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Calling Upon Your Courage Through Stoicism

By September 23, 2021 October 29th, 2021 No Comments

Today Mark is talking with Ryan Holiday (@ryanholiday) about Stoicism and the four stoic virtues—especially courage. Ryan is well-known marketer and expert in Stoicism and how it can be related to modern life. He is an author and has written several books about marketing and philosophy, including his most recent work Courage Is Calling: Fortune Favors the Brave. He also operates the Daily Stoic website and is the host of the Daily Stoic Podcast. Listen now for some insight on conquering fear and facing courage in this VUCA world.

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This is Mark Divine with the Unbeatable Mind podcast. Thanks so much for joining me today. Super excited to have you here.

Welcome back if you’re a recurrent listener… again, I appreciate your time and attention. I don’t take it for granted.

And if you love this show, please refer to a friend and it. Helps to rate it. So if you go to iTunes or even amazon now, where it’s found, you can rate it. Again, that’s helpful to help other people find it.

Today I’m super stoked to have a good friend and one of my favorite authors, Ryan Holiday. He’s become a legend for bringing stoic philosophy to our modern chaotic world.

If you haven’t read some of his perennials – “Obstacle Is the Way,” “Ego Is the Enemy” and “Stillness Is the Key” – please put them on your list.

He’s also got a great work called “the daily stoic,” for every day. You can wake up and get a little stoicism hit. I love your online platform too. I know that’s in collaboration, but it’s great to get those emails every day, too.

So, Ryan, great to see you again. I’m super stoked. We’re gonna talk about your book that’s coming out which is really cool – those of us who have studied stoicism and know about your work, know that there’s four kinds of cardinal virtues or higher virtues that the stoics have really kind of harped on.

Courage, wisdom, justice and temperance. And so it’s really neat to see you kind of finally come around to like, “hey, why don’t we do a series that includes all these?”

And so courage is the first one and your book “Courage Is Calling” which I was fortunate enough to get an advanced copy of – it’s great. Really, really good.

Of course, I would expect nothing less from you, but courage is something near and dear to my heart as you’re aware.

Ryan: Sure.

Mark: Being a Navy SEAL and having written about it. And so it’s just so cool to see all the different ways that you can kind of slice up courage and look at it through different lenses – I’m excited.

You break it down into three major categories – fear, because you could almost claim that fear is the absence of courage or vice versa – and then you get into actually what is courage and the acts of courage. And then an interesting section called “the heroic.” I guess that’s going beyond courage.

Ryan: Yes.

Mark: So cool, but let’s just catch up for a bit.

Ryan: Okay.

Mark: I’m curious like what’s been going on with you for the last year? You’ve been hunkered down writing obviously – we talked just a tad bit – but what’s going on with your life?

Ryan: It’s been a crazy, awful-slash-wonderful year. So, I’ve got two young kids – we started the pandemic with two kids under the age of four – my youngest has now spent more than half of his life in some form of this pandemic, quarantine, lockdown life.

So on the one hand it was… like you, I make my living traveling around, going to things – I sell books in bookstores. So there was obviously a moment in early 2020 where I was like, “where is this going? It’s gonna be awful.”

And then on the other hand I’ve never been so productive, never had so much time with my family it’s sort of really made me reevaluate what my life ought to look like day-to-day, to get the best out of myself.

So everyone kind of talks about things going back to normal. I kind of want some version of this to be normal – without the massive ICU and hospital surge, I would like this to be normal.

Mark: Yeah, I agree. Let’s get that out of the way. The new normal should be one where people are more courageous, because they’ve had to be resilient… they’ve had to – sometimes for the first time in their life, they’ve had to step up and be like “oh, I gotta take charge. I gotta figure stuff out. I gotta pivot I gotta buck up.”

And also, “I gotta ask better questions.” Like you said, “what is it that is most important in my life?” Obviously, your kids come first.

Ryan: Yes, well I think also people have really had to… when we talk about the four virtues – as we were saying before we started – they’re all very related to each other, right? So how does courage intersect with the other virtues?

So, I think one of the things that the pandemic really made clear – or should have made clear… if it didn’t, you missed the memo… but how interrelated all of our lives are. And how our actions affect each other.

And I think it’s very easy to go through the world thinking about your stuff, what’s important to you, what you want…

And not think about all the people who are affected by that. And conversely, I think we’ve also gotten a sense of how courageous and important certain people are that we take for granted – like, neither of us work at a grocery store and have had to deal with the awful… or flight attendants and have had to deal with the crap that people put them through every day for the last 18 months, in these really stressful times.

So, I think it encourages the currency that makes the world work, and I think we’re really experiencing both the necessity of courage, and also, we’re seeing the consequences of what happens when we have failures of courage.

Mark: Yeah, one of the things that I always come back to, when I think about courage is the root of the word – “Coeur” – which means heart, right? And so you could almost – and I’ve related this before either my gums flapping or in one of my books – that fear actually comes from the head or the mind, right? So if fear is coming from bias or a false expectation appearing real – that’s head thinking.

And westerners are pretty much mostly taught to head think. And so courage – one way kind of at a meta-level to look at courage is getting out of your head and getting into your heart. And saying, “what would the heart do? What would the heart say?”

“What would love do in this situation?” As opposed to my little ego-brain, or the fear-based brain, or the amygdala triggered brain, right? “What would love do?”

