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The Daily Stoic

14 Nov 2026 · 1h 12m · 24 chapters

Episode artwork

The Hardest Part of Questioning What You Believe | Tim Miller

In short

Tim Miller (Bulwark) and the host discuss how to decide when changing your beliefs is courageous vs self-indulgent, and how political/media incentives reward “performative outrage” and audience capture rather than real engagement. They also debate moral responsibility: whether intentions matter more than results, and what it means to participate vs stay silent when you think a cause is wrong.

Guest backgrounds

Tim Miller is host of The Bulwark podcast and author of Why We Did It, described as a “Republican road to hell” travelogue. He previously had a successful corporate/marketing career before writing and political commentary. The other speaker is a Daily Stoic Live host and writer who says he also left a prior career for conscience-driven work.

Key claims

Online outrage is often manufactured for followers and profit; it can be disconnected from real-world offense. “You have to say something” because others will—yet some commentators can refuse to perform outrage. Coalition politics sometimes requires accommodating “fragile” or disagreeable people, but there are red lines (e.g., immigration “ice camps,” Islamophobia, anti-Semitism). Moral weight often falls on enablers, not only misled actors.

Notable examples

Twitter rage profiteers; Jesse Watters refusing to pretend outrage about Caitlin Clark/WNBA; Cheesecake Factory “offense” as performative outrage; Lincoln/Cato/Stoic examples; Vietnam-era Gulf of Tonkin and non-resignations; Scott McClellan quitting over Iraq; Kyrie Irving as a case of intention vs impact; Haley Stevens endorsing a Republican amid anti-Semitism concerns; RFK/Elon Musk coalition fragility; Trump monuments vs moral legacy.

Written by AI. May contain mistakes.

Chapters

0:55

Transitioning Careers for Conscience

Discussion on changing careers due to personal conscience and fulfillment.

“Talking about Tim Miller, he's the host of the Bulwark podcast, which I'm a big fan of.”
1:32

Navigating Audience Reactions

Exploring the impact of political views on audience engagement and business.

“I was hit very hard by his book, Why We Did It, a travelogue from the Republican road to hell.”
2:54

The Insular Nature of Online Discourse

Analyzing how online discourse can be disconnected from real-world interactions.

“Even if 50 % of people in England were lowercase c conservative, they're not 50 % Republican.”
4:06

Niche Content and Rage Profiteering

Discussing niche content creation and the concept of rage profiteers in media.

“I forget who I saw that first alerted me to the fact that people were upset about your pax simidelfinger thing.”
6:46

The Nature of Outrage in Media

How media content often stirs outrage for attention and engagement.

“And so, you know, and then whatever, 100 ,000 people that read your stuff and 10 ,000 people that pay you, like, that's a big audience.”
7:48

Authenticity in Political Discourse

The importance of authentic political discourse versus performative outrage.

“Like, it's a non event and they're trying to spin it into an event.”
9:06

Coping with Modern Media Challenges

Strategies for navigating today's media landscape without succumbing to outrage.

“You know, like, it's a horrible job to wake up and have.”
14:00

The Outrage Cycle in Media

Explore how media outrage is often manufactured and its implications.

“That's maybe an assumption that's like not in evidence that you can't not.”
16:44

Audience Dynamics and Authenticity

Discuss the struggle between catering to audience expectations and personal beliefs.

“Now you have a pension for what is the point of the power if it's always about preserving the power for some future day when you get the power?”
20:00

Fragility in Public Figures

Examine the fragility of public figures in response to criticism and its political ramifications.

“I wrote a book about Trump, about how I don't like Trump.”
Show all 24 chapters
24:07

Navigating Political Coalitions

Insights on the necessity of political coalitions and the complexities involved.

“And like, that is what great, I mean, Lincoln does this incredibly well during the civil war.”
28:00

Navigating Political Alliances

Explore the challenges of building coalitions across political divides.

“But just as a hypothetical, like that, I think would be a red line for me.”
29:20

Personal Political Journeys

Discuss the personal transitions in political beliefs and their implications.

“disingenuous was before I made the switch.”
30:40

The Complexity of Intentions vs. Outcomes

Examine the value of intentions behind political actions compared to their outcomes.

“So switching sides, like wasn't that hard.”
36:57

The Moral Weight of Political Decisions

Discuss the ethical implications of political choices and enabling behaviors.

“The people who are encouraging that person, but have doubts.”
39:10

Reflections on Political Failures

Consider the challenges and failures faced by those opposing harmful political figures.

“I mean, Scott McClellan, who probably any listener that's one day younger than me does not know who that person is.”
42:00

The Dilemma of Right and Wrong

Exploring whether to do the right thing is based on potential success or moral integrity.

“who we felt like we were doing the right thing and advocated and advocated strategies that we thought might be helpful for stopping him or containing him.”
44:42

Historical Perspectives on Failure

Discussing the failures of historical figures like Cato and Napoleon and their implications.

“Like we had this, somebody, it's weird how we know they, but somebody asked Napoleon about Cato and he's like, what should Cato have done?”
47:26

Cultural Lessons from Leadership

Analyzing how modern leaders like Trump and Musk influence societal values and behaviors.

“The fact that thousands or hundreds of years later, some of the specifics of that get lost and we go like, this is where Napoleon's mistress lived.”
49:42

Ambition and Accountability in Politics

Examining the dynamics of political ambition, accountability, and the consequences of leadership choices.

“like even if they're disingenuous, this goes back to the question about intention, like even if they're disingenuous about it, like that is an important victory for stopping kind of the cascade, I think.”
52:48

The Changing Landscape of Political Values

Reflecting on how historical events shape current political values and the risks of cowardice.

“I mean, what are they getting out of it?”
56:05

The Political Landscape of Courage and Cowardice

Explore how political bravery and cowardice have evolved over time.

“You know, you see this all through, you know, the World War II era, the civil rights era, right?”
1:01:50

Reflections on Political Identity and Power

Discuss the implications of political identity and the loss of humility in leadership.

“And like, I do think it requires a kind of a strong sense of self to be able to have that.”
1:10:01

The Impact of Personal Action in Politics

Learn how individual actions can have a greater impact than political discourse.

“And we should vote for those people and we should hold our politicians to that standard.”
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Transcript

Automatic transcript. May contain errors.

0:00Ryan Holiday: So I just got back from two weeks in New Zealand and Australia. I was on tour for Daily Stoic Live and we stayed in two different places in Bondi Beach. I would wake up every morning, go for a long run. And it's been one of my favorite places for like a decade and a half. Actually, it made me think while I was there that the very first time that my wife and I went to Australia, part of how we paid for that trip was we listed our house on Airbnb while we were gone. That was something we would do back then, especially as I was making that transition from marketing, my corporate career to writing, is that when I would travel for talks, we would list our house on Airbnb.

0:35Ryan Holiday: We had this little house in East Austin, and that's how we covered the mortgages. When we were gone, people would stay in it while we were out of town. If you have space and you're going to be away, maybe that can be a memorable place for someone else to stay. Your home might be worth more than you think, and you can find out how much at Airbnb.com slash host. My guest and I today have a lot in common. Talking about Tim Miller, he's the host of the Bulwark podcast, which I'm a big fan of. We have similar stories in that we both sort of turned our backs on the life career that we had before, that we were successful in, but at some level didn't sit right with our soul.

1:14Ryan Holiday: But much more interested in that sort of turn, that story. How do you decide to make a big change because of your conscience? How do you know when it is courageous and right as opposed to self-indulgent or irrational and impulsive? I was hit very hard by his book, Why We Did It, a travelogue from the Republican road to hell. And he and the bulwark have a bunch of great sub stacks and newsletters, which I subscribe to. And you should, too.

1:51Ryan Holiday: you know what's weird about twitter is it's like because i'm not on it at all yeah and so like they'll just tell me that like this thing yeah it's actually an illustration of how insular and crazy that world is that it can happen and not do like it doesn't bleed over to real life like at all right you're not even aware yeah i mean do you we've talked about this before but Like, have you seen any, like, dip in audience because, you know, of people mad at you over various politics? I mean, I'm sure. I don't know how you would measure it exactly. I mean, I'm sure it's not good to say things that some people don't like.

2:30Ryan Holiday: Like, if it's a percentage of the population and a percentage of people don't like, I'm sure that's not great for business. The thing I always find funny is people go, like, you're going to piss off half your audience. There's this weird, very American view that, like, first off... everyone who consumes everything is evenly split. Democrat, Republican, or Trump, no Trump. And then also that the rest of the world doesn't exist. Because it's not 50-50 in England. Right, sure. Even if 50 % of people in England were lowercase c conservative, they're not 50 % Republican. So there's this weird thing where people think you're somehow committing career suicide.

