Ryan Holiday: Think Like a Stoic, Timeless Leadership Principles for Modern Entrepreneurs | Leadership | YAPClassic

18:04Ryan Holiday:Of course. American Apparel went way too far way too many times. And one of the problems with courting controversy is that sometimes you get it for things that you don't deserve. I remember one of the things that was sort of an eye opener for me is is this sort of activist or or artist or whatever. They started making fake American apparel ads and they would Photoshop this like onto billboards and street corners onto pictures of them. And then they would send those pictures to websites and then people would get mad about American apparel ads that didn't exist. And then you go, OK, well, on the one hand, it's cool that we've created something that's so provocative and newsworthy that people are willing to talk about it.

18:48Ryan Holiday:But here we are getting in trouble for something that not only we didn't do, but is fake. Right. And so I talk about this in my first book, which is about media manipulation. You know, you can feed a monster and it starts off really small and friendly, but then it becomes this big, scary, dangerous thing. And then maybe it eats you. And I think that that definitely happened at American Apparel.

19:11Hala Taha:Yeah. So you just mentioned this book that you put out. So you went from like media manipulator to media whistleblower in this book. And you were just talking about how you can basically manipulate the media. And now everything's gotten so much worse. That was 2012 when you put out that book. Now we have AI. Social media is way bigger than it was. And people not only can manipulate what clothes you buy, but also politics, the economy, all these things. So talk to us about, you know, how things have gotten worse since then or some of the concerns that you may have.

19:41Ryan Holiday:Yeah, I remember when Elon Musk took over Twitter and he eliminated the verified check mark, right? That day, a sort of a prankster created a fake account for Eli Lilly, the drug company, and he put out a tweet that said insulin will now be free. And their market cap dropped billions of dollars in an instant. And so what I was talking about in that book is the way that, on the one hand, this sort of exciting and unregulated world of social media and new media and all these tools, it makes it really easy to break through the noise and to stand out and to create a brand for nothing. It also creates a lot of vulnerabilities if you have a big and valuable brand to be attacked, to screw up, to have things that are not true get spread about you.

20:27Ryan Holiday:And so, yeah, what I was trying to do in that book is kind of tear back the curtain and go like, look, this is how it really works. And this is probably not an ideal system for anyone. And my goal in writing that book was really like I just didn't that's not what I wanted to do with my life. And so I took all the things that I knew that I'd seen that I'd sort of read about and I sort of put it all in. I just said, look, this is it. And that was part of it for me. That was my first step towards becoming a professional writer, which is what I'd always wanted to do.

21:01Hala Taha:And is there any way to use like these concepts that you use to infiltrate the media for good?

21:07Ryan Holiday:Of course. A tool is a tool. You can use an ax to chop down a tree or you can use it to murder someone, right? Or you can accidentally cut off your hand. But the tool is not good or bad. It simply is. And if you're, you know, trying to change public opinion, you have to understand how public opinion is formed. If you don't understand the sort of levers of power, if you don't understand the logic of where people get their information, you're going to be doing what I think a lot of good people who are trying to do good, unfortunately, find themselves struggling with, which is they go, my work is so important.

21:43Ryan Holiday:It matters so much to me. It's going to make a positive difference in the world, but nobody cares. And I can't get anyone to write about me. I can't get anyone to talk about me. I can't get anyone to try what I'm doing. If you don't have a good eye for marketing and the ability to break through and communicate what you're doing, it doesn't matter how great your product is.

22:05Hala Taha:Yeah, it's so true. So you went to writing about the media to then stoicism and personal growth. So what was the turning point there? How did you find out about that philosophy? And what made you kind of switch to talking about personal growth?

22:19Ryan Holiday:I always wanted to write about ancient philosophy. That was what I was fascinated with. That's what I loved. That's what something Robert and I connected over is sort of we just love, you know, ancient history. But I understood that, you know, publishers weren't exactly lining up to give book deals to kids in their 20s who had dropped out of college to write about an obscure school of ancient philosophy. And so I went and I had a career where I made money. I developed a bunch of relationships. I developed a platform. I published a book about a different topic. All of this was setting up, you know, getting in a position where I could have a little bit of power and say about what I did next.