Ryan: Well, I had Alexander Vindman on the podcast, recently… he’s the whistleblower who overheard the call with the president and the president of Ukraine. The call that got trump impeached. He’s the one who heard something untoward that was inappropriate, and he blew the whistle.

And so he’s not only a combat veteran, but also a whistleblower – who ends up losing basically his military career over this. Goes from anonymous sort of national security figure to controversial public figure that he didn’t want to be.

And he was saying that one of the things he learned – he’s a Russia expert – he was saying that one of the things that Americans struggle with, in relation to the soviets he said, is that we self-deter. So we’re almost always stronger, almost always in the moral right in our relations with say Russia, but we let them get in our heads about what we should do.

So we let them effectively psych us out. And he’s like, “this is obviously a mistake.” And he was saying as he was deciding, he knew that by going public with what he knew, he would almost certainly get the president impeached, and that he would probably lose his job over it. That he – Vindman – would lose his job over it.

But he said he had to remember that he was like, “I think this is the right thing.” He’s like, “this is what my training tells me. This is what my loyalty oath obligates me to do.”

He said, “but the key was to not self-deter. Not to come up with reasons why it was a bad idea, or why I shouldn’t do it, or why other people didn’t want me to do it.”

He just had to do the hard, scary thing – and let the chips fall where they may.

Mark: Yeah, that’s an interesting story. I love that, and that’s a big part of leadership is doing the hard, right thing… and we’ve heard that talk about the difference between leadership and management, but when it comes to leadership it takes courage to do the hard thing. Because there’s a lot of risk – with Vindman, there was risk to his career, risk to his reputation – maybe risk to his life – who knows? In those levels of power.

And so it’s really interesting to think of courage in all these different ways. And I look at it like a holographic kind of projection. Like, you turn the hologram this way and you see courage as stepping up and doing the right thing in the face of risk. And turn it the other way and you see courage as just being in the moment and being willing to take a step forward into the unknown.

And so I love the book, because you’ve got some great stories – that really kind of flip the lens just a little bit. And now we can look at courage from a different perspective.

And I like that about your writing style, because you give a lot of like easy to read kind of vignettes – your chapters are like three or so pages, and you can get the whole of it in one little sitting. And then you’re like, “ah, that’s interesting.” And you can reflect on that.

Almost like a journalistic style. It’s very interesting.

Ryan: Well, I think that’s what’s hard about courage and ultimately why I structured the book that way – courage is not one thing. Not only is there physical courage and moral courage, of course. But different situations demand different kinds of courage, right?

Sometimes courage is charging ahead. Sometimes courage is holding back, even though that’s scary, right? Sometimes courage is speaking up. Sometimes courage is keeping a secret.

Like courage can be all these different things. And so I felt like if you try to define courage as one clear thing, you’re probably going to fail – although to me the definition of courage is “when you put your ass on the line,” right? Physically or morally. Like professionally, personally…

It takes courage to start a business, it takes courage to tell somebody that you love them because you could be rejected. It also takes courage to run out onto the battlefield or run into a burning building.

But instead of trying to define it as this one thing for all situations, I tried to just look at lots of different examples of courage big and small… major moments, minor moments… well-known moments and sort of secret moments…

And sort of hopefully give the reader just some sense of like, “oh I could do that,” right? “I could do that in my own life,” because ultimately that’s what it’s about.

Like of course, we need Navy SEALs, and we need security experts, and we need civil rights leaders. We also just need people who are brave enough to be themselves. Brave enough to raise kids in this crazy world. Brave enough to focus on self-improvement. Brave enough to start their own business.

Like, we need all forms of courage. And I think very rarely would you say – in any situation – that we have too much courage.

Mark: I agree with that 100%. And I love that vision. I’m 100% in alignment with it. Gandhi said, “be the change you want to see in the world.” It’s kind of difficult to have the level of impact that a Gandhi has, but what if we had a million or 100 million people being the change by taking courageous action?

So we’re looking at courage at scale here, right? That’s what we’re talking about with this book…

Ryan: Yeah, you take something like the civil rights movement… of course Martin Luther King – incredibly courageous – multiple assassination attempts, etc.

But what we forget is all the people who registered to vote and lost their jobs over it. We forget all the people who were just in those marches, who were beaten by the police… we forget all the people who put themselves out there and made themselves targets. We forget a lot of the people who died for that exact thing.

And so when we think about courage, we often think of leaders – we think of Churchill “we will fight on the beaches, we will fight on the landing grounds.” And of course you need those courageous leaders.

But you also just need the ordinary courage of individuals who just do what they need to do in their actual lives. Day-to-day.

Mark: Right. But it’s true also that courage is contagious, just like fear is contagious. And so you could have an individual that perhaps is more prepared, because preparation favors the bold – so someone might be more prepared.

And then their courage then can inspire. So it’s like the idea of leading from the front – their courage can spark courage in others, which then sparks them to take whatever action is appropriate or reasonable for their level preparation and their physical structure and all that kind of stuff.

Ryan: Yeah, there’s a great quote – it’s attributed to Andrew Jackson, we don’t quite know if he said it or not – but he said, “one man with courage makes a majority.” And I love the idea that it starts with you.

Like, right now maybe nobody thinks x, y or z, right? Like, if we think about the civil rights movement again – this is like one lady decides that she’s not going to walk to the back of a bus. And this kicks in motion the Montgomery bus boycott, which unearths Martin Luther King as a social justice leader.

