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Ryan Holiday: Provoke With a Purpose — Transcript

Read the transcript of Caitlin's interview with Ryan Holiday where they talk marketing, provocation, and philosophy.
by Natallia Darozhkina | Nov 23 2017

Ben Schuman-Stoler: Welcome to Simplify. I’m Ben Schuman-Stoler.

Caitlin Schiller: And I’m Caitlin Schiller. Simplify is for anybody who’s taken a close look at their habits, their happiness, their relationships, or their health, and thought there’s got to be a better way to do this.

BSS: In today’s episode, Caitlin talks to Ryan Holiday, and… Well, how would you introduce him actually?

CS: Alright, so he’s an author; you may know him from Trust Me, I’m Lying, or The Obstacle is the Way.

BSS: Isn’t he best known as a marketer and strategist, but also as sort of a shit-stirrer, provocateur?

CS: Well, he certainly associates himself with figures who have kicked up controversy, like Tucker Max and American Apparel. But more recently, he’s become a bringer of philosophy to the masses, which is quite a departure.

BSS: This is where it gets really interesting. He advocates Stoicism and – for anyone who doesn’t know – classically Stoicism was about prioritizing self-control, fortitude and overcoming any destructive emotion, basically logic over emotion.

CS: Yeah.

BSS: But nowadays there’s like this modern strain of Stoicism that he’s been a big part of bringing it to the fore. And that focuses on being aware of what could be blocking you, overcoming obstacles and it requires a certain amount of, I think, self-awareness and wisdom.

CS: Yeah, lots of big questions here.

BSS: We also want to remind you, guys, that you can tweet at us. I’m @bsto. And you’re at…

CS: @CaitlinSchiller

BSS: Cool.

CS: Yeah, that’ll be fun. Oh, and don’t forget to stick around after the interview, we’ll make a book list for anybody who wants to go deeper into what we talk about in this episode.

BSS: Alright then, let’s get the tape rolling. Here’s Caitlin Schiller and Ryan Holiday.

Ryan Holiday

Caitlin Schiller Interviews Ryan Holiday

CS: So thank you for taking the time to talk today. I’ve been really looking forward to this.

Ryan Holiday: Yeah, I’m excited!

CS: Great! Could you do me a favor and introduce yourself?

RH: Yep. My name’s Ryan Holiday. I’m an author and media strategist. I’ve written 6 books on topics from media manipulation to ancient philosophy and I live in Austin, Texas.

CS: Cool. OK, can you talk to me a little bit about how media manipulation and ancient philosophy work together? How do you bring those two things together, if you do?

RH: I’m not sure that I do or that one could. As a writer, you know, my job is to tackle the topics that interest me, that are fascinating, and that I think are relevant in today’s times.

My first book was an exposé of sort of how the media system works – sort of a bit of a tell-all as well, having worked with a number of very controversial clients over the years. When I wrote the book in 2011-2012, I thought this is a fun if not alarming side of the internet.

And then my next book was about ancient philosophy, specifically Stoic philosophy, which was just something I was also very personally interested in and had some personal experience with.

So, the books don’t necessarily overlap, although I would argue that Stoicism – which is a philosophy about sort of inner discipline and clarity and sort of peace within the chaos of the world around you – would be a very relevant philosophy in a time of manipulation and dysfunction and noise.

CS: I think that’s true. Who is your audience?

RH: Yeah, that’s always a tough question. As a writer, you want to say, as many people as possible or you want to say, people like me. I try to go into every book with a very specific audience in mind.

But, for instance, if you’re writing a book and you write it in one way and it alienates another group of people, it doesn’t matter how popular it gets, you’re never going to reach them.

So, you have to know who a book is for. And I think you also want to think about, you know, who is a book not for. Which is something not enough people do with their work.

CS: That’s kind of a controversial tactic. It seems like you, do you like controversy? I don’t want to peg this on you, but it seems like it’s something that you sort of enjoy. You work with Tucker Max. You’ve been involved with American Apparel. Is controversy a good strategy? Because it seems like stirring it up is something that you either enjoy doing or you have a very high tolerance for doing.

RH: It’s probably a little bit of both. I mean, you know, controversy — seemingly for most people – has this overwhelmingly negative connotation whereas provocative can sort of be on both sides. What I’m trying to do is generate discussion with my work because I think that’s the whole point. If you’re not generating a discussion, chances are you’re not interacting and reaching people the way that you want to.

