Afford Anything - Courage and The Consequences of Inaction, with Ryan Holiday

Episode Date: October 2, 2021

#341: Imagine a line. Cowardice exists at one extreme end of that line. Recklessness exists at the other extreme end. And in the balanced middle, you’ll find courage. Today’s conversation is about courage. We’re not talking about inspiring physical acts of bravery in this episode; rather, we’re discussing moral and social courage. The type of courage you need to make an investment. Buy a rental property. Invest in stocks. Start a business or side hustle. Retire early. Travel overseas. Have a difficult but diplomatic conversation. Express your feelings constructively rather than bottling them up inside. Raise an issue with immediacy rather than hesitation. Break bad news to someone. Ask for help. Launch an initiative. Try something new. We’re talking about the type of courage that’s required to become a better, bigger person in your work, your relationships, your life. We’re having this conversation with Ryan Holiday, the bestselling author of a series of books on Stoic philosophy. Enjoy. Resources Mentioned: Courage is Calling, by Ryan Holiday affordanything.com/realestate affordanything.com/viplist For more information, visit the show notes at https://affordanything.com/episode341 Learn more about your ad choices. Visit podcastchoices.com/adchoices

You can afford anything, but not everything. Every choice that you make is a trade-off against something else. And that doesn't just apply to your money. That applies to your time, your focus, your energy, your attention, anything in your life. That's a scarce or limited resource. Saying yes to something implicitly means saying no to all other opportunities. And that opens up two questions. First, what matters most?

Second, how do you align your decision-making? with that which matters most. Answering these two questions is a lifetime practice, and that is what this podcast is here to explore and facilitate. My name is Paula Pant. I am the host of the Afford Anything podcast. And today, we're going to talk to Ryan Holiday about courage. Best-selling author Ryan Holiday is known for his writing on Stoic Philosophy.

He has gained massive popularity with his books. The ego is the enemy and the obstacle is the way. amassing about half a million followers on Twitter, which is not something a lot of philosophers can say. Today he joins us to discuss courage, not physical courage, not the acts of valor that we read about in inspiring headlines. Those acts are important too,

but today's discussion centers around moral courage, doing what is right, particularly when it comes at a cost. This is a concept that we can apply to every facet of our lives, from the way that we make decisions about our money, our businesses, our careers, our relationships, our families, anything that matters will require moments of moral courage. And to explore what that means and how to develop that, we talk to Ryan Holiday. Before we get into this conversation, I have one, two quick announcements, both of which I will

elaborate on at the end of the show. The first is that in the next two weeks, I will be live streaming three times, including live audience Q&A, to discuss some of the most common questions and fears around real estate investing. So if you live in a high cost of living area, if you're wondering if this year is a good time to start, given the market currently, If you're not sure how this type of investing plays into your financial independence timeline, those are the concepts that I will be live streaming about and you can sign up for free at afford anything.com slash real estate. That's announcement number one. Announcement number two is that I offer a course 10 weeks long, very high touch. We give our students a lot of support.

It's a course on real estate investing. We only open our doors twice a year. the last time we're opening our doors this year. If you are interested, go to afford anything.com slash VIP list. The deadline is October 14. We close our doors at that point, and they will not be open again for the rest of the year and for about probably another five or six months. So again, that's afford anything.com slash VIP list. With those two announcements out of the way, we turn our attention to Ryan Holiday. For this discussion on moral courage. Hi, Ryan. Hi, how are you? I'm fantastic. How are you doing? Doing excellent.

Great. You recently wrote a book called Courage's Calling. It's about the importance of courage. This is not a concept that most people in the day-to-day world necessarily think of. It tends to be heroism and courage and bravery, tend to be concepts that we think of in specific contexts. How does broadly speaking, a concept-like courage applied to the average person who's listening to this episode right now. Well, that's a really good point. We do tend to think of courage as like, well, I'm not a soldier or, you know, I don't run into burning buildings to save people because that's not my job, right?

We think of courage either in like the military sense or basically what we tend to think of physical courage. When we hear that word, we think physical acts of bravery. But of course, there's always been two domains of courage that they call it physical courage and moral courage, moral courage being, you know, standing up to your boss, blowing the whistle on something you've seen, sticking to your beliefs. But at the core, all forms of courage, whether it's physical or moral or some combination of the two, it's really about a willingness to put your butt on the line, right? like whether it's for someone else or it's for something you believe in, whether it's putting up money to bet on something, like a business idea that you have, or it's about trying something that most people think will fail. To me, courage is that. It's the willingness to risk something for something. And I think it's, if you see it as sort of simple and as boiled down as that, it becomes more clear why we need this in the course of, our life, whoever we are, whatever it is that we do professionally.

