Jordan Klepper: How to Talk to People You Disagree With (Without Losing It) | PT. 1

Summary

The Daily Stoic Podcast Episode: Jordan Klepper: How to Talk to People You Disagree With (Without Losing It) | PT. 1 Host: Ryan Holiday Guest: Jordan Klepper Date: March 4, 2026

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Episode Overview

In this engaging episode, Ryan Holiday speaks with satirist and Daily Show correspondent Jordan Klepper about the art and challenge of talking to people you fundamentally disagree with—without losing your composure or giving up your sense of curiosity and humor. Drawing on stoic principles and Jordan’s real-world experience engaging with political extremists and conspiracy theorists, the conversation explores emotional restraint, the roots of misinformation, the impact of media diets, and the search for genuine community in a fractured, entertainment-obsessed culture.

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Key Discussion Points & Insights

The Stoic Art of Restraint and Curiosity

• Ryan frames the topic using Socrates as a model of restraint and curiosity, noting how hard it is to stay cool when confronted with nonsense or offensive opinions.
  • “If stoicism is the idea of controlling your emotions, not immediately reacting, it's actually super important. Because when you're hearing nonsense from another person... all this requires a lot of restraint.” (01:10)
• Jordan emphasizes that his role, both as an interviewer and comedian, is fundamentally about not losing it and instead sitting in discomfort to allow people to reveal themselves.
  • “The job is not to lose it. Step one. Step two is like the gold is on the other end of that awkwardness.” (12:01)

Improv, Interviewing, and the Value of Silence

• Jordan shares a foundational Daily Show lesson: let the interviewee talk, even through awkward silences.
  • Recalls advice from Jason Jones: “Shut up and let them talk. Sit in that space.” (12:31)
• The discomfort with silence, especially for those with a “Midwestern niceness,” is overcome by recognizing its investigative utility.

Understanding Conspiracy Believers and “Group Think”

• Jordan and Ryan unravel why so many cling to talking points and conspiracies:
  • People haven’t had to articulate or critically examine their views because those views were mostly echoed within homogenous friend groups or media bubbles. (14:31–15:04)
  • Much speech at rallies is performative; it's about being part of a group identity, not deeply held belief.
    • “This isn't who you are. You just like being here. You like feeling like you're a part of something.” (16:15)
• Conspiracies become hobbies, filling a void left by disappearing community activities, especially for older people.
  • Anecdote: “You have the best hobby a 65-year-old woman in the Midwest can have.” (21:19)

Media Diets, Entertainment, and the Loss of Reflection

• Discussion of media literacy, especially generationally—older generations assume anything in print or online is true, not appreciating the publisher/consumer divide on platforms like Facebook.
  • “The dumbest person you know, the only way they can talk to you is by publishing information to you, at you.” (18:52)
• News and politics have become a form of entertainment; monoculture used to be art or literature but now politics, pop music (Taylor Swift), and sports are the remaining shared spaces.
• Reflects on how even substantive news is overshadowed by the 24/7 cycle and hyper-partisan, performative commentary.
  • Ryan: “We have conflated that with being informed. But in a way, that might be the most uninformed person.” (29:51)

The Need for Deliberate Consumption and Reflection

• Both agree that real understanding requires restraint from constant updates in favor of slower, more thoughtful, and historical perspectives—primarily through reading books or waiting for information to settle.
  • “You should find out what happened after it has happened, not as it's happening.” (39:10)
• Jordan shares how, to foster his own opinions, he deliberately delayed reading the news in the morning to allow space for genuine thought.
  • “I had to put it down and say my first thought every morning was Maggie Haberman's thought. It was like, this isn't my thought.” (33:47)

Sports, Escapism, and the Search for Community

• Both reflect on how sports (and formerly other shared cultures) provide low-stakes communities and emotional outlets that are largely lost to fragmentation or politicization elsewhere.
  • “We want to be a part of something. We want to feel like we've won. We have crafted these safe spaces where you can do that and then you can walk away and it isn't your entire identity.” (24:36)
• Both lament how even sports have been monetized and splintered, mimicking the fracturing pressures of political culture.

The Pitfalls of the Modern Media Landscape

• The constant need for content and persona shapes even journalism, incentivizing hyperbole and “manufactured takes” similar to debate show theatrics in sports.
  • “Journalists. Hedges gets slightly more hyperbolic. And you just feel that. And you see it. And just the systems in and of itself that we were getting all this information in the sports, they just feel so inherently broken.” (28:43)
• The discipline to avoid the “background noise” and carve out creative or reflective space is highlighted as rare and essential.

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Notable Quotes and Memorable Moments

• On Letting People Talk:
  “Shut up and let them talk. Sit in that space.”
  — Jordan Klepper, (12:31)

• On Why People Repeat Talking Points:
  “Repetition is their certainty.”
  — Jordan Klepper, (14:52)

• On the Appeal of Group Identity at Rallies:
  “This isn't who you are. You just like being here. You like feeling like you're a part of something.”
  — Jordan Klepper, (16:15)

• On Older People and Facebook:
  “Your neighbor's an idiot. The dumbest person you know, the only way they can talk to you is by publishing information to you, at you.”
  — Jordan Klepper, (18:52)

• On Conspiracies as Hobbies:
  “You've gotten on the Internet and it's fun. And it is fun going down rabbit holes like that. You're discovering something, you have your own little mysteries, you talk to your friends about it. And this has suddenly become your hobby.”
  — Jordan Klepper, (21:19)

• On Overconsumption of News:
  “We have conflated that with being informed. But in a way that might be the most uninformed person.”
  — Ryan Holiday, (29:51)

• On Reflection vs. Information Overload:
  “We've replaced reflection with, like, constant attention.”
  — Jordan Klepper, (32:42)

