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The Daily Stoic

11 May 2025 · 33m

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Wisdom in the Face of Censorship | Sharon McMahon and Ryan Holiday

In short

In this episode, Ryan Holiday discusses his recent experience at the U.S. Naval Academy, where he was scheduled to speak about wisdom but was informed shortly before his lecture that it was canceled due to his intent to address censorship and the removal of books from the academy’s library. The conversation, hosted by Sharon McMahon, explores themes of censorship, free speech, and the importance of historical honesty in education.

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0:00I'm recording this on a Monday, and Monday is our grocery store day in our family. I usually pick my kids up from school and we go over to Whole Foods, get all our groceries for the week. Although here very shortly, we're going to go over there to get our Thanksgiving turkey because they've got a bunch of great options. Turkeys start at$1.49 a pound if you have Prime with organic birds at$2.99 a pound. And they only carry no antibiotic ever turkeys that will bring quality to your table at a great price. Whole Foods has great everyday prices on all your Thanksgiving essentials, whether you celebrate with a massive family or just a few close friends.

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1:20Welcome 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.

1:58Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So I've lived out here a long time and been coming into this town of Bastrop for a long time. And I passed this thing on the way in. It's a church. And there's like a big, old, white, sort of farmhouse-y looking building. It kind of looked like a schoolhouse. And it turns out that's what it was. I'd never stopped. I saw it had a historical marker. And then I was reading Sharon McMahon's book, The Small and Mighty, and she talked about these things called Rosenwald schools. Basically, the founder of Sears gave away most of his money and he gave them away to people like Booker T.

2:39Washington. And this is right after the American Civil War, as they were trying to educate this whole generation, this whole race of people who'd been kept unfairly in bondage of trying to teach them. and these things called Rosenwald schools popped up all over the country, but particularly in the South, funded by him. They were schoolhouses. And it turns out there's one like right near me. And I passed by this so many times and I didn't ever stop to look at it. I never went in it. And I didn't really even know what it was. And that's like my favorite thing about reading is when I'm reading a book and then I'm somewhere, I'm traveling.

3:14I love interacting with history that I've been learning about. So we finally stopped. I posted this on Instagram to the bane of my wife's existence. We stopped. She took a picture of it. And I was like, oh, I was just reading about this. Right. And actually, Sharon is one of my favorite people. You might have seen her on Instagram. She's Sharon Says So. She's basically like America's government teacher. She was for many years a high school government teacher. Now she runs this nonpartisan fact based Instagram account called Sharon Says So. That's teaching what we desperately need right now in this country, which is basic civics.

3:48And Sharon was on the podcast several months ago. I loved her book. As I said, when I interviewed her, she was one of the few guests that my in-laws, even though we've had some incredibly famous people in and out of the studio over the last couple of years, that my in-laws were like, we heard Sharon's coming. Can we meet her? And they went and actually saw her talk. She gave a speech at the Paramount Theater in Austin. Anyways, all of this led up to the thing you've probably heard about now, which is when my talk got censored at the Naval Academy and in a Branding List New York Times op-ed about it.

4:20Anyways, Sharon reached out and asked me if I would come on her podcast. Actually, we did it as an Instagram Live where we would talk about like the importance of access to information, which the Rosenwald schools were all about. The importance of free speech, the importance of the free exchange of ideas and how these basic facts are enshrined in our government. But also what I so loved about her book is how each of us plays a small but essential role in reinforcing these norms, in showing that we actually believe in these norms, in having to fight for these norms. So we had this great 30-minute quick conversation about this very idea and how it pertains to Stoic philosophy and how it pertains to being an informed citizen these days.

5:07I asked her if I could run it here. So that's what we are running. You can check out Sharon's podcast. Here's where it gets interesting. You can follow her on Instagram at Sharon Says So. And you can check out her sub stack, The Preamble, and definitely check out her book, The Small and Mighty, which I have raved about. I rave about it in the conversation. I've told so many people about it, and it's inspired me. And as I said, it just widened my horizons about where I live. I will give that to you now. I hope you enjoy.