How do we know when we are being courageous versus when we are not? How do we develop the self-awareness? Number one, to recognize that the circumstance calls for it, which may not be readily apparent, and number two, to self-assess whether or not we have risen up to the task. Well, not to get too deep into it, but I think it's even trickier than that, right? How do you know, if you are sure you are being courageous, how are you sure you're being courageous for the right thing? You could be immensely selfish.

There's a story about a Spartan warrior who, in the middle of this battle, he rips off his armor and he fights even without armor. And when he comes back, instead of the being thrown a parade or, you know, they put a statue up of him, he's actually fined by the city's elders for being reckless, for endangering a Barton asset unnecessarily. And that's just like a more simple example. What if someone is courageously fighting for an unjust cause? So I get all of which is to say this book is actually the first book in a four book series that I'm doing. And it's on what they call the cardinal virtues, being the core virtues of Stoic philosophy. Courage is the first virtue, but the next virtue is

self-discipline. And the third virtue is justice. And the fourth virtue is wisdom. And the point is all of these virtues fit inextricably with each other. They're difficult to separate. So, you know, we're talking about courage and we can really talk about what courage looks like and what it means. But it's impossible to separate courage from wisdom, which goes to your question is, how do I know I'm being courageous? And then that's impossible to separate from justice, which is how do I know that I'm being courageous about the right thing? And then the final part is, how do I know that I'm expressing the right amount of courage, not too much, not too little? And so this is really a difficult challenge to do.

But it's why we have to be thinking about it consciously. We can't just sort of, oh, I'm just going to trust my gut on this. In the absence of trusting your gut, what are the other options? Well, there's a story I tell in the book that I like, just go to this point of trusting your gut. But Theodore Roosevelt is president, and he decides to invite Booker T. Washington to dine at the White House with him the first time that an African American has been invited to dine at the White House. Obviously, they've been in the White House. They've built the White House, but they've never been invited to dine as the guest of a president.

And Booker T. Washington is the most well-known African-American figure in the country at that time. And the civil rights leader and just a wonderful human being. And as Theodore Roosevelt is considering this, thinking about inviting him, he says he gets this moment of hesitation. He thinks about what this means for his reelection prospects. He thinks about his southern relatives. He thinks about just what the newspapers are going to say. So he has this moment of hesitation. But he says that actually it was precisely because he hesitated that he knew he needed to do it.

He said he felt sick and ashamed of himself that he even considered those reasons for not doing it, and that's why he did it. Is this a hard and fast rule? You should only do what you felt a hesitation to do? No, because sometimes the hesitation is what's saving you from needlessly plunging off a cliff. But I do think this idea of, okay, the things that we're afraid of, we're often afraid of them because there's that voice in our head that's saying, well, what about this? and what about this? And do you really want to get into this? And that's, that is the voice of cowardice

in our head that we need to sort of push through or power through. I loved that story in the book. And the thing that struck me when I read the letter that Teddy Roosevelt wrote was that when he felt that hesitation, not only did he feel ashamed that he felt it, but he hastened. He actually hastened to do it. Yes. And I think he says, and that's how, why I knew it needed to happen, not just for himself. This wasn't just like, oh, I'm a glutton for punishment. I'm going to do it even though I'm going to get criticized for it. I think he realized that because it would be controversial and that people would be frustrated that he did it or it struck him as why it was the just and proper thing to do, that this was exactly what the country needed, what needed to happen. Now, look, was Theodore Roosevelt

perfect on the issues of race? Absolutely not. Did he make a whole bunch of other mistakes. Did he hold a number of beliefs that we would today think of as not just regressive but outright racist? Yes. So I don't want to make it seem like he was somehow a perfect person. But in this one instance, he does not allow that sort of voice that, well, what will happen if deter him from doing what was obviously the right thing to do? And in the example that you just mentioned, it sounds as though the concept is that rather than trust his gut, He valued principle over gut or valued principle over voice of doubt. Yes, that's right.

You know, I was talking to a friend of mine who has a big podcast and he was talking about there's all these issues happening in the world. And you know that not everyone is on the same page about them. And so you try to talk about what you talk about and you go, okay, but if I talk about this, this other thing that's important to me that's happening in the world that I feel obligated to speak up or out about, there's a certain. amount of my audience who's not going to be interested in that. There's a certain amount of my audience who's going to be upset by that. And you can have very strong business reasons for not doing a thing.

To not do something because you're afraid of it costing you money is a really bad reason. In fact, there's a great expression I love that says it's not a principle if it doesn't cost you money. Right. So like when we think about courage, if it was. It wasn't scary if the outcome was obvious. Like if Theodore Roosevelt knew for certain that it wouldn't cost him the election, that it would age well historically, that it wouldn't cause a bunch of drama or difficulty. If starting the business was a guarantee, if success was guaranteed, well, then it wouldn't require courage and doing it wouldn't be courageous. So the fact that these things are scary or hard, there's a show my son likes, and they have this song when they talk about, you have to be scared to be brave.