• On Media and Entertainment:
  “Television is not a medium by which you can communicate intelligent thought.”
  — Ryan Holiday, referencing Neil Postman, (35:17)

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Timestamps for Important Segments

• 01:10 – Ryan frames the stoic challenge of restraint in heated conversations.
• 02:05 – Clip of Jordan Klepper’s classic interviewing style at rallies.
• 11:38 – Ryan asks Jordan directly: How do you not lose it at rallies?
• 12:31 – Jordan details the importance of silence and space in interviews.
• 14:31–16:51 – Analysis of group identity and performative belief at political rallies.
• 17:33–19:03 – Media literacy, generational divides, and the proliferation of misinformation online.
• 21:19 – The rise of conspiracy theories as hobbies among the elderly.
• 24:36 – The community role of sports and safe outlets for emotion.
• 28:30–29:49 – The parallels between sports commentary and news media spectacle.
• 32:42–34:16 – The shift from reflection to over-involvement with the news cycle.
• 35:17 – Discussion of Neil Postman’s ‘Amusing Ourselves to Death’ and media limitations.
• 37:13–39:27 – Why waiting for facts (and avoiding news in real time) is more productive.
• 41:31–42:38 – On the leader’s need for distance from the daily news cycle.

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Conclusion

This episode presents a candid, often humorous exploration of how to stay rational, empathetic, and even amused when engaging with people who hold opposing (or fantastical) beliefs. Jordan Klepper’s method—rooted in silence, patience, and genuine curiosity—mirrors core stoic techniques: tamping down emotional reaction in favor of understanding and self-restraint. Both he and Ryan Holiday highlight the importance of cultivating media literacy, carving out quiet reflection, and sustaining meaningful communities outside of politicized monoculture.

The episode serves as both a guide and a philosophical meditation for anyone seeking to keep their cool—in conversation, in media consumption, and in life.

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Transcript

[Ryan Holiday]

Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice and wisdom, into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Think about Socrates going around in ancient Athens. He was pretty smart, although he sort of played the humble fool. He was pretty smart and most of the time he knew that people were wrong and he knew that what they were saying was laughable. So his curiosity, his questioning, his restraint. Right. He's restraining himself from dunking on these other people. He's letting them work through the solution themselves or asking them to really explain what they think so he can learn from it. That's not an easy thing to do. I think culturally we pay some lip service to the idea of like, talking to people we disagree with, getting viewpoints from people maybe you don't know or maybe you even don't like, but like, we're sort of glossing over how like, difficult that is. Like, I don't just mean, like, it's difficult to get out of your information budget, but like, if stoicism is the idea of controlling your emotions, not immediately reacting, it's actually super important. Because when you're hearing nonsense from another person, when you're hearing something offensive from another person, when you're hearing something from someone that you know a lot about and you know that they're wrong, all this requires a lot of restraint. So that's why I was really excited to talk to today's guest, because he's one of the best people in the world at this. If you've watched the Daily show anytime in basically the last decade or so, you've probably seen Jordan Klepper. You've either seen him as a correspondent or you've seen him more recently as a host where he is absolutely crushing it. You've definitely seen his viral interviews at political rallies and protests. Here's a little jump cut of him being very good at what he does.

[Jordan Klepper]

Barack Obama had big part of 9 11. Which part? Not being around, always on vacation, never in the office. Why do you think Barack Obama wasn't in the oval office on 9 11? That I don't know. We'd like to get to the bottom of that. We don't even know if he's a citizen. Yeah. If you don't look at the birth certificate, there's almost no evidence there. Exactly. So there's nothing Barack Obama could do to prove that he was born here. If there was maybe witnesses that were attendants at his birth, like his mother, would you Listen to his mother.

[Ryan Holiday]

No, no.

[Jordan Klepper]

She has motivation to lie. So you don't trust Donald Trump's birth certificate either? Yeah, because he's been here forever. Well, how do you know? But how do you. What's your proof? Well, his parents, but no, but they're biased. I'm talking about, like, people who could

[Ryan Holiday]

be in the wrong way.

[Jordan Klepper]

They be biased. Well, like, I'm just using your logic against you.

[Ryan Holiday]