23:01Ryan Holiday:And that's what that transition was designed to do. So I think, You know, some people go, how'd you go from writing about, you know, public relations and marketing to ancient philosophy? Well, it wasn't like I just woke up one day and said, hey, I want to do the opposite of this. It was it was a plan. I was working towards having the freedom and leverage to control my own destiny and to talk and write and, you know, make content about the stuff that I wanted to make content about.

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26:27Hala Taha:So we've never covered stoicism on the show. And I know very little about it. Like I just researching for this interview is when I learned about it. So we're going to go deep on this. I want you to tell us about all the different principles. So first of all, how do you define a good life in stoic terms?

26:43Ryan Holiday:Well, the Stoics believed that life was unpredictable. Life would be full of adversity and challenges and difficulties. And that one had to cultivate kind of an inner strength, an inner sense of purpose and values that could guide you through the inevitable ups and downs of existence. And so Stoicism, to me, my definition as I've tried to introduce people to it over the years is this idea that, look, we don't control what happens, but we control how we respond to what happens. And so I actually do think it's a philosophy, it's an approach to living that works well as an entrepreneur, as an artist, as a creator, as a small business owner.

27:30Ryan Holiday:And so what I've tried to do is take these ideas from the Greeks and Romans, you know, going back 23 or 24 centuries and make them applicable and accessible to the kinds of things I was going through as an executive, the things you might be going through, you know, running your own show or that, you know, somebody who's just trying to figure out their way in the world is going to need, but not think, hey, what can ancient philosophy teach me about?

27:57Hala Taha:Yeah. And it is ancient, right? It's 2000 years old. So what makes this stand the test of time? How is this still relevant 2000 years later?

28:06Ryan Holiday:Well, I think sometimes we think that the ancient world was this thing that happened for like a brief period, but the ancient world was thousands of years old, right? So Marcus Aurelius, the emperor of Rome, one of the most well-known Stoics, he comes to Stoicism like 500 years after it was started. So it was ancient philosophy to him, a man whom to us is an ancient philosopher. So for hundreds of years and now thousands of years, The Stoics were entrepreneurs and athletes and actors and soldiers and politicians and husbands and wives and sons and daughters, human beings trying to make their way through an unpredictable, random, frustrating world.

28:55Ryan Holiday:And these lessons survived to us. They weren't just speculating about stuff. They learned it running the Roman Empire. They learned it leading troops into battle. They learned it recovering from a shipwreck or being sent into exile. So what the Stoics teach us is not like abstract ideas, but really sort of hard won practical wisdom about how you deal with the hand that life deals you.

29:24Hala Taha:So I thought a way that we could kind of break down some of these complex ideas is to do it quickfire style.

29:31Ryan Holiday:All right.

29:31Hala Taha:So you have three main disciplines and then you have four cardinal virtues. So I thought we could kind of go through each one. You could tell me what is the key takeaway, the key learning for each one. Does that sound good?

29:44Ryan Holiday:Let's do it.

29:45Hala Taha:Okay. So discipline, let's start with the three main disciplines. Discipline number one, perception.

29:51Ryan Holiday:So in The Obstacle is the Way, I sort of break this art of turning difficulty or problems into an advantage or into an opportunity. and it's built around these three stoic disciplines, which is first the discipline of perception. That's how we see things. That's our judgment about things. Then there's action. What are you going to do about it? And then will is like, how do you endure? How do you survive? How do you get through tough stuff? So a quote from Mark Sreelis that sort of encapsulates this. He says, objective judgment now at this very moment. Then he says unselfish action now at this very moment.

30:30Ryan Holiday:Then he says willing acceptance now at this very moment. That's all you need. That's a stoic formula for taking something that is challenging or heartbreaking or painful or discouraging and flipping it upside down and turning it into something that, you know, in retrospect, you're like, I'm glad this happened. I was able to do X, Y, or Z because of that thing happening.

30:57Hala Taha:Can you go deeper on just how to turn obstacles into opportunities? Because I know that you talk a lot about that.