And I remember hearing that as I was writing the book and thinking, that's actually very well said, right? Like if you're not scared, if it was obvious, if there was no risk involved, then bravery is just not a part of this equation. Speaking of being scared, one of the concepts that you write about in the book is the notion of fear. And it's interesting because you talk at a biblical level about be not afraid, but also fear the Lord and how those are apparent contradictions until you dig into them and then you discover that they're not. And that can be applied not just to Christian doctrine, but in a variety of universal context. Can you elaborate on that? Yeah. And I'm saying that from the perspective of someone

who's an agnostic. I think it is interesting to see that be not afraid is like the most repeated phrase in the Bible. And it's also a repeated phrase in the Odyssey. And so much literature is about the idea of not being afraid. And yet, the Bible also talks about, you know, fearing the Lord. And so what is that? I think, you know, you talked about principle earlier. What Theodore Roosevelt was actually afraid of was not the chatter of the newspapers. It was letting himself down. Or in his case, not being like one of the people from history. or even his own family who he admired and strived to be like. So I think that's an important part.

When we think about fear or when we think about things we're afraid of, we are often afraid of the consequences, right? Like, well, will this be bad for me? What will this cost me? What will people say about me? But we seem to be less afraid of like, well, how will history judge me in the future? Or how will I feel about myself in the future? the excuse, well, I was afraid, does not age well.

Not just with other people, but with ourselves. When you look back at the things that you didn't do because you were afraid, because you thought of the consequences, because you were putting your safety first, very rarely are you like proud of yourself? You're like, I'm so glad I chickened out, right? You think instead, what was I so afraid of? That's so ridiculous. the risk was so minimal.

And yet I deprive myself of X, Y, or Z, or I embarrassed myself or worse, I brought shame to myself. I did the wrong thing instead of taking the opportunity to do the right thing. So I think the tension between be not afraid and fear the Lord is don't be afraid. You don't need to be afraid. There's a plan, right? But the other part of it is, if you're going to be afraid of anything, be afraid of falling short, be afraid of not living up to what you're capable of or what is expected of you. Can you talk, since we are talking about fear, can you talk about the concept of cowardice?

How do you define it and how do we recognize it, both in ourselves and in situations? Cowardous is not fear, right? Cowardous is not fear because fear is just being afraid. What matters is, like, it becomes cowardice when the action you take is about that fear. Right. So I heard a great definition of cowardice is that cowardice is when out of fear we fail to do our duty. So like I don't like roller coasters and I don't like heights. So I'm not a coward for not jumping out of an airplane on my birthday every year to parachute down. Right. I'm not a coward for not skydiving because there's no reason for me to skydive. Right. Now, if there was something. on the line that I needed to do that for and I didn't do it because I was afraid. That would be different. I don't enjoy the sensation of, you know, my stomach dropping so I don't seek out roller coasters. That's not cowardice. But let's say I was writing this book or one of my other books

and I was pulling my punches. I wasn't saying what I really thought because I didn't want to offend people or I was not sharing things that I knew or felt. because I was worried what someone might think or I was trying to present myself a certain way, that would be cowardice, right? Because my duty, my job as an author is to put myself out there. The job of the book is to be the expression of what I think and feel. And so if out of cowardice, I fail, if out of fear I fail to do that, then we would call that cowardice. You also talk about how fears other identity is shame. Can you elaborate on that? Well, what do we fear most, I think, you know, other than death or perhaps even more than death. There's a great Jerry Seinfeld line about how we'd rather be in the casket than delivering the eulogy at a funeral because we fear public speaking more than death. I think at the core, what we fear more than anything is what other people will think. So at the root of so many moments, moments of cowardice in our own lives and in history was really this not wanting to be rejected,

not wanting to be laughed at, not wanting to be seen as different or unusual. So again, when we talk about physical or moral courage, of course, to be a Navy SEAL requires all sorts of courage. We're very lucky to have those people in the world. But there is another part of courage, which is just to be different in a world where there's a lot of pressure to be like everyone else. You know, so the courage to march to the beat of your own drummer to be different, to be difficult, to be unique, to insist on what you like, what you think, what you need is really, really important. I would guess the, I would say the other part where shame and courage are interrelated is perhaps counterintuitive, but also the courage to ask for help, to be vulnerable, to speak up when you are struggling.

