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The Daily Stoic

15 Oct 2026 · 10m · 5 chapters

Episode artwork

BONUS: Toxic Masculinity, Cancel Culture & Politics

In short

How Stoicism can help with annoying disagreements, toxic masculinity, cancel culture, ego/humility after early success, and “politics” about how humans should be treated; plus brief AI/agentic-era work and ad reads.

Guests

Ryan Holiday (author; “Obstacles the Way,” “Ego Is the Enemy”).

Key claims

you can have peace by choosing “no opinion” (Mark Aurelius); toxic masculinity platforms weaponize disaffection and should be replaced with positive role models for young men; cancel culture resembles ancient Roman exile/shaming and needs grace, while modern “cancel culture” can become a self-serving attention loop; humility comes from recognizing early luck, avoiding ego, learning mistakes once, and treating feedback as information; “agree to disagree” fails when advocating harmful treatment of people.

Notable examples

Andrew Tate, Matt Walsh, Ben Shapiro; Russell Brand; Seneca’s execution; Epictetus’ ban; “cancel culture” as exile/shaming.

Written by AI. May contain mistakes.

Chapters

1:23

Finding Peace in Disagreement

Explore how to maintain peace when faced with differing opinions.

“I want to say that your book, Obstacles the Way, helped me finish my master's thesis.”
2:34

Toxic Masculinity and Role Models

Discussing the influence of toxic masculinity and the need for positive role models.

“It's a hard thing to do to just shut up, you know, to just focus on your stuff.”
4:21

Social Conscience in Stoicism

The importance of social conscience and equality in Stoic philosophy.

“Being any kind of person is hard, right?”
7:49

Cancel Culture and Stoicism

How Stoicism can inform the conversation around cancel culture.

“How can Stoics or Stoicism help reverse the negative effects of it?”
9:39

Navigating Political Disagreements

Discussing how to handle interactions with people holding opposing views.

“I read Obstacle is the Way and I came across an interesting theme in it.”
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Transcript

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0:00Ryan Holiday: AI isn't just opening new business opportunities, it's changing the way businesses get work done. Questions they ask, the decisions they make, the routine tasks that can be handed off. That's the idea behind NetSuite Next, the next generation of NetSuite, with AI woven into the tools that your business already relies on. NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also shaping how people and teams work together.

0:36Ryan Holiday: That shift is underway. And that's why there is a new expert created business guide for you. It's called Aligning for the Agentic Era, how AI is changing everyday work. And right now, it's totally free. It can explain how AI can reshape work across your entire organization and how businesses like yours can prosper from it. If your revenues are at least in the seven figures, get this free business guide aligning for the agentic era at netsuite.com slash stoic. The guide is free to you at netsuite.com slash stoic. Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world.

1:22Hi, Ryan. I want to say that your book, Obstacles the Way, helped me finish my master's thesis. Oh, congratulations. Thank you for that. I want to ask you about when you know something or someone is like annoying you or whatever, but you can't accept that they don't maybe agree with you, how to kind of have peace with that and not let it kind of take your own peace away? One of my favorite quotes from the Stoics, it's in Meditations. Mark Sreo says, remember, you always have the power to have no opinion. He says, things are not asking to be judged by you. Now imagine this is being said by a person whose opinion was literally law.

2:04He had the life and death power over people. And here he is reminding himself to live and let live, that he doesn't have to let things bother him. He doesn't have to try to change everything. He can just let some things be. And now this sounds like not much of a power. You always have the power to have no opinion. But how many people do we know that have no such power? Right? I mentioned Elon Musk earlier. Elon Musk is a incredibly powerful, incredibly wealthy person. But has he ever had an opinion he was able to keep to himself? Not that I know of. It's a hard thing to do to just shut up, you know, to just focus on your stuff.

2:39That's what I try to do in my life as best as I can. Something I'm going through with my kids, like I'll be like, oh, wait, I don't need to have an opinion on whether this show is good or not. You like it. I like that expression. You don't have to yuck someone else's yum. Like you like it. So it's good to you. It's not something I need to convince you of otherwise. And so having fewer opinions is something I'm trying to practice and will be forced to practice over the next few years, I suspect. Great question. As a father of two young boys like yourself, I'd just be interested on your thoughts and insights particularly on the rise of what we call toxic masculinity, the likes of your Andrew Tate's, Matt Walsh's, Ben Shapiro's, etc.