31:02Ryan Holiday:Yeah, that's the idea is you go, OK, look, there are always things that we can do in response to a situation. Is every obstacle a chance to succeed professionally and increase our profit margins? No, sometimes, right? Sometimes. but every situation is a chance to learn. It's a chance to grow. It's a chance to change. It's a chance to connect with people. It's a chance to be a good person. And so what the Stokes are saying is that every situation in life is an opportunity to practice virtue. It's an opportunity to be excellent, not always in the way that you want, right? A business partner, you know, robs you blind.

31:46Ryan Holiday:Is that a chance to grow your business? No, your business is going to be, negatively affected by this. But is it a chance for you to practice standing up for yourself? Is it a chance for you to practice forgiveness at some point? Is it a chance for you to practice determination and creativity as you dig yourself out of this hole? Yes, you can do all of that. So when we say the obstacle is the way, what we mean is this situation is going to present you opportunities to do things that you wouldn't have done ordinarily. And in that, you can be made better.

32:23Hala Taha:Can you talk about related to perception, how it shapes our reality?

32:27Ryan Holiday:Yeah, the Stoics have this great line. They say, you know, it's not things that upset us. It's our opinion about things. And realizing like as an entrepreneur, there's no such thing as a good market or a bad market. There's no such thing as a good call or a bad call. There just is. Life is objective. And then we have opinions about things. We put things into categories. We say, oh, what they said was rude, right? Or a reporter writes an article about you. And you go, was it a good article or a bad article? No, it's just words on a page, right? And then we decide that we've been helped by it or hurt by it.

33:03Ryan Holiday:And understanding that you have the power to define things and to decide what they mean to you, that's what the discipline of perception is about.

33:12Hala Taha:And I know emotions is core to all this and figuring out how to deal with our emotions. What do we need to know about that?

33:19Ryan Holiday:Well, I think when people hear the word stoic, they often think emotionlessness. I don't think that's what it is. Were the stoics trying to be less emotional? Yes, because we very rarely make good decisions out of emotion. Our emotions can blind us. So the stoics were trying to put those emotions to the side for a second and see what we're really dealing with to see it as clearly and as objectively as possible. But they still love, they still get excited, they still get afraid, they still have the full spectrum of human emotions. They just try not to be blinded by those emotions, particularly when we're making tough decisions.

33:56Hala Taha:When I was learning about stoicism, and I know a lot about Robert Greene's stuff, there was parallels. But stoicism is kind of like manipulating yourself. and Robert's stuff is kind of like manipulating other people's perception to persuade them or influence them.

34:14Ryan Holiday:That's interesting. Yeah. You know, one of the things the Stoics say is that the greatest empire, right? Like Robert's books are like how to build an empire. That's what he's talking about. But the Stoics would say that the greatest empire is command of yourself. How many people are extremely powerful, extremely wealthy, extremely famous, but they're not in control of their own lives. They're not in control of their moods. They're not in control of their desires. They're not in control of themselves, period. And so for the Stoics, sure, they wanted to be important and significant and achieve things, but they tried to conquer themselves first.

34:54Ryan Holiday:And I think that's a really important part of the philosophy that you notice there for sure.

34:59Hala Taha:So you also talk about these cardinal virtues of Stoicism. There's four of them. Do you want to tell us about that?

35:05Ryan Holiday:Well, look, the Stoics are saying that everything is an opportunity to practice virtue. Well, what do we mean by virtue? The Stoic virtues are really simple. They're courage, self-discipline, justice, and wisdom. So when we say that everything's an opportunity, that's what we mean, that, you know, a business setback is a chance to practice self-discipline. Now you really got to, you know, run this operation lean. Somebody just stole money from you. This is a chance to practice justice, right? Either holding them accountable or forgiving them. Courage, this is the chance to stand up, to keep going, to put ourselves out there.

35:44Ryan Holiday:And then wisdom is sort of the trump card, I think, here, because wisdom is our ability. Wisdom always allows us to turn obstacles into opportunities because we can use them as a chance to learn, if only about ourselves, right? And so that's what the Stoics mean when they talk about how we always have the chance to practice virtue. Everything is gonna demand from us or has a chance for us to demonstrate courage, discipline, justice, and wisdom.