Courage is not being invincible and not having vulnerability or weakness either. But what prevents us from saying like, hey, I'm having trouble or I don't know or I can't do this. I need help. What prevents us from doing these seemingly, you know, minor statements compared again to running into a burning building is we're really afraid of being judged. Hmm. And so how can a person develop bravery? How can a person start in an actionable way to be less afraid or to perform acts of courage in spite of their fear? Well, I think we can start with, and the way I try to build this book and all my books, is about studying people who were courageous. There's a long fellow poem, and he says, you know, the lives of great men all remind us, we can make our lives sublime. I love the idea of like, who are your heroes? Who do you admire?

Who do you look up to? Whose example are you following? I think that's a really important part. And it can be easy to look around and see, you know, everyone else sort of not ruffling feathers, nobody else standing up, nobody else doing anything and be like, okay, I don't, I'm not obligated to do anything here. I don't have to do anything. But when you have steeped yourself in the history and examples, when these sort of characters that I build the book around, are real and true to you, you feel called to follow in their footsteps. And I think that was something I thought a lot about during the pandemic. One, it was wonderful to be able to live with and talk to these

figures from Florence Nightingale, Winston Churchill, to the 300 Spartans, you know, as I'm writing the book. But remembering that, hey, as difficult as the last 18 months have been, you are by definition the direct descendant of people who survived much worse, right? We come from a long, unbroken chain of evolutionary success stories. We wouldn't be here without being descended from people who survived the Spanish influenza and survived World War II and survived the Great Depression and survived all the way back to the Antonine play, which Marcus Aurelius lived through. We are the descendants of generations of survivors.

And I think sort of seeing yourself as an error to a tradition as opposed to just some ordinary person from Phoenix, you know, who's nothing special, is an important way to sort of reframe sort of who you are and what you're obligated to do. at the risk of being overly analytical, is there any way to quantify this? To quantify courage? Yeah, courage, bravery, any of these concepts. We've been talking about concepts at a high level. Particularly this audience, there are many people who love spreadsheets live in them. That's their love language. Is there any way to track, to manage, in any way quantify improvement in these domains?

I don't know. I mean, one of the things I do talk about is I don't want you to think of courage as this all or nothing thing. Like, I am courageous or conversely, which I imagine a lot of people do, they go, I'm not courageous. Because I failed here or there, I now see myself as a coward or scared or whatever. I think a better way to think about it is like more often than not, what do you do? do you go towards the fear or do you go away from the fear? You know, there's that cliche, like do one thing every day that scares you. Again, that's a cliche, but it's a pretty good rule. So if you want to think about quantifying it, it's like, how are you challenging yourself

on a daily basis? What is the thing that you are doing that is getting you out of your comfort zone, that's preparing you, that's building this muscle of courage? And if you're not doing that, you've got to imagine you're probably either atrophying or going in the wrong direction. If we think about it in terms of luck, hopefully you will be unlucky and never have to express true courage or heroism, right? Like, hopefully there will never have to be another invasion of Normandy. Hopefully there won't have to be another major civil rights movement or whatever. hopefully we don't need these things. And so therefore, the moment of being an Englishman or English

woman during the Blitz will not be required of us. Hopefully our future generations will not have to live through something like the COVID-19 pandemic. But if it did happen and it does tend to happen, what have you done in the way of preparation? There's a reason that troops are sent through drills and war games, and they have to keep in good physical condition. There's a reason that firefighters trained over and over and over again for exactly the kind of thing that happened on 9-11. And that's why, despite the immense terror and uncertainty in chaos of that moment, so many brave men and women did their jobs. And there's actually an FDNY like sort of slogan that's in a lot of firehouses, and it says, let no man's ghost return and say, my training, let me down.

So I think if we're thinking about quantification, we should be thinking more in the, maybe it's more in the realm of preparation. What are you doing day in and day out to build the muscle to prepare you for a lucky or unlucky moment where, you know, sort of real bravery is required? And to the extent that preparation is the daily work, you write in your book about how courage is a habit. Yeah. Well, when we're talking about more often than not, what are you doing? It's, again, do you want to be the person who you worked your way up through the company, never rocking the boat, never speaking up, never proposing anything, even the slightest bit risky, always being conservative, always standing. on your boss's good side. And then when you is your view that suddenly when thrust into a position of power influence, you're going to flip a switch and be the sort of bold visionary that you

expressed absolutely zero hints of possessing? Probably not. And I think this is really the problem. We wonder why, you know, leaders or or executives or even politicians struggle to do the obvious right thing, it's because they didn't get where they are by doing that. They got there by doing the exact opposite. You do have to make it a habit within reason, right? You think about someone like Tim Cook, who succeeds Steve Jobs. Now, if Tim Cook was a bold visionary, a transgressive leader, like in the mold of Steve Jobs, probably he and Steve Jobs wouldn't have gotten along very well, and he would not have ever been in a position to be the next CEO. So it's a tension.