Which leads to all these changes that now – everyone agrees – were obviously necessary. But that was not the case at the time… I tell the story in the book there’s this moment where Martin Luther King is arrested for trying to integrate a department store. This is right in the 1960 presidential campaign.

And so he gets arrested by these authorities in Georgia. And they’re like, “we got this dude,” right? Like they sentence him to four months on a chain gang, but everyone was pretty sure they were gonna lynch and murder him. They were like he’s disappearing into the bowels of the segregationist justice system; he’s probably not coming back out.

And so Coretta Scott King – Martin Luther King’s wife – calls both Richard Nixon and John F Kennedy -because they’re both running in a very tight election, ultimately an election decided by like 30 000 votes.

And she said, “what can you do? My husband is going to be murdered, what can you do?” And Richard Nixon – who was personal friends with Martin Luther King… they’d work together in the Eisenhower administration – says, “look, this is a really tight election. I can’t get involved.” He’s like, “I don’t want to grandstand, I can’t get involved. I need to win the south. I’ll help later.”

And John F Kennedy said, “I’ll do what I can.” And he called Coretta Scott King and comforted her. And then he called the judge and the governor of Georgia, and he ends up helping to secure Martin Luther King’s release.

But this ultimately wins him the presidential election – just two phone calls that his opponent was too afraid to make. But that again – in retrospect – of course, it’s the obvious thing you should make this phone call.

Mark: Yeah.

Ryan: But Richard Nixon psyched himself out. As you said, his heart knew what he needed to do. But “how will this play in the election?” In his brain, convinced him not to do what could have nearly sent a man to his death.

American Apparel


Mark: That’s kind of interesting, right, because then you can also… I mean, you also have to have a keen intellect and think about your thinking, right? And so to me, it’s like the holy grail is to be able to think with heart and head. It’s like – I don’t know if you knew this – but the term Kokoro we use for one of our SEALFIT crucibles – the 50-hour hell week sim – and that word means to merge your heart and your mind into your actions.

And so it’s kind of the essence of what we’re talking about. “Have courage, but don’t leave logic behind.”

I think it’s cool – you have a story about how logic can defeat fear. So that seems to be a little conundrum of what we just talked about.

Ryan: Yeah, it does. I mean, oftentimes what we’re afraid of is this sort of vague, poorly defined mish-mash of emotions and fears.

And so part of what we have to do with the mind is break that down and go what am I really dealing with, right?

I’ll give you an example – I tell a story at the end of the book, about a moment when I wasn’t courageous enough… I was asked to do something unethical at work, and I sort of objected but didn’t sufficiently object.

Mark: This is the American Apparel story?

Ryan: Yeah.

Mark: Great story. Thanks for sharing that, by the way.

Ryan: I appreciate that. It was a not a fun story to write. But this is my point – so I wasn’t willing to do it – but I didn’t want to speak up too loudly about it. Because even though it was unethical, and I knew it was wrong. And I said it was wrong.

I didn’t want to lose my job over it. But if I step back and I think about it – as I should have then – if you can lose your job over this, is that really somewhere that you should be working?

So we often convince ourselves we go, “well, I don’t want to do it because it’s bad for me for the following reasons.” But we don’t really think about how it’s also bad for you to not do anything, right? Like the status quo is also untenable.

So what we’re really just saying is, “I don’t want to deal with it. I want someone else to deal with it.”

And that’s kind of to me the definition of cowardice – is when you refuse to do your duty and then somebody else has to carry your weight.

Mark: Wow – I don’t want to say anything too controversial now, but what that brought up for me is my nephew came out a few years ago and trained with me and ended up making it into the Navy SEALs – so he’s now at SEAL team four – great guy – SEAL team two, actually… I can’t remember… maybe it’s eight. Whatever.

He’s out there. He’s doing it, right? And I was thinking about him this morning and I sent him a text of “how things going?”

And he says, “good.”

I said, “how’s the attitude of the team?” Thinking wow, I wonder what the guys are thinking about this chaos in Afghanistan. And all this controversy.

And I got a surprise email back he said, “well we’re coming out of a period where attitude is not great. We lost 22 guys because they refused to take the vaccine.”

And I was stunned. I’m thinking wait a minute, wait… and this is just one SEAL team. 22 Navy SEALs that spent a minimum probably of four or five years training to become a Navy SEAL. That the government invested a million dollars to train to be an elite special operator.

And I’m looking at both sides of this going what the f, right? Like, what are we thinking throwing these guys out? And what are you thinking – you had to take a vaccine and you get jabbed for everything for every freaking country you go to, so what’s the big deal?

They lost their career over this. Like what… so that’s to your point… like, just think it through – pause, think it through use some logic, and consider all the different ramifications.

Ryan: I’m so glad you brought this up, because you’re the exact kind of person I want to talk to about this.

I’m thinking about doing a piece – there’s kind of a perverse courage in what you’re just talking about. Like, to lose your job over a principal is a hard thing to do, right? To go like, “I don’t want to do that. You can’t make me do that. And are there going to be consequences? Then I’ll take them.”

And I even tell a story about Helvidius Priscus – one of the stoic senators who basically stares down the emperor of Rome and says, “I don’t care if you kill me. I’m not going to do what you say.”

But there’s something strange about this anti-vax mentality… where it’s got all the markings of courage, right? Like they’re going against the crowd, they’re willing to pay the consequences, right? They’re risking their lives for something they believe.