36:13Hala Taha:Like you just mentioned, these philosophies are really great for entrepreneurs because we have uncertain environments. We've got to keep our cool in the highs and the lows. So I wanna ask you some follow-up questions related to entrepreneurship in particular. So you talk about a more fatty, if that's how you say it. Is that how you say it?

36:32Ryan Holiday:Yeah.

36:32Hala Taha:Tell us about that and why entrepreneurs can use that as they, you know, come across failures and setbacks.

36:39Ryan Holiday:You know, acceptance, which is what Amor Fati is about. Acceptance means a love, Amor Fati means a love of faith. Acceptance can be a hard sell to entrepreneurs because they're sort of like, well, I didn't get here by just accepting things. And so it feels passive or it feels weak. But actually you did get here because of acceptance. You accepted that it's raining outside. You accepted that you're going to need to raise money to start your business. You accepted that most people are busy and don't care about what you're doing. And that's why you designed a marketing plan. That's why you designed a fundraising plan.

37:16Ryan Holiday:That's why you got an umbrella, right? You have to accept reality before you can set about changing it or you can set about succeeding despite it. And so Amor Fatih is this idea that instead of resenting things, instead of dreading them, instead of wishing they were otherwise, you accept them for what they are, you embrace them, and you're like excited about it. It's like turning the have to into get tos. It's deciding to embrace it and love it and to love the challenge of it. To me, that's what it's about anyway.

37:54Hala Taha:So it's love of fate is the translation, right?

37:57Ryan Holiday:Yes.

37:58Hala Taha:And so basically it's saying it's going to happen no matter what and you should just be okay with it. Why be upset about it?

38:05Ryan Holiday:Am I understanding that correctly? I think that's part of it too. Look, did you think you could start a business and never have a down quarter? Did you think you'd never have to fire anyone? Did you think you'd never be criticized? Did you think you'd never make any mistakes? Like, that's preposterous. This is part of it. This is what you signed up for. This is how it goes. You should love that. If you really love this, if this is really what you're meant to do, you love that shit too. And you love that it's all part of it. And you're excited about the no's. And you're excited about the setbacks.

38:38Ryan Holiday:And you're excited about the problems that you get to solve. Because that's part of it. Yeah.

38:43Hala Taha:It's hard when you're like, I'm an entrepreneur. I have a business. I have a social agency. I have a podcast network. And in the beginning, it really is hard. You feel like, oh, no, I lost a client. The first time is always hard. And then after a while, you're just like, it doesn't matter. Like, this is just the ebbs and flows of a business. You know, nobody's going to stay forever. No employee is going to stay forever. And that's just how it goes.

39:03Ryan Holiday:Yeah, that's that's life.

39:04Hala Taha:So decision making is something that stoicism can really help us and especially making clear headed choices.

39:11Ryan Holiday:Yeah.

39:12Hala Taha:Tell us about that.

39:12Ryan Holiday:Yeah. To me, a key part of stoicism, like when you hear someone is philosophical, you don't mean that they know a lot of ancient philosophy. Like when we say, oh, that guy's really philosophical or she's really philosophical, what we mean is like, oh, she sees the big picture. She's calm. She's not easily rattled. Right. And that's what stoicism is really helping us get towards the ability to see the forest for the trees, to see what's really going on, to sense what's actually important, what's actually true in a given situation, as opposed to what a lot of people are, which is blinded by what's happening around them right now, distracted by noise, blinded by their emotions, you know, and they're not philosophical.

40:03Ryan Holiday:You know, they are only seeing part of what's in front of them. And so, yeah, I think stoicism is about making good choices, seeing things clearly. That's what the discipline of perception is really supposed to help us do.

40:15Hala Taha:So I know you tell a story in your new book, which we're going to get into later on, but I think it's relevant right now about Truman making a really hard decision. How is this related to being clearheaded, justice, all the things that we talked about?

