Let This Be Our Legacy | Robert Greene's Stoic Lessons (That Changed Ryan Holiday's Life)

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1:49Just go to dailystoic.com slash premium to sign up right now or click the link in the show descriptions to make those ads go away. Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. On Tuesdays, we take a closer look at these Stoic ideas, how we can apply them in our actual lives. Thanks for listening, and I hope you enjoy.

2:25Let this be our legacy. It's always been about winning, even back to the ancient Greeks. That's why people trained for the Olympics. It's why they traveled to compete in the Olympics. It's why the spectators watched the Olympics. So naturally now, many centuries later, whenever the Olympics come around, we tend to place a big emphasis on winning and individual glory. We obsess over world records and historic performances. We track how many gold, silver, and bronze medals each country has won. We read and watch the stories about the training regimen and sacrifices of the Olympians who do whatever it will take to get the gold.

3:04But as the Stoics would remind us, it's not just winning that counts. That there is sometimes another plane of greatness that an athlete can reach by an injury they overcome and finish despite, by the political gesture they make on the medal stand, by the way they treat a competitor. I tell the story in Right Thing Right Now about a Japanese equestrian, Shunzo Kido, in the 1932 Summer Olympics in Los Angeles. He was competing in a 22.5 mile 50 obstacle race that he didn't normally run after a teammate was injured and had to drop out. Improbably, with no proper training for himself or his horse, Kido was in the lead, clear of the pack after jumping over the second to last obstacle.

3:46But what he did next was even more improbable. He pulled up the reins and dropped out of the horse. Out of nowhere, he gave up a chance of gold and glory for himself and his country. Why? He could feel that his horse was struggling and sense that even just a few more seconds at full speed would kill the horses across the finish line. As the plaque on the Friendship Bridge along the Mount Rubidoux Trail commemorating this unprecedented display of sportsmanship reads, Lieutenant Colonel Shunzo Kido turned aside from the prize to save his horse. He heard the low voice of mercy, not the loud acclaim of glory.

4:24In a world that often glorifies winning at all costs, this story reminds us of a deeper, more enduring value, the importance of compassion and integrity. The Stoics believe that how we treat others, especially those who cannot speak for themselves, reveals our true color, our true character. Chrysippus and Early Stoke who competed as a distance runner would make this point about cheating. The competitive drive might be what motivates an athlete, but to cheat or to hurt someone else in order to fulfill it is to miss the point. It's easy to get caught up in the pursuit of glory, but the real test lies in how we act when no one is watching, when the stakes are high, and when the choices are difficult.

5:03In the end, the victory over oneself, the triumph of one's principles is what counts. the satisfaction of not only giving your best, but being. So let this be the legacy that we strive for, not just in sports, but in everything we do. And if this episode sounds a little different, it's because I'm recording it on my phone at an Airbnb in Australia, where I was just watching the Olympics. I've been here, I just gave those two talks, one in Sydney, one in Melbourne. And it's been fascinating to watch the Olympics from another country's perspective. Like I was watching Australian women's field hockey.

5:39And I was watching Australian women's diving. I've watched the Olympics from the perspective of another country. It's been really interesting, right? It just sort of reminds you, so easy to forget because there's so much nationalism tied up in the Olympics that these are the best athletes from this country and they're proud of them. Actually, it's been quite heartwarming to watch the Australian television announcers, just how nice and friendly and supportive they are of the athletes. You made us so proud. We're so happy for you. It's just, it's been a fascinating sort of cultural experience for me.

6:11Anyways, I just gave my talk the other day. I'm heading back to the US very soon. I'm going to be doing talks in Toronto and Vancouver, then London, Dublin, and Rotterdam in November. You can check all that out at ryanholiday.net slash tour. I would love to see you. It was awesome. I've had so much fun down here and it was so cool. I spoke to 2000 people in Sydney, like 16, 1700 in Melbourne. and I've never gotten to do something like that. So often when I get talks, it's like a corporate audience or it's at a conference, but to see like 2 ,000 fans of the Daily Stoic, so many of the people told me to listen to the podcast, it was just awesome.