And yet I can’t help thinking of a quote from Lord Byron the poet he said, “the cause makes all that hallows or degrades courage in its fall.” And I think what he meant is like what cause you’re fighting for determines how valuable or admirable the courage was.

Was Robert E Lee courageous under fire? Were there all sorts of courageous fighters in Nazi Germany or imperial Japan?

Yes. But they were fighting for a horrible cause. And when I think about the things people are willing to risk to not wear a mask or get a vaccine – which not only helps them, but objectively helps other people – vulnerable people.

And I say this, just having gotten news that the father of a friend of mine, who was vaccinated, died of covid late last night. Because he’s a cancer patient, right? And was immunocompromised.

It’s like people understand courage, but only superficially so. You just talked about incredibly brave people who have been under unimaginable stress…

Mark: The most courageous – you would expect – in the world…

Ryan: Yeah. The other example I think about – people know about the My Lai massacre in Vietnam. So not only was that horrible, but what I think is particularly interesting, is like almost all the members of the platoon refused to testify against the guy who ordered it, right?

So again, it’s courageous to plead the fifth and not incriminate a friend of yours… but you’re defending a mass murderer, right? You’re missing the point of what courage is supposed to be for.

Mark: Yeah, I think the modern version of that – and we can come back to the vaccine issue – is Eddie Gallagher, right? So yeah, in one sense you’ve got the physical courage to go to combat time and time again, and to serve your country, and to put yourself in danger.

But then there’s this moral courage which gets a little fuzzy, because there’s my moral code and then there’s the moral code of the Iraqis and the Taliban… or whatever… ISIS and Taliban.

And there’s even your moral code and the moral code of the person to the right of you, even though that ethos may mesh, it’s not going to be entirely in alignment…

Ryan: And the courage of the profession or the omerta or whatever… like

Mark: You’ve got that overlaying on it, so there’s a lot of different attributes that if you do not practice the self-awareness that the stoics talk about… the constant introspection and looking at “what is really the reality of what’s going on here? What’s really true here? And is there a principle that kind of supersedes my principle, which might be a relativistic story or belief from my culture that may not survive the test of time.

So that’s what we’re talking about here… true courage is a combination of integrity as well as a moral ability to look at moral issues from a higher perspective than your limited cultural context, or life context.

And so, there’s no word for what we just said there really that I’m aware of, right? It’s tricky.

And so these t people who are like, “I’m not going to take the vaccine,” well their information and their little moral code says that’s the right thing to do. But they’re not considering the fact that they’ve committed to serve their country. The American people are counting on them, they’ve spent millions of taxpayer dollars to get them trained up. They’re letting their teammates down…

There’s so many perspectives that they just ignored, and they threw that out the window. I’m sure some of them maybe thought through that, and they said, “Well, I still believe that this vaccine is going to turn me into a zombie,” or whatever they’re thinking… I don’t know…

Ryan: Yeah.

Mark: But it’s fascinating to me because again – back to the Navy SEALs – like, we’ve been stuck 100 million times with all this different crap. Like, we’re basically petri dishes for whatever they think that we’re going to come to face with overseas. So what’s one more thing?

Ryan: It is tricky, because like… it’s always – for instance – hard to judge historically the context in which someone made a decision, right? It’s never clear.

And so we have to accept that there’s a spectrum of values, and that people can do something you totally disagree with and end up still respecting the courage, right?

I think John McCain is a great example of someone who politically I often disagreed with. But you can’t help but respect that the dude did what he thought was right all the time, right?

Mark: Yeah, Joe Manchin’s the current version of that on the other side of the aisle, right?

Ryan: Yeah, and you can be frustrated – you can be immensely frustrated and still respect that this dude is sticking to some sort of higher principle.

I think what’s tricky on the vaccine thing is we’re not talking about a range of political – “is this better, is this better.” We’re getting as close to you can get as objective science – overwhelming information.

And I think more importantly – and this is what I think I’ve really struggled with in the pandemic- and it’s been it’s been hard for me to figure out how to process.

But look, if you want to speed on an empty road because you don’t care – you’re so brave that you’re not afraid of a car crash – by all means, right? If your behavior doesn’t have negative consequences for someone else, we can have some room for disagreement about whether something’s a good idea or not.

The problem is when we talk about vaccines or public health in a situation like this, we’re talking about something where you’re a Navy SEAL… you’re in great health. You’ve already probably been exposed to worse viruses, right?

So this isn’t about you. This is about my grandmother, and this is about a child cancer patient. This is about somebody who has to get blood transfusions on a regular basis, right? These are about people who are really struggling.

And I think where it’s so strange – whether it’s with the police or… for instance I volunteer, I spent a bunch of time working at a vaccine clinic here in the small town that I live in in Texas. Because our vaccinations rates are very low.

And I remember like very recently a police officer came in and finally got vaccinated. Now this guy’s been able to be vaccinated since December in Texas. And he just got it.

And so on the one hand, I’m happy that he got it. But I was thinking about it, it’s like, “this dude would jump in front of a bullet, run into a burning building, risk his life on a daily basis… and yet he’s fine walking around as a vector for a virus that endangers precisely the people he’s sworn to protect.”

And I think the hardest part to swallow is he’s interacting with those members of the public on a daily basis. And not doing everything that he can to keep himself and them safe. And that’s where I sort of come down on the vaccine thing.