40:28Ryan Holiday:I mean, that's what leaders do. That's when Truman has that sign on his desk that says the buck stops here. That's what he's talking about. Like when you're low up in the organization, you can kick the decisions up or down. You can make it your employee's problem. You can make it your boss's problem. But ultimately, the boss is the decider. The boss has to choose. And if you don't have a strong set of values, if you don't have good judgment, if you don't have the ability to see things clearly, what they actually represent, what they mean, you're going to not make good decisions. You're going to get in trouble.

41:03Ryan Holiday:And so, you know, look, the Stoics weren't these sort of academic philosophers who just read books. They were leaders. They ran organizations. They ran empires. They led troops into battle. They were making real decisions in the real world. And they understood that this was a skill you develop the only really way you can, which is by experience.

41:25Hala Taha:I love our listeners to hear stories. And you talk about Roman Emperor Marcus Aurelius. Marcus Aurelius. I only read it. I never heard it. So it's funny.

41:39Ryan Holiday:I tell that story. I tell a story about that with Truman in the book. Truman was famous for mentioning mispronouncing words and people would make fun of him. And then somebody realized, oh, it's because he grew up not around a lot of smart people. He didn't have a traditional education. He'd never heard these words said aloud. He'd only read them. And I always consider that a badge of honor. That means I'm that means I'm like reaching, you know, it means I'm punching above my weight. And so I love that. Yeah, it's Marcus Aurelius.

42:11Hala Taha:Marcus Aurelius. Yeah. So he was an emperor, which kind of is like being a CEO running a company. So share the story about him in general? Like what leadership principles can we take from him? What can we learn from him?

42:24Ryan Holiday:Well, I mean, look, he's the chief executive of the largest empire in the history of the world. He oversaw something like 50 million people, thousands, tens of thousands of square miles. It was enormous. He was the most powerful, important person in the world. And he struggled, as I think we all do. I mean, his reign was an unending series of troubles. There was floods, There was a plague. There were natural disasters. There were wars. He had health issues. He was also a father and a husband and did to deal with, you know, Murphy's law. What can go wrong will. But he tried to see this as an opportunity.

43:05Ryan Holiday:He tried to he said, good fortune is what you make for yourself. It's one of my favorite quotes from him. He's like, by doing good things, by thinking good things, by treating people well. And so what we see in Marcus is one of the few examples. You know, there's that expression about how absolute power corrupts absolutely. It's one of the few examples where that doesn't happen. And it doesn't happen because of his grounding in Stoic philosophy. He would journal every day. He was still reading. There's a famous story about Marcus Aurelius. Towards the end of his life, he's seen leaving his palace in Rome.

43:39Ryan Holiday:And a friend stops him and he says, you know, where are you going? And he says, I'm off to see Sextus, the philosopher, to learn that which I do not yet know. So even as an old man, he still saw himself as someone who was learning on the job, who had room for improvement, that he was a work in progress. And in this way, he's one of the greatest human beings who ever lived.

44:01Hala Taha:That makes me feel like, man, like I wish like Trump would get into stoicism or something. We need that in our leadership.

44:07Ryan Holiday:I'd be happy if he read one book ever. I don't think that's going to happen. Look, there's a great stoic line that I think applies not just to him, but to so many leaders. Epictetus, who wasn't the emperor of Rome. Epictetus was a slave whose philosophical writings would influence Marcus Aurelius. But Epictetus would say that it's impossible to learn that which you think you already know. So if you're someone who is humble, who is hungry and trying to learn, you will continue to learn. If you are someone who thinks that you're just naturally brilliant, if you think you're better than everyone else, if you think you're perfect, you can't learn.

44:49Ryan Holiday:You become frozen in place. And I think that's a trait that defines a lot of really mediocre to outright bad leaders, which is they're so egotistical that they can't get any better.

45:02Hala Taha:I was just going to say, it sounds like you're talking about ego. And I feel like entrepreneurs have a lot of problems with ego. A lot of the times it's what got us to where we are now, but it's not going to help us get to where we want to go. So talk to us about how ego can be our enemy as entrepreneurs.

45:17Ryan Holiday:Well, I think it's important we make a distinction between confidence and ego. I think confidence is something you learn. Confidence is something you develop. And ego is like, you know, is stolen or ego is on much shakier ground. So again, look, Socrates is considered wise because he knows what he doesn't know. Egotistical people think they know everything. They think that everything is about them. They think they're better than everyone else. They think the rules don't apply. And this is why they end up almost always overreaching, causing drama, getting sucked into conflicts, you know, missing warnings.

