Interview: Ryan Holiday

By: Cock Rock Posted in Interview, Podcasts on Tuesday, August 7, 2012

Trust Me, I’m Lying by Ryan Holiday

Here’s the transcript for an interview I did with Ryan Holiday. I’d post the audio but the sound quality came out terrible. HotRecorder would make Barry White sound like Eazy-E. It’s just as well, Ryan and I talk about ideas that merit a more concrete format.

Also, it’s a long interview, so get ready to concentrate. I was going to post it in several installments, but then I realized you guys aren’t idiots.

Mark Derian: Hey everybody, welcome to this special edition of The Brazen Heads. We have with us in studio—across the country, in studio… the whole country is our studio, I suppose—we have with us Ryan Holiday, author of the new book, Trust Me, I’m Lying. What’s up Ryan, how’s it going?

Ryan Holiday: It’s great, thanks for having me.

MD: Yeah man, thanks for doing this.

RH: Of course.

MD: So I bought nine copies of your book, because I wanted to read it nine times, and it turns out that if you buy nine of your books, then you will do a half hour phone call. And we could talk about anything I want, I suppose. I guess you give great marketing advice, which I probably need, but we’re not going to go there. Because I think what’s interesting about you is that you are into philosophy.

RH: I am.

MD: I wouldn’t say that’s your thing, but you would consider yourself a Stoic.

RH: Yeah, it’s one of the topics I’ve studied. I don’t know if I would identify as a Stoic. It’s something that’s changed my life a great deal and I do a lot of practice in it.

MD: You’re a practicing Stoic. Wow, I’ve never heard it said that way before. It kind of makes it feel like a religion. Like you go to a Stoic church or something.

RH: Well that’s interesting because I don’t think it’s an ideology. It’s a set of spiritual exercises or ways of looking at the world. So I don’t call myself a Stoic, I just use those tools in my life along with—and this is another Stoic idea—I use principles of other things that I think can make my life better, too. It doesn’t really matter where it comes or what it is, but if it makes you happier or healthier or more invincible to random events or fate, then I think it’s a good thing.

MD: Yeah, I’ve always considered philosophy to be self-help for smart people, or maybe self-help is philosophy for dumb people.

RH: No, I think that’s exactly what it is. People believe that philosophy is what you do in a university classroom, or a philosopher is only what a philosophy professor is. But the great philosophers like Cato, Seneca, or Marcus Aurelius, were philosophers because they lived creative, successful lives.

MD: Yeah, well a lot of that is philosophy’s fault. It’s really done itself in by emasculating itself. I read this new ebook—do you know who Sam Harris is?

RH: Yeah, uh huh.

MD: Well, I read this new ebook by him called Lying, and he talks about Kant’s view of lying and the categorical imperative, and Kant’s stance is you should never lie. And this isn’t some small philosopher, this is the most influential philosopher of the last 200 years, and even Sam Harris, Mr. “open to new ideas,” Mr. “tolerant of everything”—well, except Christianity and Islam—says, well, this is unsustainable. You can’t live like this.

So philosophy has really done itself in by sitting in the ivory tower and laying commandments on people not unlike Moses coming down from Mt. Sinai and saying, “no, this is just how you should live, and who cares how it works in real live?” Even if Nazis are knocking at your door looking for Anne Frank, you tell them the truth because it’s your duty.

RH: Yeah, I would totally agree. I don’t think philosophy has done itself much service. And I think a lot of people who get a benefit from calling themselves philosophers don’t get much benefit from people like you and me from having access to the subject. They want you to pay 30 grand a year to get a degree in philosophy, when in reality there’s only about five books you have to read to be as knowledgeable about philosophy as they are.

MD: Whoa, whoa, whoa, let’s not go too far. I was a philosophy major in undergrad, so let’s try not to make me feel too bad about the time I wasted. Let’s talk about how it was totally helpful, and how it’s totally helped me get tons of jobs. Let’s keep the conversation there. I would appreciate it for the sake of my ego. It’s pretty strong, but I can’t take those jibes quite yet. That’s really pushing it.