Mark: Yeah, it is interesting we can kind of pin this conversation in a bit – but two comments about that – like for me, you’re right I’ve been exposed to everything… and I was even exposed to covid I think in Germany – December 31st of 2019, when I was at an event and the producer of the event had just come from China, and he was sick as a dog. And half the people in the event ended up in the hospital with respiratory issues.

And I was like, “I don’t feel too bad, but I don’t feel 100%”

At any rate – so I held off for a while – not for political reasons, just because I felt like the human body is going to provide the best response.

Until we had to get together with some clients, when the restrictions were lifted and I’m going to be with clients. And I’m like, “oh no, this isn’t going to work. I’ve got to go get vaccinated.”

And I was like, “okay, that’s no big deal.”

That’s one point that it’s like you said, if you’re not going to hurt anyone else because you’re living in a cave, fine. But if you’re going to be out interacting – especially if you’re in a role as a leader – then think differently.

And the other thing is, if you’ve decided to serve your country or your community as a first responder, that’s a whole different thing, right? So if you don’t want to get vaccinated, then resign. Don’t wait to be fired, like those SEALs. I don’t know what they’re going to do with them, like that’s crazy…

Anyway, I know it’s probably controversial, I’ll probably have some people say they’re not happy with my podcast and whatnot…

Ryan: But this goes to the other point, right? Which I think we could use as a segue-way… which is there’s lots of people that I know that have very strong opinions in line with what we’re talking about – who don’t want to say things because they don’t want to upset their audience.

Mark: Correct. I was just thinking that. It takes courage to have this conversation on a podcast.

Ryan: Yeah, it’s either reckless or it has some courage – but I get that email all the time. I’ll say things that people disagree with, and they’ll go, “why did you mention that? You must have known that it would upset some percentage of the audience.”

And my answer is usually – if I’m being nice, I’ll say it nicely, if I’m frustrated, I’ll say it a little bit more bluntly…

I say, “look, I didn’t build this platform and become a writer to not say what I think is true…”

Mark: That’s right…

Ryan: “…to avoid negative consequences for my business. In fact, my whole obligation as a writer is to say what I think people need to hear, not what they want to hear.” It’s better business to tell people what they want to hear, as you know.

But you might as well quit, as we were saying… if you got into the business of writing to not write what you think, it’s time to hang it up and find another job.

Mark: I totally agree. And there’s too much of that going on in social media and people kind of tap dancing around issues.

Another thing that could be a kind of a fun hot topic is the chaos in Afghanistan – just like with the vax issue – I’ve trained myself to be able to see these things from multiple perspectives.

Ryan: Sure.

Mark: Like, there’s no way that I think we needed to be there anymore fighting a war per se.

And then I can flip my perspective and say, having said that – we have been in Germany, we’ve been in South Korea, we stayed in Japan… we’re all over the world with a presence. And we don’t have a solid presence in that region, so what’s the difference between those things and leaving a small presence here.

And I saw what my teammate Jocko Willink put a little video out and he said, “this is what I would do if I was president,” right? And so I thought about, “like, what would have been the courageous thing for me to do if I was in the leadership position. The big one.

And I would have declared victory, because just like every disaster has an equal part victory, I would have declared victory – because look what we did over there for 20 years. We provided opportunity, we provided stability, we provided freedom for women to go to school and have a career.

For 20 years. And it was just the very beginning – seeds of more freedom for a population that never experienced it. So choose those good things and declare victory around those.

Ryan: Sure.

Mark: And then just working with our allies, say, “listen, let’s keep a security footprint here so that these seeds that we planted can grow to flowers and trees. And not get all thrown away – by just whisking away in the dead of night and letting the Taliban or perceived enemy take back over and crush all those freedoms.

So I think that yes, it was right to pull out – but the more courageous thing would have been to just be a little bit more patient, a little bit more thoughtful, and to do it in a way that was victorious for the people that were benefiting. Which was a lot.

Ryan: Well, you know what I think is also interesting – and this goes to the virtue of wisdom – which is the fourth virtue. I think what you just expressed is perfectly said, because you could boil what you just said down to – it’s real fucking complicated, right?

And it takes some courage and wisdom to accept…

Mark: And temperance, right? (laughing)

Ryan: Yes. That it’s not clear-cut and that it is complicated and that leaders have to make… I think Truman was told by one of his advisors that “all the decisions you make, are bad decisions,” right? Because all the easy clear-cut decisions, they never even make it to you.

Mark: Right. You just have to make the least worst decision…

Ryan: All the choices are between evils at that level. And I think… I actually really appreciated Biden’s most recent speech where he said, “look, it wasn’t about pulling out or not pulling out. It was about escalating or pulling out,” right? And he was saying, “that’s the reality on the ground.”

What struck me also – and I think this also goes to the idea of courage he said look – and again not as a veteran… I say this all with a certain amount of humility – but he was saying that, “look, if Osama bin Laden had attacked us from Yemen and we’d invaded Yemen instead… would we be talking about Afghanistan at all right now? No, because Afghanistan is not part – it’s a landlocked country with very little resources… it’s not to our vital national security interests.”

Which I thought was a reasonable point and of course people can disagree. But I think you look at Vietnam – and president after president got the same binder about how hopeless that cause was. And general McMaster wrote a great book about Vietnam early in his career.

Like the presidents were not brave enough – and I would argue the generals were as well – were not brave enough to lay the facts out on the table and make the uncomfortable decision to leave. And a generation of young men mostly – but also the enemy combatants and innocent civilians – lots of people died, because no one could stop something that really shouldn’t have continued on as long as it did.

