The Daily Stoic - Moral Courage Isn’t Always So Simple

Episode Date: May 4, 2025

The call for courage keeps returning, over and over. What matters most isn’t what we chose before, but what we choose right now.Listen to the talk that Ryan was supposed to give at The Naval Academy: Apple Podcasts, Spotify, YouTube 📚 Check out the Virtue Series 3-Book Bundle which includes Ryan Holiday’s books: Courage is Calling, Discipline is Destiny, and Right Thing, Right Now 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to the daily Stoic early and ad free right now. Just join Wondery Plus in the Wondery app or on Apple Podcasts. Even the smallest business can face big risks. Get a business insurance quote in minutes at zensurance.com slash podcast and receive a $20 gift card. Zensurance policies starting at $19 a month. Be protected. Be Zen. Welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like here or recommend here at Daily Stoic and other long form wisdom that you can chew on on this relaxing weekend.

We hope this helps shape your understanding of this philosophy and most importantly, that you're able to apply it to your actual life. Thank you for listening. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. You probably heard about this incident at the Naval Academy where they asked me to remove some slides and I didn't. They probably wanted me to just quietly go away and I didn't.

And so I wrote this New York Times piece about it. And then I filmed the talk and I put it up. And we ran it as a podcast episode. So maybe you listen to it. And it's been nice and gratifying to be able to say, hey, it didn't work. You didn't get to shut this down. I'm not gonna obey in advance.

I'm not gonna quietly go into the night. I'm gonna take a stand and I'm gonna show, hey, my principles matter here more than access. And people I really admire, Admiral Steph Reedus sent me a very nice note. He said, I'm proud of you. This is a former commander of NATO, someone who I admire,

someone who I look up to, his books, we carry him in the bookstore. He's a great writer, one of my favorite sort of business leadership writers. Some politicians I admire. The response has been over one, I mean, some people just called the bookstore just to say, hey, I'm sure you're getting a lot of hate for this,

but I just wanted to say good job. Like that was incredibly gratifying. And people, you know, said some stuff about, you know, this is you living what you talk. And I'm not listing all this to pat myself on the back. I hope that's clear, cause I want to get into why I'm bringing this up. I felt like it was a little unfair

how positive this stuff was, because I know myself, right? I know that I haven't always done this. I know that there have been moments when I was afraid, even when they called and they said, hey, we want you to take this out. I thought about it, right? Like it wasn't black and white, it wasn't immediately clear.

I said, hey, is this, you know, is this a language thing? Like, are there some ground rules you wanna lay? I don't know if I was thought I could get myself off the hook or if there actually was a compromise. I don't think there was. And I don't think I would have accepted it. But the point is these things are hard. They're not clear.

They're not easy. They're not obvious. And even when I made the decision, even I said, hey, guys, I'm not taking this out. You know, there was part of me that hoped there was still a way forward. There was a part of me that wasn't sure. I mean, I called my wife Samantha after and I said,

did I make the right decision? And I asked because I wanted to be reassured because I wasn't totally sure, right? And I'm saying this because doing the right thing is hard and it's scary. And these are the reasons we don't do it. We tell ourselves excuses, we make excuses. And I know this from experience

because I have been that person in the past. If you read Courage is Calling, you know this. If you know anything about my story, I had a complicated in many ways messed up stint in my 20s where I worked for some people I shouldn't have. I went along with some things that I shouldn't have. And it continues on past that. I mean, I look at conversations

with people where they were talking about someone else and I should have said, hey, don't do that. That's not okay. Don't do that when I'm around. There are just all sorts of moments in my life where I've not had that moral courage. I think we all have. And when I think about those moments,

I think about how my excuses didn't age well. Now I drew on that here and it made it slightly easier. That's the thing, it's kind of a habit. You either develop the habit of doing it or you don't. And I felt like when I wrote Courage is Calling, I didn't want anyone to infer that I was saying I was like these people. Because if anything, I'm further from these people

than I am like these people. And if anything, I'm further from these people than I am like these people. And I open, let me grab it here. I open the afterword of Courage is Calling with a personal story, one that was scary to write, I will say, because there's always some risk when you're being vulnerable and real, that you are taking your life in your hands or your career in your hands, your reputation in your hands.

And I talk about a real failing of courage. making your life in your hands or your career in your hands, your reputation in your hands. And I talk about a real failing of courage. And that's what I wanted to bring to you today. In Alcoholics Anonymous, they talk about doing a ceaseless moral inventory. It's not just about moments where you did the right thing and you want to see, look how great I am. But we have to look always in the mirror and go, where did I fall short? Where could I have done better?