He was in Austin for a live show a couple of months ago, and so I asked him if he wanted to swing by the bookstore, which he did, and I wanted to talk to him about that. Like, how does he have that ability to stay calm, to stay curious, to stay funny? I think a lot of it comes from the improv training, which maybe there's something that he can teach us in this polarized world because he's able to not just talk to people he disagrees with, but often, oftentimes get them to make the strongest argument against their own point by not jumping in, by giving them just enough rope to hang themselves. And I'm not saying that's what we should do. We should go around making people look foolish. I'm just saying there's something there and it's something I wanted to ask him about. And I think you're really going to like this conversation because we talk about keeping our cool. We talk about conspiracy theories, talking about the way that conspiracy theories have become kind of a hobby for some people. Bad media diets, good media diets, and much more. I'm really excited to bring you this. Jordan is a writer, a comedian, a correspondent for the Daily Show. You can follow him on Instagram at. Jordan Klepper. You can check out his upcoming live show dates. He is amazing. Very, very funny. @officialjordanclepper.com. I don't know if you've seen a video or a talk from me lately, but you can tell I'm kind of on a sweater kick. I don't know why exact exactly that started, but the problem with this sweater kick is like, finding ones that actually look good that I like and I'm not paying like an absurd, let's call it unstoic amount of money on them. And that's where today's sponsor comes in. Quince. They've got great design, great styles, great fabrics, everyday essential that are effortless to wear. They're not too hot, they're not too cold, they're not too thin, they're not too thick. They work with top factories. Cut out the middleman. So you're not Paying for brand markup or fancy retail stores. Just great sweaters and clothes that you'll like. And you've probably seen me wear them in some of the daily Stoic stuff. I got this Mongolian cashmere sweater. I got 100% organic cotton sweater. They're comfortable, they're high quality. That's always the thing. Stop overcomplicating your wardrobe. You don't need a closet full of options. You just need some great staples that actually work. And right now, if you go to quince.com stoic for free shipping, you also get 365 day returns. That's a full year to build out your wardrobe and love it. And you will now available in Canada too. Don't keep settling. For clothes that don't last. Go to Q U I-N C-E.com stoic for free shipping and 365 day returns. Q-U-I-N-C-E.com stoic so I am recording this in an Airbnb. I'm out doing a little speaking gig and didn't stay in a hotel, stayed in an Airbnb. And let me say this place is pretty dated. I'm sure it was fancy and cool when it came out, but it's got a lot of old wood stuff. It needs a refresh and maybe your house needs a little refresh if you want to upgrade your space with quality pieces that work within your budget. Plus enjoy fast shipping and easy assembly options. Well, you should check out Wayfair because Wayfair makes it easy to find exactly what fits your style and needs. Wayfair makes it simple to narrow down to exactly what works with your style and budget. They've got filters on the site to narrow down the search to the size and the material and they've got thousands of five star reviews to help you shop with confidence. I've always had a great experience with Wayfair. We just decorated our house and part of our office with some stuff from Wayfair. Items big and small are shipped right to your door. With installation and assembly services available. You can find furniture, decor and essentials that fit your unique style and budget. If you head to Wayfair.com right now to shop all things home, that's W A Y-F-A-I-R.com Wayfair every style, every home. You work a full week and then you're like the weekend is actually the more stressful time for you.

[Jordan Klepper]

Yeah, I think during doing these standup shows for sure. I mean my schedule is strange in that, like, host week is a chaotic week and there's no space and time. Non host weeks. I'm in the office working kind of on call and also prepping for other stuff. And so that was what this week was. And then, yes, knowing that, like, oh, I'm gonna jump on the road and do a couple shows. And then also we have a field shoot that's happening on Sunday, and that's based around the news, which is always changing. So we're going to Portland, and we're watching the news out of Portland, whether or not federal troops are coming in or out. We're watching Chicago to see if I'm going to Chicago. So suddenly, the week was fine. The weekend is just a bunch of things up in the air that I just kind of get on a plane, pack some books, and I'm like, all right, I'm going to go. I don't exactly know if I have all the flights to get home, but I know I'm going out and I'm doing these things here.

[Ryan Holiday]

And that's not even thinking about the fact that. And maybe it's helpful that you're not. You have to do the performance each time.

[Jordan Klepper]

Yes.

[Ryan Holiday]

Right. That's just like the logistical stress. Stress of being at the place that your name on the marquee says you're gonna be there.

[Jordan Klepper]

Well, I have to remind myself, and luckily, I mean, the ego test in me. You walk into a space that has your name on a theater. It's an easy reminder.

[Ryan Holiday]

Sure, sure.

[Jordan Klepper]

But it is a reminder. You're like, oh, the thing I've been stressing about or anxious about is actually the thing I like to do and the thing I'm exc. Excited about doing. As long as I've planned some space internally to realize that, then I'm great. And frankly, that's what happens with these shows. You show up and you have to show up early to do a tech. And my show has some technical elements to it all. And after you finish that tech, you got an hour and a half to just realize what you're there for.

[Ryan Holiday]

Yeah. To do the thing.

[Jordan Klepper]

To do the thing and then be ready for the thing.

[Ryan Holiday]

Yeah. And that you can end up spending. I try to remind myself. It's like I'm spending all this time worried about whether I'm gonna make the thing or whatever, but I'm not. I could just be putting that energy into, like, the thing. Like. Well, like, I'm not. I'm spending the time thinking about checking flight aware or whatever. Not. I could just Be working on what I'm gonna do when I'm there, if I'm lucky enough to get there.

[Jordan Klepper]

And I mean, I think you get good enough at. You know, I've been doing versions of this for decade plus. And you get. You also realize that some of your most relaxing times take place on that flight. Some of your best reading takes place on that flight. Some of the only time you have to yourself and not have the responsibilities of being a parrot happen to the hotel for the 40 minutes right there. And so I have to keep teaching myself. But I have gotten better at realizing, like, you're getting little buckets of time that have stress all around them and all the edges, but enjoy those spaces and remember to. To take advantage of it. And I think I'm better at that now. So even if I'm thrown into a chaotic three days, I understand that in those spaces, how not to go completely crazy.

[Ryan Holiday]

Yeah. All I was thinking about. Cause I flew out early yesterday morning and then flew out late last night. All I was thinking is, like, I'm going to take two naps in the same day.

[Jordan Klepper]

That is. That's a dream.

[Ryan Holiday]

Yeah. Emma. I think first my wife was, like, sympathetic, and then I think she realized. She's like, no, no, no. You're taking two naps.

[Jordan Klepper]

That's the tough part is you have to be. I'm all for communication within a relationship, but, yeah. Sometimes you complain about life on the road, and then you articulate life on the road to somebody who's not on the road, and they're like, oh, you got two naps today. Oh. And all. And you just. You ate tacos all day. Oh, a crowd of hundreds of people clap for the things that you said. Oh, that was. That must be so tough. Oh, are you sleepy?

[Ryan Holiday]

Yeah. You're calling and you're like, I don't know if I should get room service or I should walk down the road to get something to eat. And then she's like, I've eaten nothing but beef jerky today.

[Jordan Klepper]

I also, like, I can't not talk about, like, any media that I've ingested over the few days I'm gone. So when I go home to see my wife, if I watch, like, any movies at the hotel, any movies on

[Ryan Holiday]

the flight, that's cheating. Yeah.