3:26And particularly their negative attitudes towards women and how you guide, let's say, your sons on the appropriate actions with the fair sex. Yeah, that's a great question. One of the reasons I feel so strongly about this and why I talk about these things is I have two young boys and I also just so frustrated with the way that people who have platforms and influence over young men have decided to deploy those platforms, to use it to call out and inspire the worst in people. Look, if you want to use your platform to tell people to get active, to read great texts from history, to aspire to do things, to be ambitious, take care of yourself, to make your bed, all that's awesome, right?

4:10And I think young men especially are desperate for that advice and desperately need positive outlets and role models because there are not enough of them out there. You know, being a young man is hard. Being any kind of person is hard, right? And when you look at the stats, young men are struggling. In the United States, two-thirds of college graduates are women. Just young men are struggling across the board. And I think because of that struggle, it makes them a very ripe target for sort of reactionary figures to pander to them. And as all sort of cultures have struggled with over the years, to take those disaffected young men, weaponize that disaffection to say it's this group's fault or it's this part of society's fault or to direct it at a common enemy.

4:54That's what like demagogues do and have always done. So I think that's why I feel so strongly about talking about some of this stuff and talking about it in a positive way. Because I feel like I'm one of the only people that has not a mostly male audience, but has a male audience that hasn't gone in that direction. There's definitely a few exceptions. I think Rich Roll does an incredible job. There's a bunch of people I like, but I think this space is failing young men particularly. I just find in the Stoics that I admire a strong social conscience. And that to me, that strong social conscience has to also include equal treatment for all people, all genders, all orientations.

5:29and to really sincerely care about that as if it as is important to you as your own equality and success to me. That's just part and parcel of being a decent human.

5:40Ryan Holiday: So I have a bunch of traveling I'm doing through the end of the year on Daily Stoic Live Tour. I just got back from San Diego. I like to stay in the places that I'm staying. I like to book places on Airbnb so I can be like a local. I not only do some of my best writing, but I learn about things that I wouldn't have known otherwise. When I was just in San Diego, So I took a walk along the water. I bumped into someone who recognized me and they told me about their favorite local bookstore, which was like two blocks from where I was staying. And I never would have known about it if it wasn't for that encounter.

6:09Ryan Holiday: It was cool to me to think that I have helped facilitate that experience for many, many people coming to Austin over the years. The first house that I bought in Austin when my wife and I first moved here, we would list it on Airbnb and it helped me make the transition from my corporate life to being a full-time writer. So if you're gonna be away, you should maybe think about listing your place on Airbnb. It can be a great way to earn extra cash while you travel. It can offset the cost of your trip or maybe even go towards whatever you're doing next. If you've got travel coming up, check out Airbnb.

6:40Ryan Holiday: Your home might be worth more than you think and you can find out how much at airbnb.com slash host. Benjamin Franklin said time is money in 1748. That was his advice to a young man. 278 years later, some of us, depending on what you do, are still spending part of every month typing receipts into a form. It's bad use of your time. That's bad use of company time. Expense reports are tedious. It's not what I want my employees doing. Well, Ramp makes collecting and submitting expenses super simple. With Ramp, expenses submit themselves. You just text or email your receipt and Ramp categorizes codes and submits it.

7:21Ryan Holiday: And when you book business travel with Ramp, they find the best flights and hotels you're actually allowed to book. You don't find out later that your company is only partially going to cover it. Ramp is the only finance platform that employees and finance teams both rave about. And companies have saved over$12 billion with Ramp. Time is money. Save both with Ramp. New customers get$250 off at ramp.com slash daily stoic. That's ramp.com slash daily stoic. So I'm thinking that cancel culture is really awful. Sure. How can Stoics or Stoicism help reverse the negative effects of it? Look, they had cancel culture in ancient Rome.