Where was I not the person, as Mark Schreiber said, that philosophy wants me to be? And I'm telling you about how I fell short because I think we learn more from these moments. And I want you to understand that if you have fallen short, well, you still get to make the next decision. The call is coming again and again and again and again. And what matters is not what we did then,

but what we do now. And there were again, big moments and small moments in my twenties when I was not that person. And that's what I'm gonna bring you today. We're gonna do this afterward from Courage is Calling. Let me just seamlessly get into it. By the way, you can grab the audio book on Amazon or I can sign your copy of Courage is Calling. Let me just seamlessly get into it. By the way, you can grab the audio book on Amazon or I can sign your copy of Courage or Justice

or Discipline at store.dailystoic.com. And then the Wisdom Book, which is one of the books I was gonna talk about at the Navel Academy, I believe you can grab that at dailystoic.com slash pre-order because we're just putting it up for pre-order now. So here's me talking about that exact struggle and how I myself have fallen short of it many times. Afterward, I was maybe 23 years old when Dove Charney,

the CEO of American Apparel, asked me to leak naked photos of a woman who was suing him. I told him I would not. He believed that these pictures and the accompanying texts would exonerate him. To a certain extent, he was right. They also constituted what we now call revenge porn. I said I wanted no part in it. At the time, I felt a certain satisfaction with myself for this moment of moral courage.

As I've gotten older and having written the pages you've just listened to, the choice holds up, but it also seems shamefully insufficient. On the one hand, defying Dov Charney was not something people did at American Apparel, not if they wanted to keep their job, let alone stay on the boss's good side. On the other hand, why didn't I turn around, walk out the door, and never look back? Why didn't I quit on the spot? Why didn't everyone?

Why did I still want to keep the job? I remember walking into his office a few weeks later and witnessing a video call between him and reporters from major media outlets where they viewed the photos. I had stopped only my participation in the scheme. I had done nothing to actually prevent it from happening. Within minutes they would be splashed across the internet and the press. Why did my courage fail me? It's a question I have asked myself many times since, because it was not the only moral quandary that I found myself in in American Apparel.

I told myself that I stayed over the years because I wanted to protect the people who worked for me. I stayed because I thought I could make more of a difference by staying, because I believed in the mission of the company, and it was doing good in the world, because I wasn't like the others or like him. And to a certain extent, this was all true, but we can always find reasons not to do the

hard but right thing. At that age, walking away from money, from the most important job I'd ever had, disrupting the plans I had for my life, that all weighed very heavily upon me. The irony in retrospect was that at that very moment I was already making plans to do something much scarier, to transition away from the corporate world and become a writer. I believe I was afraid of what severing my lifeline would mean. I hesitated over being without a salary.

I was deterred by the uncertainty, by the leap in the dark. But in hesitating, I put myself and my safety above what was right, above other people. For three more years, I remained with the company as an advisor and a strategist, which mostly consisted of running interference for the employees whom I could help and preventing the car from crashing into a ditch. I prevented

bad decisions from being made. I steered decisions in a more ethical direction. I tried to rein dove in. I kept the thing going in my own small way, helping thousands of garment workers to keep making a living wage. I also continued to get paid and as a result, I can't fully escape complicity for the bad that did happen. A profile in courage I was not. In 2014, after I had established myself as a writer of three books, events took a sudden turn. Dove, whose grasp on reality had been intermittent

before, spiraled. He was living on a cot in a warehouse. He struck an employee. He would rant like a lunatic. He had driven the stock price to the lowest it had ever been. The lawsuits continued because he could not stop himself. During Dove's descent into madness, I frequently had discussions with some of American Apparel's board members about the state of affairs inside the company. As the reports grew worse, the board eventually decided to move on their CEO. I had begun to argue that Dove needed help in the way that Nero had needed help, that removing him was the only way to do it. It had taken me too long to get there, but once I made the decision, there wasn't any doubt it was the right path. On the day I ended

my book tour for The Obstacle is the Way, I got a call from Dove, and then from his number two, the board had finally fired him. Could I have made a difference if I had advocated for this earlier? Or would I have been fired? If I had quit in protest in 2011, would it have sent a message or gone without notice? If I hadn't held my fire, I wouldn't have been around for the pivotal moment when it did come. Or that's what I tell myself. Dove, unaware of my efforts, tried to purchase my loyalty in those desperate moments.

I will buy you a publishing imprint, he told me. Could he have delivered on that promise? Probably not. It didn't matter because I was not interested. I had crossed my Rubicon. I flew to Los Angeles and began a new role trying to rebuild the company and save it from Dove, who instead of walking away with millions, decided that if he couldn't be in charge, he'd rather

attack what he'd spent his life building. It was a race to stop him from burning the whole place down. There was a hostile takeover from Wall Street, then a poison pill from the board. It was hardly time in a war zone, but it was chaos on a level that I'd never seen. I had to brave criticism and intrigue and all sorts of other nonsense. I would sit and be interviewed for a number of investigations. I showed them where bodies had been buried and money had been wasted. I convinced other people to share their stories and protected them from retaliation.