3:11Ryan Holiday: Because you do a lot of global stuff. I don't even talk about that. Yeah. And like, I think people forget that if you don't speak up about something because you don't want to piss off a percentage of your American audience, you'll piss off part of your international audience. It's like, like, imagine if you're a Canadian and you're a fan of my stuff. Right. And you never mentioned what's happening here. Yeah. And so if you're an average Canadian and you just assume that like someone you're reading in the U.S. is a fan of an authoritarian strongman saying he's going to turn your country into the 51st state.

3:47Ryan Holiday: Like that's also bad. Right. Yeah. It's not just bad for business. It's just genuinely bad. And you should say something. Bad soul work. Yeah. I'd be curious because you probably saw you probably recognize some of those people that are getting angry. I have no conception of who these angry people are. Do you know what I mean? Like the sort of professional Twitter shitsters. Yeah, I forget who I was. Was it Will Chamberlain? I forget who I saw that first alerted me to the fact that people were upset about your pax simidelfinger thing. Yeah, man, again, I do think that there is a category of people that really follow all this stuff like sports, you know?

4:29And there are people that fit every niche. You know what I mean? Like we've had lately this weird uptick in like people kind of from the DSA left influencer class like going after us. Yeah. Because not really me, but like some of my colleagues have, you know, aren't really huge fans of Abdul and, you know, I've picked on various things that some folks have said. And it's like, I don't know, like you said, the gap between that and the real world. Like I was at a No Kings thing in New Orleans and a guy comes up to me and he's like, you and Piker are my two favorites. Ostensibly opposite people. Within this coalition, there's this huge like discourse online and I've talked to his son and like, you know what I mean?

5:14And so I do just think that there are people that both pick a tribe like Blue Red, but then within that, pick like, I'm the nationalist conservative, I'm the pro-Israel conservative, I'm the socialist liberal, I'm the moderate liberal. And they get in fights, and their business model is getting in fights online, and cooking fights and finding outrage. You know what I mean? And they do have some followers, but it's in the grand scheme of things. It's not huge percentages of the electorate or anything.

5:48Ryan Holiday: I think that's the thing that people don't know about. Just in the way that there's like somebody specializing in every niche you could possibly imagine for content. Like, oh, I'm going to be like a woodworker. I'm going to be this. All these different niches that you are like. You're amazed that someone just makes content about like fixing lawnmowers or whatever, right? Because somebody somewhere, they don't realize that there are people who just pick out insane niches that like it wouldn't actually exist on paper. like trad wives, right? Like, obviously there are some trad wives, but it's like, hey, I'm going to pick that character and perform as that person.

6:22Ryan Holiday: And then that's going to be my social media business. And there are sort of like, I think I call them rage profiteers in my first book. Like their job is just to pick the most outrageous position that that character would take and then profit from the anger and the attention that comes from. And you don't need that big of an audience, right? Like, if you have 10 ,000 people who pay you 10 bucks a month or whatever, I mean, you can do the math there. Like, that's a seven-figure job. And so, you know, and then whatever, 100 ,000 people that read your stuff and 10 ,000 people that pay you, like, that's a big audience.

6:55And it looks big online. Like, in the grand scheme of things, it's not that big. You know what I mean? Yeah, yeah. That's a small town in a big country, right? Yes. And you see this in the Abdul discourse. There's this pullout today in the New York Times where it's like, among Kamala Harris voters, he's up 96 to two. And like, you have all this conversation happening on social media and on cable news, like about the two, you know? And, and I just like, that's, it is the job to try to disentangle, right? Because that's not always true. Like sometimes if people are really mad about something online, it is reflective of something that's happening in the broader society, you know?

7:32Ryan Holiday: But it's like, their job is to take, just in the way that like, I think you see this very clearly when you're watching sports, where it's like Stephen A. Smith wakes up and he's like, Like, what's the take I can have that will be outrageous isn't the right word, but most counterintuitive or interesting. And then somebody else is taking me and that the job is to just sort of create the conversation where most people have no opinion about this whatsoever. Like, it's a non event and they're trying to spin it into an event. And and like you're watching people do that professionally. And then so you think like, oh, I'm trending on Twitter.

8:09Ryan Holiday: and it's like no no just some people chanced upon your thing and decided this would be good for them to have an opinion like i don't think anyone was actually offended that i don't like ken no of course not no i mean i think that what uh you know i mean maybe his daughter or something like weirdly is campaigning with him but like crazy but i you know what those guys are doing then think about the business like what was i just talking about like okay to have a good life you're trying to get 10 ,000 paid subscribers, right? So if they host that and they find two Ryan Holiday fans who liked your books, read your books, who are Daily Stoic fans, but also are for Ken Paxton, you know what I mean?

8:51Then they think, okay, I can accrue those two guys. You know what I mean? Like, I'm going to... And like, that's good business for them, but like meaningless in the broad scheme of things. You know what I mean?

9:03Ryan Holiday: But also just bad for the world. I mean, it's a shitty thing to do. Oh yeah, horrible for the world. You know, like, it's a horrible job to wake up and have. And some people have decided that, like, yeah, my job is to have basically destructive political takes to get attention. Sort of like, how can I appeal to the worst in people, the most retrograde opinions? And, like, because there is a percentage of the population that would like to have that part of their brain scratched. It's the fakeness that bothers me. I actually almost don't even mind. Like, if people have genuine retrograde opinions or genuine bigotries, then that's actually worth hashing out.

9:42You know, like my view on my show on The Bullwark is, and I said this after, when did I make, I came to this decision actually after the Biden debate, because there are a bunch of people that were kind of in my camp, like more moderate type people that liked Joe Biden, that like after that debate were on MSNBC or on social media. trying to spin it, saying stuff, and then kind of getting mean, getting mad at the left, people criticizing him, like they're trying to circle the wagons around him. And there were a couple specific examples of people who did that publicly and then would call or text me and have the exact opposite opinion.

10:22And I was just like, sorry, you're not on the show anymore. That's not what I'm trying to do. I actually don't care. And so that's why it's hard for me to find MAGA people because I think that a lot of MAGA people, whether it's your middle finger thing, whether it's the Cheesecake Factory, pretending to be upset about, like, the business on the right is a lot of fake outrage. There are, though, genuine, like, the idea of America First right-wing conservatism is a coherent ideology. It's not mine, right? And so there are some of those folks out there, and I do try to have them on, right? And, like, and hopefully that helps in a small way of, like, you know, if we can raise votes of, like, the authentic socialists and the authentic America Firsters and the authentic classical liberals, and have a discussion, like, okay, like that's at least a more healthy environment.

11:08I mean, it's hard though. It's like a whack-a-mole situation.

11:10Ryan Holiday: It's interesting to me how similar those people turned out to be, you know, 10 or 15 years ago, the sort of feminist blogosphere that would just get offended about everything. It was sort of professional, like pearl clutching, which ironically leads to this sort of cancel culture and then some of the PC backlash that we have. how similar the sort of right wing ecosystem is to that now. Like, because I don't think a single human being was offended by the Cheesecake Factory joke. Right. But like the system says, no, no, no, we can't leave that there because we might be able to fool some people into being offended by it.

11:47Right. I mean, this started, well, it started way before this, but this was like super acutely after Charlie Kirk was killed. And I was on the side where I thought that like there was some horrific rhetoric around that. And, you know, I just was like really grossed out. And, um, I understood people that were fans of his or admired him that were like really mad about like kind of the reaction to that in some quarters. I do under, like genuinely mad. But then it kind of evolved into this thing where it was like, if you are a teacher at a school in Arkansas and you posted on Facebook a meme, it's like maybe a little over the line, but kind of fine in the grand scheme of things.

12:32Or even, forget a meme, even posted something that was like just, I thought that what he stood for was reprehensible or just kind of opposed his ideology. People started coming. It was literally the inverse of what they had complained about during, you know, kind of peak woke. Right. Like they started coming for people and trying to get them fired and canceled over like having opinions that were, you know, maybe a little rough around the edges or maybe not. And in a lot of cases, like not. And so and like now, I think that was kind of a serious version of it where you could see how they were totally bad faith in all of those criticisms of because they just wanted to use that power against their foes.

13:11And like, that's a serious example. Then the Cheesecake Factory is like the performative version. You know what I mean? I'm like, no one is actually mad about this, but we have to do it to feed the beast.