5:36Thanks for squeezing me into your busy schedule. No, it sounds like you were busier than me today. I am really excited to chat. And one of the things that I wanted to talk to you about is about your recent scheduled appearance at the U.S. Naval Academy. First of all, just to set the stage a little bit, if you guys are not familiar with Ryan Holiday, you really should follow him. He has written so many incredible books about stoic philosophy, and he was going to be speaking to students at the Naval Academy about the concept of wisdom, right? Yeah. Okay, tell me more about what the speech that you were supposed to be giving was about.

6:16The last four years, I've been doing a series of lectures on the cardinal virtues. So I did courage, and I did discipline, then I did justice. And then on Monday, last Monday, it was supposed to be wisdom. And I owned a bookstore here in Texas. You were nice enough to come out when you were doing your talk at the Paramount. You might remember, but on the window of the bookstore is a line from Rage Against the Machine, the rock band. And it says, they don't got to burn the books. They just remove them. Favorite songs, favorite song lyrics. And we put that up when they started removing books from the library here at the high school in the little town that we live.

6:50So I've always believed that, you know, generally people should have access to ideas. And that when we're in the business of censoring and removing stuff, we're almost certainly screwing up. And so I was supposed to give this talk at the Naval Academy. And about a week before I talked, I read in the New York Times that they'd removed something like 400 books from the university library that were deemed to be too woke or supporting various DEI policies. Now, 400 sounds like a lot. Also, it doesn't sound like a lot when you realize there's something like a half a million books in this library. So the idea that any one of these books is somehow, you know, a statement of policy preference is ridiculous.

7:26This is a library for warrior scholars, as well as the many brilliant professors and teachers that are there. So I felt like I couldn't give a talk on the subject of wisdom, the cardinal virtue that I was speaking about, and not address this very timeless and unfortunately very prevalent tendency to get rid of books that we disagree with. And so I was going to talk about that briefly. I wasn't going to call anyone out or humiliate anyone, but I was going to say, hey, we shouldn't be doing this. Not only shouldn't we be doing this, it's the opposite of what we should do. And I was going to tell the story of the great James Stockdale, a graduate of the Naval Academy, who was later sent to Stanford to get a master's degree.

8:13And you can read these letters he sent home while he's studying there about his excitement to take this class on Marxist theory. and not because he's a Marxist, but because he thinks that communism, which it was then, was the primary geopolitical threat to the United States. And he wants to be familiar with it. He's doing what Seneca, the Stoic philosopher, calls reading like a spy in the enemy's camp. And my point was, if one of the revered heroes of the Naval Academy can sit down and read Lenin and Marx in the midst of the Cold War, you're telling me that today's midshipmen can't read Maya Angelou or Stacey Abrams' memoir or this book about the history of the Ku Klux Klan in the Naval Academy Library.

8:59I mean, it was absurd on its face. So that's what I was going to talk about. And what happened, to make a long story short, is they called me about an hour before my talk was supposed to go up and said, hey, you've got to remove these slides. We don't want to wade into the middle of a political fight. And I said, look, I understand that. And if you want to talk about, you know, some ground rules by which, you know, you don't want to get anyone specifically called out. I'm all about it. But I can't come here and give a talk about courage and a talk about doing the right thing. I can't put a sign on the window of my bookstore that says removing books is the same as burning them.

9:36And then and then just do it just because you, you know, don't want don't want anyone to have their feelings hurt. And so, as you can imagine, that led to the talk, the offer to give the talk being quickly rescinded. And I flew home. Here we are. Yeah. Like, didn't it happen, like, just very shortly before? Like, you weren't there ready to go on stage in short order. I was ironing my shirt, to tell you a little behind the scenes. I was about to walk over to go give the talk. And what had happened is I'd sent the slide, like, maybe this is naive, so I'll own that. But I sent my slides over the night before, as one does.