45:55Ryan Holiday:And it's also, I think this is a big thing. Egotistical people are very easy to manipulate because you can flatter them. You can deceive them. You can tell them what they want to hear. A humble person, a confident person, they don't mind being disagreed with. They seek out divergent opinions.

46:15Hala Taha:They're not threatened by talented people. Look, that was one of the problems at American Apparel.

46:22Ryan Holiday:Dove, who was brilliant and very successful, was reluctant to hire other competent people around him because he thought they would constrain him. He thought they would challenge him. He wanted to like like, look, on one level, it was absurd that I was the director of marketing at a publicly traded company at 21. It worked out OK in my case, but but there were just a lot of people there. And again, myself included at times who are just unqualified to be there. But because we were less threatening, that's why we were there. And that is a recipe for building a dysfunctional organization and team.

47:03Hala Taha:It's so true. You really got to make sure you've got smart people around you that know more than you. But to your point, if you're too egotistical, you end up with people, knuckleheads that don't know what they're doing so that you can just tell everybody what to do.

47:16Ryan Holiday:Yes.

47:16Hala Taha:So we're entrepreneurs. A lot of the times you don't have a boss and it's sometimes hard to have any sort of accountability. We got to just wake up and decide we're going to do this, have our own motivation. Can stoicism help us with that?

47:31Ryan Holiday:Yeah, look, that's what this virtue of self-discipline is all about. And I do find people struggle with that. I think a lot of people experienced that during the pandemic. Suddenly they were working from home. Suddenly there wasn't a boss looking over their shoulders and then they realized, oh, I have to be the boss. No one can make me do any of this. No one's going to remind me about any of this. I get to choose what order I do things or what I do and don't do. There's a part of me that doesn't want to make the right choices. And stoicism is about holding yourself accountable. It's about doing the hard thing.

48:03Ryan Holiday:It's about pushing yourself. It's about growing. And so, yeah, that requires that willpower. One of Seneca's lines, which I think about a lot, he says, we treat the body rigorously so that it's not disobedient to the mind. One of the reasons I have a physical practice, I run or bike or swim every day or I lift weights, I do hard stuff because I don't want to do hard stuff. What you learn in the gym, what you learn on the road is that there's the part of you that doesn't want to do it, that wants to huddle under the covers, and the part of you that's glad afterwards that you did it. And you have to fight to get from here to there, right?

48:42Ryan Holiday:The part of you that wants, that doesn't want to make one more call, that doesn't want to do one more draft, that doesn't want to have interview one more candidate. That's the part that you have to conquer. You have to get over to get to the other side, to get to that next level of performance or success.

49:01Hala Taha:Okay. So last question on stoicism, then I want to get into your new book for a little bit before we close. Is there one principle that you wish that you'd known in your 20s or 30s during your career? I know you're still in your 30s.

49:14Ryan Holiday:That's a good question. I mean, look, I would say that my 20s were very intense and my 30s have been very intense. But the more I slow things down, the more deliberate I am, the more intentional I am, the better I seem to do and then also the happier I am. And, you know, I just look back and I go, why was I freaking out about that? Why was I in such a rush back then, right? Why did I think this was such a huge deal? And it's only with time and experience that you are able to slow down a little bit and get that perspective. So if I could give myself the ability to relax a little bit, I don't mean relax my standards.

49:57Ryan Holiday:I just mean to not be so high strung. I think I would have done better and I would have enjoyed it more.

50:04Hala Taha:I remember when I was 25 and I was like, I used to feel like I was so old and I'd be like, oh, I'm too old to do that. I feel so old. I'm too old to do this. And then looking back, I'm like, what was I thinking? You know, I wasn't too old to do anything. And I feel like young people feel older than they are all the time. And it's not till you're in your 30s when you're like, what was I thinking?