[Jordan Klepper]

Yeah.

[Ryan Holiday]

Yes. Yeah.

[Jordan Klepper]

Well, then I break down. I give her. I hold onto. I'm like, should I tell her my opinions on these four films that I saw? I'm like, no, that's just gonna make her upset. And then 20 seconds later, I'm like, I need to tell you about this romantic comedy that I watched for the third time. You want to hear my opinion on it? Like, no, but I do it and I lose a little bit of credibility because of it.

[Ryan Holiday]

Yeah. Yeah, right. You were. You have it so hard. You watched three movies over the weekend.

[Jordan Klepper]

It's like, I watched Goodfellas again and I got, you know, I saw it in a whole new light. Do you want to talk about that? And. No, she doesn't.

[Ryan Holiday]

Oh, man. So I was thinking about the kind of comedy you do when you're at these rallies and stuff. How do you not lose it? I guess this is basic improv, but it seems like it would require a lot of restraint to let someone hang themselves the way that you often do.

[Jordan Klepper]

Yeah. I mean, I think the job is not to lose it.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

Step one.

[Ryan Holiday]

Sure.

[Jordan Klepper]

Step two is like the. The gold is on the other end of that awkwardness.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

One of the first things I learned at the Daily Show, I did one of these sit down interviews. And especially when you're doing a sit down interview, a more traditional one with somebody who you might not agree with, it gets awkward.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

And as somebody who comes from an improv background and also a Midwestern niceness, like the silence in conversations is death and rings and hurts.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

And so I usually want to talk through those. Give people space to. To clamp onto something and. Yes. And their ideas. And I was told by, I think, Jason Jones, like, my first week at the Daily show was like, shut up and let them talk. Sit in that space. And so that was like, it had to unlock something for me. But it was like, oh, remember, your job out there is to create enough space, enough comfort for people to reveal themselves. Sometimes by over talking, some times by overthinking. But let that be so that's my mindset going in. Then beyond that, I do think I have legitimate curiosity about these things. And I also understand the mechanism. Sometimes there's hateful, terrible things that are said that make me upset. More often than not, that doesn't make the final edit. I'm not perfect out there. I've gotten into heated arguments over things that don't make good TV or stuff we don't want to put on TV because there's hateful rhetoric that we're not gonna amplify. But more often than not, what I see is people working through a narrative they haven't articulated yet because they just read it or they've heard the president say it and they're articulating that in real time. And I also see them performing for the cameras because they feel a need to be more certain than they normally are. And I think I have empathy for that moment. And so as much as I'd like to be like, how can you believe that? I think I know how you can believe it. So I'm not surprised by how they could believe it. I'm just surprised by what they're articulating.

[Ryan Holiday]

Or they don't really believe it. They're saying it out loud for the.

[Jordan Klepper]

Like they're performing it.

[Ryan Holiday]

Yeah. Or they have this kind of gut instinct. And then it seems like sometimes your job is to get them to put it into words and then it falls apart. Which is, by the way, like, why you're supposed to be reflective in your life. You're supposed to journal and talk to people about things because you realize that some of the things you think are nonsense.

[Jordan Klepper]

Yes.

[Ryan Holiday]

But not everyone's doing that.

[Jordan Klepper]

That is. I think that's spot on. This is. For the most part, it's people who have only heard this talking point echoed from their friends.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

They're not talking to other people who are challenging them.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

And they hear a president who's often not challenged by the media in a way that they have to articulate a point of view.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

And so they just assume this thing that they're saying right now is just settled law. They haven't had to agree upon how they got there. They just agree upon it because it's been told to them over and over again. Repetition is their certainty.

[Ryan Holiday]

Well, that's the thing that the Daily show pioneered, that like sort of jump cut of the talking point across 50 different shows, local, national, different. And you're just like, oh, that somebody came up with that phrase and distributed it. And then people got it and it seemed it felt true. But it falls apart if you subject it to the slightest bit of scrutiny.

[Jordan Klepper]

Yeah. More often than not, I feel like I'm running a propaganda focus group where it's. If I go out there, like, I know what these talking points are. Let's see how they bubble up, how deep they've gotten. And sometimes they don't get as deep as you think they will. Sometimes there's conspiracies that the news talks about that doesn't grab hold anywhere. But you also realize a lot of this stuff does grab hold sometimes because it is. It answers some question people have. But more often than not, it's just the language, the words now that they can use to be a part of the conversation.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

I think that's where some of it is, where I get upset. I don't want to paint a picture. Like, I don't. But where I have that empathy is that I don't think you believe all of these things. This is just the admission of entry, is that you talk about these things now.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

This isn't who you are. You just like being here.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

You like feeling like you're a part of something. You like cheering for this guy. And all of your neighbors are doing that, too. And now we're going to talk about. Okay, now let's talk about inflation. You don't want to talk about inflation. You want to get a corn dog. You want to feel good. You want to watch the parade. And now some asshole from New York wants to talk to you about inflation. And so you're grabbing from the things you've heard about inflation. And you have to pretend, because there's a camera there, that there's a certainty you have about this, and this is who you are, but who you are is really somebody who. Who wants to be a part of a group, wants to cheer on that famous person who's right there and wants to. Wants to not feel left out of the conversation.

[Ryan Holiday]

Yeah. That's interesting. Yeah. You. You realize that the stuff trickled down from somewhere. And like, one of the things I. This metaphor I love from Epictetus, he was talking about how a really good money changer in the ancient world could take a coin and, by banging it on the table, tell if it was counterfeit or not. They knew the sound of the. The metal that had been diluted versus the one that hadn't. And you realize, like, some people are not good at that. And. And they. Or. Or they only get. If you've only experienced counterfeit information, then it seems real, because that's the standard by which you get pat. Like one guy saying something is, to you sufficient.