10:14You give a lot of talks. You don't send your slides over the night before for approval. You send your slides over so the tech person can load them up. And so that's what happened. I'd sent the slides over and, you know, they'd made their way up the chain of command. And some people were very alarmed. And they made up, ironically, a very political decision, right, to suppress criticism from a private citizen of a policy that, by the way, they were following. I think I understand that if you're an officer in the armed forces and the commander in chief or coming down the chain of command gives you an order, unless that order is in itself illegal, your job is to follow that.

10:52So I get their position. But my position as a private citizen, as a voter, is that this is insane. And I'm not not going to say that just because I've been invited to speak somewhere. In fact, I feel like maybe you can tell me if you disagree, but I feel like my obligation is to as a private citizen is thus greater to say things that I don't think a uniformed military officer is is in a position to say and probably isn't appropriate for them to say. Yeah, I totally agree with what you're saying. And the idea that criticism of a governmental action is being suppressed, like you're not allowed to come here and criticize us.

11:33That is the opposite of freedom. Yes. That is the opposite of freedom of you can't criticize the government. That is a slippery slope, my friends. A slippery slope is exactly what happened, because I imagine that the superintendent of the Naval Academy, who I did not talk to, so I wouldn't imply otherwise, no one gets in the position where they're running a university, especially an elite university like the Naval Academy, because they like removing books from a library. Right. She she did not want to do this. She would not have asked to do this. it was the order that she got. But in following that order and not pushing back against it publicly or privately, next, her and that administration there is in the even stickier position of having to suppress criticism of the decision because it's a bad look.

12:25Like the optics of it are inherently bad. And so that's that tricky situation where I think sometimes people think, oh, hey, I'm going to go along with this. So in the future, I'll be in a better position to do the right thing. What actually happens, and I say this from experience, having done the wrong thing, when you don't speak up, when you don't do what you know is right, when you go along with a policy that is problematic, what actually happens is you find yourself having to double and triple and quadruple down on that thing, and you get much further from where you want to be. And then kind of once you're in it, it's hard to get out of it.

13:02I love what you had to say too about James Stockdale and this concept of reading like a spy in the enemy's camp. There seems to be this idea that if we are exposed to an idea that we disagree with, that that somehow diminishes us, that that somehow is so inherently harmful that we must have sort of big brother government to protect us from said, you know, air quotes, harm. And I'd love to hear you talk a little bit more for somebody who's not familiar with the James Stockdale story or about this concept of, you know, reading like a spy in an enemy's camp. I want to hear you talk a little bit more about who he was and why that concept is important.

13:46Well, and look, I think it's worth pointing out because apparently it doesn't go without saying. Maya Angelou is not the enemy, you know? These books that were removed, you can disagree with some of the arguments and I haven't read all 500 books, I'm defending their right to exist, not their ideas in them. And I'm certainly defending people's right to read them and agree with them or disagree with them, right? But when Seneca is saying, we read like a spy in the enemy's camp, he's not just paying lip service to this idea. I think it's worth pointing out. If anyone here has read Seneca's letters, which is one of the most remarkable philosophical texts you'll ever lay hands on, you'll notice that he, the Stoic philosopher, quotes more than any other philosopher, Epicurus, the head of the rival Epicurean school.

14:31And it's remarkable that he does this because we're so used to taking only supporting arguments for what we believe, right? I think everyone knows what a straw man is. The opposite of a straw man is what they call a steel man. That means engaging in good faith with your opponent's arguments. And by the way, stipulating and recognizing when they get it right. Seneca has another great line. He says, I'll quote a bad author if the line is good. And I think you found this, your book does a good job of this too. A lot of the figures that you talked about were not perfect. They were not all good. They believe some great things and some bad things.

15:11And an adult is able to celebrate the good and acknowledge and discuss the bad. And so Stockdale, to go to what we're talking about, when he gets this graduate's degree in the humanities, He studies Marx. He studies world history. There's no doubt this is the early 60s. He's getting all sorts of information that's critical of America, that's critical of America's mistakes. And you know what he's doing? He's engaging with it as an adult. He's not a sensitive little snowflake. He has his prior beliefs, but he's willing to question them and have intellectual intercourse with people who believe differently.

