Stoicism with Ryan Holiday - Part 1

26 Jul 2025 · 42 min

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Podcast Summary: The James Altucher Show - Stoicism with Ryan Holiday - Part 1

Episode Overview James Altucher interviews bestselling author Ryan Holiday in a candid discussion about creativity, ethics, and the changing landscape of media. The conversation dives into the challenges creators face in expressing themselves authentically in today's polarized world.

Key Themes

  • Creativity and Silence: The importance of allowing creative ideas to develop before sharing them publicly is emphasized. Holiday explains that discussing ideas too early can hinder their evolution.
  • Social Media and Algorithms: The shift from chronological feeds to algorithm-driven content has transformed social media from a space for personal expression to one dominated by extreme opinions and engagement metrics.
  • Ethics in Expression: The tension between having an opinion on every issue and remaining true to oneself is explored, alongside the ethical implications of silence in the face of injustice.
  • The Nature of Writing: Writing is described as a medium that requires discipline, tension, and a deep commitment to crafting meaningful narratives, contrasting it with the spontaneity of other forms of art.

What You’ll Learn

  • Creative Momentum: Sharing ideas too soon can disrupt their development.
  • Algorithmic Influence: Social media's focus on engagement over expression can distort personal narratives and opinions.
  • Podcasting Challenges: The long-form nature of podcasts can sometimes be less rigorous than other media, leading to the spread of misinformation.
  • Artistic Integrity: Balancing artistic freedom with audience demands can lead to a loss of creative autonomy.

Timestamped Highlights

  • [00:00] Writing Without Talking About It: Discussion of the importance of not revealing ideas until they are fully formed.
  • [10:00] Social Media’s Shift to Opinion Farming: Examination of how social media has changed the dynamics of opinion-sharing.
  • [14:00] Are Podcasts Dangerous?: A critical look at the implications of podcasting in the current media landscape.
  • [37:00] Writing as the Hardest Artform: The challenges and intricacies of writing compared to other artistic mediums.
  • [39:00] Why Great Writing Still Matters: The enduring importance of well-crafted narratives and their emotional impact.

Key Takeaways

  • Creative Process: Allowing ideas to mature before sharing can lead to more profound and impactful outcomes.
  • Navigating Polarization: Creators must find a balance between engaging with pressing societal issues and maintaining their authentic voice.
  • Evolving Media Landscape: As media evolves, the responsibility of the creator to manage their influence and audience expectations becomes increasingly complex.
  • Value of Writing: The rigor involved in writing makes it a uniquely powerful medium for conveying thoughts and emotions.

Additional Resources

  • Ryan Holiday’s Website: [ryanholiday.net](https://ryanholiday.net/)
  • The Daily Stoic by Ryan Holiday: [Buy on Amazon](https://www.amazon.com/Daily-Stoic-Meditations-Perseverance-Wisdom/dp/0735211736)
  • James Altucher on Twitter: [@jaltucher](https://twitter.com/jaltucher)

Conclusion This episode provides valuable insights into the struggles of creativity and the ethical responsibilities of creators in a digital age characterized by noise and rapid information flow. Both Altucher and Holiday emphasize the importance of maintaining integrity and authenticity in one's work amidst the pressures of audience expectations and algorithmic influences.

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Transcript

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0:30And with LinkedIn, of course, you can feel confident that you're getting the best. Based on LinkedIn data, 72 % of small and medium businesses say using LinkedIn helps them find high-quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn. Post your job for free at linkedin.com slash altature. That's linkedin.com slash altature to post your job for free. Terms and conditions apply. This message comes from Capital One. The Capital One Venture X Business Card has no preset spending limit, so the card's purchasing power can adapt to meet business needs.

1:09Plus, the card earns unlimited double miles on every purchase, so the more a business spends, the more miles earned. And when traveling, the Venture X Business Card grants access to over 1 ,000 airport lounges. The Venture X Business Card. What's in your wallet? Terms and conditions apply. Find out more at CapitalOne.com slash VentureXBusiness. Today on the James Altucher Show. It wasn't until I was like midway through it that I figured it out that it was about ego. I nailed that. So I usually like just don't talk about it until it's like well underway and it exists. You can't write a book for the sake of writing a book.

1:47That's how bad books are written. One of the traps of our time is that you have to have an opinion on every issue. I think people have to get along before they can have any sway on someone's opinions. But who's actually benefiting from you? Well, yeah, who has the audience, right? Do you have the audience or does the audience have you? What kind of success is it that you actually have less freedom once you've achieved it? This isn't your average business podcast, and he's not your average host. This is The James Altucher Show.