13:20Ryan Holiday: But yeah, it's economically the incentives make it impossible to not pick up the thing, right? It's like there's money laying around. And by choosing not to be offended, you're choosing not to pick up those followers, right? It's like they can't not do it. When the model is, I chase what's in the zeitgeist, you're not actually a free actor who sort of has real opinions. And like, there's this sort of audience capture. Your audience is this sort of angry group of people who want to be angry at certain other groups of people. And you can't not say it. Because someone else will say it. Yeah, that is true that someone else will say it.

13:56I do think, though, that... That's maybe an assumption that's like not in evidence that you can't not. Just one example recently I saw is Jesse Waters, who I don't like a lot. was on TV and Fox was doing this thing this summer where they were getting really outraged about fouls against Caitlin Clark and being like the refs are biased against her and WNBA's racist and then so become... And finally, I think there were like three or four days in a week where it was on the rundown of his show and Jesse Watters on Fox just goes, guys, I'm not... I'm skip... You can skip me. I'm not going to pretend to get outraged about this.

14:36I don't watch the WNBA. I'm not going to pretend to care about this. And that clip did pretty well, I saw online. And I don't know, like I, you know, on our side, on the Trump stuff, like one thing that I said after the 2024 election to the audience was I was like, there's gonna be a lot of stuff to be outraged about the next two years. I'm not going to pretend to be outraged about something I'm not. Like Trump does something. Trump makes fun of John Husted's ass. And like, I'm not going to talk. I'm not going to like, you know, start rending my garments about how the office of the presidency is being sullied.

15:06Like, you know, there's stuff to be really upset about, you know, with the internment camps and et cetera. We could talk about them. But like, people appreciate that. And I don't know. I even think that there is not as big of an audience on the right, but there would be an audience on the right, I think, for like a genuine America first kind of commentator. But I just think it's like, it's too easy not to do it. You know what I mean? These guys all take shortcuts. You know, they all take shortcuts because it is easier to do pretend outrage. And, um, and so it's, we don't really know. You know what I mean?

15:40It's kind of like, I would like to see somebody that is talented try it.

15:45Ryan Holiday: Well, I always think about it. It's like, do you have an audience or does the audience have you? Like, are you talking about what you want to talk about, what you think is important, or are you playing to the crowd? There's actually, there's actually funny, there's a line in Mark Sreos' meditation. He says, I'm up on the stage and he's like, I can sort of feel what the audience wants and they want me to do demagoguery, right? And he's like, just because the audience is stupid doesn't mean you have to be stupid. And he's just reminding himself that he gets to decide what he says. And I do think people struggle with that.

16:17Ryan Holiday: I think people struggle with the idea of like, hey, I think it's very true on the audience side. Like, hey, I worked really hard to get this podcast or this book or this sub stack or whatever it is. Like, I'm the one that decides what goes here, not like what's trending. And then I think you see this on the political end where it's like, what exactly did you become a senator for? Like, why did you get a job where you have six years of job security or, you know, you do a number of terms in the House. Now you have a pension for what is the point of the power if it's always about preserving the power for some future day when you get the power?

16:56Yeah, I kind of, I'll be curious what you think about this, because there is something about human nature that makes it hard to buck this. You know what I mean? Like, you really have to try. I give myself, like, I see the comments, you know what I mean? I know what people's feedback is, I see the stats, I know what types of episodes people want, you know what I mean? And so you have to try, and I will find myself, I work really hard not to do this, but I will find myself, like, pre-budding my argument if I know that there's gonna be some segment with the audience that doesn't like it. And I really try to not do it.

17:28Because the type of person that comments is different from the whole listener base. And a lot of times, you know, like episodes that the commenters complain about the most are the ones I get the most texts from, from like my college buddies. They're like, I liked that episode actually. And so it's good to serve both. But like, I, you know, have been in therapy and have a decent sense of self, and I'm like really trying. You see how people lose it. And then like on the politician side, like we just have this Haley Stevens story this week. I think it ties to Fetterman, ties to a lot of these Democrats who buck the party on certain stuff, big time on Israel, but also on other cultural issues on transgender stuff.

18:05They get really negative feedback over it. Aggressive negative feedback, particularly on social media, particularly in their mentions. Sometimes at grassroots events, they'll get booed or whatever. Haley Stevens mentioned this when she talked about endorsing Mike Rogers. At the first press conference, she's like, I was booed at a Democratic thing as if that is the reason to endorse somebody from the other party. But like, that is just obviously part of their part of, you know, what is pushing them away from the Democratic coalition. They are overreactive to negative feedback from people and they struggle to process it.

18:42And the other side's just like, all right, well, come on over here then. I do think that's a really human.

18:46Ryan Holiday: Isn't that the Elon Musk origin story that he wasn't invited to like an electric vehicle summit? It's like you're the richest person in the world. And not getting invited to a thing that you probably would not have enjoyed going to is going to flip your entire ideology. Yes. It's insane when you say it, but people say it like it's not insane. Yeah. What is that, though? I think there's a fragility, and then I think it starts like a cascade. You're pissed, and then you're seeing all the other slights you've been enduring. Yeah. And then I do think the come over here, the water's warm is a very attractive thing to people.

19:21I simultaneously think this is a fragility and it's a weakness. And I kind of want to mock them because whether they be the senator, Elon Musk, because it's just like, guys, you know, who cares if some people don't like you? That's part of the business. You became a public figure, you know? And now you're going to totally throw in with people who are anathema to your stated political views before. So you want to make fun of him. On the other hand, I do look at Trump and I think, this is a good political skill. I mean, there's not much I have to compliment Trump about, but if I, like right now, said, Ryan, this has all been a joke.

19:59This is all with my whole why we did it. It was all, I was all wrong. I wrote a book about Trump, about how I don't like Trump. And, you know, I've been watching him this year and I'm so impressed with the reflecting pool. And like in my back right there, I've got a MAGA hat and I'm doing a heel turn right now. You could join the club right now. boom, he'd invite me to Mar-a-Lago right now. And like the Democrats don't do that. And I almost feel like there's some middle ground there where it's just like being so rigid that you're not welcoming to people if they have views you disagree with is a flaw.

20:28And obviously the Trump thing is like, because he has no principles. So that is revealing of an underlying weakness that he has, but that serves him politically.

20:38Ryan Holiday: Well, I think it's particularly clear in politics is politics is coalitional, right? Especially in the United States, you have to create this coalition of different figures. And it's usually whoever has added one or two new coalitions that because politics are so evenly matched in the US. But I think sports is a great example of this. Like in my book, An Ego, I wrote about Kyrie Irving and LeBron James. I think it's so fascinating that like Kyrie Irving basically blows up the Cavaliers because LeBron James gets to like travel with friends on the team plane and he doesn't. Like he's like, I'm rookie of the year.

21:13Ryan Holiday: I'm the guy. And then you came here. Yeah. And then everyone's like, LeBron James is amazing. Now, I think as an outsider, as a fan, you're like, what a fragile little baby that you blew up this team for that. But as far as like an organization goes, and as far as LeBron James goes, this was a huge mistake. Like, sometimes people in the team are fragile and need handholding and you need to be, it's like Kyrie Irving's ego blows up the team. but also LeBron James's ego of not being aware of what it's like to be LeBron James and to come into town and overshadow someone. Like you have to have the ability to soothe those kind of ruffled feathers and bring people in.

21:53Ryan Holiday: And like, he didn't do that. And he's like sort of surprised that this guy's mad and hurt. And I think like what great leaders do, and you see this in sport, like sports, I think one of the reasons you sometimes see people in sports be a little bit more sort of Trump accepting than you would think is that their whole life is around making accommodations for completely crazy people who they think can serve their purpose in this one area. So the idea of like writing someone totally off is like, it makes sense like in real life, but like in sports, like, again, this is both a failing and a reality of sports where it's like, this person could be a monster but if they can you know if they can run a good passing route you'll you'll bring them back and so so i think there there is something in in life and leadership that's a little bit of a tricky skill that sometimes like the crowd is not good at which is like how do you forgive accept accommodate adjust for these types of people it's hard to know where the line is too yes you know what i mean like you mentioned elon i mentioned rfk I think about this like probably once a month.