15:51And my belief is these midshipmen are the elite of the elite. They're the most talented, brightest young men and women in this country. And I will say my time giving these talks at the Naval Academy has been one of the honors of my life. And I would say one of the things that gives me the most hope for our country, because it's an incredibly diverse group from all different walks of life who have decided to, instead of going to Harvard or Yale or Stanford, they're going to a university that comes with an obligation of service. And anyways, my point is, these people are going to be the commanders of submarines and battleships and fighter jets.

16:32They go on to run enormous organizations. You know, Admiral Stavridis, who is a graduate from the Naval Academy, a great author, he becomes the supreme allied commander of NATO. So these are leaders of leaders. the idea that they're too fragile to be exposed to some books about diversity, equity, and inclusion is, if we believe that, let's shut this whole thing down right now.

17:07We just took our kids to an outdoor performance at The Nutcracker. They had a snow cone, and then they went insane in the car ride home. And one of the things I try to remind myself when that's happening is that I don't control my kids' behavior, especially when they're too far gone like that, but I do control how I respond, right? That's stoicism, but it's also what Dr. Becky talks about. Dr. Becky is a clinical psychologist and a best-selling author, and she founded Good Inside, which is there to give parents practical, actionable tools for handling those everyday challenges with confidence.

17:42My wife introduced me to Dr. Becky's books. I love them. I've recommended them a million times. I've had her on the podcast. And as it happens, Dr. Becky is hosting two live Q &A events for good inside members. I am one of them. She signed me up for it about a year and a half ago. I've loved it ever since. On December 1st, you can join Dr. Becky for her How Not to Raise Assholes event, which is about avoiding entitlement and raising kind, empathetic kids. And on December 15th, she's hosting her How Not to Lose It Over the Holidays event, which I'm sure we could all use. As I said, I'm a big fan of Dr.

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20:12Well, and also, please note, the only books that were banned, because I've been through the list of the books, they really have to do with race in America, right? We're not banning porn from the Naval Academy. We're not banning books about Nazis from the Naval Academy. We're not taking other allegedly bad ideas, even if an administration thinks it's a bad idea. We're not taking other potentially harmful concepts and removing those from the library. It's specific to this one topic that somehow some of America's best and brightest, most civically minded people, because as you mentioned, these are incredibly elite students who then have to serve their country in the Navy.

21:01afterwards, after they are done with their education. They don't just get to take the degree and leave. They're not just incredibly bright. They're also perhaps some of the most patriotic. They care the most about the country. And for us to say, here are some ideas that are just so bad that we can't allow you to be exposed to them while also allowing them to be exposed to other bad ideas. That is very telling. It's very telling. And I think it says like so much. And it almost, by the way, it seems like they just did a control F search of the library catalog and looked for the word black. I'm not even joking.

21:40They asked ChatGBT, what are some woke books we should remove from the Naval Academy library? And then I think it gives you a sense of who the type of person and the type of education they're dealing with that's leading this is that they don't even have the familiarity with American history or American literature to go, hey, this is the list. Let's get rid of Maya Angelou from that list because it's going to look badly. We might be able to get people to roll over and accept, you know, the removal of some of these obscure, more leftist, you know, academic history books. But Maya Angelou is a treasure of American letters, You know, Oprah Winfrey is her number one fan.

22:23The idea that people aren't going to be upset, anyone would know that. And I think the reason they didn't know that is they have also not read Maya Angelou, right? And so there's a blind leading the blindness to it, I think. And you're right. These are people who are going on to be leaders, right? They're going to be the next generation of leaders in America. We're not trying to indoctrinate them with anti-Americanism, but if they're going to help America become what America is capable of becoming, I don't think it's unreasonable that we would give them the unvarnished truth about who America has been in the past.

22:55That's how we that's how we don't repeat mistakes like the Ku Klux Klan and the Holocaust. And, you know, I quote I wrote a New York Times op-ed about this. And one of the the the people that I talked about and he was going to be in the talk as well. This none of this controversy is new. There was a big backlash during the Cold War about what books were in American embassies during the Red Scare. And right after he's elected, there's a press conference where a reporter is asking Eisenhower if he's going to remove the Communist Manifesto and other books from the libraries at American embassies.