2:26So what have you been mostly up to? I know you have a book coming out in October. Yes, I do. I think it's October. So I'm finishing that. And then, yeah, starting to think about the next one. What do you think is going to be the next one? I know, I'm just not saying. Okay, I respect that. I think talking about it sometimes kills the energy a little. No, totally. I think, well, it's two things. Talking about it is a way to kind of get credit in advance. Yeah, it's like that go green hit. People are like, oh, it's so amazing. You know, whatever. I try to avoid that. But also I find that it's very discouraging to me because if I had my arms wrapped around it, I'd have probably done it already.

3:06I'm still like thinking about it. And so if I like describe it to you, it's going to sound stupid. And then your reaction is going to influence my… You know what? I'll be able to tell you exactly what it is and what it's about when I'm almost done. And if I'm doing it now. I feel like you were able to do that before, though. You had such a solid grounding with Ego is the Enemy and the whole series of Stoicism books. I think you were able to more... When there's a concept that is just really solid, I think you don't have that problem. Yeah, but see, Ego is the Enemy started as a book about humility.

3:50So if you're like, what are you working on next? And then I'm like, I'm doing this book about humility. Because I'm the expert. You'd be like, oh, cool. Good for you. I hope that does well. You know, and I'd be like, it wasn't until I was like midway through it that I figured it out that it was about ego. I nailed that. So, so I, I usually like just don't talk about it until it's like well underway and it exists. I think that's good. Like, I think, you know, I wrote, I wrote one to two books a year from 2003 to 2021. Yes. And then I haven't, so this is like the first time as an adult that I haven't written a book.

4:25in a couple of years. You feel backed up? Very much so. But I think you have to be true to yourself. You can't write a book for the sake of writing a book. That's how bad books are written. You've always seemed to me as someone who sort of is compulsively creative. Like I thought when you were doing your comedy stuff, I saw that as like, oh, actually, social media, writing online and doing books, James is like, no, he's just having to mainline it like directly from the source. Like you were like trying to get to the most unadulterated form of like expression, reaction, expression, reaction. That's sort of what I saw you chasing there.

5:08Yeah, I never thought of it that way, but you're right. A book, there's a very long waiting time between starting the book and getting the dopamine hit from releasing the book. But in standup comedy, you get that hit or not every day. And if you don't get it one day, You just go back the next day or the next hour and, and go for it. And that's true. And also it's, it's a very high pressure creativity. Like I need material for tonight. And so you have to be writing every day. And you see, you notice this with comedians, like even like take someone like Jerry Seinfeld, who's so successful as the greatest television show creator ever.

5:46He would say, if you say, well, what do you do for, he would say, I'm a comedian. Like comedians are comedians at the core. And ultimately, I was not a comedian. So that's not my core. But for comedians, that's their core. No matter what else, Kevin Hart, more of a movie guy and a production guy than a comedian. But he's a comedian at the core. Yeah, no, I think you're someone who has things to say. You have a point of view or a voice. And I think I've watched you. I was thinking about this on the way here. I would have started reading your stuff in 2010. So it's crazy to me that it's been 15 years.

6:19And I was realizing one of the first articles I read from you was an article you wrote about not going to college or dropping out of college. And I realized that that article hit me because I was still relatively close to having done that. Like, that's how long ago it was in my life that I was like, oh, this guy's like speaking to this thing that I did that I'm still not sure if it was the right decision or not. Because I don't know the end of the story yet. And so you've always struck me as a person who has strong opinions. and you've been trying your hand at lots of different outlets with a whole bunch of success.

6:57You sort of succeeded in each one of the mediums, but that you're like a point of view guy. That's what you are. Yeah, point of view. It's an interesting thing, point of view, because, and that means something different now than I think it meant 10 years ago or 15 years ago. Like now there's only two points of view and you're either like... What, woke and anti-woke or what? Or just like, you know, either Trump or anti-Trump or whatever. And like, I have actually like no interest in that. And so then the question is, what's ethical? Like, do you need to have an interest in that? Like I was talking to Mehdi Hassan and he was like, you need to have an interest in this.

7:36And, but I was more like, you know, I'm more interested in how I can become a better person. and then as just a side effect of that, that if people relate to that, then how other people become better people. Sure. And it's like different layers of where you should focus. So if I focus on, let's say, this other layer, then it might distract me from how I can become a better person. Like maybe how I become a better person by convincing people to have one stance or another when I don't even know. Like Ukraine's a great example. I have no clue other than what people tell me about what's going on in Ukraine.

8:12And so I can have a stance based on what people tell me. But then in terms of me then regurgitating that stance, I'd rather talk about what makes what adventures I'm going through that make me a better person. Yeah. Yeah. I mean, one of the traps of our time is that you have to have an opinion on every issue. Well, but people say silence is violence. So they make you feel like it's unethical if you're silent. Well, and it's hard because there is some truth to that, right? If they're taking people away to concentration camps and you don't have an opinion because you're really into physics, that you're complicit in that happening.