23:01I just am like, Kamala really should have tried to butter up RFK. I mean, she's from Brentwood, you know, they're both LA life, they probably have some celeb friends, throw him a bone on something. He was right about some things, about the food supply and healthy eating, ignore the vaccine stuff aside, like throw some of its quackery aside. and you know in the grand scheme of things maybe indulging the fragilities of Elon Musk and RFK would have led us to a place where we don't have measles back right now those are two big pieces of the coalition and maybe it wouldn't have worked though you know what I mean you don't know it's a counterfactual like maybe those guys had become so you know consumed by their resentments like there was no amount of coddling that was going to help and I think that's possible but i do feel like in retrospect it was kind of worth the worth the efforts and that is

24:03Ryan Holiday: like not my nature at all but it doesn't have to be your me as the individual i can say fuck rfk i would never have them on my pockets and i and i tell any of my friends that do that i think it's a colossal mistake to platform this noxious terrible person with an ungodly amount of blood especially if you are prepared to challenge yes exactly that being i am not in charge of a political coalition though. Right. And like, that is what great, I mean, Lincoln does this incredibly well during the civil war. Like, like he could have easily written off the border states. He could have written off some of the sort of copperhead democratic politics.

24:37Ryan Holiday: He's, he understands that he can't afford to lose one person. And like, even his cabinet is full of like snakes, basically like call it team of rivals, but some of them are like actively plotting to take the presidency from him. And he's good at keeping them in there. I think Churchill was good at, at these coalitions, like politicians. So the Lincoln thing, though, I'm sorry, I have to history nerd on you for a second, though, because maybe he overdoes it, though. And yet he replaces his VP, who is anti-slavery, the first VP, for the reelect, and replaces him with Andrew Johnson, who is a racist, thinking that that will help expand the coalition.

25:17He gets killed. Johnson becomes the president, and the reconstruction nightmare happens, had it been Hamelin that But maybe he doesn't win re-election, right?

25:25Ryan Holiday: Maybe that's exactly the argument you're making, which is like, would Kamala Harris have been better off winning the election, having promised RFK a cabinet spot and then immediately firing him when he proves himself to be a cook? I was going to promise him a cabinet spot. I was going to give him something. Right? And like, that is a skill. I mean, the Lyndon Johnson line is like, do you want Hoover pissing out of the tent from inside or do you want him pissing inside the tent from outside? That is the skill of politics. Yeah. And like some people have that skill. The people that don't, like people like me, should not really be in politics.

25:58Ryan Holiday: That's why we're podcasting. Like my job is to write about things, I think, with a kind of like moral clarity and straightforwardness. And that's different than the art of politics, which is deals and compromises and working with personalities. I mean, I do think that that's right. And I don't know though, like, we're in a moment right now where just there are a lot of moral kind of red lines that get crossed and you have to navigate that stuff. You know what I mean? And you have to say, okay, what is too much for me? I got to, like thinking about the Hailey Stevens thing the other day, she is concerned, her stated reason, is concerned about anti-Semitism.

26:39I don't know, to the extent that that's genuine or not, let's just put that to the side. But her stated reason for basically leaving the Democratic Party and endorsing this Republican is anti-Semitism. And I'm concerned about rising anti-Semitism. I think it's real. I definitely think that there's rising anti-Semitism in the country. When I was posting about this on social media and commenting about it, I was like, okay, but to endorse somebody on the grounds of like you're opposed to bigotry and now to go endorse somebody else. Who is a bigot. Who is trafficking in Islamophobia and over and, you know, and has had RFK campaigning for him, talking about how Arabs are stupid and all this stuff.

27:13And also who would be a vote to fund Trump's like ice camps, which is everything else you believe. Everything else you believe. Right. But like for me, like the ice camps, like is really just something that I do personally deeply care about and is a red line for me. and so you know and i so i posted that and you know some of the whatever some of the right-wing people that don't like me were like this is fake you don't really care about these camps and whatever you're just looking for an excuse to be for abdul and i'm like no this is really aligned for me i feel it'd be very tough for me for if like a politician this politician isn't going to exist but just hypothetically like emerges in 2028 and they're like hey i agree with tim on everything except i do want to keep the camps you know like i do like the mass deportations worked Like Trump has done really well on immigration and I'm a nationalist and, you know, that person doesn't exist in our world.

28:00But just as a hypothetical, like that, I think would be a red line for me. You know what I mean? And so like those things have to exist. And, you know, Elon has certainly crossed that in a lot of ways. And I think that the next Democratic nominee is going to have a lot of tough questions on that challenge of like, how do you build a coalition back together where you have to grow Kamala's coalition? You have to gain people that work for Trump. And all of them are going to have some type of pretty icky either association or track record or policy past.

28:32Ryan Holiday: That's tough. But you've had to do that. Like in 2016, right? Like you had to, you basically switched parties. Sure. And so how do you think about that? Because I see some of these people and sometimes I wonder if I'm being unsympathetic or if I'm being hypocritical where it's like, because you and I have this in common where we sort of like turned our back on our old profession or some of the people that we used to know. and like it's hard to know whether it's sincere and genuine and i just disagree with them or if it's hypocritical and malicious or sort of profit driven right like and you don't you don't know yeah i mean there were a lot of hard elements of making that switch like this kind of moves into more of an easy element which was the like the the period of time where i was faking and being disingenuous was before I made the switch.

29:27You know what I mean? Like, I do think that there are some, and I think people misunderstand this about me, like, you know, a funny thing that when I support some progressive thing, people are like, you used to be a principled conservative. And I was like, that's actually not me. That there are, those people exist, George Will. Like, they're definitely, I've got some colleagues like Mona Charan. There's some people that are, were conservative, believed in social conservatism and limited government. And they opposed Trump, not really on policy grounds, but on character grounds, and had to make real concessions to go along with the Democrats who disagreed with them on whatever that would be, abortion or size of government or foreign policy.

30:03You're Lynn Cheney's or whatever. Yeah, yeah, Liz Cheney. It was a great example of that. That wasn't really me. That's what I write about. I was a hack. I liked politics because I liked the game of politics. I liked the sport of it. And I ended up coming in the form of Trump face-to-face with like the like most outlier worst possible outcome of my idea of my ideology and actions. And I got to, you know, not everybody's as lucky as that, right? Like they get to see, you know, what damage like my own failings might lead to and cause. And I was just like, no, like, no, I don't want to be a part of that.

30:40Right. So switching sides, like wasn't that hard. Like, sure. Do I disagree with the Democrats on some stuff? Like, absolutely. But like, not any fundamental, like deeply seated principled issues, right? It's like, it's kind of differences of kind or character or like size and scope of government, right? Sure. And so, you know, that journey is like a little bit different than what somebody, like I mentioned, like a Mona Charan would have to do, who's like trying to, okay, I'm trying to judge what the extent of my concessions can be from my principles. And I do think that Democrats in 28 are going to have to face that challenge a little bit.

31:20Yeah.

31:20Ryan Holiday: No, it's hard when you see someone taking an unpopular or controversial stand or they're leaving what was comfortable and supportive and going. So I admire it on one level, but also you're wrong. Like again, I think you saw this during the pandemic. Some people got a little bit out there, not a little bit, very out there on their sort of conspiracy theories and you're like they same thing you were asking me like do you think about like whether this would cost you to say i'm sure kairi irving is like thinking about like hey this could cost me my nike deal it's going to cost me a season playing for the nets and he's like willing to do it anyway on some level you admire that also like you could not be more wrong like you could just not be more wrong like like you're just you're an idiot that's your problem like i I was thinking about the Haley Stevens thing watching it.

32:09Ryan Holiday: Like, I can't imagine that was an easy decision. Or do you think Robert E. Lee pacing his house and he's like, do I side with my state or do I side with my country? You know, like you put aside the monstrousness of the issue that's putting those two in conflict with each other. And you can empathize if you've ever had to make one of those like, I'm going to go out into the wilderness decisions. Yeah. And then also though, like, is it, is it actually admirable in the abstract or does it have to be correct? That's what's hard about it. Makes it hard to judge. Yeah, this is related to something I really try to grapple with a lot, especially and have been during the Trump era, which is like the extent to which intentions matter, you know, or whether like the results or the, you know, your stated views in the case of Kyrie Irving matter.

32:57Like, did Kyrie influence people in a way that made them risk their lives? Like, does that matter, that result? Or does like the intention that you're discussing matter? And, you know, I think because people ask me about like Bush a lot vis-a-vis Trump, I struggle with it. Because I'm like, well, on the one hand, I think that W really did believe the kind of maximal... It's hard for people to actually believe this, but I think he believed, in his heart of hearts, the maximalist version of neoconservatism, which was like, I'm going to bring freedom to these people around the world who are suffering right now under authoritarian regimes and under Islamist regimes or whatever, and we're going to do that using the military.

33:38And I think he believed that it was going to work. And it was a disaster. And it caused unimaginable pain and suffering, both for people there, but also our soldiers. Probably led to Trump, right? Ropes of world. Seriously. And so it's like, well, so does his intentions matter at all, actually? And then you look at Trump, and this is more true about the first term than this term, because he's causing unbelievable lots of damage. He's got two years left. But in the first term, it was like, okay, up until COVID, at least, in particular, It was his intentions were horrible. Yeah. And he was corrupt and he's lying all the time.