6:46I hope to see you in one of those cities. And then this story, the one I just told about this Japanese horseman, it's one of my all-time favorites and I love to run wherever I go. I've been running a lot here in Sydney, but I went to college in Riverside, California and that's where that Mount Rubidoux trail is. And the first time I saw it, I'd never even heard this story. And it's such a wonderful, lovely thing. And I wish it was more well-known, probably the events of World War II kind of raise some of the cultural goodwill there for a Japanese officer. But I've always loved that story. And I wanted to put it in Right Thing Right Now.

7:19You can check it out. It's in part three of Right Thing Right Now. And if you're listening in Australia, I just signed like 200 copies of Right Thing Right Now for Gertrude and Alice, a little bookstore here in Bondi. or you can come grab a signed copy in those dates I'm doing in November at ryanholiday.net slash tour.

7:44A little over 15 years ago, I dropped out of college to apprentice under the great Robert Green, strategist and thinker. Authors sold millions of copies, 48 laws of power, 33 strategies of war, mastery, the laws of human nature. And Robert taught me how to write, how to think. He opened doors for me. He got me a job at American Apparel where he was on the board of directors. As I've gone on to write my own books, start my own businesses, Robert has always been there teaching, advising, answering questions for me. He's shaped the whole course of my life because Robert is actually a closet Stoic.

8:17People might not know this from the controversial themes in his books, but he knows the Stoics. He's read the Stoics and he's helped me understand the Stoics in so many ways. And that's what we're going to talk about in today's episode.

8:29I remember I walked into Robert's house shortly after starting to work for him and he showed me his famous note cards. He showed me the Robert Greene note card system which I use to this day to organize all my books and do all of my writing even outline many of the videos that I do. For Robert he was saying that it starts with the research and you have to create a system to synthesize and organize the information that you read not just as you're doing a specific project, but across your whole life. This is what a commonplace book is. We can think about Marcus Aurelius' meditations being Marcus Aurelius riffing and talking and recording things.

9:04You have to do that. Robert's books, if you think about how meticulously organized and story-based Robert Green's books are, it's because of this note card system, which he's been doing for years and years and years. He records all this information, he stores it, and it allows him to move the pieces around. It's a very difficult system. There's no question it could be done more easily, faster online. But the point is the system is hard. The point is the system takes a lot of time. The point is the system has multiple points of redundancy. You're writing things by hand. This is the analog. This is the work that goes into making something great.

9:38It's not about clicking and copying and pasting and taking this from over here. No, it's a painstaking process. It's the accumulation of years of research and insights and experience. And then the organization that finding the patterns, the connections between things, that's what has unlocked Robert's work. It's also what's unlocked my work. But this process of keeping a commonplace book is a practice that goes way back to the Stoic. Epictetus said we have to write these things down, talk to people about them, riff on them. And that's what Marcus Rios is doing in meditations. It's what I'm doing in my note cards.

10:09And it's what Robert did in his. And I'm so grateful that he opened me up to this system because none of the things I've done since would be possible without it.

10:19When we talk about this idea of the obstacle is the way, no one is better at doing that than an artist. I remember I was going through something really tough, really painful, and Robert Green looked at me and he said, you got to remember, Ryan, it's all material. He's like, that's the joy, the benefit of being a writer is that you get to take the worst things that happen to you and you get to transform them into material, into lessons, into ideas, into things that help you and other people. You think about the 48 Laws of Power. Robert Green, for the first 40 years of his life, things did not go the way that he wanted them to go.

10:48He was kicked around. He went from job to job. He never really found his calling. He never locked into anything. He got abused. He got manipulated. All of that was forming and shaping, incubating the ideas that would become this incredible book, The 48 Laws of Power. So you think you want things to go a certain way. You want them to be easy. You don't want to have your heart broken. You don't want to have things stolen from you. You don't want to be betrayed. You don't want to hurt yourself. You don't want to have setbacks, but also you do. If you can decide, like an artist, to transform the things that happen to you into something good.

11:17Mark Schruess says, what you throw on top of a fire becomes fuel for the fire. It transforms it all into flame and brightness. That's what an artist does. That's what a stoic does. That's what Robert's done. And that's what I've tried to do. And that's actually what shaped the idea of The Obstacle's Way.