[Jordan Klepper]

Yes.

[Ryan Holiday]

And if you haven't sort of learned sort of the basic academic or intellectual rigor that we tend to apply to things, if you're used to, like, a Bill O'Reilly history book, you know. You know, you're not. That's not subjected to the same standards that a normal history book is.

[Jordan Klepper]

Yeah.

[Ryan Holiday]

And so it can ring true, but it's just woefully insufficient or it's very diluted.

[Jordan Klepper]

I also feel like we are. I mean, I know I'm 46. It's. I feel like I grew up believing that anything I saw published, written down, or on television was most likely true. That's where official words got distributed. And so I think I understand the digital age somewhat, but I still feel like I look at people who are specifically older than me, who believe that even more than I do, and something that they read online in any kind of format, to them is truth. That's sort of how it has always been, or at least how they've always understood it. And I think about places like Facebook where, again, the admission for entry for Facebook is that it's not that you sign up, it's that you publish. So these are not. They're not people who are communicating on Facebook. They're publishers. Your neighbor's a publisher. That person's a publisher. And you approach that information with the same veracity as you would, your neighbor's an idiot. Yes, your neighbor's an idiot. The dumbest person. You know, the only way they can talk to you is by publishing information to you, at you.

[Ryan Holiday]

It's weird, because I remember we talked about this when I was on your show. Remember the things my parents warned me about on the Internet, and the irony of that basically happening to them and their. Their generation. I remember I was talking to my dad one time, and he was telling me this thing that just from him telling it to me, I could tell was from the Onion, you know, and, And. And. And you go, oh, okay, there. There really is kind of just a media literacy issue here, or just a set of assumptions that don't work in the media environment that we currently live in.

[Jordan Klepper]

They were. They were afraid we would look at boobs.

[Ryan Holiday]

Yes.

[Jordan Klepper]

And they ended up listening to boobs. Now here we are.

[Ryan Holiday]

Well, they. They were afraid of scams. They were afraid of, like, radicalization. They were afraid of strangers. They were afraid of all these things. And that's kind of exactly what happened.

[Jordan Klepper]

Yeah. And then. Then they got time on and nobody to connect to, and so they jumped into this thing too, woefully unprepared.

[Ryan Holiday]

Yeah, well, that's. Yeah. The irony is, like, nobody has more time for social media than the people who are most vulnerable to it.

[Jordan Klepper]

I ran into some. Some lovely older ladies in Wisconsin and was. Was there to do a rally. And again, had an expectation at this rally that it was actually. It was. It was just after Roe v. Wade was being overturned. I thought people were gonna be really adamant to talk about that. And I show up in the Midwest. I'm from the Midwest. Show up in Wisconsin, and we see these sweet older women. I'm like, oh, these are some sweet old ladies. I wonder what they're gonna Wanna talk about probably Roe v. Wade, women's rights to some degree. And they immediately jump into conspiracies, concerns about who's Alive, who's dead, JFK Jr. Some wild, far fetched like hologram death stuff. And those are the things you don't prep for back in New York. You get out there and you're like, oh, wow, I had no idea. And in talking to him about it, you're like, oh, this is your ho. It's not knitting, it's not doing crochet. You guys are retired. You've gotten on the Internet and it's fun. And it is fun going down rabbit holes like that. You're discovering something, you have your own little mysteries, you talk to your friends about it. And this has suddenly become your hobby. You take it to a place where you suddenly become a publisher to all of your other friends and then you become an influencer to people at a political event. And you have the best hobby a 65 year old woman in the Midwest can have.

[Ryan Holiday]

Yeah, there's not a lot to, I mean, my grandmother would just watch church, you know, just a lot. And you go, oh, this is your board, you know, and it's this sort of intersection of the collapse of community and the rise of these sort of forms of entertainment. And you just become vulnerable to it

[Jordan Klepper]

and it's, I mean then it all becomes entertainment.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

And then you're like, oh, of course. Well that's, we have nothing but access to this entertainment. The news has become entertainment. It becomes the only monoculture there is right now is this big story of this big orange man who's affecting the world around you.

[Ryan Holiday]

Politics and Taylor Swift are the two things that everyone knows about.

[Jordan Klepper]

It really is. Everything else is niche. Yes, we could talk Trump or Taylor and people have an opinion on that.

[Ryan Holiday]

And football. Yes, those are our own. And you do realize, oh, these things are actually very, you need things like that. And what happens when everyone is in their own little world and we don't have things that we can. And I think you know, this is also like the monoculture used to be literature, like, and then for instance, for a while it was music, but like it was at least a form of art. And politics is important, but it's not art. Right.

[Jordan Klepper]

It is people's lives. It should be roads, bridges, things like that that are important. And I think there's also a misunderstanding as to what government is. When you, when you suddenly gamify it, you are so devoid of or so far away from that, that original intent.

[Ryan Holiday]

But if it was supposed to be literature. Then we're. And then we're even. Movies, Right. Are at least it's. It's art. So it's designed to teach and explain and put things up for everyone to think about. And then you have this kind of common culture that you can reference. And then when a huge movie is only seen by like a small fraction of the population, then you lack the ability to take these kind of references or have these stories that, like, bind you together.

[Jordan Klepper]

Yeah, you need that coffee. You need that water cooler talk. I've actually, I've refound sports. I mean, I was a sports kid. I was a fan, a Michigan kid, and played sports, loved sports. And as I got maybe deeper into the arts and moving away, I felt less of a need to follow sports. I became somewhat cynical about sports and about the fandom around all of that. And then I realize I lack in my life that community, that driving force, also that escapism. And I've refound that, especially in the last year and a half when I don't want to engage in the monoculture of the news. And I want to just, like, I want to feel something, I want to emote. That has very little consequences about what I root for, what I yell for that can put me a part of a team and connect me in a way that is really like. Like low stakes but high emotion. And I hadn't realized how much I was missing in the community that something like sports brings. We want to. We want to cheer. We want to be a part of something. We want to feel like we've won. We have crafted these safe spaces where you can do that and then you can walk away and it isn't your entire identity. And that has felt like, oh, for so many people and for me as well, like sports or politics has become that. And that's such a dangerous space to be in.