34:16And the actual result of his policies did not cause the pain or suffering of people that was equal to the Iraq War. And so it's like, okay, well, which is worse? And I always was somebody who very much thought the intentions matter. And my confidence in that got a little shaken during the last decade.

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35:25Ryan Holiday: My favorite thing about shopping about Wayfair is the reviews. You know, you buy stuff online sometimes and then you get it and it's way smaller than it looked or it's garbage. You know, you want to see real photos from real people so you know what you're actually buying. When refreshing your home this holiday season, Wayfair delivers exactly what you need. Head to Wayfair.com to shop all things home. W-A-Y-F-A-I-R dot com. Wayfair, every style, every home. I grew up in Sacramento, going to Lake Tahoe. And one of the things I'd always noticed is that there were like brands that the locals knew and used, like people who actually they're not tourists.

36:01Ryan Holiday: And then slowly but surely it'd catch on with the rest of the country. And there's a brand that is out of Jackson Hole, Wyoming. They'd been at it since 2011. 15 years in, the locals are still loving it. And now it's spreading. I just got a new jacket from them. Samantha got one too, like sort of a puffer down jacket. I've been wearing it because we've been traveling a lot. I was over in London. Even in Australia, we took the jackets because it was getting spring there, but it was still cold on a couple of days. And it's been great. It goes right in the suitcase. Easy to fold up. And, you know, ski season being here, you can gear up now the way locals do.

36:44Ryan Holiday: Go to stio.com slash stoic for 20 % off your order. That's stio.com slash stoic. S-T-I-O dot com slash stoic designed and tested in Jackson Hole. Well, I think what that brings up is if that person is a true believer or is sincere, but maybe stupid or crazy or just not getting good information, then the moral weight of it actually falls on the people who are somewhere in the middle. Right. The people who are encouraging that person, but have doubts. right like I've been so this book I'm doing now is all about Vietnam and like the interesting thing about Vietnam is all the people who knew and didn't say anything just all along the way like all the way down Johnson basically sees what happens in Gulf of Tonkin he's already pre-written this resolution and he uses this thing as an excuse maybe he thought it in the moment that something was happening but within days he is very aware that nothing happened yeah And he said, but I already got the thing.

37:50Ryan Holiday: Congress already gave me the green light. I wanted to do like, but he's not the only one that knows, but nobody's willing to say anything. And so like McMaster's points out in his book, like not a single member of the Joint Chiefs of Staff for like 15 years of the war resigns on principle. Like people who thought the war wasn't being executed harshly enough and people who thought it was lost and needed to be, not a single one resigned on principle. And so they're all knowing that the thing is not going to work and that it's not working. But everyone is preserving their access and power and reputations.

38:28Ryan Holiday: And they ask one of the Joint Chiefs, they're like, why didn't you resign? And he said, well, it would have been a story for a couple of days. And then I would have been not on the Joint Chiefs of Staff anymore. So like everyone is saying, like, I'm not stepping up and saying something because I want to prevent something worse from happening. And then you're like, but Vietnam was the worst thing. It could not have gone any worse. Okay. Like millions of people died. It was the worst thing. Yes. And so there is this, I think the real moral weight of it is not the bad actor or the misled person, but it's all the people that enable that person or continue to mislead that person because they want Twitter followers or they want to be press secretary or whatever it is on that line.

39:11I think of a Bush-Iraq example. I mean, Scott McClellan, who probably any listener that's one day younger than me does not know who that person is. But he was White House press secretary. He does quit over Iraq. Yeah. Quits, doesn't want to spin it anymore. I think I'm right about this. I'm going from memory. I'm pretty sure Ari Fleischer, who is just still an awful hack to this day on Fox, replaces him. There might have been somebody in between. But McClellan quits, and I'm at the beginning of my career at this point in Republican politics. and Ikea like the things that people said about him at like parties in DC and it was nasty like people were horrible to him he ends up I wish if I knew we were talking about this I would have prepped this but I think he ends up I want to say at like a seminary school or something like definitely some type of higher educational thing and like kind of just reboots his life and I'm like this is an underrated kind of hero of the Bush era now.

40:08And in my formative time in politics, everybody was like, they use all these other moral words to try to make him seem bad, like he's a traitor, or he was kind of a dick about it. I think he was. Or he released private correspondence and that showed him to be not trustworthy. And so you can see how people like cloak and rationalize like not doing the right thing.

40:35Ryan Holiday: And that's also how they disincentivize other people from doing it. By making it impossible for that guy to have a soft landing. Right. They keep other people in the plane, so to speak. Yeah. I think this is an interesting question that I've been thinking about on the book that I'm working on because it's all about Stockdale and Stockdale knows like he's in the Tonkin, the day for all of it. And he leaves the reprisal rate. And so, you know, he's probably saying to himself, it wouldn't have made a difference. Like if I had tried to do something, If I had resigned, if I'd smacked on my wings and walked out, which is true, it probably wouldn't have.

41:08Ryan Holiday: But the question is not whether quitting would do anything. The question is whether participating is good or bad. Do you know what I'm saying? Like the question is, is not like if I quit, will it stop the Vietnam War? The question we have to ask is, should I bomb another country for what I know is a made up pretense? And that is this. So it's not like, hey, if I speak out about this political figure or this issue, will I single handedly turn the tide of history? It's what do I want to participate in or not participate in? Yeah. Well, thank you. This is good therapy for me because this is something never Trumpers have to grab.

41:48with a lot recently because we failed. Yes. You know what I mean? And you get this a lot. You mentioned Liz Cheney earlier and this is part of that kind of discussion. And it's like, okay, you know, there was a category of people who we felt like we were doing the right thing and advocated and advocated strategies that we thought might be helpful for stopping him or containing him. And like, it just didn't work. Like, it just didn't work. And, you know, who knows what might end up working is just him stepping on ranks. you know, and like doing such a bad job as president in the second term that people, you know, suffer consequences of his actions, right?

42:25But, um, you know, I, at some level, did it work in 2020? Maybe like the Biden coalition, I did think included a lot of never Trumpers, a lot of suburban Republicans, like of our types of people, um, you know, but then Trump comes back. Right. And in some ways you look at it and then, you know, in my really dark night thoughts, it's like, it probably would have been better for him to beat actually you know because there's something of four years in the wilderness like you gain a lot of time to plan and plot nefarious plots and and you know had he just won that anyway um who knows

43:01Ryan Holiday: right who knows but um but that's like do you only do the right thing because it will succeed or do you do the right thing because it's the right thing that's like the question right like i think about to go back to the stoics like cato is the guy who stands against caesar and he fucking loses. It's like he loses as hard as you could possibly lose. It ends with him disemboweling himself. Okay. Hopefully that isn't enough. He commits to, he so loses and he refuses to give Caesar the pleasure of pardoning him. So he disembowels himself and he fails. He fails even at this. So they rush and they hear him, they hear him fall on the ground and the doctor rushes in and they sew him back up and then he wakes up, you know, did I die?

43:49Ryan Holiday: He did, no. So he has to rip it open again. Oh my God. So it's this brutal, it's as humiliating a failure as you could possibly have. Yeah. I'm feeling pretty good now. But like, you know, 2000 years later, it's what inspires the American founding. Like the lone guy fighting for a republic over despotism. I guess my point is, first off, you don't know how it's going to go. Like nobody, the idea that like you get to see the fruits of your labor or the movement that this, that sometimes you're, you live long enough to see the triumph of your movement. Sometimes you don't, right? Like should Melville have not written Moby Dick because like people didn't like it in his lifetime?

44:28Ryan Holiday: Or should he sit down and write the book that he thinks is good and like believe that it's good? So sometimes you get to see it. Sometimes you don't. And like the idea that you would only do it if you're rewarded for doing the right thing. It's just, just kind of a crazy. So what should Cato have done? Maybe nothing. Or maybe just smoked pot and check out. He could have gone into exile. I mean, it's funny. Like we had this, somebody, it's weird how we know they, but somebody asked Napoleon about Cato and he's like, what should Cato have done? And he's like, oh, who did he help? Like, I think it ultimately validates Cato that Napoleon is like, that guy's a fucking loser.