8:47And so obviously at some level, silence is violence. At the same time, the idea that everyone should have an opinion on everything all at the same time is partly what you could argue there's also a form of violence in that. We used to have this impression, and this is like a very 20th century opinion, that, or sort of worldview that authoritarian governments were about depriving people of information and enforcing sort of silence or whatever. And now what authoritarian regimes realize is that it's much easier to allow an ungodly amount of information, contradictory information out in the world, and then people just get confused and tune out or they don't, they're able to tell themselves whatever is comforting, right?

9:35And so part of, you could also argue that noise is violence because what it allows for is people to do sneaky shit or to do not sneaky shit, but just to do it in such a way that they get away with it. And so I think the idea that everyone should have every opinion all the time and be talking about it all the time is also wrong. There's some middle ground that each individual and then certainly each person with a platform or brand or an audience has to figure out the right amount of also. It's true. I guess in all that you just said, all that's true is the has to that you said in the last sentence there is where I wonder, like, what do I have to do?

10:18Like, I'm not obligated to my platform. Well, that's true. You don't have to do anything. And that's what makes it an ethical choice. Right. But then that's interesting though. Right. So there's a line where, of course, if I'm a physicist and that's all I'm interested in, but my neighbor is going to a concentration, I have to speak about that. That I could see. But, you know, I sort of, honestly, I sort of missed like 2011 and 2012 because nobody actually cared whether Barack Obama or Mitt Romney won. I mean, people did. Like if you're a Democrat, you wanted Barack to win. If you're a Republican, you wanted Mitt Romney to win.

10:50But nobody talked about it. I remember every other election. I don't remember 2012's election day. Well, look, in normal times, most people don't have to be political because there's an Overton window where, you know, okay, they might disagree this way or this way, but there's a sort of a box that we're all in relative agreement that these are the sort of assumptions. I think the problem is what has happened is what we're now sometimes calling political issues are actually sort of fundamental like social contract issues. And they're actually, like, I think sometimes people think I'm political and I'm actually not really talking about the passage of SB 112 or, you know, like the name of some law.

11:39Like I'm actually talking about philosophical issues and our politics have gotten so toxic that we're not talking about politics, but we're talking about bedrock philosophical things. Do you know what I mean? And yeah, I agree with that. Particularly the toxicity. Like I feel people, I feel, I feel like the problem now is people can't have conversations like, and, and like I have, I'm pro-choice, but I have a business partner who's pro-life and we've been business partners since 1999. Like he's kind of in the background of a lot of my business stuff. And we've never once had an argument, even though we've discussed pro-life, pro-choice stuff, like he adopts kids.

12:19Like he puts his, you know, his life where his opinion is. And I strongly disagree, but we never, there's no point in arguing because like he's got his view. I'm not going to change his mind and he's not going to change mine, but people still, I think people have to get along before they can change, you know, have any sway on someone's opinions. Yeah. I do think a part of it is probably rooted in the fact that what social media is built around is the solicitation of opinion, right? Like it is, it requires you, it, the fuel of social media is opinion and judgment. I would say now, but like 10 years ago, I don't think that was the case.

13:01Like I could talk about, Oh, here's the 10 things I did when I was broke and depressed to kind of overcome that. And that would get attention because people believed me and they trusted me and they would know my story or learn my story and then they would want to repeat or emulate what I did. So the big switch and like Jonathan Heights talked about this, but so like they say like social media is bad for kids or whatever. Actually, when you look at the data, it's not like social media has been around a long time. It's actually not like the level of mental health levels or whatever they track in kids that sort of see the spike.

13:34It's actually not like the day Twitter is invented or the day Facebook is invented. It's right when the social networks switched from a chronological feed to an algorithmic feed. Yeah, I agree. And so I think about this even with podcasting, which I'd be curious to have your take. I'll talk about that in a second. But the switch from chronological to algorithmic or even what TikTok does, which is switch it even from the social graph to purely the viral graph, right? Is the switch from, hey, I like that person. I want to follow them to this is what's being surfaced to me based on what the algorithm thinks will be the most engaging to me and based on what other people are sharing.

14:21And so it breaks social media from being this way to follow different people or things that you're interested in to being this thing that surfaces the most extreme, the most invigorating, the most outrageous, whatever, right? That's the fundamental switch. And that's why it goes from, yeah, people talking about their interesting lives to like sort of all politics, all division, all culture war stuff all the time. Yeah, and you're right. So, and then not only, the problem is the algorithm exists almost as an entity. So it's not like I'm tweeting something controversial so people are going to follow me because of the algorithm.