11:34It's funny, when I dropped out of college, people thought I was crazy. They thought I was throwing my life away. They thought I was going to come to regret it. But I knew because I wanted to be a writer that there was nothing better than apprenticing under a great writer. and in Robert's amazing book Mastery, he talks about how everyone has to undergo a long apprenticeship. You have to learn from someone who's further along than you, who's mastered that thing. That's the fastest way for you to become a master. And so watching Robert, how he organizes his day, I remember I would just ask him questions like, how does the index in a book work?

12:06I asked him how the note card system worked. I asked him what books to read. Working for Robert was difficult. It wasn't particularly lucrative. Although he would have to remind me to invoice him because I knew that I was getting the real payment was in being able to ask him questions, was in the access, was in getting to watch him work, right? So you have to find out in your life who's further ahead than you, who's going to be the model. Seneca talks about how you have to choose yourself a Cato. It's because without a ruler, you can't make crooked straight. Robert Greene was the ruler that I measured myself against, that I straightened myself out again.

12:42And that long apprenticeship, which went on from basically my 18th or 19th birthday to this day, but I worked for him on an almost daily basis until my mid, late 20s. And if Robert Greene asked me to research something right now, I would drop everything and do it because I know that I would learn something by seeing how he thinks, how he works, by having access to his world. So you have to find that apprenticeship. You have to stick with it. It's going to take longer than you want. It's going to be more painful than you want it to be. But that's how you learn things. and all the greats find a model to learn from, find their Cato, find their Robert Greene.

13:17And I'm so lucky that that happened to me.

13:23It's funny though, like when I did drop out of college, I was terrified. Of course, knew it would work and thought it would work and I wanted to do, but I was also terrified because I listened to those other people. And I remember another mentor I had pointed me to a page in the 33 Strategies of War where Robert Greene talks about acting before you're ready. In the 48 Laws of Power, he talks about entering action with boldness. And that's something I learned from that critical point. I wanted to be timid. I wanted to see, could I not drop out? Could I just do this on the side? And I was like, no, I got to make a bold gesture.

13:52I got to take a big risk. I got to bet on myself here. And Robert allowed me to do that. But also his work and his ideas, it encouraged me to do that. When I was having lunch with him and he said he needed a research assistant. And I said, I'll do it. I'll do it. I'll do it for free. He said, I'm not going to let anyone work for me for free. But he said, I think you've got a shot to do this. and I think you can do this. He bet on me, I bet on myself. I took this big risk, but we enter action with boldness. Sometimes we act before we're ready. That's what the Do It For Jew of Courage is about. You're afraid, but you do it anyway.

14:21You do this scary thing. If it was safe, if it was guaranteed, if it was easy, everyone would do it.

14:30One of the ideas I took from Robert is that success is a lagging indicator. He said once that creativity is a result of all the previous work that you put in, the books you read, the notes you took, the conversations you had, things you watched, the places you traveled. The first 40 years of Robert's life didn't seem like they were going anywhere, but actually he was reading and thinking and observing and jotting things down. And then he has this meeting in Italy where he pitches the 48 Laws of Power to Eust Elfers, the packager of the 48 Laws of Power. And all this stuff comes pouring out of him and this world-changing, you know, publishing changing enormous success comes out of that up until that point it would have seemed like Robert wasn't going anywhere and then after that point it would have seemed like it came out of nowhere but no it's a lagging indicator of the work that you put in and in fact when I was thinking about writing my first book on Stosan I got this offer for a book deal and Robert said you're not ready you need to go put more work in that was one of the hardest things I've ever had to do to turn down a book deal but Robert is right.

15:35Timing is everything. The apprenticeship you put in is everything. The time you put in is everything. And so The Obstacle is the Way, which did come out several years later, is the lagging indicator, is the culmination of those extra years of work. Had I rushed it, had I done it sooner than it should have been done, I'm not sure that book would have been the same. The experiences wouldn't have been the same. I wouldn't have had the hard, painful lessons that ultimately formed the ideas in that book.

16:03Obviously, at the core of Robert's writing is this idea of being strategic. People think it's about manipulation or Machiavellianism, but really, it's actually closer to Stoicism, the idea of getting your emotions under control, stepping back, seeing the big picture. Stokes talk about having command of the greatest empire, yourself. That's, to me, the essence of Robert's books and he said this on the daily stock a bunch of times. I remember once I was asking, I was in this sort of dispute with my neighbor, it was this whole big thing. I asked Robert his advice and what he really asked me to do is step back and see not just like my position but their position and then what they would do if I did this and what I would do if they did this.