23:30And he says, absolutely not. He's like, if we're going to run a free country, we have to educate ourselves. And he says, one of the lessons that I took from World War Two is that we should have more of us should have read Hitler. And more of us should have read Stalin and more of us should have read Marx because we would have understood where they were going. Right. And so, again, Maya Angelou and these authors that were removed from the library are not the enemy, which makes this even more inexcusable. But the point is, if you're going to make America what it's capable of being, you have to understand it for its flaws and deficiencies so you can you can accentuate the good and prevent the bad.

24:11I love that. I think that's so true, that in order to fully understand something, you have to understand it from all dimensions. This is not a situation where, you know, indoctrination is never being allowed to question what you have been told. And if you're not allowed to say, is it really true that X, Y, and Z is, you know, what happened? If we're not allowed to say that, then that is the path to indoctrination. Free inquiry is the opposite of the path to indoctrination. So when somebody is characterizing the free inquiry of ideas, meaning I might read a book I disagree with to better understand the enemy, again, air quotes, to be a spy in the enemy's camp.

24:54The suppression of free inquiry is inherently anti-American. That is not what the framers of the Constitution, the founders of this nation intended for the population as a whole and certainly not for the leaders of leaders. The suppression of free inquiry is a very dangerous endeavor. You're absolutely right. And look, any time an organization does something that it knows it's wrong, you often see this revealed in the sort of corporate or political doublespeak that comes out. And so when the Naval Academy was asked and I told them, hey, you're canceling a planned and announced lecture. The idea that no one's going to find out about this is silly.

25:36So when they were asked, you know, we heard you cancel this lecture. What happened? They said, look, the Naval Academy is an apolitical institution. And we were concerned that this thing would be political. And then they said, but we're really just canceling it for scheduling reasons. Right. But I agree that the Naval Academy should be apolitical. And that's why it's so alarming that politics is intervening to remove books from the library. One of the tricky things about the times we live in is that often the accusation is a kind of confession. And when they're saying, hey, we're trying not to be political and then removing books because they're politically disagreeable, that's an accusation masquerading as a confession.

26:18but I think it says something about where we are that saying, Hey, I don't think we should be removing books, any books from a university library. That's effectively an Ivy league university for the armed services. I don't think we should be doing that. And then you're told you're being political. Like this isn't political to me. This is basic social contract, constitutional freedom. This is academic freedom and independence at its core. that's what I'm objecting to. And I hope people who are listening that maybe aren't fans of DEI as a political boogeyman, like they disagree with some of the ideas from Kendi and these other thinkers, great.

27:02You're free to do that also. But when we are removing books, if each administration is coming in and removing the books they don't like, that gets to a dark place very quickly. And it's not what what we're supposed to be doing. And it's not how you raise, you know, a generation of leaders and independent thinkers, which ultimately you want. I think people think the military is about top down control. Actually, I interviewed General Dan Cain, who's now the chairman of the Joint Chiefs of Staff on the Daily Stoke podcast several years ago. And he said people get the military wrong. He's like, I've probably given two direct orders in my entire career.

27:39He and most of the great military leaders will say that the crown jewel of American military power is the independent thinking of our officers and our non-commissioned officers. We have really smart people in our armed forces that make really great independent decisions. And for the most part, don't make ethically horrendous decisions, you know, like your Miley massacres and things like that. We have people who think for themselves and they question illegal orders and they push back when things are dangerous or, you know, strategically unsound. That's what you want. Russia doesn't have that. That's why they have blundered in Ukraine over and over and over again.

28:20The military is not a meat grinder that we feed people into. It is made up of elites of elites who are smart, who are creative, who think for themselves. You know, you said something that I really want to touch on, which is that if history doesn't make you uncomfortable, then you're not actually reading history. And I mean, isn't that the truth? This idea that we're supposed to be fed, you know, only like the chocolate cake version of history is kind of a recipe for disaster. You it leads us to and I've spoken with many members of the military about this, too. I recently had the occasion to talk to Jim Mattis, who was Secretary of Defense under Donald Trump in his first administration.