So that takes a lot of courage too. To take the hit to be like, “I’m gonna be the bad guy, and I’m gonna pull out.”

Execution is obviously a secondary discussion that matters just as much, but to make that hard decision it’s not an easy thing.

Mark: Yeah, I agree with that. And I think you could pan out and be like, all of these wars the more courageous thing would have been to be temperate and restrain yourself from the reaction of having to go in and create chaos and destruction for 20 years.

That’s a hard thing, because most people think that we were morally right to go smack down Afghanistan, the Taliban and to go get bin laden.

But any time you hit force with more force you get a negative reaction. And consider that when you think about the virtue of temperance… it’s like, “wow, we actually played right into bin Laden’s hands.”

It’s exactly what he wanted us to do. And look what we got in return – 20 years later – not a whole lot. Except for those some of the seeds of freedom that we talked about. Which is very real thing.

Ryan: And I mean it’s even more complicated than you argue… what he got out of 9/11. He does 9/11 and then we inflict a self-inflicted wound a thousand – ten thousand times – worse…

I mean, that was also what Biden talked about in the speech – 300 million dollars a day we were spending in Afghanistan. He says, “what could we have spent that money on?” And I think when you look at China and you look at the infrastructure let’s say that China has. And you go, “how do they afford all that?”

Well, they didn’t light two trillion dollars on fire in Afghanistan, right?

And I think that was Biden’s point that our enemies could want nothing more than for us to engage in forever wars in the middle east.

Mark: Totally agree. Yeah, I totally agree. And like I said, I think it was the right action to pull out and to re-apportion the money – but that’s where wisdom comes in. It’s like how we do that, right? Really important.

And to be thoughtful and judicious… that’s a tricky one too.

Anyways, there’s no right or perfect answer in these things. And that takes courage to admit you don’t have the answer. But we’re still going to take action, and you have some great conversation about… like, a term we used in the SEALs was “doubt is eliminated by action.”

So sometimes it’s just like just do something. In this case that doing something created a massive blowback, but…

There could have been other smaller steps maybe using some micro-goals that could have led to a little bit of feedback… maybe we could have had a more graceful exit.

Ryan: Yeah, I mean, jocko says like, “how do you get over fear?” He says, “you go.” Like, once you get moving, it takes care of itself, right? Like once Kennedy picked up that phone and decided to do something about Martin Luther King, it wasn’t scary anymore.

What was scary was “do I act? Do I not act?” Once you quit your job, now you’re busy trying to figure out how you’re going to feed your family, right? It’s the “do I want to leave? Should I keep going…?”

It’s the hemming and hawing that’s the hard part.



Mark: Right. So my sense is – and what you just said – that courage can be a single act, but it also can be a series of successive acts, like you say, almost habituating courage. Because courage, you get feedback, you get a little strength, a little bit of doubt’s eliminated… that leads to a little bit more courage to do the next right thing, and the next right thing.

But it doesn’t have to be. It could be a single act. Maybe your whole life was kind of made or built for this one moment. And that’s almost like the heroic courage you’re talking about.

Whereas the idea of just showing up every day and taking one courageous act after another is a whole different kind of display of courage.

Ryan: Well, I mean think about with you, when you got out of the SEALs… like, you could have just gone and got a nine to five job… or you could have retired, right? There’s any number of things you could have done that would have been less risky.

But you didn’t like start and do all the things you were doing the next day, right? You took one tiny action… like, I didn’t choose like to become a writer in this swashbuckling, bold move… like, I put up a blog on the internet. And I wrote my first article and I sent it to people.

And I was willing to look weird, and to be bad at it, and to fail at it, and any number of things, right? And so it’s about… you can’t be brave if you don’t start somewhere with something.

Mark: Right. Let’s just kind of ping on that a little bit… you started your authorship career – if you could call it that – talking about marketing and helping students if I recall.

Ryan: Yeah.

Mark: And so how did you get interested in stoicism? Which is where you really made your Mark – or more of a Mark – I would say…

Ryan: Yeah, so I dropped out of college and got into marketing. And then I sort of left marketing to write a book about marketing. and then I left my successful career as a writer of marketing books, to write about ancient philosophy, right?

But what I would say about that journey – and I think you found this in your thing too – is like the first one was the hardest, the second one was a little less hard, the third one was easier and now… like, now I don’t wonder “am I gonna be able to do this?”

Like, I know that I can pull off hard things. So you develop confidence as you go. For me stoicism was something I actually found early – right around when I was in college – but the idea that I could write books about this – that people would listen to me – that was insane, right? That was inconceivable to me.

So it was really about those small steps – like, I wrote my first article that did well, then I wrote a book and that did well, then I wrote another book and that did well.

But funny enough – when I went to my publisher and I said, “hey, I want to write this book about an obscure school of ancient philosophy.” They were like, “that sounds like a horrible idea.” And they were like, “here’s the smallest amount of money we can offer you, without hurting your feelings,” right? Like, it was less than half what I’d gotten paid for the book that I did before that.

Mark: Really? Was that “the obstacle is the way?”

Ryan: “the obstacle is the way” I took half what I got for “trust me, I’m lying.” Actually less than half.

And I asked my editor later on. I said, “what did you guys think?”

She said, “we hoped you would turn down the offer.” And she said, “when you accepted it, we hoped it would just get this out of your system, and you’d go back to the other stuff.”

So there’s always risks. And if there’s no risk, then it doesn’t require courage and it’s probably not that important.