[Ryan Holiday]

Yeah. Although. And you could.

[Jordan Klepper]

It's also dangerous to be a New York Knicks fan, too. So there's, There's. There's problems there. You're going to be let down.

[Ryan Holiday]

Yeah. Although. And then I think you're also seeing some of the forces that tore apart these other industries happening in sports, too, where it's like, like, who can afford to go to an NFL game? It's crazy. Or I mean, even just league pass is like 500 or not league pass. What is it? Sunday tickets, like 500 bucks a year or something? And it's like, I got to another streaming service just to watch football. It's crazy.

[Jordan Klepper]

It's nuts. You can't afford to go in and watch it. And then also the politics that is in there. I feel like I've also shift my opinion on that. I want some of these people I root for to have opinions that perhaps reflect my morals and the way I see the world. Although living that is so gosh darn exhausting. I definitely have gotten to the point where I just want to see somebody who's really good playing basketball. You can say whatever you want, no judgment on what you have to say, but I'm not going to hold you to the standards that I'm holding my politicians to. I want to see you excel at this thing that other people cannot do.

[Ryan Holiday]

But yeah, I was just thinking it's like it used to be free. It was free to watch football and now it's $500 a year. I mean I'm watching more games but it is weird to think like it used to be free. And then it's like no league passes this. Then you're going to have prime on Thursdays and then you got. It's crazy how. Because what they figured out that if you break stuff apart then everyone can get a little piece and you have to have all this stuff. But it used to have antennas on your TV and you could watch it for free.

[Jordan Klepper]

And the process of it used to be more manageable. Like used to watch NFL on Sunday and college on Saturday and that's it. Monday Night Football was a while. Now I am literally coming here today. I'm seeing clips from. I was like, oh, is there a Thursday night game on last night? Okay, right now they have like two Monday night. Like what they've done with all with news, what used to be nice news in high school and college to read the paper, finish the paper. And it wasn't mostly college. I started to read the paper, finish the paper and then I had the news for the day. I never thought I didn't have to think about getting News for another 24 hour cycle. Now I can't stop looking at the news in the same way that sports. Instead of just like let me engage with the NFL for one day a week, understand the narrative of it all and then step away to other things. But they get your eyeballs, they want your attention. They want 24, 7 attention.

[Ryan Holiday]

Yeah. I mean I think sometimes watching sports it helps me understand the media cycle. So you're like. Like when I turn on Stephen A. Smith and he's manufactured a thing to have an argument about and then you go, oh, this is also what they're doing on Fox right now and msnbc. And it's obvious with sports you're like, wait, why? I like watching football on Sunday. The debate about it on Monday and Tuesday and Wednesday and Thursday and Friday has no bearing on whether it's on. What's gonna happen should the Raiders do this? You know, is so and so the blank or is this the blank? You realize they're just creating ways to discuss a thing or speculate about a thing that's not changing the actual thing. The game is at noon and it will be three hours. And no amount of talking beforehand or after changes what happens. And you can kind of see that more clearly in sports that like, oh, they're trolling you. And you go, but, but insert journalist. I like would never do that to me over the shutdown coverage or whatever, you know, and it's the. But it's the same hustle, basically.

[Jordan Klepper]

Oh, it's exactly the same hustle. And then insert journalists you like, who's struggling to make ends meet. And then journalist boss is like, well, the only way to do this is you also have to have a Persona.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

So you need to go on these television shows at night.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

And so journalist has to buy new cool outfit. And then it's like, all right, I want to go on here. Here' an eight minute chalk. You're going to talk for three minutes and if you're not as exciting as you need to be, you're not going to sell the commercials after the eight minutes. So be exciting. And then journalists. Hedges gets slightly more hyperbolic. And you just feel that and you see it. And just the systems in and of itself that we were getting all this information in the sports, they just feel so inherently broken. I don't see a way out of all of these things getting so warped.

[Ryan Holiday]

Well, I mean, the way out of it is to like watch football on Sunday. Yes. Right. Or, or to like read a book about something or to watch some kind of thing that is a summary or an encapsulation. But, but like I remember growing up, I think about this all the time. My friend's family, they watched Fox News so much it was burned into the corner of the tv. Like when you would change to watch something else, you could still see that the logo on the corner. Like, like no one, not even someone who is currently in elected office should be watching that much news. Right?

[Jordan Klepper]

Yes.

[Ryan Holiday]