But yeah, I totally agree. We could go back to evolutionary psychology here. Philosophers are trying to seem like what they do is cooler than everything else so maybe we can get vagina. That’s what it is, it’s like, “how cool can we make ourselves look, while making everyone else seem lame and dumb?” This is our tribe, and this is how we get laid.

RH: Yeah, pretty much

MD: So can everything in philosophy be reduced to that? I know you have some dark views on the media based on your experience, and you’ve seen some of the base drives of the human condition first hand by something you call “one-off” journalism.

RH: Right.

MD: Which has taken over blogging, and it’s basically that a blog can just post whatever it wants with no consequences, no regard for the truth, and even if it’s wrong it doesn’t matter. Even posting a retraction of the post only makes people believe it more, which plays into certain biases of humans.

RH: Well I don’t think philosophy can be reduced to that. I think in it’s purest form, philosophy is normal human beings struggling with the gravity of existence and trying to make their way in the world, and coming up with ideas, hacks, and exercises to answer who we are and where we came from and what to do about it. And like, “hey, this thing works for me, and I think it will make your life better.” Or, “I put a lot of thought into this, and I think you might benefit from hearing it, too.” And that’s why I like ancient philosophy as opposed to philosophy as we get closer to modernity because it has too much artifice and pretense, when really philosophy is about how to live a better life. It’s not about making us smart better than others.

MD: Right, that’s a good point of philosophy. But there’s also the money grab and vagina grab that’s part of it, too. Just like in this media, which you talk about in this book, which, it goes without saying, I highly recommend to our fans. You point to the dark side of media, but it doesn’t have to be that way. Similarly, philosophy doesn’t have to be needlessly complicated to make people feel stupid. And yeah, I agree that ancient philosophy is better—actually Stoicism was the last little piece of philosophy before the rise of Christianity. Well actually I think it went Stoicism, then Skepticism, and that made the soil fertile for something like Christianity to grow

RH: Right, well I forget who said it but it goes something like, right around the time of Marcus Aurelius was the last time man stood alone in the universe. It was the last time before we had Christianity through which humans explained and analyzed the world. Christianity became our lens. But the difference between the media and philosophy is that philosophy doesn’t tell us about what’s happening right now, it’s supposed to tell us about more timeless truths. So you can read a book that was written 2,000 years ago, but you’re not going to read journalism that was written 2,000 years ago. And what I discuss in the book is that the channels through which we’re given current information inherently corrupts that information, rendering it completely unreliable.

MD: Yeah, media’s not like philosophy, but my point is that there should be more philosophy in journalism. What we try to do here on The Brazen Heads is, yeah, we talk about current events, but we also talk about how those current events relate to more abstract ideas. So even in 5,000 years when somebody does listen back to this, they’ll say, “I have know idea of this event these guys are talking about, but the way they’re relating it to this idea…”—you know this is my fantasy. It will be some guy’s job in 5,000 years to study The Brazen Heads.

RH: Yeah, I agree.

MD: So there should be more philosophy in the media, and I think if there was more philosophy in the media—here’s my contention—there would be much less of this one-off problem you talk about in blogging and websites like Gawker and Huffington Post.

RH: Yeah.

MD: Because the story now is all facts. Yes the facts matter, but there’s another conversation to have. When the facts are tempered by commentary—hey, maybe even rational commentary, you never know—that would lend itself to more relaxed media.

RH: No, I agree. I think the journalist’s job is to get us the truth, and it’s to tell us what we’re supposed to do with information. Unfortunately, they think their job now is to get us information as quickly as possible, and it’s up to the users to decide if it’s a value. And so you don’t get context, or connection to abstract ideas, or why you should care about something. And philosophy is really good at that. It tells us how to interpret and make use of things. Journalism, as it’s gone away from that, has basically just become entertainment.