15:00It's we're both catering to the algorithm. Like now people tweet because they know it feeds, this giant algorithm monster and that people then are also praying down to, like, I'm going to go to the algorithm monster to look at all, to feel exciting and interesting. Well, instead of being a point of view guy, like, here's what I think. What happens, I think I've seen this happen to so many people I know. They were sort of a point of view person. They had an audience, they were putting stuff out. And then they touch upon an issue or they say something or they connect in some way. And then they become all that all the time.

15:37Right, which I think is very limiting. I feel like when I began the podcast, it was about what I cared about and what I was interested in. And I keep it that way. I mean, I've had some drift in different directions, but so many people say, oh no, you will get so many more downloads and followers if you pick one side or the other and you just go all in. I can't do it because A, I'm not that interested in that. And B, I don't think I serve anybody. If you're just preaching to the echo chamber, who's actually benefiting from you? Well, yeah, who has the audience, right? Do you have the audience or does the audience have you?

16:17Right. And I think that's what happens. And that's always the challenge with every writer. Like if you're just like, oh, I have to write books about stoicism because that's what my audience wants, then you just became a slave to your audience. Totally. And the challenge for any creative is to not be a slave to your work. Yes. I mean, that's why you see like... That's why you got into it. It was for the expression not to be corrupted and controlled by some algorithm. That seems like, what kind of success is it that you actually have less freedom once you've achieved it? Yeah, I mean, you can argue the brain.

16:51There's a built-in algorithm in the brain. It's like Joseph Campbell's Ark of the Hero, you know, the hero's journey. And you have to cater to that structure in the brain that appeals to heroic journeys. But that's about it. Well, I'm thinking about writing this article that I was once very bullish on podcasts. And now I'm increasingly beginning to think they're very bad for you. And I think part of it is the switch from a feed-based universe. If you think about podcasts five or ten years ago, a podcast is something you subscribe to. It's long form. It's the ads are pre-sold. So whether an episode does a million views or five, or sorry, a million listens or 500 listens, like you already sold it, right?

17:42It's not sort of sold in this real-time marketplace. It's primarily conversational. And so I thought those are all relatively positive elements of a medium that I think are designed to produce intelligent, good information. Now, what happens is podcast goes from being just audio to also video. And video, like people, a good chunk, 30 % to 40 % of the people who are consuming this episode will be watching it on YouTube. That's why I have this studio, right? But YouTube is inherently algorithmic. So it becomes how the thumbnail of the episode and the title of the episode and how many comments it generates and the watch time.

18:26All these other forces are now operating on you as a content creator. And then I would say the other thing is they now sell real-time ads in your thing. So for people to understand, you plug in this little chunk of code and they sell ads in that code. So if the episode blows up, they serve more ads. If it doesn't, whatever, they serve less. And so there's a greater sort of connection between content and profit. it. And then I think the other thing that I'm realizing is that, like, when McLuhan said the medium is the message, what he was saying is that, you know, and Postman talked about this too, whatever the medium goes towards or elicits from the creator or is most conducive to, it shapes the kind of content, right?

19:13And so, like, it's very hard. I think people think that podcasts are good because it has like two people who disagree talking with each other or it's like maybe um you know people outside the mainstream or whatever actually what i think a two-hour conversation is really good for is bullshit like it's very like you don't i'm not going to have you here and then like hold your feet to the fire for two hours that's like that'd be incredibly awkward on a personal level do you know what i mean also boring and well yeah sort of that too. But I guess what I'm saying is that what the friendliness of the medium actually allows crazy people and bullshit artists and manipulators and whatever who are good to use the medium to introduce shitty ideas or untrue things.

20:03But do you think that's true for every medium? Yes, but it's harder to insert outright nonsense and bullshit into a mainstream newspaper than a three-hour conversation where both people are smoking weed. Do you know what I mean? And also, you have to understand with podcasts, I'm talking about audio podcasts now, you have a captive audience because they're either in their car or they're at their gym. That's where people consume podcasts. And so they're not switching while they're driving. They're not switching while they're on the treadmill. So you have, it's probably more than most media, you have a captive audience.

20:37Yes, and so you can kind of do these meandering long form, Like, I just, when I hear people talk about things that I really know about, I'm like, this is, they're not even close, you know? And so it's interesting to watch people as, and I think any medium as it develops, it's, there's this kind of innocence and purity in the early days. and then people who need access to an audience get really good at figuring out how to sort of inject themselves into... I think Robert F. Kennedy Jr. is a great example of a person who's just utterly full of shit and probably like literally insane who has figured out that, oh, this medium is conducive to spreading my type of thinking because it's fundamentally unrigorous and there's fundamentally a captive audience.