You don't need to be doing that. And I think we have conflated that with being informed. But in a way that might be the most uninformed person. So I told you I was at this Airbnb here in Maui on this trip we took and oh man, the mattresses were not good. I did not sleep well, the kids did not sleep well. I wish that they had Helix Mattresses. If you've ever slept on a Helix, you'll know why so many people love them. Basically you take this Helix Sleep quiz that matches you with the perfect mattress based on your personal preferences and sleep needs. We've got the midnight mattress at our house. It's you know, medium firmness, not too firm, not too soft. And that's probably why it is their top selling model. Helix is the most awarded mattress brand tested and reviewed by experts like Forbes Wired. They've got free shipping, seamless delivery and the whole process is super simple. They deliver the mattress right to your door with free shipping in the US and you can rest easy with the happy with Helix guarantee that ensures seamless returns and exchanges risk free customer first experience. The Helix guarantee is designed to ensure that you're completely satisfied with your new mattress and includes a 120 night sleep trial and limited lifetime warranty. Just go to helixsleep.com stoic for 27% off. That's helixsleep.com stoic For 27% off. Make sure you enter our show name at checkout so they can know we sent you helixsleep.com stoic well, here we are well into a new year and it's worth taking some stock. Who do you want to be this year? What changes do you want to make? How could you be better? That's where today's sponsor comes in and it's where something I have been doing myself now I guess since college, which is working on myself with a therapist. And although I used to when I lived in la, drive an hour in traffic to sit down in someone's office for an hour. Now I do it on the phone, I do it while I'm walking, I do it in the car. I do my therapy online. And BetterHelp is the world's largest online therapy platform and I'm not the only one. More than 6 million people have gotten help through BetterHelp. It's just easier to keep the appointment. It's less of an imposition, cheaper, it's more efficient and I honestly find it easier to just get into the stuff you're there to get into when I do it remotely. BetterHelp will match you with a therapist based on your preferences. You can easily switch at any time at no extra cost. You can click the link in the description below. Or you can just go to betterhelp.com daily stoic to get 10% off your first month of therapy.

[Jordan Klepper]

You mentioned it earlier. It's that what we've. We've replaced reflection with, like, constant attention. And so, yeah, because attention felt. Reflection felt passive, or at least to me, can sometimes feel passive.

[Ryan Holiday]

Sure.

[Jordan Klepper]

I. I think back to, like, my. My college mentality when I was first interested in the world around me and getting information and the idea of watching the news in and of itself felt like eating vegetables, but in a way that was like, oh, the more that I do, probably the more in tune I will be if I watch the Sunday shows now. Well, now I'm more involved with the world around me.

[Ryan Holiday]

Smart people do this.

[Jordan Klepper]

Smart people do this thing. I will engage in the thing that smart people do. And I can do it full time. And now it gives me this. This Zhujian, this energy. And now I'm part of the conversation. But we do miss that. I watch it on Sunday, I understand it on Sunday, and I think about it for a few days, and I have my own opinions about it. That was actually the thing that I gave myself as an assignment when I had my own show where I was waking up every single morning, have to sort of craft what the show and the narrative was going to be. I was exhausted by the news cycle, and I just realized I would wake up so early and the first thing I would do is grab my phone and I just start looking at the news and start reading. And I was like, I had to put it down and say my first thought every morning was Maggie Haberman's thought. It was like, this isn't my thought. I'm reading an opinion on what happened. I have zero opinions on what happened in this day. I need to at least give myself an hour to take a freaking shower, think about something, and reflect and give yourself space to have your own opinion before it gets filtered in by somebody else's.

[Ryan Holiday]

And why are you gonna ruin your day before it started?

[Jordan Klepper]

I know, but still, that, that college mentality of like, well, I need all. If I don't have all the information, I can't be articulate about what's going on.

[Ryan Holiday]

Yeah. And the idea is like, the information is out there. What. Actually, what we need more of is more sort of insight or understanding about what it means. And most people are not cultivating the habits or the practices or the wisdom that will allow them to. To do anything about it or understand it or put it in its larger context. Like yeah. How many people even know how the system works but then are watching the negotiations happen in real time?

[Jordan Klepper]

Right. What do you do? How do you differentiate? Well, how do you find space to reflect that information?

[Ryan Holiday]

I try to read mostly books like I try not to watch any television news that. Yeah. I think. Have you read Amusing Ourselves to Death?

[Jordan Klepper]

No.

[Ryan Holiday]

I mean, the reason the Daily show is great is because it is designed to be entertainment. It's embracing entertainment. But his point that basically television is not a medium by which you can communicate intelligent thought is really as spot on as it can get.

[Jordan Klepper]

I think that book holds up as that is articulates our day and age as completely as you can.

[Ryan Holiday]

Yeah. And you realize, oh, okay, this is just not where I'm going to get good information.

[Jordan Klepper]

Right.

[Ryan Holiday]

And so I just try to think about like where is good information going to be found? It's probably, obviously I'm biased as an author, but like in a book, I'm having to work for a long time on something that I need to hold up, you know, because it's not going to come out for a year. So I've already, I'm already having to say this information has to have a shelf life up more than one year, then it has to be worth paying for. Right. It's not free.

[Jordan Klepper]

Right.

[Ryan Holiday]

And then it has to be worth the amount of hours that it takes the person to consume. And I think writing is a pretty unforgiving medium in that it. You have to spend a lot of time getting it. All right. So I have to spend a lot of time thinking like. So I just think about that as being the medium by which you're going to get the least sort of sensational and the most thoughtful and then the longest lasting information. So I try to, when I'm trying to understand stuff that's happening, I want to read about times where this has happened before or the underlying sort of influences of this thing so I can consume it and understand the basics of it in as least sort of partisan or incendiary or contemporary way as possible

[Jordan Klepper]

in regards to current events.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

How does that drip come to you? Will you. For instance, we have, we have a peace plan that is being worked out as we speak right now with Israel and Hamas. There's a lot going on. People are talking about it. Are you, are you going to places to find out about that? Are you curious about that? Are you blocking yourself off from that?

[Ryan Holiday]

Well, I think it's interesting, right. It's like they first started talking about it like three or four days ago. And then this goes to the sports thing. At some point, the deal will happen. But in the, the interim, five days are the worst days to find out what's happening. Right, Right. Because, like, it's changing. It's coming into existence. It's like, I'll meet your baby after it's born. I don't, I don't need to be in the delivery room. I want to. I obviously wanted to be there when my kids were being bor. But, like, the process was horrendous.

[Jordan Klepper]

I don't know. You could be a bad friend. You could use that logic. I'll meet him when he's three. All right? When he can walk. I'll get a coffee with him when he can walk and drink caffeine.