45:07Ryan Holiday: He didn't make a difference. his sort of principled stand didn't stop Caesar. And it's like, I think ultimately, like the fact that the people who bend the knee and go along with it, there's no evidence they have made any positive difference whatsoever. They've kept nothing bad from happening. It's as bad as it could possibly be, I think is the ultimate sort of indication of like, I'm not going to be a part of anything I think is wrong. That feels good. I'm with you and I think it's true. So, counterpoint, Napoleon, I was in France this summer for his first time in Paris, and you know, I was walking around the Arc de Triomphe, which people from all around the world were walking around, taking pictures, seeing the Arc de Triomphe, which is, you know, Napoleon's monument to himself.

45:54And Trump is thinking about doing the same thing now in DC. And you know, I don't know, what percentage of the people going there were like thinking about Napoleon's moral failings and like who actually won the battles and you know. Sure, but what good does it do Napoleon?

46:11Ryan Holiday: There's a lie in meditations where Marcus Sturlus goes, it's worth remembering that Alexander the Great and his mule driver both died and the same thing happened to both of them. So the monument's still there. Who gives a shit? You know, Marcus Sturlus has a monument too. There is a - Trump gives a shit and he's going to be happy it's there. But this is my point. There is a like a two or three hundred foot monument of Marcus Aurelius in Rome. It's this of his of his martial victories. It's this marble carving of his victories over the barbarians. It had his statue on top. So you might go, you know, he says it doesn't matter, you know, but but it's still there.

46:47Ryan Holiday: Well, actually, it falls into disrepair. And then in the 15th century, a pope sort of uncovers it and goes, oh, this is so cool. Knocks Marcus off the top, puts St. Peter or St. Paul on top, and then puts an inscription on the bottom congratulating himself for restoring the monument, which he says was the monument to the victories of Antoninus Pius. So he attributes it wrongly, makes it a monument to someone else. I guess my point is, it doesn't fucking matter because they're all dead. What matters is like, did you feed a generation of people into a meat grinder to appease your vanity? And like, I would say that's bad.

47:29Ryan Holiday: The fact that thousands or hundreds of years later, some of the specifics of that get lost and we go like, this is where Napoleon's mistress lived. Isn't that cool? it's like no he was as fucking shitty as a person as there could possibly be that's true i mean moving it outside of you know kind of my own grappling with my own choices and whether you know i matter and kind of existential dread i do think that to that point though like the failures of what like these guys bring it back to now to present day like trump failing matters to me in part because of, I do think that like these things have momentum and energy.

48:14Yeah. And I was already seeing in the culture, like the fact that Trump won and that Trump's argument won, like, were we doing this last year? Like, I think one thing that we would be grappling with is that there were a lot of people out there in the world, in America in particular, particularly young men who look at this and are like, well, this is what I should be doing. Yeah. Right. Like screw the rules, you know, screw, you know, being kind to people or being generous. Like the path to success is to, you know, just bulldoze everything. And like you have in Musk and Trump, like these just two models of that, right?

48:50Like through their own kind of will and determination and unwillingness to... Sociopathy. Yeah, sociopathy, but also just kind of unwillingness to like care about anything. You know, so many people would have quit after all the bankruptcies or, you know, to the Rock of it. Most people would have quit after the Access Hollywood tape. They were humiliated and they would have walked away. Right. And so there was like this lesson in the culture that, you know, that that is the way to, you know, rewards and even just rewards, right? That it's worth it. You know, this is all now we're in Machiavelli territory.

49:23But like, I do think that his failures now are important, not for like the success of the Never Trump movement, but like as a broader lesson.

49:34Ryan Holiday: Well, lesson aside, also, they're just bad and they're doing bad things. It would be good if they were not able to do bad things. I just mean like that means a stopping of the perpetuating of it. Right. Like even if even if there's the modest element of the Republicans deciding like, OK, like we need to at least signal to people that we want to, you know, return to a time where we take accountability for our crimes and failures because the public is so mad about the crimes and failures of the Trump administration. like even if they're disingenuous, this goes back to the question about intention, like even if they're disingenuous about it, like that is an important victory for stopping kind of the cascade, I think.

50:15Ryan Holiday: Yeah. You know, I was thinking about this because it strikes me one of the big misses of the founders was this idea that ambition would check ambition, right? That all the office holders would jealously guard the prerogatives of their office. I was thinking about this because I was talking about Robert Caro's book, Master of the Senate. The idea that like Mitch McConnell would become the head of the Senate for many years, the Senate majority leader, and then he would use that power not to expand the power of the Senate. Like his primary, if you were like Mitch McConnell, was it all worth it? He would say, it was all worth it.

50:51Ryan Holiday: I can't talk, but if he could, he would say it was all worth it because look what I did to the Supreme Court, which like the founders would find insane. Lyndon Johnson would find it like your primary legislative accomplishment is that you strengthened the counterbalancing institution. That's like insane. And so what like I just that institution wasn't counterbalancing him. I think this would be I think Mitch McConnell's I think. But I'm saying he has no legislation legislative accomplishments to crow about because that is the failure of the founders. The idea that like the Senate majority leader would be vying for power with the president, who would be vying for power with the chief justice of the Supreme Court, each of whom thinks they're the most important guy or woman.

51:36Ryan Holiday: There's some recent failure of that. And I think about this like - They did see it coming though. They had fear of the parties. You know what I mean? And I think that probably, and this gets fixed, this is why when we start in doing democracies places, they don't copy our democracy, they copy other countries, right? Because the multi-party system is not perfect. And like there are other issues in the parliamentary system, but it does guard against this in a way that having just two factional parties doesn't. And that was, they warned about that, but I think that now we really need Bill Kristol here to do the Federalist Paper stuff, but that then goes back to where you were, which was like, okay, well, if there's a small lower house and the upper house and the Supreme Court, there are other checks, the states are like, there'd be other checks and balances.

52:25Ryan Holiday: I just think it's so interesting that these people work their whole lives to get some form of power and then are like, I'll give it to this guy. It's psychologically interesting and historically interesting that seemingly sort of ambitious, those people would just roll over so easily at their own expense. I mean, what are they getting out of it? It's crazy. I feel power. That's in the book. I did cover this. I got this part down. In DC, it is almost better to be right next to power than in power. Because, you know, power has all the weight of the responsibilities and the choices and the policy outcomes, right?

53:13And a lot of these guys have one or two things they care about that they did want to get through. But besides that, it is, you know, I've got my staff, I've got my security, they call me Mr. Leader, you know, I get to be on the Air Force One, you know, I get to be at all these historic moments, I'm gonna get a bust. You know, I think about like Kevin McCarthy, who's just the Speaker of the House for Trump for a little while. Total failure. Knew what Trump was doing on January 6th was wrong, said it at the time, flipped, went fully in with Trump, gets to be the speaker, is pushed around by the rank and file members of the House, was one of the weakest speakers in American history, but he gets the bust.

53:59Right. That's ultimately the accomplishment that he cares about. Yeah, the kids and maybe, you know, grandkids, friends, you can go to the Capitol, you can see the bust you know Trump's going to invite you to the lighthouse you know you can get a ride on Air Force One after it

54:19Ryan Holiday: proximity to power gets you some of the perks of power without the downsides of power which is responsibility accountability failing yeah right and you know I do think this is like we're a big dynamic country it is hard you know what I mean like people say they want change. Like, there's this kind of revealed preference versus stated preference. But, like, a lot of times, big changes are not popular, you know? And if you make a big decision, there's gonna be some, now we go back to where we were earlier, there's gonna be some constituency that's mad at you. Even, especially in this two-party system, even within the Republican constituency.

54:58You know what I mean? It's like, you help Ukraine, the isolationists are mad at you. You know, you don't, the neocons are mad at you. You know what I mean?

55:07Ryan Holiday: And so it's much better to ride around in a golf cart. And maybe that was the feature of the system, which it was designed to be a bunch of people temporarily doing their duty, like jury duty, not a career. They were farmers that came in. You know what I mean? I was just reading David McCullough's book about the Panama Canal. And then I was going back and reading about Carter deciding to give the canal back and how hard he had to work to get the passage of the canal treaty. And then it basically devastates the Democratic Party. Like a huge number of the senators that vote for it are not reelected.

55:42Ryan Holiday: Wayne Morse, who's one of the two senators who votes against the Tonkin resolution, doesn't get reelected. And like that's a feature, not a bug of the system. And I don't know. That's hard for the individuals to understand. And the systems evolves and incentives evolve and people see that, right? Like over time, you know, and I think this goes back to like the lessons, right? You know, there was a period of time where there was enough countervailing examples of politicians being rewarded for taking brave stance. You know, you see this all through, you know, the World War II era, the civil rights era, right?