16:39You know classic sort of strategic empathy, the ability to see the big picture and to see cause and effect. Robert makes this contrast between strategic heaven when you're thinking big picture, when you're thinking multiple moves ahead and tactical hell. A lot of people live in tactical hell. You could argue that stoicism is about getting out of tactical hell. Tactical hell is when we're emotional, when we're reactive, and we're just thinking about the immediate urge or desire or feeling or emotion that's in front of us. We want to get to a place where we're strategic, right? Where we're in command of ourselves and we're in command of the situation.

17:12We're determining what happens next as opposed to just letting the things happen to us.

17:20At the end of the 48 Laws of Power, which is seemingly these laws about how to act, the final law is seemingly a contradiction of all the other laws. It's assume formlessness. People wrongly think stoicism is about rigidity, about making things a certain way. Stoicism is actually flexibility. Epictetus talks about the art of acquiescence. I think Robert's books are good about this. You know, it's funny, even the laws, right? each law, here's people violating the law, here's people observing the law. And then what does it say? It's reversal of the law when you do the opposite. And so if you take stoicism to mean like gripping really tight at things, wanting them to be a certain way, I think you're gonna be kicked around by life.

17:59You're gonna eventually run up into something that's more powerful than you that's gonna break you. I see Marcus Aurelius in meditations as actually being really flexible, being pragmatic. Although he's idealistic, he has virtues, he has things he won't do, So he also has a sense that he, even as this extremely powerful person, has to be flexible. You don't get your way all the time. Things do not go the way you want them to be. It can't be rigid. You have to assume this form. The highest form of mastery is the ability to be flexible, to adapt, to change, right? To adjust to the situation or the context.

18:32That's something Robert's always reminded me of is don't try to be rigid. Don't try to project the laws onto things. Don't try to project your expectations, your view on things. Be flexible, adapt, and adjust.

18:47You might think, given that the first law in the 48 Laws of Power has never outshined the master, that Robert and I might be in conflict with each other. I think, to me, this is the greatest example of what Robert writes about and then who Robert is as a person. The 48 Laws of Power, we have to remember, is not Robert's prescription for how the world should be. It's Robert and all of human history compiled to show how human nature tends to be, how things tend to go, what people in power tend to do. You don't have to do these things, but you have to be prepared for people to do these things to you.

19:22You have to be prepared for certain things to happen, patterns to emerge, right? This is what the laws of human nature is also about. And so what I have loved so much about Robert, what's impressed me so much is what a cheerleader and selfless patron of my career he's been. He helped me get my first book deal. He introduced me to book agents. He's blurbed my books. He's given me advice. I feel like I've repaid him where I can. But he has selflessly supported and rooted for me and given me advice and had to put up, I'm sure, obnoxiously with people asking him about me in interviews when they should be talking to him.

19:58about him and his work. So for me, that's such a great insight into Robert. He knows the law. He knows how other people typically behave in this situation. He knows what he could get away with, but then how he comports himself, the standard he holds himself to is something higher than the 48 laws of power, more virtuous than the 48 laws of power. And I've just always tried to pay that forward now with people who work for me, with mentees that I've had, with apprentices that I've had. Just because this is what powerful people often do, Robert isn't saying you should do that. He's just saying you should be prepared for that to happen to you.

20:29And so I feel also in debt for Robert for what an advocate he's been for me, how many doors he's opened, and just how fundamentally decent he's been to me.

20:42Robert, I tell people, is like a monk. He's hard to get a hold of. He works incredibly long hours. Even though he's extremely successful, not complacent, He doesn't spoil himself. He stays on the task. And he works for years and years on his books. I mean, I watched him work so hard on the laws of human nature that he ended up having a stroke. He says this too, that the book was responsible for this devastating stroke that he had. And then what did he do? He goes to this incredibly difficult, grueling rehab regimen so he could get back and market that book, which would become the fastest selling of all of his books.

21:18Nobody works harder than Robert Greene. Nobody is more disciplined than Robert Greene. Nobody is better at ignoring distractions than Robert Greene. Robert could be on a million corporate boards. He can make a fortune speaking. But mostly what he does is research and write, research and write. And that's why he's written these books that have sold so much that will still be here in 100 years. It's because Robert is disciplined, like so disciplined. He is an embodiment of that virtue of discipline. He has command of the greatest empire, as we were saying, not just in strategic situations, but with himself, with his career.