But if you have become sort of a risk-averse bureaucrat inside your company, when you do and you tell yourself, oh, it's because I don't have any power or any influence, well, what's going to happen when you do have those things? You're going to magically transform. That doesn't tend to be what happens. We'll come back to this episode in just a minute. But first, the holidays are right around the corner. and if you're hosting, you're going to need to get prepared.

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your business. Fifth Third Bank has the big bank muscle to handle payments for businesses of any size. But they also have the FinTech hustle that got them named one of America's most Innovative companies by Fortune Magazine. That's what being a fifth-third better is all about. It's about not being just one thing, but many things for our customers. Big Bank Muscle, FinTech Hustle. That's your commercial payments, a fifth-third better. One of the precursors to everything that we're discussing is recognizing that you have agency.

Can you talk about how and why that matters? Well, it's a fun tension because the stoics say that are a key task in life. is to determine what's in our control and what's out of our control. And the reality is a vast majority of things are outside of our control. But that we can take this too far. We can start to believe that everything is systemic, everything is bigger than us, that it's all about averages and odds. But of course, if everyone believed that an individual couldn't make a difference,

that would become effectively true. So agency is the belief that you can control your destiny to a certain extent, that you can change things, that new things can be invented, that new things can be made. There was an interviewer who was speaking with Charles de Gaulle, the leader of the free French. And he said, you know, weren't you in a minority in all the things that you did? And he said, yes, but I knew that one day that would cease to be so. And I don't think he thought that just magically everyone would change their mind and come over to his side. I think he believed that he had the power to convince people, to will into existence the future that he wanted to live in. This is really important.

If you don't think that you have a chance, if you don't think it can be done, you're right in that you will not be the one who does it. And it may not get done. Now, of course, just because you believe you can do something doesn't mean you can. But I think this idea of agency is really the belief in our own power and ability, talent and skill to direct the course of our lives. It takes courage to believe that. It's easier to be cynical. It's easier to say it's rigged. I don't have a chance. It's not my fault. It's hopeless. It's sadder, but it's easier because then you don't have. to do anything. You have an excuse for why you don't have to do anything. If we find ourselves succumbing to those thoughts, how do we pull out of it? I think this goes back to the idea of heroes. Look at the individuals who have made a difference. Look at the people who had it much harder than you. Look at what they were able to accomplish. Look at your own life. Look at people who were at the same crossroads as you were, whether it was

in college or before that, people you grew up with, people you were. have been in relationships with. Look at people who weighed the same amount as you, and now you've lost weight and they haven't. It's not hopeless. Your life is a testament to the power of agency. This also goes to the idea of averages, right? You know, sometimes we'll go, oh, it's hopeless. The odds are stacked against it. I'm reading a book about the New England Patriots. When the New England Patriots were down 28 to 3 in the Super Bowl against the Atlanta Falcons, the probability of them winning the game was something like 99.6%. It was 99 to one odds that they could not win. And yet we do know what happened. They did win. They pulled off one of the most astounding comebacks in the history of sports.

The point being, people defy the odds all the time. You have defy the odds many times in your life. The fact that you are alive, that life exists on this planet is the most unlikely thing to have ever happened. And so when we think about agency, it's important to look at the demonstrable historical record of individuals and ourselves. And remember that this thing isn't sewed up. This thing isn't totally outside of our control. and that people who believe they can make a difference are the only people who end up making a difference. We've talked a bit about heroism, but we haven't elaborated on it. What is a hero?

Well, if fear is the first battle, right, I'm afraid I don't want to do it. Courage is, here's how I'm going to do it. I'm going to take the risk. Heroism is something at a higher level. So one of the examples I use in the book, I think there's a good way of seeing the distinction. When Michael Jordan leaves basketball, he's the greatest basketball player in the world, perhaps the greatest fall time, he walks away from basketball at the height of his career to play baseball. What he wanted to do, what he thought would be a fun challenge. And you can imagine that

everyone in his life sold him is a terrible idea, right? It's too risky. You'll never make it. Athletes don't do this. Think of all the money that will cost you. And he did it. And he played. He was good. he ends up coming back to basketball. We know the end of that story. But it takes courage to have done that, courage and bravery to have defy the odds, defied expectations and criticism to pursue what he wanted to pursue. Heroism, though, there's nothing particularly heroic about it. He was doing it for himself. He wanted to play a different sport, and he used his power, talent, and resources to pursue that. But what about a few seasons ago when Maya Moore, the equal dominant basketball player in the WMBA, walks away at the height of her career.