MD: Yeah, do you think that part of the problem—no, I’m not going to say that, that’s would be a leading question. I’ll say this. I think part of the problem is cultural. If we weren’t bored, we wouldn’t be susceptible to the media. I know just from working at home. If I’m bored with something I’m way more likely to go on Drudge Report. But if I’m exciting myself with work, I don’t care about Drudge Report, I don’t care what Arianna Huffington has to say. And also, if we cared more about philosophy, or at least thought it mattered, then philosophy would matter more to the media. I know I made those self-deprecating jokes about philosophy a few minutes ago, but I think it matters. And I love defending my philosophy degree to people, because I will be right. I will win that argument.

RH: Yeah, the existential vacuum contributes to places like Gawker and the Huffington Post, and yes, the readers have a role in the problem. Readers think they need to be updated constantly and get their news in 140 character increments. And they’re so unhappy in their own lives that they take great pleasure in tearing other people down, shitting on them, and writing angry comments. So yes, there’s plenty of blame to go around here.

And I think that the more you read philosophy, the longer term your outlook becomes. The more you read philosophy the more you think, “okay, what am I doing with my life, what am I doing with this brief thing I’ve been given,” and so the less you’re concerned with looking at Kim Kardashian slide shows—

MD: Whoa, whoa, whoa, Kim Kardashian slide shows might be interesting. Let’s not go that far, Ryan.

RH: Well, I will go that far. And the more you’re happy with yourself, the less you’re reading blogs and tearing strangers a new asshole.

MD: Yeah, nobody who’s happy with their life never goes out of their way to hurt somebody. I was at a bar about a month ago and this chick’s anger at me was so overblown that I just looked at her and was like, “You must be the least happy person ever.” There’s nothing else that would explain you trying to make me feel terrible. Or you have a crush on me, either one. But the way you’re so angry with me after only knowing me for 30 seconds, you’re anger isn’t about me. It’s about you. You must be miserable and I really do feel sorry for you.

RH: Totally.

MD: And that’s exactly the way I feel when I look at YouTube comments. Why is YouTube the worst as far as comments go? You can’t go six or seven comments on YouTube without somebody being racist or comparing someone to Hitler. I dunno, there’s just something weird about YouTube.

RH: Yeah, I think it’s the anonymous nature of it. And you’re not trying to build a reputation on the site. Forums are usually better because everyone knows you. But you comment on this video, you’re one of 6,200. And another part of it is, look, there’s a huge portion of society that’s miserable and filled with hate and just awful and they’re generally not part of our worldview or our existence but they do exist. The internet is the great equalizer since we’re all now swimming in the same pool for a change.

MD: Alright, cool. Now this is a good segue to get back into your Stoicism. You just said that large portions of society are miserable and cruel. Is it this view that lends you to stoicism? Because stoicism did develop from Cynicism, and the founder of—well, maybe not the founder, but one of its adherents, was Diogenes. And we all know Diogenes as the guy who walked through the agora with a lamp looking for an honest man.

RH: Right.

MD: So much of Stoicism stems from, maybe not a poor view of man, but a poor view of the world. And when you have a poor view of the world, you begin to detach yourself from external possessions, and life becomes about your internal state, your internal motivations. So do you think that’s what got you into Stoicism? Or tell me I’m wrong. What is it that really rung true for you with Stoicism.

RH: Yeah, I don’t know if I’m cynical. I think I’m pretty realistic. The reality is, if you want to go back to YouTube, in the Roman days people would go to the Coliseum and watch animals tear humans apart. Just like you go to a YouTube comments section and see people figuratively tear people to pieces. That’s always been a part of us and we all have those instincts that drive us. Hazlitt says the sway of the wild beast rises up inside of us, so when we see what’s happening, we almost cannot help but get caught up in it. And some people have more control over their impulses, but it really comes with practice.