21:26And it doesn't, you don't go to a podcast to get political or medical advice for the most part. But if your favorite comedian is interviewing that person, now you're, that's being downloaded directly into your brain in a way that I think if he was forced to defend himself on television or in a debate or, you know, in an op-ed, it would fall apart. It's true because like, you know, I had him on my podcast and I knew I am for vaccines, but I don't know anything. I don't know any facts. And he knows a lot. And then we were going to talk about his autobiography, but then he goes for 20 minutes on this stuff.

22:08And I just don't know how to, I'm not, I can't respond to it. I don't know how to respond. And you're not, you're like, we got three hours left in the, or two hours left in this interview. I'm not going to be like, well, that was bullshit. You're not going to say that, right? And you're not. you're not 60 minutes or something where your job is to be hostile if they're, you know, like it's not an interrogation. And so what it does is I think it enables stuff to spread. It's an unfair playing field. And so I don't know, when I hear people tell me that they listen to lots of podcasts, I usually go like, I might turn, I might switch the ratio.

22:48I think podcasts are good. if you read a lot, if you talk to lots of smart people, if you have other information inputs and you also have a strong base of knowledge, I think podcasts can be great. They can be additive. But if you're just like a long-haul truck driver and you just do nothing but listen to podcasts all day, I think it will destroy your brain. It's bad for you. What should a long-form truck driver… I think audio… I mean, think about the… Like an audiobook and a podcast sound essentially the same. Right. But the amount of effort that goes into one versus the other, it's not even on the same planet.

23:26Right. Because an audio book will take you, let's say, two to three years. Yes. And it has to be worth paying for. It's designed to last for a long period of time. It's been at least edited. Like the person went over it several times. There was an editor and a copy editor and a legal review. And then the press, you know, there was a process. It's not a perfect process, but there was, it's the result. There's some stress applied to it. And then what a podcast is for the most part is a thought literally coming off the top of that person's head.

24:07Take a quick break. If you like this episode, I'd really, really appreciate it. It means so much to me. Please share it with your friends and subscribe to the podcast. email me at Alcatra at gmail.com and tell me why you subscribed. Thanks.

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26:36And with LinkedIn, of course, you can feel confident that you're getting the best. Based on LinkedIn data, 72 % of small, medium businesses say using LinkedIn helps them find high quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn. Post your job for free at linkedin.com slash altature. That's linkedin.com slash altature. to post your job for free. Terms and conditions apply. Well, I wonder then what makes a medium maybe useful or interesting in some way is how much tension there is in the creative process.

27:17Your point is in a podcast, look, we could just sit down and start talking and yes, it's going to be interesting. We've known each other a lot. Well, hopefully it'll be interesting. We've known each other a long time. We've developed a whole industry around podcasting, but a book, there's a lot of tension. It's like what we were talking about earlier. You, oh, what am I going to write about? Oh, is this good? Is this bad? I'm halfway through writing about it. Should I tell people, should I change this topic completely? Should I throw this away? It's probably awful. My wife hates this book. And it's this huge tension that it's like a battle for years until you give birth.

27:52And podcast is not that way. So even like a TV show, like you mentioned 60 minutes, okay, they've got a whole meeting of 30 people get together and decide, okay, well, who's going to be a good guest? And then you five research this, you five research this, get all the notes together, and hopefully please God, it'll be a good show. And then they have a 45-minute interview that they're editing down and deciding what shots to go here to set that they're getting it down to a 14-minute piece or whatever, right? There's just a whole... The idea of just sort of unedited, like, here it is. Again, there's something refreshing about that, and that's why I like listening to them.

28:31But there is also, yeah, the ease of, there's a reason people like making them. It's because it's the easiest of all the things to do. But sometimes the conversation's great. Like I did just watch Joe Rogan had on Magnus Carlsen, who's the greatest chess player in history. And Joe, you can see, doesn't really know anything about chess, but is fascinated by somebody who's the greatest in history at a skill. And a skill that's so culturally significant. And so their conversation was fascinating because Joe is such a great conversationalist and is a genuinely curious guy. Whether or not you always agree with him, that doesn't have to do with his skills as a podcaster and conversationalist.

29:15So there's a reason he's the biggest. Yeah. And Magnus, who's not a conversationalist, almost by definition, he's a chess player. But Joe was able to get out this stuff that Magnus has really thought deeply about for decades. And that was interesting to me because it is so spontaneous. Well, then what's the one, who's the actor that he had on? Oh, did you watch any of the Terrence Howard one? No, although it's funny, I had never seen Terrence Howard really in a movie, but then I watched after that, I watched a little bits and pieces of it. And then I watched Hustle and Flow with Terrence Howard, John Singleton directed and great movie.