She takes a year off and then now I think it's been two years to help free a man from prison who had been wrongly convicted. That's heroic because what she is doing is taking all the same risks as Michael Jordan, but it's not for her. She's not getting anything out of it. I mean, she feels obligated to do it's the right thing to do. But to me, this is a higher plane of courage because we're risking something for someone else. One of the correlated concepts with heroism is the notion of valor.

What is it? Valor to me is another way of expressing this kind of heroism where you're willing to die for a principle. You're willing to give everything that there is. And, you know, it's interesting, right? Whenever you watch or read about one of these kids, they're often kids who are, you know, getting the Medal of Honor or something, you know, they go, or somebody who, you know, jumped in front of a train and saved someone from a train track or whatever. I just did what anyone would have done. And it's like, we know that's not true or we wouldn't have medals, right? Like, if this was actually common, it wouldn't be special. And it's precisely because it's so rare that we recognize it.

And we celebrate it, hopefully to inspire other people to follow in their footsteps. But yeah, this idea of really putting yourself out there when the primary beneficiary of what you're doing is not yourself. I talk a little bit about the decision that CVS made several years ago to stop carrying cigarettes. This costs them several billion dollars annually. what's remarkable about it is that it doesn't it not only reduces sales of cigarettes like at CVS by definition, but from the research, the sales of cigarettes nationwide go down because cigarettes are harder to get, so people just smoke less or cigarettes are more expensive, and so people just buy fewer of them. And so when we think about what does CVS get out of this, like nothing.

Right? CVS gets nothing. They just didn't want to be that company. And again, when we talk about heroes, that's something that we shouldn't just go, why don't more companies do stuff like that? To me, the question is, well, what sacrifices have I made in my business or my career, my industry for which the primary beneficiary was not me? Would it be accurate to say that valor is the concept and the hero is the individual

or entity? I think that sounds right. I like that. And so how do you know, since sometimes your own motivations may elude you, how do you know if a particular act of courage is in service to someone else or somebody besides yourself or not? It can be easy to deceive yourself. Oh, totally. When we talk about heroism, what we're really talking about is this idea of selflessness. I think about my grandfather, landed at Normandy. When he enlists, they were like, hey, you're going to be gone for an indefinite amount of time. You're going to not know the odds of survival are decent, but not guaranteed. And he said, all right, sign me up. So heroism is when we risk something and we risk that thing and the primary beneficiary is what the Stokes referred to as the common good, right? Other people,

the whole, your children, society. What are you risking and is the payoff there for humanity as a collective? Or are you not willing to risk it because you don't want to be possibly disadvantaged or imposed on in some way? And that relates back to the concept that you talked about at the beginning of this conversation, which is that courage is the first of four. with justice and self-discipline and wisdom being the other three. Yeah. And I think self-discipline is a really interesting, underrated virtue because, let's say,

you are willing to quit your job to go start a business. Is it courageous to do it the day you have the idea? Or does it require some courage to plan and save and prepare? Right. So the idea for me of self-discipline is like what is the right amount? What is the timing? Can you hold your fire till the absolute right moment? Can you pick the right cause?

All these virtues are very related to each other and again, difficult to separate from each other. There is no, you know, courage doesn't matter if it's not in the pursuit of justice. You need wisdom to know what the just cause is, but you need self-reveillance. discipline to know what the right amount of courage is and how to apply it and when, you know, when to apply it. They're difficult to separate for sure. And they're, they don't exist as parlor tricks, right? You know, a really self-disciplined person whose self-discipline is merely applied to doing lots of sit-ups so they can have a perfect physique. You're sort of like, well, okay,

I mean, I guess it looks good, but what was the point? Would it be accurate then to to say that too much courage could border on recklessness? And not only could one say that, that is what Aristotle says like 2,000 years ago. Aristotle has this concept of the golden mean. And he actually uses courage to illustrate how all virtues, he says, are a midpoint between two vices. So he says, on the one end, you have cowardice, but the opposite of cowardice is not courage. the opposite of cowardice is recklessness. And in the middle you have courage.

So I like that. It's the virtue is like, what's the right amount? What's the right amount? Just as, you know, a lack of self-discipline is not good, but so would, you know, an addiction to working out or an eating disorder or something, right? Too much discipline is also a vice. So it's about what is the moderate amount, you know, nothing in excess, as the Greek said. It's about getting to that sort of perfect midpoint that's really essential.

How would it work with the other two? What would be too much wisdom? I mean, certainly, you know, wisdom pursued for its own sake becomes kind of a, you know, vanity. Are you pursuing information you can actually use or are you just piling up facts and figures? So ignorance on the one end and then just loads and loads of impractical, theoretical, abstract information is not of much use either. Justice is where it gets tricky. You know, Marx really says that there is no sort of opposite of justice in that sense. Like justice is what we're aspiring towards.