50:24Ryan Holiday:Yeah, look, especially if you're ahead of the curve, right? Like, especially if you're a driven, talented young person, you feel like, you feel old already because you're doing stuff when your friends are out partying or whatever. But yeah, you have so much time and you are still so early in the game. But it's only with the passage of time that you can understand the passage of time, right? And so that perspective that I have now, I wish I could give to myself a little bit more earlier.

50:54Hala Taha:Okay, so you have a new book. It's called Right Thing, Right Now. What was the aim in writing this book? What was the new information that you wanted to share with everyone?

51:01Ryan Holiday:Well, I've been working on this series about the cardinal virtues now for almost six years. So I did one on courage. I did one on discipline. And then this was the one about justice. And I think when people think of justice, they tend to think of the legal system. They think of whether something is against the law or not. But justice is how you treat people, the standards you hold yourself to, the morals you adhere to. And I guess I would ask every entrepreneur on this call here, what is the point of doing your own thing if you're not going to do it well and if you're not going to do it right?

51:38Ryan Holiday:You're the decider. You're the boss. You get to decide what you pay people, what materials you use, the quality control that you insist on. If you're not going to try to use that to make a positive difference in the world, what are you doing? You know, there's so many ways you can make money. And if money was all you cared about, you should just go work in finance. You know, it's less risky and the upsides are probably higher. If you've decided to make something, it's because you want to make something that doesn't exist. You want to do something the right way. And you should let that guide you.

52:14Hala Taha:I know in the book that you argue that doing the right thing is the hardest path. So why do you think that leaders, entrepreneurs struggle with making the most ethical decisions?

52:23Ryan Holiday:Well, because we also have a bottom line, right? We're also trying to be profitable. And if you're deciding between using this supplier, which is made in a sweatshop in some foreign country, and then this one, which makes a higher quality product but pays its workers a living wage, that suddenly is not simply an ethical issue, but it's also a P &L issue. And I actually remember at American Apparel one time, someone was suggesting that Dove move the factories overseas. And he looked at him and he said, if all I cared about was making money, I'd have become a drug dealer.

53:02Hala Taha:And I think about that all the time.

53:04Ryan Holiday:It's like, oh, yeah, I chose not to. By definition, you've already chosen not to do a bunch of super unethical, but potentially profitable things. So here, as you're making a decision, don't let profit be the only thing you're thinking about because you have other values. And as an entrepreneur and as a leader, I think you have an obligation to try to make the world a better place.

53:29Hala Taha:Do you feel like there's a difference between doing the right thing and doing the smart thing?

53:33Ryan Holiday:Yeah, sure. I mean, look, if all I was thinking about was selling books, would I have written a book about justice? No, there's other other topics that are more straight down the middle. Like my book on discipline, you know, a lot of people want to learn about discipline. A lot of people need discipline. A lot of people are trying to overcome obstacles. You know, there are other topics that I can write about that I know will do better. But this is the one that I felt called to do. This is the one that was important to me. This is the one that was creatively fulfilling. This is the one that I I think no one else has done.

54:09Ryan Holiday:So it's weighing those other concerns. So is it the smartest thing to do? No. But is it the right thing to do? Is it what I want to do? Yes. So that's what I'm doing.

54:22Hala Taha:Back to stories. Harry Truman, he ended up dropping two atomic bombs on Japan. And he became a very hated president.

54:32Ryan Holiday:Yes.

54:33Hala Taha:Talk to us about that decision making and how it's related to justice.

54:36Ryan Holiday:Well, Truman is a is a character in the book for precisely this reason. He's in some ways one of the most ethical and least corrupt of the American presidents. One of the most thoughtful in some ways, one of the most progressive. He desegregates the armed forces. He challenges the Southern Democrats in his own party as as he begins to tackle race. and, you know, one of the only presidents not to make himself very rich while holding the office. In fact, the reason there is a presidential commission is that Harry Truman was so principled out of office and refused to cash in on having been the president that they thought he might end up bankrupt.

55:19Ryan Holiday:And so Congress allocated a pension for him. On the other hand, as president, he had to make a lot of difficult decisions. That's what being the president is. And the decision to drop the atomic bomb is one of the obviously most morally consequential choices of the 20th century. One of the flaws for Truman is that I don't think he ever really thought of not doing it. It was a project he inherited from his predecessor. The military was united in its recommendations that they drop it. And so he sort of, I wouldn't say went along with it, but never really contemplated the idea that there might be another way to end the war.