21:49His work ethic is just unparalleled. And again, when you see that when you're young, when you see the virtues embodied in someone, the Stokes would say, nothing is more encouraging than that. And so to be able to watch Robert not just talk, but walk the walk is the big part of it for me. And it's something I've tried to shape my career and my career decisions around.

22:12So when I was thinking about leaving American Apparel, I had lunch with Robert Greene in Silver Lake in Los Angeles. I remember we're sitting there and I said, you know, I think I want to be a writer. I don't want to do this anymore. I'm ready to go. And he said, well, how much more time do you have at American Apparel? Because I promised them I'd finish in certain projects, like six months to a year. And he says, okay. I said, okay, let's call it a year. He's like, Ryan, you have to understand in life, there's two types of time. There's a live time and dead time. Dead time is you sitting around just marking off days of the calendar to one year from now, and you're free to go to your thing.

22:44A live time, he said, is how do you get the most of every single minute of that time? Who's every person you want to meet in the next year? What's all the research you're going to get done? What's all the planning that you're going to do? What's all the reading that you're going to do? What are favors you're going to bank? I said, how do you make this year the most alive time that you possibly can? And I remember I went home from that and I wrote in a little note card, I wrote alive time versus dead time. And I put that on my wall. I actually wrote a whole chapter about it many years later in Ego is the Enemy.

23:12But the idea of alive time versus dead time, and I'm pretty sure he's the one that told me the story of Malcolm X in prison, how Malcolm X seized that alive time, transformed himself in the prison library, turned himself into this crusading civil rights leader that he would become. Prison could be dead time. Work could be dead time. It doesn't matter what you're doing. It could be dead time if you're wasting it, if you're just letting it go. But anything can also be alive time. The time at the airport, the time stuck in traffic, the time on a tour of duty or deployment. It doesn't matter. You want to transform every minute into a live time.

23:45You want to be learning. You want to be asking questions. You want to be forming relationships. You want to be using every single second. So when I did leave and suddenly I was on my own, I wasn't getting paid anymore. I didn't have the safety net. Actually, I did have the safety net because of what I'd spent that last year doing. So I think all the time, ever since a live time versus dead time, it's probably the single most important piece of advice Robert Greene ever gave me.

24:10One of the worst phone calls I ever got in my life. I was sitting in my house in Austin. I get a phone call and it's this voice I can barely recognize. And then I see it's Robert Green. And he says, Ryan, I've had a stroke. I'm in the hospital. Robert was driving with his wife and he started acting strange. She said, pull over the car, pull over the car. She pulls over the car. She calls 911. Paramedics thankfully get there in just a few minutes. Robert Green is in the midst of a devastating stroke to which to this day, he's still recovering. He actually dies in the ambulance. I think we could have lost this great mind, this great man, this great friend, life can just cut you down like that.

24:46This way, the Stoics say, memento mori. Remember you are mortal. You could leave life right now. They say, let that determine what you do and same thing. The good news is Robert hadn't left anything on the table. He said an incredibly productive, amazing life filled with good work and good people, but it could have been it. Death is this thing that's scary. Yes, but it's something I think that all of Robert's work is about facing those uncomfortable, difficult, unpleasant things, staring them in the face, getting comfortable with them, figuring out how to utilize them, respond to them. And I think that's what stoicism is about.

25:17And it's been so inspiring to watch him claw his way back from that, to fight against the adversity and difficulty that's been the consequences of that stroke. But mostly the lesson I take from it is that life is short, live while you can, do what you can, memento more. When I wrote The Daily Stoic eight years ago, I had this crazy idea that I would just keep it going. The book was 366 meditations, but I'd write one more every single day and I'd give it away for free as an email. I thought maybe a few people would sign up. Couldn't have even comprehended a future in which three quarters of a million people would get this email every single day and would for almost a decade.

25:53If you want to get the email, if you want to be part of a community that is the largest group of Stoics ever assembled in human history, I'd love for you to join us. You can sign up and get the email totally for free. No spam. You can unsubscribe whenever you want at dailystoic.com slash email.