t suck the joy and the fun out of it. Don’t let anxiety rule. Don’t be so insecure. You got to settle down, calm those nerves, work through that anxiety. Don’t let it ruin your life or your opportunities.

Ryan Holiday’s Expensive Habit - Ryan Holiday’s most expensive habit in his youth wasn’t drugs or partying, but anxiety. - He was constantly worried, likely due to his childhood, and often ignored the Stoic principle of focusing on what’s within one’s control. - This anxiety made him overly sensitive to feedback, stressed, and generally less enjoyable to be around. - Looking back, he realizes this anxiety stole the joy from a time he should have enjoyed more. - He now advises younger people to learn from this and enjoy their present moments, especially if they are in a career with a limited timeframe, like professional athletes. Transcript: Ryan Holiday Look, I had a very expensive habit when I was young. Wasn’t drugs, wasn’t partying. It wasn’t fancy stuff. It was anxiety. I was just worried all the time. I picked that up in my childhood probably. And I was ignoring that critical stoic lesson about like, is this in your control or is it not? And so I just sweated things more than I needed to. I stressed more than I needed to. I got places way earlier than I needed to. I took feedback way harder than I was just too sensitive, too worried to what about this and this and this and this. I was extrapolating out too often. And that made me really fragile. It made me hard to be in a relationship with, my wife tells me. It sucked a lot of the fun and enjoyment out of this period that I should have had more fun doing.

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Don’t Let Anxiety Win - Don’t suck the joy and fun out of your pursuits, especially in your younger years. - Don’t let anxiety and insecurity control your actions and decisions. - Work through your anxieties and insecurities instead of letting them dictate your experiences. - Calm your nerves and settle down to avoid missing out on opportunities. Transcript: Ryan Holiday Don’t suck the joy and the fun out of it. Don’t let anxiety rule. Don’t be so insecure. You got to settle down, calm those nerves, work through that anxiety. Don’t let it ruin your life or your opportunities. Ego is the enemy. I have it tattooed on my arm. I knew that as a kid who’d gotten a lot of crazy, awesome shots very early, that I wasn’t going to be destroyed by anything but myself. If this went to my head, it would ruin me. If I got complacent, it would ruin me. If I thought I was better than other people, the rules didn’t apply to me, that I was special, that was the end of it. Remember, it’s impossible to learn that which you think you already know. That’s from Seneca.

Ego is the Enemy - Keep your ego in check; humility and self-awareness are crucial for learning. - Be confident, but acknowledge your weaknesses and strive to improve. Transcript: Ryan Holiday Ego is the enemy. I have it tattooed on my arm. I knew that as a kid who’d gotten a lot of crazy, awesome shots very early, that I wasn’t going to be destroyed by anything but myself. If this went to my head, it would ruin me. If I got complacent, it would ruin me. If I thought I was better than other people, the rules didn’t apply to me, that I was special, that was the end of it. Remember, it’s impossible to learn that which you think you already know. That’s from Seneca. Zeno felt that the worst trait in one of his young students, the thing that was the biggest impediment to knowledge, he said it was conceit. You can’t learn that which you think you already know. You need to be confident. You need to know what you’re good at, but you also need to have the self-awareness to know what you’re not good at. And you need to have the humility, the openness to want to know what you don’t know, to want to get better. If you think you’re perfect, it’s true in the sense that you cannot get any better. Humility, openness, self-awareness, self-criticism, that’s energy you want working towards you when you’re young. Superiority, specialness, entitlement, all that shit, that’ll break. And nobody has time for it. Successful people don’t want to be around egotistical upstarts.