29:04And one of the things that they talk frequently about is that people actually can handle the truth. They want to know the truth. And there's far more damage that happens when we lie to people with some sort of sanitized version of what we wish were real. And you talk about this too, that when we're so overcome with what we hope to be true or what we wish to be real, that we're not seeing things as they really are. No, I think that's totally right. The ability to deal with reality on reality's terms, I think is the mark of an adult. But I would also say like, look, when you study history, there's darkness to it and contradiction and embarrassment and shame, American history being no exception.

29:54But when I read American history, and I've read it extensively, I read from all different sources, and when I see the darkness and the sadness, I don't go, oh, I'm a white person, I have blood guilt on me, and I hate my country, and I hate myself. No, I relate to the small and mighty characters that you profile in your books. When I tell my kids how history goes, and I explain what the good people did and the bad people did, and how even there was bad people on the good side and good people on the bad side. What I'm doing is trying to get them to identify with the good people, the people who didn't always win, but were trying, you know?

30:33And like, when I read about American slavery, I don't identify with Thomas Jefferson. I identify with Frederick Douglass, and I go, he's my guy, right? And I think when we talk about uncomfortable truths, I think especially somewhere like the Naval Academy, they're not like my country right or wrong. They're identifying with the good virtues in the person. And then they're able to see the vices or the flaws and go, hey, I don't want to make that same mistake. So I'm going to do things differently. That's why we study history. And you can learn just as much by studying somebody's foibles and flaws and mistakes as you can from studying only the times they were embodying virtue.

31:20If you don't understand what went wrong when they didn't embody a virtue like wisdom or like courage, then you're robbing yourself of important lessons. That's totally right. And look, this is some of my criticism of the sort of more the very far left interpretation of history, even the sort of Howard Zinn version of history, where when you only catalog the horrors and the contradictions and the hypocrisies, you end up with this kind of nihilism. Right. Like, look, Vietnam was a war started for no real reason and continued for 30 years for no real reason. It is a black mark on American history.

31:57But but in that blackness, there is someone like James Stockdale, who was heroic and virtuous and and worth studying and learning from. So so you don't just look at history and go, this is gross. This sucks. Nothing matters. What you do is you look for the good and you look for the bright spots. You look for the green sprouts. You look for the people who were trying to swim against the current. And you elevate those stories to provide a model for future generations to swim against the negative currents of their own time as well. We're going to run out of time, but I want to hear from you. Why did you feel so strongly about continuing forward with your speech as was?

32:41Why did you feel like I need to record what I was going to say and I need to bring this to light and write it out of the New York Times? Why are you here today? Like, why is this such an important issue for you? Well, thank you for asking that. Thanks for having me. I think it's two things. So people have been so nice. Well, not everyone, but most people have been so nice in their reaction to it. And they they've said some some, I think, very generous things about me and this little standard that I took. I have not always done this in my life, right? Like in my 20s, I worked for some controversial people.

33:14I was put in ethically fraught situation. I didn't always make the right choice, but I feel like I learned from that. And I feel like my study of history, we sort of pick our heroes. Doing this talk about Stockdale, this guy, if he had done the expedient thing, if he had gone along with what was being asked of him at any point in his time as a POW, he would have gone home. He would have been spared torture. And he said, no, I'm going to stand on principle here. And it felt morally bankrupt and contradictory for me to hold him up as an example and then immediately contradict that example. Right.

33:47So I felt that, but it's been a process for me. Like, I understand I'm in a position to take a stand in a way that a civil servant or a career military officer is perhaps not. So I thought about that too. But at the core of Stoicism is this idea that we control some things and we don't control other things. We gotta focus on what we control. And as it was happening, I go, look, I don't control that they're forcing me to make this choice, but I do control what choice I make. and then I don't control whether they allow me to speak or not, but I do control whether the message disappears or not. And so I said, look, I have to take my lumps here.