But I do think mercy probably applies in there, if not compromise, the ability to get something done in real life as opposed to, you know, the impractical, perfect scenario. Maybe that's where we start to find justice, you know, needs a moderating influence. But I haven't written that book yet. So I don't have a great answer for you yet. It seems imprudent to have a conversation about courage, heroism, valor, without also discussing the notion of sacrifice. How would you define sacrifice? and how do we know it when we see it and accept when sacrifices must be made? Yeah.

What are you willing to pay for this thing that you believe in, right? What are you willing to put up? It doesn't always have to be your physical safety, but it could be a hit to your reputation, could be work, it could be commitment, could be effort. But I would argue that courage inherently demands sacrifice. and heroism often demands what we now call the ultimate sacrifice. I think the idea that none of this is free, right? The fear is free, not doing stuff is free, although it sort of can cost you spiritually

in the end, but the idea that like you have to risk something, you have to pay something, you have to put something on the line that is what courage is about. Like I was saying earlier, if it was guaranteed, if you knew as a foregone conclusion that it would work out, you're talking about a situation that courage doesn't pertain to. The whole point is that we don't know. We don't know. It could go either way. It could work, could not work, but you're willing to try. And we need people who are willing to try. You know, we need more people who are willing to try, especially on, the problems that seem impossible or unwinnable. Or, you know, we have that expression, no good deed goes unpunished.

Like, we need people who are like, I don't care. People who are willing to accept the punishment in order to do what's right, what's principled. Yeah, because where would we be without those people? I think if you, that's a good test as far as courage goes. Like, what would the world look like if everyone accepted the excuse that I'm about to accept? ah, but I could lose in the primaries, or ah, I've got young kids, or, ah, I don't like the spotlight.

Or, eh, you know, our opponents are too big. No one wants to hear this. You know, the cause is not popular. Where would we be if everyone had accepted that excuse? All the progress we've made as a society, as a species, has come from people who had the courage. in some cases people who heroically, you know, gave everything in opposition to that kind of resignation. Well, thank you so much for spending this time with us. Where can people find you if they would like to know more about you or your work?

Oh, yeah. Well, thanks. It's always good to talk. You can check out my stuff at Ryanholiday.net. And then I send out an email every day totally for free about Stoic Philosophy and these four virtues at dailystoic.com. Thank you so much, Ryan. What are some of the key takeaways that we got from this conversation? Here are five. Key takeaway number one. Ryan explained the concept of four inextricable cardinal virtues, the anchor-stoic philosophy. Courage, self-discipline, justice, and wisdom. These four virtues cannot be separated.

There is no such thing as courage absent of wisdom. For one needs to be. the wisdom to know that it is being done for a just cause, and one needs the self-discipline to know that you are remaining balanced. You haven't tipped the scales too far over to the side of cowardice, nor have you tipped the scales too far over to the side of recklessness. Courage is the first virtue, but the next virtue is self-discipline, and the third virtue is justice, and the fourth virtue is wisdom. And the point is all of these virtues fit inextricably with each other. They're difficult to separate. So, you know, we're talking about courage, and we can really talk about what courage looks like and what it means.

But it's impossible to separate courage from wisdom, which goes to your question is, how do I know I'm being courageous? And then that's impossible to separate from justice, which is, how do I know that I'm being courageous about the right thing? And then the final part is, how do I know that I'm expressing the right amount of courage? Not too much, not too little. And so this is really a difficult challenge to do, but it's why we have to be thinking about it consciously. We can't just sort of, oh, I'm just going to trust my gut on this. And so the first key takeaway is that these four virtues embody separate concepts, but none can exist or live without one another.

They are interdependent. And so if we want to exhibit any one of these virtues within our lives, in our careers, in the businesses that we run, in the investment choices that we make, in the way that we show up as landlords, as side hustlers, as small business owners, if we want to show any one of these four virtues in the way that we approach that work, then we need all of them. That is the first key takeaway. Key takeaway number two, don't trust your gut, because sometimes your gut is a coward. sometimes your gut doesn't want to do the thing that's uncomfortable.