56:21And so you tell yourself a story as a politician that I'm going to do the right thing here and I'm going to be lauded for it. And, you know, the guy that lost his seat over the Panama Canal is probably telling the next person running, like, don't. It's probably not worth it. You know what I mean? Like, it really wasn't worth it. I wish I was still a senator. I don't care that much about the Panama Canal on balance, right? And then you go through a period of time where you now see the opposite happening. You know, back to the Trump thing where like people are rewarded for the opposite. I mean, at least recently.

56:51You know, and there's a period of time where people are politically rewarded for cowardice.

56:56Ryan Holiday: Although it's funny, you talk to a lot of these ex-politicians and they're not like, my life is horrible. They're like, oh, it's so much better. Like there is the things people will do to debase themselves for a job that privately they'll tell you they fucking hate is pretty crazy. Yeah, I think that there's another revealed preference or stated preference. There was this Chris Christie interview that I thought was like so revealing when he was kind of talking about his journey with Trump. And, you know, Chris Christie, I like to bring this up a lot because, you know, I don't like Chris Christie that much and people forget it.

57:30It's lost history. But he was like the first normal Republican to endorse Trump, actually. After the New Hampshire primary, Trump wins. they're still kind of thinking Marco or Ted Cruz is not great but you know what I mean somebody besides Trump will get there and Christie is the first person to be like I'm going to stand with Trump and endorse him and Trump humiliates him anyway he's being kind of introspective on this podcast interview I was watching and he says this thing about leaving the governor's office and he talks about how he's like it's just one day you know I'm in Drumthwaka that's what the governor's residence called in New Jersey and you know then the next day the lights are off yeah nobody's calling me yeah you know i need to figure out what to do with my day and i you know i miss the the spot i miss the juice i was sorry to forget exactly the phrase he is but i write like he missed the rush of like being in the mix yeah and i do think that there's a lot of fear like maybe eventually politicians find ex-politicians you know find themselves fulfilled in family life and doing other endeavors right but I think that there's a fear in a period of time where it's like man I think the lights are going to turn off like that like I'm not going to have a staff I'm not going to have the security I'm not going to have access I'm not

58:47Ryan Holiday: a lot of things from me that takes some character and self identity like you know what I mean like that your identity is not the job it's not the power and by the way like I think that is a fundamental mistaken assumption they're making which is like that you were powerful. It's like, no, no, no. The governor is powerful. The president is powerful. The Senate is powerful. And you were temporarily occupying that seat. We, the people gave you this power. You are not important. Right. And so there's this ego where you fuse your identity to being referred to as senator or congressman or, you know, whatever.

59:26Ryan Holiday: And then you're worried about losing something that was not actually yours. All right. So I'm just finishing up this tour here in Australia. And I thought it'd be warmer here than it was. And so I thought maybe, you know, I'd be a little overdressed. But a bunch of the sweaters I got on Quince are what I wore on stage in Sydney, in Auckland, in Melbourne. That's one of the weird things about this Daily Stoic stuff. It's like I had to be on camera, I had to be on stage more than I thought. You know, if it was just me, I'd probably be wearing basketball shorts and a band t-shirt most days. but I got to dress up a smidge.

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1:01:53Ryan Holiday: there's a story about truman like as he leaves the white house his car stops at a traffic light for the first time in eight years and then reporters ask him you know so you might think oh that's that that identity like the athlete leaving that transition these reporters they go so what was the first thing you did you know when you got back home to springfield and he was like i took the suitcases up to the attic and he said that with like pride like he's like he's harry Truman, who was temporarily president. And like, I do think it requires a kind of a strong sense of self to be able to have that.

1:02:26Ryan Holiday: And maybe the problem is we elect people that don't have that or people who don't have that are attracted to the office, like a moth to a flame. And then they can't be without it. I don't know how to get that back. I mean, like, I'm decently optimistic about moving past like this soft authoritarian moment. I just, I think that the amount of suffering that's being wrought in the country. Trump has lost the ability to even pretend that he cares about regular people. He used to be really good at pretending to care about the forgotten man and the regular guy. And I don't know if it's old age or just he's been in there so long or the bubble or whatever, but he's not even good at faking it anymore.

1:03:07And so I do think that we'll be able to move past it. There's something, though, like there was a cultural norm and value that we honored from, I guess I can't speak to before Truman, but like certainly from Truman through like H.W. Bush, basically, even into Clinton a little bit. And where it was like the presidency, you know, was -

1:03:29Ryan Holiday: And we were living in the shadow of decisions that Washington made. Yeah, right. Of like resigning his commission, resigning the presidency. Calling himself Mr. President instead of his excellency or whatever. Like there was this - More example is powerful. Yeah, there was this example that was like, hey, it is actually noble and good that the president is humble, that the president is not above everyone else, that the president has limits on their power. And I do think that we've lost that totally. And like even on the left, like I think about like a democratic presidency in 29, there's not going to be anybody saying to the president, like you really could use a little humility and like put limits on.

1:04:09And like maybe the first thing you should do is start putting limits on the executive power because who knows where the next Trump might come from. Like that would actually be a very valuable thing for somebody to do in 2029. Is there going to be someone that has the Panama Canal level gumption to say, hey, okay, sure. Yes, we're going to try to do Medicare for all who want it or something. Or like we're going to do something that like is responsive to people's economic concerns. But like also we need to make reforms like limits my power and that I'm not going to go pedal to the metal on advancing a bunch of kind of left executive orders.

1:04:47Ryan Holiday: There's no incentive to that. Well, that's the tragedy of Biden, which is that you had an old, potentially single-term president with a long history in Washington of being a decent sort of norm-respecting person who could have done that and didn't. You'll never get that. It's not just the, you know, what did Trump destroy, but why did Biden have a chance to re-establish and model that he didn't? And this ties to the age, actually. Like, he was too personally feeble and weak to do it. Honestly, that seems meaner than I mean it to be. But, like, you know, you have to make kind of some sort of bold reforms that go against, because it goes against coalition interests, right?

1:05:32Like, there are going to be Democratic activists who are like, hey, you've got to do this student loan reform via executive order. you promised it, you know, or, hey, you got to do that, this thing or that thing. And to be able to stand up to them and say, hey, no, and bring people along and say, hey, yes, we're going to we're going to work on, you know, these political priorities and, you know, that that are responsive to what Democratic base voters want. But like, I'm also going to, you know, change the way that these that we do business. And I'm not going to do what Trump, you know, we're not going to just go back and forth between, you know, right-wing authoritarianism and some kind of like lefty, progressive, like soft, you know, executive power administration.

1:06:15But he couldn't, yeah. Even if he wanted to do that, like -

1:06:19Ryan Holiday: But it goes back to the real villains are the enablers, right? Like, I don't think he thought that's what he was doing. And so the people with, I think the moral weight also falls on the people who didn't deliver the truth, who whispered things in his ears, who brought those agenda items to him and like... And it goes back to the original sin, right? Of like, if he would have said he was a one-term president, which was a risk in its own right, and who knows, could have risked bring Trump back? There are no easy answers here, but his neighbors, including his wife, were not on board with that. They wanted power.

1:06:51They wanted access to power. If you do that, like some people say, oh, well, if you say you're a one-term president, then you're automatically a lame duck. You can't get stuff passed. And that's one way to look at it. But there's another way to look at it where like you could do some like big political reforms without like worrying about, you know, what you're standing, what's going to be next time. And that could be some stuff that left people wanted, like you could have pushed to make D.C. estate and then like, oh, Republicans are pissed about this, but who cares? I'm not running again, you know, and simultaneously push to, you know, put in pardon reforms, which would which would mean he couldn't have pardoned his own kid or, you know, like other stuff that could have created some guardrails around Trump.

1:07:30Ryan Holiday: and no. The irony that even in their 80s, people are not able to go to YOLO. Like, you know what I mean? Like, we all think at some big moment we're going to do the thing. And it's like, if you're not doing it now, you probably are not going to do it. Like, everyone thinks they're, I'm going to be Mike Pence. I'm going to be the person at the last minute who steps in. And it's like, you're not Mike Pence. We don't need you to be Mike Pence. We need you to be a regular person doing the right thing right now. That's what we need more people to do. The ego of like, no, no, no, I'm the special person who's going to be the double actor.

1:08:06Ryan Holiday: So at the last minute, I can be the, no, just do it now. We'd be better if we did it now. There's a lot of literature about this. If you don't want to read, you can watch the movie Blow or something. You know, a lot of things about people was like, I'm going to do the right thing after one last, you know, bad act. No, the Biden, the ego thing, we talked all about the Republican guys that goes to Biden. It existed until even after he quit. Like the story from, gosh, I hate to not credit whoever it was, one of the books was he calls Harris on the morning of her debate with Trump. He has heard from some people that she was distancing from him on this thing or that, and he wanted her to stay in line.