To me, what’s always rung true with Stoicism is I was always a self-reliant person. I was always independent and private. Even when going up. I was never estranged from my family, but I never totally fit in and I was never doted on by my parents. So to me, when I picked up The Meditations for the first time, the message of, this is your life, you’re responsible, you’re on your own, no one is coming to save you, you have to be accountable, and at the end of the day, you have to answer to yourself for what you do and what you will do, and there’s no reason why you can’t be great at it. So I think that’s what I latched on to. I read as many books, listened to as many lectures, and I talked to as many smart people as I could about it. It became a transformative point in my life. It crystallized what I think a lot of us intuitively know, but we don’t realize that a lot of smart people have struggled with this and made a lot of headway with this over the last 2,000 to 4,000 years.

MD: That’s interesting. It sounds like you got all the good points out of Stoicism. Because I would call Stoicism a philosophy for the downfall of civilization. It teaches people you’re not to desire, and yeah, you’re on your own, but there’s a negative connotation with that. As an individualist, I love that stuff, but Stoicism grouped it together with being congruent with the fact that nothing good is ever going to happen to you. And I don’t think it’s a coincidence that this was the major philosophy that led to the downfall of Rome, and I think it paved the way for something like Christianity. Skepticism helped a lot with that, too.

RH: I think it would be false to attribute the fall of the Roman Empire to Stoicism. I think it’s the philosophy that is a response to a decaying and decrepit society. It says, “look, this is the attitude you need to have to get along in a vicious world.” And I don’t think it’s a coincidence that in times of strife and difficulty, Stoicism has sort of risen again, from the Gilded Age to today to the fall of the Roman Empire. People are looking for a way to cope with a world they cannot understand. And I think Stoicism does a good job with that.

MD: Well I would say that Stoicism is at least a major contributing factor. But if it wasn’t Stoicism that demolished the Roman Empire, what was? What gave rise to a world in which Stoicism flourished?

RH: I think the political context had more to do with the fall of Rome than the philosophical context. Rome became an unruly, corrupt, overtaxed empire that lost the guiding principles that drove the expansion of the empire. When those things collapsed, it couldn’t support it’s own weight, and that’s what caused the collapse of the empire more than anything else.

MD: Yeah, this is getting pretty dark.

RH: Yeah, these are hard things.

MD: But it’s important to talk about these things. And we have talked about the potential downfall of Western Civilization before on this show, and my point to the fans is always: look, civilizations come and go, that’s just what happens. But the point is individuals live on. Don’t put too much credence in, “oh, there has to be a western civilization.” No, there doesn’t. There just has to be you, a thinking individual, who can possibly create value for other people. That’s what should really be a keystone in your life, not, “oh, what if the American government goes belly up?”

RH: Right, I think that’s a great way to put it.

MD: Alright, now in your book, Trust Me, I’m Lying, you say that much of the media acts the way it does because it’s responding to how people are biologically. For instance, there’s a cognitive bias that ascribes too much truth and meaning to something we see, and then to use all subsequent facts, even if they’re contradictory, to support that first thing we see. And I’ve heard Michael Shermer talk about this, do you know who he is?

RH: No.

MD: He’s a major skeptic guy; he’s probably friends with Sam Harris. But he talks about how this bias developed on the African plains millions of years ago. If we see a rustle or hear something, it’s more advantageous to our survival to go with it and believe it. (Edit: The negative consequences for believing something to be true are small, but the negative consequences for believing something to be false are large.)

RH: Right, of course.

MD: So if the problem with the media is biological, what hope is there to fix it?