56:00Ryan Holiday:On the other hand, you know, he would say, if you asked him, he would go, look, my obligation is to the mothers and fathers of American soldiers who, as per the current estimation, several hundred thousand of them would die in a potential invasion of Japan. And so as the American president, who is my obligation to when I make this decision? Is it to the men and women who voted me into office whose children I am sending into battle? Or is it to the people of Japan? And we would say that there's a tension between these two choices. And ultimately, he makes the decision. I don't say in the book whether I think it was the right or wrong one, but without a moral compass, without a sense of our obligations and our duties and responsibilities.

56:51Ryan Holiday:A country, a nation, the world is in very rough shape. And I think we're seeing now what happens when you put someone in the Oval Office whose primary obligation seems to be to themselves and doesn't see themselves as really having any ethical constraints in any way and actually has kind of a penchant for revenge as a list of enemies they want to punish, you know, that's where you really get yourself into trouble.

57:20Hala Taha:Well, let's end this interview on a high note. So what is one daily habit or mindset shift that we can do to do the right thing, even when it's difficult?

57:30Ryan Holiday:Look, the most basic practice in Stoic philosophy is journaling. The Stoics spend time every day thinking about things, talking to themselves, talking to page about what they're struggling with, about what their values are, about what's important, about what their options are. And I think adding a journaling practice into your life as an entrepreneur is not only going to help you slow things down, not only help you get perspective, but it's going to root you in your values, in your principles, in what's important in a way that basically nothing else can. And so if I could leave everyone here with something that would be, it would be this idea of a journaling, a philosophical journaling habit.

58:16Hala Taha:So philosophical journaling habit, like what questions would we ask ourselves? Like what, what's, how does that differ from regular journaling? Just cause I never heard of it.

58:23Ryan Holiday:Yeah. Yeah. Look, if I'm not talking about, here's what I had for breakfast, you know, uh, here's what so-and-so said to me yesterday. Um, here's what my goals are. Uh, And it's more like, how can I be better? Where am I falling short? What's my duty here? How can I resist this or that? How can I do more of this or that? To me, it's kind of having a dialogue with the self where we're trying, as we said earlier, to fight from where we are to where we want to be. That's what we're trying to journal about and ask ourselves about.

58:58Hala Taha:That makes sense. OK, so I end my show with two questions that I ask all of my guests. This has been an awesome conversation. What is one actionable thing our young and profiters can do today to become more profitable?

59:10Ryan Holiday:Well, look, is profit simply making more money or is profit also getting more efficient? And so I would ask myself, hey, where am I wasting a lot of time? Like where what are the biggest time sucks in my life? And this is a very key stoic practice. The stoics talk about how we never let someone steal money or property from us, but we let people steal our time. And so how can we be more protective of our time, which is our most precious of resources? I try to do an audit of my schedule and my time and get more effective and efficient with my time because that creates the ultimate form of profit.

59:52Hala Taha:And so true. Time is the most valuable asset that we have. What is your secret to profiting in life? And this can go beyond financial. at all?

1:00:00Ryan Holiday:Hmm. What's my secret? I don't know if I have a secret, but I'm trying. I try to I try to do what I'm supposed to do every day. I try to show up, try to work hard. I try to give my best. And then I don't think that much about outcomes. I just focus on what I control, which is what I'm putting out there, what I'm putting in there. And I let the rest take care of itself.

1:00:23Hala Taha:It's obviously working for you, Ryan. Where can everybody learn more about you and everything that you do.

1:00:28Ryan Holiday:Yeah, I send out a Stoic inspired email every day at Daily Stoic. There's a podcast version of it also. And then I do a parenting one as well. It's called Daily Dad, which you can check out at DailyDad.com or Daily Dad on wherever you get your podcasts.

1:00:42Hala Taha:Amazing. I'll stick all those links in the show notes. Ryan, thank you so much for your time.

1:00:46Ryan Holiday:Oh, my pleasure.