[Ryan Holiday]

I actually, I need to meet fewer babies and more older children.

[Jordan Klepper]

That's fair.

[Ryan Holiday]

But you know what I mean, the messy part is now I'm having to follow it like five or six times.

[Jordan Klepper]

Right.

[Ryan Holiday]

Like, I remember, I think I wrote about this in my media book where I was saying, like, you know, people are like, the great thing about Wikipedia is it's always being updated. It's like, yeah, but I'm not reading it as it's being updated. I'm only reading it now. So if it's wrong now, I'm wrong. Like, I don't.

[Jordan Klepper]

I'm not going back to see what people think about Sandy Koufax again and again and again.

[Ryan Holiday]

Yeah. I'm not checking in on this Wikipedia page as it's getting better. Like, it's got to do the job now. And so, so I just think, like, unless you run a hedge fund and your job is to speculate on news or you are in fact a politician who's in the mix on the thing. Although I do think it's interesting, like, whatever, you should be consuming as little real time information as humanly possible because it is of almost no value to you. You should find out what happened after it has happened, not as it's happening.

[Jordan Klepper]

Right. You don't need to fill up the hours of your day with speculation.

[Ryan Holiday]

Yes.

[Jordan Klepper]

And you can wait for information.

[Ryan Holiday]

There's a great Chuck Klosterman piece about sports where he is visiting a bunch of teams during training camp and he was amazed that they were watching ESPN like that they had. He was like, you would you think they have better information? But they don't. And there is something uniquely terrifying about Trump's media diet. Like that he watches a lot of news. The CIA put out this book during the first Trump presidency that was A history of how the different presidents have taken the presidential daily briefing, which is the greatest collection of intelligence in the world. And every president has had a different relationship with it. But it's like he prefers Fox and Friends to the presidential daily briefing. And that is terrifying because they are so far downstream from what is what we know, what is known by the smartest people. Like, this is intelligence paid for in blood and treasure. And he's like, but what is Pete Hegseth's replacement thing? And so I just think most people should not be consuming speculation about what's happening. We should wait until it's been figured

[Jordan Klepper]

out, especially if you're the commander in chief. I mean, I do think that's what's happening in Portland right now. Sending troops because of the things that he was watching, which was video from five years ago. What's curious about even hearing that Klosterman detail is what I imagine. And knowing politicians who are obsessed with being on television and watching television, like, I think they will tell you the story that they're trying to stay updated on the conversation, that they're watching information. And I'm sure that's what some of the sports stars might say is like, well, that's what I want to know. I want to know this prognostication. But I think they're watching it for vanity. They want to see themselves on television. They want to be a part of that conversation. That still there's this utter need for fame and to be reflected on tv. And that is, I mean, clearly that's. Trump wants to see people talk about him. He doesn't care about the information that's there as long as it's about him positively. It's not the information outside of it.

[Ryan Holiday]

Totally. The job of the leader is to be making big picture, long term decisions. So in a sense, they should actually be as removed from the conversation as possible. If you're gonna make great art, you shouldn't listen to what's popular right now. You should understand people, you know, or, or art historically. Otherwise what you're going to make is derivative and reactive. And it's like, weirdly, journalists and politicians should be, are, are the people who consume the most news. And they should. There's an argument, I think, to be said for them consuming the least amount of it.

[Jordan Klepper]

I think you're right. I think it's gonna be a tough sell for those guys.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

But I don't think you're wrong. Put them in, put them in padded rooms. Have them just think about stuff working

[Ryan Holiday]

together, which is it requires a certain discipline because it's so easy to default to it and you have to go wait in. Oi. You need to know it's background noise. Like you're aware that it's happening, but it can't be driving your day to day understanding of things because it's. It's. Yeah, that's the tail wagging the dog.

[Jordan Klepper]

Yes, we have a. It's. Functionally, at the Daily show, one of the most comforting things is once you get into writing the show is that you aren't aware of what is happening during the day. And again, we have to be immersed in the news cycle day in and day out and what's happening, but also how it's being told, which is overwhelming. And sometimes, especially when I did my first show, I found it very overwhelming because I had this idea that I need to know everything, which left no space for any kind of creative take on it. But you reach a point, and it's very early on, where we make some early decisions about what we think is important. And then you just become a creative space. And there are people who are aware of what the conversation is, but they don't need to update you on everything that happened. They update you on things that happen that are of import. And then so that that seven hour space where you're like, oh, we are just being creative about the things that we know is the most fruitful space that we have. And if somebody comes in the door and says, I mean, for a learned person, it would be something important that happened. For the Daily show, it's like, Donald Trump's penis fell out. We have to talk about this. And so it's like, stop the presses. There was a penis on tv. We must rewrite the show. So that's sort of our breaking news. But it gives us that space which is so crucial.

[Ryan Holiday]

I bet the time you're doing the show itself is probably some of the most present. It's like, you know when you come out of a movie theater and it's gone from like daytime to nighttime and you're like, whoa. You know, because you were like fully engaged in a thing when that's probably your, ironically, your least connected and most connected time. Because you just spent it with this group of people doing this thing, channeling your emotions and feeling into the performance, not being like, well, what are other people doing?

[Jordan Klepper]

And literally the fact that they're like, put your phones away. Yeah, something 200 people, we're here for 40 minutes, no phones, we're going to do a thing. I mean, it's remarkable.

[Ryan Holiday]

Yeah.

[Jordan Klepper]

Rare. I mean, in the performative world, it's such a nice thing, but it does feel like such a rarity. I mean, even in basic conversation with people and what have you, you rare get the luxury of a handful of people in a room where they're all actually listening to what's happening.

[Ryan Holiday]

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 it would really help the show. We appreciate it. And I'll see you next episode.

[Jordan Klepper]

Sam.