8:00It was called exile and it happened all the time. There's a whole generation of Stoics that were known as the Stoic opposition and they were either exiled or executed. This is how Seneca meets his end. The reason Epictetus is teaching philosophy in Greece is that there is a blanket ban on all philosophers in Rome around the time he gets his freedom. Look, public shaming, piling onto people, being very unforgiving, you know, making someone's worst moment, who they are as a person. Yes, that kind of cancel culture is not great. We need more grace in this world. We're all imperfect. Seneca talks about this.

8:39He says, like, we're all fucked up and awful. And the only way we're going to survive is by being kind and patient with each other. That being said, I feel like cancel culture has become a rallying cry, largely of people who it would be wonderful if we could cancel and they went away. And so this idea of, you know, like Russell Brand gets accused of a bunch of horrendous things and then becomes like a right wing cancel culture warrior is very self-serving and transparently manipulative in my eyes. So there's something about where we're going as a society where we're like, oh, because polite society is horrified at what this person has done.

9:19And rightfully so, I'm actually going to instead of saying rightfully so and being like, I'm not going to be a fan of that person's work anymore. We decide to make them this kind of like antihero. I feel like it's created this toxic feedback loop where like the worst people get the most attention. And so I'm more worried about that than cancel culture. I'm reading your book now, Ego's the Enemy. I read Obstacle is the Way and I came across an interesting theme in it. As you were successful when you were younger, I wanted to ask you as someone that's quite relatively young, how do you iterate when something doesn't go your way and how do you keep yourself humble despite having a lot of success at a younger stage?

9:58Thank you for that. Yeah, I think I was always very cognizant of how lucky I was to have some of the opportunities that I had early on. And my main goal was not fucking them up and not letting them go to my head. When I looked at other people that had started off strong or gotten similar lucky breaks, what happened? It wasn't that someone came along and took it all away. It was that they alienated people or took it for granted, got complacent, like lost their minds. You know, I understood that ego was this kind of toxic force that would make whatever I was trying to do harder. And I think that's true at any level of success you have.

10:35But it is particularly hard to bear in young people. If they're choosing between two people to give an opportunity to, the asshole is the one they're going to pass on first, you know. And so I was just thinking a lot about how do I not regress towards the mean? That's a mathematical proof for certainty that all things regress towards the mean. How do I not do that? How do I stay where I am? And to me, that was mostly about staying humble, staying clear-headed, doing the work. But yeah, you're gonna make mistakes. You're gonna screw up. I did that a lot. But I wanted to make sure that I only made those mistakes once, that I didn't make the same mistake over and over and over again and need to make it bigger before I learned the lesson.

11:14And I wanted to make sure that when I did make a mistake, I took the feedback, not personally, but as information I could use to get better. How do you deal with people on the day-to-day who are on the far opposite spectrum and believe in everything that you feel like is wrong with the world, but they are actually decent people, but they just believe, in our sense, wrong thing? Look, I live in a small town in rural Texas on a dirt road. I have plenty of interactions with people that I disagree with on lots of things. Not that I'm on the far left myself. I have not. That's why I live in rural Texas.

11:53I feel like I have pretty down the middle views. It's just segment of society has gotten more and more extreme. I will say I don't buy the distinction or the benefit of the doubt that you can believe and advocate for horrible things that have horrible real effects on real human beings and then go, well, we just agree to disagree. That's what I mean. Like people go, why take a stand? You know, why embrace the divisiveness? Sure. Like there's lots of totally normal policies on all sides of the spectrum based on real data that people can have lots of opinions about. I don't talk about politics ever in that sense.

12:29I don't talk about tax policy. I don't talk about educational policy. There's none of that. But when it comes down at the most basic level to how we treat human beings and what the social contract obligates us to do and not do, and what history tells us to be very wary of and to be very emphatic about nipping in the bud, that's the kind of politics that I feel obligated to talk about.

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From the publisher

In this bonus episode, Ryan answers questions about handling other people’s opinions, toxic masculinity, keeping your ego in check, politics, and cancel culture. Have a question for Ryan? Bring it to one of his upcoming live shows!


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