I cleaned up long-standing messes and canceled policies that never should have been there in the first place. I comforted people. I tried to make things right. I worked long hours far from home while my wife waited patiently alone as we attempted to salvage the ruins of the company. It was exhausting. But not every battle is able to be won. The new corporate leadership hesitated at a critical moment. There were employees who needed to be fired, who had been corrupted over the years. When they were kept on out of a fear of upsetting anyone, Dove was able to sabotage the company through them.

Then the hedge fund that bought the company relented under his pressure and brought Dove partly back into the fold. I had warned against this repeatedly, so I quit on the spot, giving up the rest of my contract. He had been fired for reasons that had been denied and excused for too long. The idea of then reversing course was unconscionable to me, but the turnaround experts were certain they knew better. The company

would end up filing for bankruptcy twice. More than 10,000 people lost their jobs. I tell a longer version of this story. This was an experience that informed my book, Ego is the Enemy. I've received death threats for my writing before, but none of them rattled me the way that Dove's clownish goons did over the phone that summer. You go from working for and admiring someone thinking you believe in the same things to realize that you had blinded yourself. You realize that you debased yourself. You realize that most of it was a lie. And suddenly you're worried about your safety, going about your business as if your car and your office are bugged. There was sadness and fear, but there was also a surprising amount of certainty.

It felt so much better to leave, much better to do the hard thing than the morally conflicted years, as interesting and fun as the times had been. It was far more rewarding, too. been is far more rewarding too. You know those creepy stories that give you goosebumps? The ones that make you really question what's real? Well, what if I told you that some of the strangest, darkest, and most mysterious stories are not found in haunted houses or abandoned forests, but instead in hospital rooms and doctor's offices? Hi, I'm Mr. Ballin, the host of Mr. Ballin's Medical Mysteries. haunted houses or abandoned forests, but instead in hospital rooms and doctors' offices. Hi, I'm Mr. Bollin, the host of Mr. Bollin's Medical Mysteries, and each week on my podcast,

you can expect to hear stories about bizarre illnesses no one can explain, miraculous recoveries that shouldn't have happened, and cases so baffling they stumped even the best doctors. So if you crave totally true and thoroughly twisted horror stories and mysteries, Mr. Bolland's Medical Mysteries should be your new go-to weekly show. Listen to Mr. Bolland's Medical Mysteries on the Wondery app or wherever you get your podcasts. You can listen early and ad-free right now by joining Wondery Plus in the Wondery app or on Spotify or Apple podcasts. or Apple podcasts. As American Apparel imploded, I read a lot of Seneca. He's a fascinating figure because for all his beautiful writings about stoicism, courage,

and justice especially, he also worked for Nero. Had I been a minor 21st century equivalent, a writer who didn't live by their words? In a sense, yes. Indisputably, I had fallen short. I had compromised. Should have known better. I could have been braver. I think a big part of it had been the slow boil of it. You start with a set of assumptions made based on the facts as you understand them, or even on compromises you're willing to make. Nero was a teenager when he met Seneca. I met Dove when I was a teenager.

Things change. You learn more. Events happen. But if you're not willing to make decisions, hard decisions, as you grow and things change, then you're a coward. A lack of agency is contagious. We used to talk at American Apparel about how we were all watching the Dove Show.

No one even talked about doing anything about it. It was like we were all passive observers of our own surreal lives, right down to the hours and hours we were forced to sit and watch him rant and rave. Sometimes he was brilliant. Sometimes he was appallingly malevolent. It's as if it never occurred to anyone that we could do something about this.

Maybe we expected that somebody else would, that the adults would save us. And as we got older, as Seneca grew powerful in his own right, it conveniently escaped us that we were the ones who needed to come to the rescue. Confidentiality agreements, severances, car leases, friendships, compartmentalization, our own daddy issues. He was the boss and his signature was on our checks. You have a personal connection and it blinds you.