RH: What I say is look, when the media used to have time to think of an idea for a day or a week or a month or sometimes a two-year investigative piece, we were a little more insulated from those first impressions. So journalists were more able to dedicate a career to conquering some of those impulses, thinking through them, and creating checks and balances against them. A journalist would sit down with his editor and maybe take a few days to even talk about an article. The editor would say, “well, I think this is good, but maybe you jumped to a conclusion here, let’s at least talk about it in this way.” Today, reporters have to publish five or 10 articles per day, which is preposterous. And reporters are incentivized or paid to exaggerate the significance of their pieces, because that’s what gets the most page views. And the reality is we tend to believe what we read, so journalists and writers have a responsibility to ensure what we’re reading is good, accurate information and commentary.

MD: A responsibility that can only be born from philosophy, is my point.

RH: Yeah, both. In the book I discuss how the rise of subscriptions in newspapers created good incentives, but it was also pressure from journalistic clubs that created some sort of identity and purpose that reporters took from their job in the early 1900’s, until Woodward and Bernstein. Journalists used to see themselves as being very important for society, and they took a lot of pride and honor in what they did. When journalist did this, they made a better product than they do now, when everyone is trying to line their pockets as quickly as possible to get a bigger piece of the pie, and do crappy work because of it.

MD: Right, and it matters less in a society that doesn’t care about philosophy.

RH: Of course.

MD: And I get that there may be a biological component driving page views on Gawker, and similarly, there’s a biological component to being afraid of heights, or of falling. But there are free climbers—free, soloist climbers—who scale Half Dome without any ropes or harnesses. And they spend years suppressing that adrenal response that comes from being high up on the side of a cliff.

RH: Right.

MD: And if they can do it, we can do it when it comes to suppressing our need to refresh Drudge Report every three minutes. Well actually, Drudge Report refreshes for you. So maybe the Huffington Post. We can maybe not see what Alec Baldwin has to say this week. We can maybe chill out on this and look at our own lives for a little bit and concentrate more on what we want to do. If some guy can climb Half Dome without an adrenal response, we can have the internet without an “I need to be updated” response, too.

RH: Right, and we have to embrace the difficulty and hard work that goes along with that. In addition, and I bring this up in the book, we have to do away with the preposterous notion that news and information is going to come cheap and easy and fast. It’s not.

MD: Man, it’s tough. How do you motivate people to do that? Maybe if we figured out a way to have studying philosophy get you laid more. That would bridge the gap.

RH: Well what I try to do in the book is to show the cost. This cheap and easy information is actually very expensive, and it’s costing us a lot. So I hope the consequences are somewhat of a motivator, but I think you’re right, the aspirational messages are always a bit more motivating.

MD: Right, what you say in the book is good, but people don’t make decisions based on logic. This has been shown in people who have brain damage in the emotional centers of their brain. They can’t make any decisions at all. You can sit them down in a restaurant and give them a menu, and they’re like, “I don’t know what to do.” So there has to be an emotional element. Like I said, I just read that book by Sam Harris on lying, and his point is, well, you shouldn’t lie. Well that doesn’t matter, people don’t take, “I shouldn’t lie” out into the world and then not lie. There has to be an emotional drive. Which, I think, is being really comfortable with yourself. You have to be a master at dealing with uncomfortable emotions. That’s how you become honest. Sure, you also have to believe lying is wrong, but that’s just the cherry on top.

RH: No, I agree.

MD: Okay, well, even if you don’t, I still appreciate the fact that you would say that.

RH: (laughs) no, I’m actually lying.

MD: Well that’s okay, I’ll still take it as the truth. On podcasts, that’s all the truth needs to be. You can lie to me, just pretend it’s the truth.

RH: Correct.

MD: But I will say, just to give myself a plug, we said that one of the solutions to the media mess is more philosophy in journalism, which is what we do here on The Brazen Heads and my website, Anything you want to plug?

RH: Yeah, you can find me on I recommend books on philosophy life and you can check those out on my site if you like them.

MD: Alright man, well cool. Thanks for doing this, we appreciate your time, and take care.

RH: Alright, I’ll talk to you soon. Thanks again.

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    About Cock Rock

    I am Mark.

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