29:47Of course. But you're like, oh, okay, the same medium that's so conducive to getting something interesting out of, a great chess player also can allow a person who's clearly bipolar or manic or just like not well. Love him, but mentally ill. Yeah, you're watching it. You're like, this is not like if you watched a not well person being interviewed on CNN, you would turn it off. Like it wouldn't work. It doesn't work in the format. But the podcast medium is so forgiving that it allows a not well person to act like they're well. And millions of people listen to it and they go, oh, he really said something there.

30:25And it's like, no, this person, like this person should have been politely, you know, escorted to a doctor's office. Well, and the problem is the millions of people listening are not like just sitting at their homes and then they move on to the next podcast. Then they all go on Twitter and talk about it. And you have literally, it's 50-50. These 50 are defending and saying, yeah, he invented Wi-Fi. And then the other 50 is like, no, that guy has a problem, but they're not, you know, no one's ever going to cut. Oh, like, oh, I just read an anonymous person on Twitter and he changed my mind completely.

30:57Like that's never been said. Yeah. So, you know, it's, it's interesting in that way. And at the same time, then you get a completely different feeling when you read a good book where that there was that years of tension, like, oh my God, how should I sculpt this sentence and this part of the story? And like you said, it's edited over and over and over again. You know, the, what's the classic example, you know, Ernest Hemingway, his first book of short stories or no his first his very first book um what's the farewell to arms was that his first book uh anyway whatever sun also rises sun also rises he said he edited it like a hundred times yes see that you you there's like 50 endings yeah yes no totally it's all that's there and i would say honestly i think most people would be better myself included if we like listened to more music and fewer podcasts do you like because there's something music you know what music is no opinions right or if there are opinions it's mostly about humanity it's about life itself it's not opinions about uh culture war stuff for the most part in fact those songs are probably bad yes so like even like Kendrick Lamar okay you just did the Super Bowl show and he had this this song you know not like us I love the song but I almost felt when he mentions Drake in the song that okay I really love the whole idea of the song but I don't know what your personal beef is with with Drake, you know, and, and I have no clue at all.

32:22Like, well, I barely know who you are, but I like this song and I really wanted to hear good lyrics. Like you listen now to like, let's say Led Zeppelin and the lyrics, how do they even write those lyrics? It's so beautiful to me. And they're also, you know, they're so personal, but they bring up these, you know, feelings in you that are like, Oh my gosh, I forgot. I had these feelings listening to these beautiful lyrics how do they write those how do they write those songs i don't even understand how they how robert plant and i'm just using him as an example there's millions of great songwriters not millions but a lot but they're so beautiful to me and i practically cry listening to them and i feel like that's not just it's just not done anymore yeah i think we're too much of the moment and trying to root things in the now as opposed to sort of rooting them in the like kind of fun.

33:12Like, what's the last, you know that Olivia Rodrigo song, Driver's License? No. She writes a song, I mean, this came out in the middle of the pandemic. It was a huge song. But she's writing a song about getting her, like the feeling of getting her driver's license. And like, it's a sad song. It's like a poppy sort of, like, I mean, it was a teenage girl singing about this. But the reason it becomes this huge hit is because that feeling is such a universal sort of modern part of coming of age. Right? I think that the great works of art are rooted in some part of the human experience, even though they're very specific.

33:49They are somehow, some version of that happened to me, as opposed to, you know. I think people think of Bruce Springsteen as this kind of like, not political thing, but that his songs are very like class conscious and political, you know. But they're actually about human beings struggling. Yeah, I never feel the class conscious thing with him. I feel like you either buy into this emotion that he's experiencing or you don't. And it's just emotional. Yes. Yeah, and the emotions are timeless. So he's changing characters and eras and different worldviews. But it's rooted in some thing that whether you're very successful, very unsuccessful, big, small.

34:38young old, there's something in it that connects with you. Like you two, they come out of this violence in Ireland and Bloody Sunday is about this violent historical event in Ireland. I didn't know that when I first heard the song, but I still was able to enjoy the lyrics because the way they're singing, the lyrics themselves, somehow you can relate, even if you have no historical context there. Yeah, well, it's also interesting when you think about these acts that are huge in non-English speaking countries like they're in they're American or British acts but then they're huge like globally so people might not even know what the song is about and so at some level it doesn't actually matter what they're singing about it matters the emotion that they're evoking in how the random words are coming together and I always again I always just wonder like how that music writing good music writing seems to me the most creative thing of all because i it's literally the one thing where i can't imagine how they came up with these lyrics and i really think these people are sort of unique like did i ever tell you when i ran into bono no so like you've met tons of famous people because of the podcast i've met tons of famous people but when you see someone like bono it's like a different experience so i'm in an elevator in a hotel and he walks in with um uh some friends and they were talking or bickering or something like that.