Mark: Yeah, do you ever have a fear that you’re gonna run out of things to say?

Ryan: No. I think the fear is more that I won’t be able to do the material justice… so I feel like I always have stuff to say, but the question is like “are you getting better?” I got to imagine athletes… you have this sort of quiet fear that like your body’s going to quit on you or something. That you’re not going to cut it anymore. I think my fear is more just like falling off.

Mark: Yeah, yeah. That makes a lot of sense.

When you wrote this book, what did you learn about courage that you didn’t know before? Or what was surprising to you that kind of came out of this process?

Ryan: That’s a good question. I mean, I think I wanted to… it’s very easy to talk about sort of military examples of courage…

Mark: They’re all over the place, right.

Ryan: Yeah, and it’s also what courage has meant for the vast majority of human history. But it came to me -as I was writing the book – just how important sort of day-to-day, ordinary courage is…

Whether it’s to get up in front of a crowd, whether it’s to march to the beat of your own drummer… whether it’s just to carve your own path in life, or to speak out about some injustice or whatever…

I read this great book a few years ago about whistleblowers, and it was called “a crisis of conscience,” but as I read the book it actually wasn’t that we have a crisis of conscience – everybody knows what’s wrong, right? Like everyone knew what they were seeing was wrong.

The problem is we have a crisis of courage. Do people do anything about it, right? That’s really the problem. People know, they just don’t do that next step.

So I think one of the things I just came away with over and over again in the book, is like not only is courage necessary, but the excuse “I was afraid” ages very poorly.

Mark: Mm-hmm.

Ryan: Like, when I told you the story about me and American Apparel… like, as I was trying to explain what I was thinking in the moment, that allowed me to make the decision I made – that sort of half-assed decision that I made.

I kept trying to explain it. And then I was just like nobody gives a shit. It doesn’t matter at all. Like, it’s either the right thing or the wrong thing, right? Nobody in retrospect goes, “ah, but at the time you were thinking about x, y and z.”

Like, nobody is going to care in 20 years that the NBA had a really strong business relationship with China. That’s not going to be the salient fact. The question is going to be how complicit were they in doing business with a totalitarian regime?

And for the NBA – insert any number of other examples, right? No one’s gonna care what your reasons were. They’re just gonna wonder why you didn’t do what you should have done.

Mark: That’s right, because you can rationalize anything away, like you said earlier. The point is to be able to pan out and take perspective.

And I love that. That’s a great… maybe it fits more in the wisdom category, but again these things are all interrelated – but a great drill for leaders is to pan out and say, “what will people say about this in 20 years?”

One of the most courageous leaders that I worked with, was a guy named Jim O’Connell he was an O6, he had retired or was on the cusp of retirement when we decided to go into Iraq in ‘03. And they literally pulled him out, to lead the war effort.

We had a saying… a t-shirt in Coronado that I really loved that I saw during SEAL training – had a picture of a glass jar and inside was a frog – which represented the Navy SEAL frogman. And underneath it says, “in case of war, break glass,” right?

And so they broke O’Connell’s glass, and they brought him back. But I remember, he liked to meet all the staff. And so I went and had a conversation with him.

And he told me about what he called “the New York times” test. And he said, “if you’re going to make a decision on Friday, ask yourself whether you want to read about it. And what you’d like to read about it in the New York times on Monday”

I was like, that’s great. I even think you should project further ahead. Five years, ten years… what is this decision gonna mean for the environment? What’s it gonna mean for my reputation? What’s it gonna mean for the company?

Look at it from multiple angles.

Ryan: Yeah, I think also it’s like your kids are going to ask you. Let’s say during the pandemic, they’re going to be like, “grandpa, what did you do?” Right? And you’re going to be like, “oh, I refused to take a vaccine, and I thought it was a hoax,” or whatever…

Right, like you don’t want to be that guy.

Mark: (laughing) I was just thinking that same exact thing… I threw my SEAL career away, because I wouldn’t get jabbed…

Ryan: Yeah. You want to say, “hey, I served my country honorably,” or you want to say, “your mom and I did x, y and z.”

The same thing as this social justice race reckoning we’re having in America, they’re going to want to know “what did you do?” They’re going to go, like, “did you get caught up in this, or that…?” Or, “what did you do with your time? What did you do with your money? What did you do with your body in the midst of what was happening?”

And again, we can all have different opinions on the specific policy solutions, but “what steps did you take?”

I think maybe another good question is like, “am I part of the solution here? Or am I contributing to the problem?” And I think this takes both courage and a strong sense of justice and wisdom to know what that is.

But how are you going to account for yourself in the future – I think, as you said – it’s a great test.

Mark: Yeah, and I think some people who really should be asking those questions are like Mark Zuckerberg…

Ryan: Yeah, of course…

Mark: The leaders of these companies that have this outsized influence on our culture. It’s just unbelievable. We’ve never seen that before.

I mean, first it was just the media in general, right? But now it’s like consolidated to just a few organizations. And those organizations have leaders. They have their own kind of sense of momentum, and their own identity as a culture.

But there is an individual in charge of those. And that’s where we need to see some courage as well.

Ryan: It’s like, yeah, what good is it to be the CEO of a trillion dollar company, and then be like, “but I’m powerless to decide what direction it goes in.” And so you’re total you’re totally right.

Lyndon Johnson – as he pushed through the civil rights act – somebody said “you know this is really going to cost you x, y and z.”