1:08:46And like, Harris is like, I'm prepping for the debate. Like, why are you like in this kind of jealous high school mode right now? Now you are the President of the United States. You did it. You were just a Joe from Delaware. You became the President of the United States and you're still worried about what so-and-so is saying about you. It's the playground. And the whole thing is insane. It should have been the opposite. As soon as he decided to quit, he should have called in Harris. That's your legacy. Yeah, and said, hey, kid. Yeah. Do whatever you need to do. Honestly, here's a white lie I would have allowed.

1:09:18That's within my moral compass. Go ahead and just tell people that she opposed the unpopular shit you did. You know, like, who cares? Like, if you're Biden at that point, it's like, you know, call in whatever Maggie Haberman and be like, I do just got to say, like, it is true that Harris was not with me on Gaza. But like, you know, she was a good soldier and I appreciated it, but I want to let her run her own race. Yeah. Like, that would have been totally helpful to both his legacy, to Harris, but just, you know,

1:09:48Ryan Holiday: this kind of ego. It's so fascinating to look at this stuff politically and go, like, why did it? and I there's this line from the killers that struck me the other day I don't know why I'd heard the song so many times and I'm forgetting what song it is but they go are your excuses any better than your senators and I was like oh yeah it's so easy to be like why is this person not speaking out oh it's because they don't want to lose your job but it's like have you ever said anything in your fucking life that has in that has endangered your job right like we we want people, we want people in Brussels or DC or wherever your state capital is to be like, noble and true and decent and courageous.

1:10:29Ryan Holiday: And then it's like, sure, that's good. And we should vote for those people and we should hold our politicians to that standard. But ultimately, the thing you have the most control about is whether you do that in your life, in any of the things you're responsible for. And like, you know, do you? So where does that leave you on the virtue signaling discourse, whereas... Virtue signaling is annoying and obnoxious, but certainly preferable to vice maximizing. Which is what we have now. I'm just trying to find the line between, you know, doing something in your life that is taking a moral stand and people self-soothing by being like, yeah, the moral stand I'm doing in my life is posting my black square onto Instagram.

1:11:09Ryan Holiday: But that's my point. Where you could have impact is not politically. Like, where you can have impact is like, Like, people talk about, you know, like, what healthcare should be. And then it's like, okay, but you have a company of 70 people. What is your benefit package? Right? Like, people have opinions on what minimum wage is. And then it's like, okay, but what do you pay? The fact that, like, I think John Mackey. Are you complaining about tipping the barista? Are you, like, giving a good tip? All of the above. No, what I'm, yeah, exactly. Exactly. And I think John Mackey is a great example of people, oftentimes the libertarians are like, you shouldn't be making us do this stuff.

1:11:50Ryan Holiday: And it's like, okay, but if you weren't made to do it, would you do it at all? Would you do it better? And I think what I've always admired about Whole Foods is he's like, no, the government shouldn't be telling me what to do, but I'm going to be pretty generous and cool and kind and try to... So the question is ultimately, I think, where do you have impact in your life and what decisions are you making? When was the last time one of your principles cost you any money like the virtue signaling of yeah like i tweet about stuff well but like what are you doing in your life where there's a cost to it yeah i think that's interesting i just say this to people a lot because i worry about this i mean thinking about my show is like it just is what i'm talking about the terrible stuff trump's doing every day like that just is what the show is and um i think that there's some value to that it's not as much which is some people think it's, you know, but like people need to know what's happening and I'm trying to have honest and interesting conversations, right?

1:12:46And so then, but then people ask me, it's like, okay, well, like, what should I be doing? You know what I mean? And it's like, I'm listening to your show. I'm watching 20 hours of MSNPF a week. I'm posting it onto Instagram. And I'm like, honestly, like maybe you can listen to my show less, really. You know, it's fine. Like, it's good. It's going to be there. I appreciate it. But, you know, if you're listening four days a week instead of five and the fifth day for that hour, like engaging in your community. Like that's probably better. A lot of people I think get this anxiety. I have friends like this in my life that like have get, it goes from anxiety to anger.

1:13:20They have like anger in their life by how bad everything is in the world. And, and they're, they're exercising that anger by like being really mean on the internet and like bitching about stuff and yelling at people and whatever, like sending, sending instagram reels around and i guess to say to them like god like man like you're not actually how like that's not serving you like this is my job like i'm doing it as a job like it's not your job like you have another job and if you want to and if you know what i'm doing is serving you in some way and you're like finding entertainment in it or comfort or education or learning yeah you need to go do something great yeah but then now like take it out take it somewhere else and I and you know but then it's like what and it's like I do understand people's frustration like there's this feeling of like you don't have control of all these horrible things that are

1:14:10Ryan Holiday: happening but probably consuming more info is not going to help it's only going to review like if you already know that these people are awful that they have no business in power that they're going to continue doing awful things that they have done unimaginable damage like you're you're probably good like you're good like I know this one writer and and they were saying like you know I find it hard to write. Like, I'm so angry about what's happening. And I'm like, well, that's like the number one way you could fight back then is like, don't let them take your thing from you. Like you're freely giving them.

1:14:42Or find somebody you're really angry about that people don't know about. Like that's what I'm trying to do. You know, when I'm like folks, like, as I mentioned earlier, it's like the immigration stuff that bothers me the most. So I try to find like individual stories that people aren't talking about and be like, I'm really mad about this story and hopefully bring attention to that. And there have been examples like these guys have back down on various, you know, horrible immigration policies that they had, in particular the El Salvador prison, which they're planning on having a massive prison in El Salvador, and now nobody's there because there's so much pushback to it.

1:15:11So that does matter. And I don't know, when we went to Minnesota to do a live show after Freddie and Good were killed, I was like blown away. There were people, like we went to, man, now I'm blanking on the name of the detention center in Minneapolis-St. Paul, but like waiting outside the detention center, like people had been getting nabbed And then some of them were then being dropped off. You know what I mean? Because either they had legal status or they weren't deportable or fail for whatever reason. And it's freezing in Minneapolis. And, you know, it's mostly Hispanic people that are just like being dumped by the ICE agents like on the street corner.

1:15:45And they're all these mostly boomers. Shout out to boomers, but not entirely like standing out there. And they were like, we've got we've got water. We've got car ride. Like, where do you want us to take you? Like we've got sweaters and coats and it's just like, that's a useful, that's like, that is taking being really upset about what's happening to action. And like, that's happening everywhere. Like, it's not like that there aren't people who are being abused by the ICE agents like in your community. It's happening everywhere.

1:16:13Ryan Holiday: Yeah, there's a line in The Unbearable Whiteness of Being, the Milan Pender book. And the woman says, like, in sort of Prague, under the communist, she says, like, it is better to help a half-dead crow buried in the road than it is to send petitions to the president. Like, you know what I mean? Like, help one fucking person. We'll make all the difference. Like, that has a real tangible difference. Like, you angrily tweeting or commenting on social media makes much less difference. Unless your job is to be a person who talks about things publicly. in which case it's different. But like... Or unless, and that is my job also, and it's maybe something I fail on, but I try to do it, which is like finding issues where I'm like, actually, here's something where if you called a specific senator, it might make a difference.

1:16:58Like we did. There was one example of the person that was in a detention center near here, in Dilley. The lawyers of the family asked if we could, you know, kind of flood Katie Britt's office. She's a senator from Alabama because Katie Britt had spoken out about how she was outranged to the Republican senator. How about she's outraged about the case of this one boy, but there was like another boy. It was the same situation and he was in there. It's like, well, if you're outraged about this, will you speak out about that? And eventually she did. And they got out. You know what I mean?

1:17:23Ryan Holiday: It's like that is like a tangible, useful thing. If that was the only thing you'd done in the last 10 years, you made a difference for one person. That's a real thing for a real person. And that's what people should do.

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From the publisher

What happens when everything you've built your life around starts to conflict with what you believe is right? In today’s episode, Ryan sits down with Tim Miller, former Republican political strategist and host of The Bulwark podcast, to talk about how ambition, ego, and blind loyalty can lead you to compromise your principles. They discuss the stories we tell ourselves to justify our decisions, the pressure to go along with the crowd, the danger of staying loyal for too long, and how to know when it's time to walk away.


Listen to Ryan’s episode on Tim’s podcast, The Bulwark Daily | Apple Podcasts, Spotify, YouTube


Grab a signed copy of Tim Miller's book Why We Did It: A Travelogue from the Republican Road to Hell at The Painted Porch | https://www.thepaintedporch.com


Instagram: @TimMillerGram


X: @Timodc


Substack: @TimMiller15


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