And that reptilian part of you, the part that seeks safety and comfort and familiarity, the part that loves the status quo, sometimes your gut reflects that and you hesitate. And so sometimes that feeling of hesitation is something that you should ignore, not always. And that's why this takeaway isn't to rebel against your gut. it's simply not to trust your gut because every now and again your gut isn't aligned with your moral principles. Is this a hard and fast rule? You should only do what you felt a hesitation to do. No, because sometimes the hesitation is what's saving you from needlessly plunging off a cliff. But I do think this idea of, okay, the things that we're afraid of, we're often afraid of them

because there's that voice in our head that's saying, well, what about this and what about this? And do you really want to get into this? And that is the voice of cowardice in our head that we need to sort of push through or power through. And so what's better than trusting your gut is trusting your principles. Let your principles be your North Star. That is the second key takeaway. Key takeaway number three. Courage requires that you pay a certain cost or you accept a certain level.

level of risk. If there's no risk, then it doesn't actually require anything of you. Now, let's take this concept and let's apply it to investing. Let's apply it to buying a rental property. Let's apply it to foraying into the stock market for the first time. Or maybe, maybe, if it's right for your asset allocation, taking on a small, reasonable exposure to cryptocurrencies, which is something that maybe five years ago you never would have considered. All of those. acts, those acts of investing, those require a degree of courage. If there was no risk, then everyone would do it. And if there was no risk, then there would be no potential reward. The same holds true when you decide to leave your career and switch to a more fulfilling,

but potentially lower paying or more volatile career. The same holds true when you decide to start a side hustle, despite the fact that you don't know where you're going to find the time to do it, or when you decide to quit your 9 to 5 and make your side hustle your full-time career, all of these things require that you pay a certain cost, that you take a certain level of risk, that you become a bigger person, a more self-actualized person than you were a year ago. To not do something because you're afraid of it costing you money, is a really bad reason. In fact, there's a great expression I love that says,

it's not a principle if it doesn't cost you money. Right? So, like, when we think about courage, if it wasn't scary, if the outcome was obvious, like if Theodore Roosevelt knew for certain that it wouldn't cost him the election, that it would age well historically,

that it wouldn't cause a bunch of drama or difficulty, if starting the business was a guarantee, If success was guaranteed, well, then it wouldn't require courage and doing it wouldn't be courageous. So the fact that these things are scary or hard, there's a show my son likes. They have this song when they talk about, you have to be scared to be brave. And I remember hearing that as I was writing the book and thinking, that's actually very well said, right? Like if you're not scared, if it was obvious, if there was no risk involved, then bravery is just not a part of this equation. And so courage demands a cost.

That is the third key takeaway. Key takeaway number four. Acts of courage relate to your ability to do your duty. It is not, you know, oftentimes people will throw around little jabs or little dares when you decline to do something that's just pointless and dumb. Oh, you're not going to eat that hot sauce? What are you weak? Like, I do it too.

It's how we tease our friends. But in all seriousness, if something is pointless and dumb, you don't have to do it. Ryan Holiday gives the example of he doesn't like roller coasters. He just doesn't like them. And so if he decides not to ride a roller coaster, that's not cowardice because he doesn't have to do that in order to do his duty to his society, to his family, to his colleagues, to his friends, he's not letting anybody down if he declines to ride a roller coaster. It doesn't matter.

But if an act of moral cowardice, for example, if a hesitancy to have a difficult conversation, a necessary but difficult conversation, if an act of moral cowardice like that curtails you from doing your duty as a member of society, as a neighbor, as a family member, as a friend, as a colleague, as an investor, as either a citizen or a resident, that is where the conversation around these cardinal virtues come into play. I don't enjoy the sensation of, you know, my stomach dropping, so I don't seek out roller coasters. That's not cowardice. But let's say I was writing this book or one of my other books and I was pulling my punches. I wasn't saying what I really thought because I didn't want to offend

people or I was not sharing things that I knew or felt because I was worried what someone might think or I was trying to present myself a certain way. That would be cowardice, right? Because my duty, my job as an author is to put myself out there. The job of the book is to be the expression of what I think and feel. And so if out of cowardice, I fail, if out of fear I fail to do that, then we would call that cowardice. And so cowardice is not declining to do something that's pointless and dumb. Cowardous is failing to do your duty. That's key takeaway number four. Finally, key takeaway number five. These four cardinal virtues, cowardice, justice, wisdom, and self-discipline are not extremes.

They all exist in the middle. Courage, for example, is the midpoint between cowardice and recklessness. And that's a bit of an eye-opener because oftentimes people forget the far end of the extreme. People will paint courage as the opposite of cowardice and portray it as a far extreme end. It is actually a midpoint. It is a point that requires an artful balance. Aristotle has this concept of the golden mean, and he actually uses courage to illustrate how all virtues, he says, are a midpoint between two vices. So he says, on the one end, you have cowardice, but the opposite of cowardice is not courage.

The opposite of cowardice is recklessness, and in the middle you have courage. And so these four concepts, courage, self-discipline, justice, and wisdom are the middle way. That is the fifth and final key takeaway from this conversation with Stoic philosopher, Ryan Holiday. Thanks so much for tuning in. My name is Paula Pant. This is the Afford Anything podcast. If you enjoyed this episode, please share it with a friend or a family member. And I'll catch you in the next episode.

Take care.