Nobody we knew called us out and if they had, would we have listened? Or would it have just driven us deeper into the cognitive dissonance? Fear in its many forms was a persuasive deterrent. It won out over courage. At least I can say that in my own case. Seneca would talk about how virtue is two parts,

the study of truth followed by conduct. If there is a third part, he said, it would be admonishment and reminders, the process of reviewing and reflecting and creating rules based on our experiences. Of course, of all the parts, conduct is the most important. My own story is evidence of that. But it is also by failing and looking in the mirror afterward that we were able to grow and learn and hopefully be better next time. That's how it went for Seneca. Eventually he did break with Nero. He went out like a hero. By the time 2016 rolled around, I too had learned from my experiences. I had a column in the New York Observer, which was owned by Jared Kushner, then known simply as a real estate developer and the son-in-law of a reality show personality. That summer, I wrote a piece that made a strong

case against Donald Trump's fitness for office. There had been no need for editorial approval of my writing up until that point, but suddenly the paper blocked the publication of my piece. A few years earlier, I would have been afraid to rock the boat or lose the money that might come from the gig. Now it didn't even occur to me not to publish something I thought was important. I also knew I wasn't wrong, which meant it was right to say it. I posted my piece elsewhere and immediately it went viral. I knew it meant my days writing at The Observer would be numbered.

Shortly afterward, I wrote another critical piece that also focused on the extreme right-wing website Breitbart. Again it was not published, so I put it out on my own. Shortly thereafter, I was informed that someone associated with the campaign had called to make serious allegations that one of my books had been plagiarized. The accusation was preposterous, but that wasn't the point. It was supposed to be a warning. They wanted me to know that they would try to ruin me if I didn't shut up. Didn't work.

If I had lost my column because of the Trump piece, if I had been forced to fight false allegations, if someone had come after me, I'd have handled it the same way I handle losing that salary, with the tools I've always had, as Marx really said. To give in to fear is to deny the talents and skills that got you where you are in the first place. It's to deprive yourself of the agency you were given at birth. In a sense, I'm grateful for the experiences at American Apparel because they taught me belatedly about the importance of listening to the voice inside yourself. In the midst of chaos and corruption, it can be hard to hear the call to courage.

Sometimes, you can only understand the perils of hesitation of not speaking truth to power after witnessing what happens to you and others when that doesn't happen. You'll find the outright intimidation I was talking about is rare. Far more effective are the ordinary incentives of life. Tell people what they want to hear and you'll have a bigger audience. Don't get political. Refrain from challenging anyone's identity. Any modern writer can look at their unsubscribe and unfollow rates and learn very quickly that to present the harsh truth is often to harm your wallet. You only have to read your fan mail when you

wade into controversial topics. Why did you say that? I'm never reading you again. I'm not perfect. I haven't always been as courageous as I wish I was, clearly. But as I've gotten older as a writer, one thing has become increasingly clear to me. Our obligation is to the truth, whether people like it or not. Like Helvidius, they might punish you for it. They might cancel you or literally even kill you for it. But as I often tell angry readers, I didn't build my platform to not use it to say what

I believe. I saved this story for the close of the book precisely because it's complicated and ordinary. 12,000 people worked at American Apparel over the years. Who was the most guilty? No one can say. If you read the stories about those leaked pictures, you'll see how murky the situation actually was. Maybe you'll read my Trump column and think I was totally wrong and it shouldn't have been published. My point in those stories was to show that courage is something we all

have to work toward in our own way, in our own lives, most of which are quite pedestrian. Samuel Johnson joked that every man thinks meanly of himself for not having been a soldier. I get that. I wrestled with that even as I wrote this book. Am I qualified? Am I allowed to write about courage, having never saved anyone's life outside of some 911 calls and giving somebody CPR on the pavement outside of a bar. I haven't always been courageous. I'm not always courageous. I hesitated even to write this chapter and some people told me not to include it.

But then I remembered that hesitation ought to steal your resolve. I can say earnestly that I am getting better at the timeless challenge of applying courage to real life. I care less of what people think today than I did yesterday. I step forward more often than I slink back. Writing and publishing this book was an example of that, but I'd like my private life and my private actions to speak louder than words. We have to stop thinking of courage only as what happens on the battlefield or on a bus

during the freedom rides. It's also just not being afraid of your boss or the truth. It's the decision to follow your own creative path. It's drawing an ethical line. It's being a weirdo if that's who you are. It's voting your conscience, not what the crowd wants or what your parents want. It's not only doing these things when destiny calls you onto the world stage, it's also as we talked about making courage a habit. Something you do in matters big and small, day in and day out, so that it feels natural in every moment, no matter who is watching, no matter the stakes.

Courage calls to each of us. Will we answer? Or maybe that's too much. Can we get better at answering? Can we step up more times than we step back? Let's start there. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much

to us and would really help the show. We appreciate it. I'll see you next episode. If you liked The Daily Stoic and thanks for listening, you can listen early and ad free right now by joining Wondery Plus in the Wondery app or on Apple podcasts. Prime members can listen ad free on Amazon Music. And before you go, would you tell us about yourself by filling out a short survey on Wondery.com slash survey.

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