36:03And Bono's just making a way. He turns to me and says, you know, look at these weirdos I'm with. And I just said something like, you know, you really got to be careful about who you hang out with. Like you're the average of the five people you spend your time with. And then as the elevator opens and they all leave and then Bono turns to me and hugs me and whispers in my ear, it's going to be okay, man. And then he leaves. That's amazing. Yeah. So it's just like he turned like this elevator ride into a work of art, at least for me. So my Bono story was I was having dinner with this guy. He runs a movie studio.

36:36And we were talking. And he was like, let's have dinner. And we had dinner at like Beverly Hills Hotel. One of the fancy hotels. Might have been the Beverly Hills Hotel. I think it was. Okay, so it's the Beverly Hills Hotel. And we're sitting there. And he goes, you know, like, you know, that's Bono over there. And I go, oh, wow, that's so cool. I was like, he's the best. And he goes, here, I'm going to take you. I'm going to introduce you to him. And I was like, okay. And so we walk over and he knows him very well. So he's like, hey, Bono. He's like, Ryan, this is Bono, the lead singer of you two.

37:05And then he goes, Bono, this is Ryan. Do you know the Daily Stoic? And he's like, no. And then I was like, why did you do that to me? I said to my friend, why did you ask Bono if I knew who I was? Yeah, but you just set him up to obviously say no. And then just sort of all the air went out of the room because we didn't, and so I shook his hand and left. But so my one Bono interaction was someone setting him up to say that he didn't know who I was. Okay, so if you were Bono there, what is the way to respond where the air doesn't go out of the room? Well, Bono didn't do anything wrong. He got set up.

37:44He didn't do anything wrong. But I'm still thinking how he could have kept... The politician's answer would be, you look very familiar. Tell me about it. Or, yes, I do. I'm a huge fan. Like, I actually did meet this politician the other day. Someone did the similar thing. Like, do you know? And he's like, oh, yes, I'm a huge fan or whatever. And I felt like a million bucks, you know? And then as I was walking away, I was like, he didn't say anything specific that would prove that he did. But I wanted it to be true. And so obviously, I suspended disbelief. And that's what great, personable, sort of charismatic people make you, can make you in the moment feel like they see you and they recognize you and they connect with you, even though they're about to do that to the person next to you and the person next to you.

38:37And that's a super rare skill. It's a rare skill. And you probably have had this experience just having a lot of politicians or actors. Same thing, by the way, politicians and actors, I've noticed. You've had a lot of politicians and actors on your podcast, as have I. And And I always, when a good actor or politician I'm having a podcast with, I always end up thinking mid-podcast, is this my new best friend? Like, are we best friends? We're going to keep in touch. Like, we're going to hang out in LA or DC or whatever. And then you never hear from them again. Or even if you go to LA and say, and text, like, hey, I'm here, like you said, or I should get in touch.

39:11Like, you never hear from them. Yeah. And they're so good at that. At first, I was like, oh, he wasn't really my best friend. but then it's like you appreciate that they have this amazing skill I wish I had that skill well no the ability to do that to someone you're interacting with that's like one elite level skill and then the way somebody through their art can make a person they're not even directly interacting with feel that way that's the most elite skill that a movie star can make themselves feel like your friend or your hero or that can connect with you through a camera, reading, you know, a script, that's an incredible skill.

39:55To elicit this sort of parasocial relationship is like, you know, magic. And I feel like you could tell when they don't have that skill. You could tell, particularly now, we don't just watch things, we then read about the things we're watching. So like, you get this third layer of analysis, whether it's a politician speaking or an actor acting. but you could tell, oh, this person's acting. I feel like this person's acting. I feel like what this politician said was not true, was not something they believe. But the really good ones, you cannot tell whether this is them or this is them reading a script.

40:30Yeah, there's no sort of artifice and it just feels natural. And then the part of it where you willingly suspend disbelief and allow yourself to enter the world or the mood or the story. And by the way, it's not just, I mean, this is like what demagogues do, right? This is what like bad leader, like it doesn't just have to be for good. What you have to do because to be, otherwise everyone's going to say that's a demagogue. Like that's an evil person. Oh, Hitler's just evil. We're not going to vote for him. No, no. He tells a story that you give yourself over to and you turn off the part of your brain that's thinking about the consequences or the risks or the stupidity of it or the contradictions of it.