And he said, “what the hell is the presidency for?” And I love that as a test too.

Like what good is it to be an author, or a Navy SEAL, or a successful business person, or a school principal, or whatever position of leadership or power you’re in… what good is amassing that amount of power -and I’ve seen this as I’ve consulted with some people in Washington – they’re always like acting like they don’t have any power, and it’s like you’re fucking congressman, you’re one of a hundred senators, you have more power than me. You don’t get to say, “this is somebody else’s problem.”

So I think, “what did you accumulate what you have for?” Hillel‘s question is “if not you then who?” And “if not now, then when?”

Mark: Yeah, I love that. It’s everyone’s moment every moment to make the best right choice they can.

Ryan: Yes, right…

Mark: So that requires reticence. It requires wisdom, it requires courage and justice.

I look forward to having more of these conversations…

Ryan: I would love that. This was really helpful for me too actually, because it’s clarifying. Because it’s easy to talk about the stuff in the abstract, and then you’re like, “yeah, but actual people had to lose friends and family members in Afghanistan,” or whatever, right?

So it’s all it’s all complicated and real.

Mark: Yeah. And everyone’s going to have a different opinion. And I think part of courage is also to be okay with disagreeing. To be okay with people having differences of opinions. It’d be super boring if we all agreed on everything, the same…

What I mean it’s okay… that’s diversity and I think as a country we kind of lack a vision. We becomes so diverse and so polarized and so segmented with where we get our news and information and how we communicate, that we kind of have lost a common vision for our future.

And that might be one of the biggest and most courageous things for us to do as a country is to figure out how to have a conversation about vision. Like, where are we going? What does it mean to be an American?

Ryan: Yeah, or the other argument is actually we’re much more on the same page than people want us to think that we are…

Mark: That’s an interesting perspective, too. I love that.

Ryan: I think the American values are relatively constant, because they’re timeless, bedrock values. I think we all really want a lot of the same stuff.

The problem is people on both sides benefit from us not thinking we’re on the same page.

Mark: That’s true, but also our political system seems to cater to the extremes. And so most people really kind of want to be somewhere around the center – swinging back and forth. I like to think that we’re moving to like a post-liberal, post-conservative perspective – it’s very Wilberian, but like I’m liberal on a lot of issues, I’m conservative on a lot of issues…

And I could give a shit about what party I’m affiliated… it doesn’t matter, right? I love the libertarian principles, and I love fiscal conservatism, and I love social justice… so how can that fit into any one party today?

And so it’s going to take courage for us as a country to figure out how to solve that gridlock. And that extreme swing left to right, left to right…

And maybe the counter to that, that you’re about to say is, “well, that’s great, because it prevents us from really doing any serious damage. Because one side undoes the other side’s progress. And they just keep going back and forth.”

Ryan: No, I mean, what I would just add to that is I think a lot of the problems that we face as a society and as a planet – whether talking about global climate change, or you’re talking about the middle east, or you’re talking about a pandemic. Or you’re talking about social justice.

These are not political issues, right? These are huge human rights, human survival issues – the pandemic doesn’t care if you’re a republican or a democrat – the pandemic is a real thing that operates under a very specific logic, a ruthless merciless logic – doesn’t care what you think.

It just matters what you do in response to it. And so I think we are way – now we’re getting into the weeds – but we’re way too politicized, when most of this stuff has nothing to do with politics. And a lot has to do with right and wrong principles, values and just sort of basic facts or science.

Mark: I agree. Yeah, and we can kind of end there by saying stoicism helps us to become self-aware, right? Know thyself. And then by knowing myself – instead of just living your life based upon the opinions of your friend, and your latest social media memes – like, really think deeply about what’s reality for you. And what’s reality in the world.

I find great wisdom in stoicism, I find great wisdom in yoga and all the perennial traditions… because you have these universal truths that kind of cross cultures, and cross time. And then they really help me kind of make courageous action, because I don’t get so caught up in the vagaries of the daily chaos and politics and whatnot…

Ryan: No, it takes courage just to live in this crazy world.

Mark: No doubt.

All right, Ryan. Thanks so much. This book comes out September 28th. Well done.

Ryan: Thank you.

Mark: We will promote it when it comes out and for your next book, I’d love to have a conversation with you on your podcast, if you’re open to that sometime…

Ryan: Anytime…

Mark: Can continue some of these interesting discussions…

Ryan: We’re on it, man.

Mark: Yeah, awesome. And I appreciate your time today. I’m sure all the listeners are gonna really have some thought-provoking moments from this podcast.

Ryan: (laughing) Send your emails to Mark.

Mark: (laughing) No send them all to Ryan. It’s your fault…

It’s all good brother. All right thanks very much. And you can find more about Ryan at, what…?

Ryan: and

Mark: Hooyah, brother. We’ll see you soon.

Ryan: Dude, you’re the best. I’m going to send you an email – I would love to have you on the podcast, that’s a great idea. We’ll set it up.

Mark: I’d love that.

Okay folks. That was Ryan holiday. Go check him out – you’re gonna love his new book “Courage Is Calling.” And like I said, if you haven’t read his trio – “Obstacle Is the Way,” “Stillness Is the Key,” and “Ego’s the Enemy,” then add those to your list and share them with your family and friends. It’s really important work.

And I appreciate you, Ryan. Thanks again.

Ryan: Talk soon.

Mark: Yeah.

For all you listeners, stay focused and until next time, be unbeatable.


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