34:25You know, I have to go, I have to slink home. I have to leave. I can't do the thing I wanted to do, but I can go home and I can record this talk. I can write it. I can use what I'm good at, which is writing. I can write up what I was going to say and submit it to the New York Times. I can do that. And I can make sure that I don't go quietly about it. And I think we're in, I think, a very precarious moment in American history here. Most of us are not presidents. Most of us are not senators. Most of us do not hold serious political power. But we do have influence over our choices and our little sphere.

34:58And you think about the president of Columbia versus the president of Harvard. One rolls over and, you know, agrees to the policies and the other takes a fight. We each have the ability to say, hey, here's the line and you're not going to get me to cross it. And I think if everyone were to do that or if we were all as a society to get better at doing that, whether we're talking about resigning on principle, pushing back, you know, being a whistleblower, etc. I think a lot of the extreme forces on all ends of our political spectrum would get pushed back into normal bounds very quickly. The problem is everyone is going along with it because they don't want to be criticized.

35:41They don't want to pay anything for it. They don't want attention. You know, they don't want to they just don't want to be in the middle of it. And I think the obligation to us all is to be in the middle of it in the areas that it's possible for us to be in the middle of it. Yeah. What would 100 year old Ryan, in retrospect, looking back at his life, where would he wish he might have made different choices and not speaking up for what is right is often a regret that people have? Every time in my life I have made a decision for reasons, you know, like I had my reasons at the time. Those reasons have not aged well.

36:22Ryan, we could keep talking, but I'm going to let you go for today. I'm so glad we were able to make time to do this. Thank you for your courage and your wisdom. No, my pleasure. And thank you for everything that you do. I'm a huge fan. And we sell so many of your books at our bookstore because it's exactly the thing people need to be reading right now. It's not that they were small and mighty. It's that you can be that, right? That's what we have to take from history, that we all have the ability to make a little bit of a difference and that the world is better when people do that. So thank you for writing it.

36:52Thank you. Thanks, Ryan.

36:56Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. I'll see you next episode.

37:18look ads are annoying they are to be avoided if at all possible i understand as a content creator why they need to exist that's why i don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like the Daily Stoic going. So if you want to support a show but not listen to ads, well, we have partnered with Supercast to bring you a ad-free version of Daily Stoic. We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast completely ad-free.

38:06No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium, and we are offering a limited time discount of 20 % off your first year. Just go to dailystoic.com slash premium to sign up right now or click the link in the show descriptions to make those ads go away.

From the publisher

Sharon McMahon, aka "America's Government Teacher", hosted Ryan on an Instagram Live to discuss his recent experience at the U.S. Naval Academy. Invited to speak on the topic of wisdom, Ryan was informed just moments before his lecture that it had been canceled due to his decision to address the removal of books from the Academy’s library. What was meant to be a conversation about wisdom quickly turned into a powerful lesson on censorship, free speech, and the challenge of living with virtue.


Sharon and Ryan talk about the importance of confronting history honestly, the controversy around books labeled “too woke,” and the scary implications of silencing ideas in places meant to shape future leaders.

After years as a high school government teacher, Sharon now runs the non-partisan, fact-based Instagram account @sharonsaysso and is the author of The Small and the Mighty.


Check out Sharon’s podcast Here’s Where It Gets Interesting and follow her on Instagram @SharonSaysSo and on X @Sharon_Says_So


Sharon's Substack: The Preamble. 


🎙️ Listen to Sharon's episode on The Daily Stoic Podcast: Apple Podcasts, Spotify


📚 Grab a copy of The Small and the Mighty by Sharon McMahon at The Painted Porch: https://www.thepaintedporch.com


🗞️ Read Ryan Holiday's opinion piece in The New York Times: https://www.nytimes.com/2025/04/19/opinion/naval-academy-speech-censorship.html


🎥 Watch the talk that Ryan Holiday was supposed to give at The Naval Academy: https://www.youtube.com/watch?v=ZcnE1-SClfg


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