41:13That's, again, a very difficult thing to do. Yeah. But then, like you mentioned earlier, how what they're really doing is just using their art to connect in such a way that you relate so much, you're like friends with them in your mind. And so then it can be said, writing then must be the hardest of all because you're at such a distance. They don't see anything but letters. I think the writer does feel it like, I'm having this experience that probably, or it's almost like maybe a survivorship bias, but you write about your experience. And if it's something that's relatable to enough people, you really do make that connect.

41:49If you have the skill of writing, it underlies all these things. You need the actual artistic skill through practice, experience, maybe a little bit of talent. And then you come up with a story that's either true or not true, but it's by magic, something that a lot of people have experienced or some people have experienced. So they relate to it or want to relate to it and they connect with you. I've met a lot of my friends now because they've read my books. Well, it's all art is magic, right? We don't really know where it comes from or why it works. But I think there's different potencies of the magic.

42:21There's something about music. It's like one note can evoke a mood, right? So there's something just extremely powerful about music. And so I think it can sometimes reach a higher plane. like I feel like there are a handful of notes in a song that are more in one song that are more evocative than all the moods that all of my books combined have ever managed to get out of someone does that make you upset? yeah I'm jealous I'm genuinely jealous of the power of music like I wish I could have come up with Hotel California sure and performed it on stage so I could actually see people responding to it yeah it's just never gonna happen for me and like comedy has something where it's like you're on stage and there's the mic and then you can, there's something about laughter specifically that's very powerful.

43:07I think writing is like, it's kind of crazy that writing works at all. Like the idea that just through strings of characters, which become words, which become sentences, which become paragraphs, and then a narrative, that you can, that I could convince someone that they should change their life in some way or that they're capable of something or that I can make them cry or that I could make them, you know, dedicate their lives to something. Like the power of the written word is incredible. It's just, I think it requires so much work to get it to do that.

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From the publisher

A Note from James:

Ryan Holiday is one of the few writers I consider a peer—not just because of the work he’s done, but because of the choices he's made along the way. We’ve both published a lot of books. We've both dealt with audiences, platforms, and the weight of having a “point of view” in a world that increasingly wants you to pick a side. This episode wasn’t meant to be a debate or an interview. It was just two people trying to make sense of the tension between creativity and truth, honesty and influence, and why sometimes the best thing you can say is nothing at all.


Episode Description:

In this candid and far-ranging conversation, James Altucher sits down with bestselling author Ryan Holiday to talk about the changing nature of creativity, writing, podcasting, and personal ethics in a polarized media landscape.

They discuss the illusion of having to weigh in on every issue, the danger of algorithmic thinking, and how to stay true to your voice without becoming a prisoner to your audience. Whether you're a writer, a creator, or just trying to think more clearly in chaotic times, this episode offers real insight into the forces shaping our thinking—and how to resist them.


What You’ll Learn:

  • Why sharing too early can kill creative momentum
  • How social media shifted from expression to algorithm worship
  • Why long-form podcasts might be bad for your brain
  • How writing differs from other art forms in its tension and permanence
  • The tradeoffs between artistic freedom, platform growth, and audience expectations


Timestamped Chapters:

  • [00:00] Writing Without Talking About It
  • [01:00] Why Book Ideas Need Time in the Dark
  • [02:00] Creative Compulsion vs. Discipline
  • [03:00] Stand-Up, Dopamine, and Daily Feedback
  • [05:00] Point of View in a Binary World
  • [06:00] Silence, Ethics, and Speaking Up
  • [07:00] Noise as a Form of Violence
  • [09:00] Political vs. Philosophical Disagreements
  • [10:00] Social Media’s Shift to Opinion Farming
  • [11:00] The Algorithm as Audience Puppet Master
  • [12:00] When the Audience Has You
  • [13:00] Podcasting’s Algorithm Problem
  • [14:00] Are Podcasts Dangerous?
  • [16:00] Podcasting vs. Books: Tension and Craft
  • [18:00] The Rise of the Longform Grifter
  • [20:00] RFK Jr., Bad Ideas, and No Fact Checks
  • [22:00] Why Audiobooks Outperform Podcasts
  • [23:00] Can the Medium Save Us?
  • [25:00] When Podcasts Work (And When They Don’t)
  • [27:00] Music and the Emotional Power of Simplicity
  • [29:00] Songs vs. Culture War Commentary
  • [30:00] Great Lyrics, Great Feelings
  • [32:00] Bono, Stoicism, and Making You Feel Seen
  • [34:00] The Parasocial Magic of Fame
  • [35:00] Acting, Politics, and Emotional Truth
  • [37:00] Writing as the Hardest Artform
  • [39:00] Why Great Writing Still Matters


Additional Resources:


See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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