So, what I like to do is to take some, you know, sacred cow or to take some poorly understood but generally held assumption. And I like to challenge it and I think that’s a great way to break through to people and also on the marketing side it’s a great way to get people to hear about something.

CS: Yeah, like finding that niche and working it in a novel way.

RH: Yes. Actually, one other note on controversy is, I think, if you know who you’re making this work for and you know who it’s not for, it allows you to play to one base and sort of deliberately tweak or provoke the other base. So, for instance, knowing that I wrote these books, my philosophy books, with the idea that philosophy has been made needlessly elite or obscure, or it’s sort of almost got a fundamentalism to it, knowing that I’m not writing for that audience allows me to not get upset if that audience doesn’t like my work.

So, if some professor of some obscure school of philosophy says, you know, what Ryan is doing is bastardizing this philosophy, he’s forgetting this, this and this or, you know, it’s much more complicated than that, “Good! I don’t like what you do and I don’t want you to reach you.” So the fact that you are telling me that I didn’t do it your way is confirmation to me that I probably got at least close to what I was trying to do.

And this is true for a lot of things, you know, and not to make this political, but when Donald Trump pisses off people who are not part of his base that means he’s probably done something that his base actually likes. And so I’m not saying that that’s a general strategy that everyone should do all the time or that that’s even what I’m trying to do. But when you know who your audience is and who your – maybe we’ll call them your-not-audience – is, it’s not going to break your heart that someone who is never going to be a fan of what you’re doing is telling you that they are not a fan of what you’re doing.

CS: Yeah. I think that’s a very true observation. It takes a lot of fortitude though to decide that that’s OK with you. How did you come to that place in your work and just in your career progression where you decided, “I do have legs to stand on and I don’t care what you think.” How did that happen for you?

RH: That’s a good question. I don’t know. I mean obviously having worked for clients that would generate protests or boycotts or backlash was maybe an exposure to it that I wouldn’t have had otherwise.

But it was always interesting you know at American Apparel there’d be some massive controversy on the internet and then, you know, you’d look at the sales over the weekend and they’d have stayed the same or gone up and then you realized, “Oh, wait, there’s kind of this echo chamber out there.” It’s so easy to talk about things that you’re upset about on the Internet. But it doesn’t necessarily follow that it actually changes people’s behavior in any real way.

And so you sort of realize that there’s kind of this professional wrestling going on about sort of making everyone seem upset or that everything’s a crisis. And then you realize that it’s not that exactly how it’s going. And so I think that that helped me a little bit.

And then also, as you get more confident in what you do and you do more of it, you realize, I was never making this for everyone. I’m making this for who my audience is, I’m making it for what I’m trying to express here. It’s not unreasonable that some people would object to that. The Stoics would talk about this too. The idea that you can control other people’s opinions or that it’s even admirable to get everyone to like you, whether that’s a worthwhile pursuit, is not the best use of anyone’s time.

CS: Yeah. You’ve developed this personal philosophy at it seems a really young age. I don’t know exactly how old you are. I’m not going to ask. I think that we’re more or less contemporaries, but I kind of think that to get to a place where you have a well-buttressed personal philosophy, something had to happen. What was the crucible for you? Why did you turn to philosophy? What made you start looking?

RH: Yeah, I don’t know exactly. I think it’s a reasonable inference that most people are not operating by any sense of philosophy either religiously, spiritually, you know, academically, whatever. They’re just kind of winging it. And I think that’s why so many people end up either being people that they’d rather not be, or ending up very far from where they’d like to be career-wise or personality-wise or character-wise. And so I think a philosophy is sort of this guiding framework that helps you operate in life.

I’ve heard Stoicism expressed as an operating system and I think that’s an interesting metaphor. If it’s not the operating system, what is your operating system? I’m not sure most people have an answer to that.


BSS: Hey guys, it’s Ben. We’re taking a quick break from Caitlin and Ryan Holiday to hear from one of you. This is Kyle, talking about how reading can be easier than it seems and how it helps him with the big questions in life.

Kyle from The Phillippines: Hey guys! I just want you to know how glad I am when I found Blinkist and, of course, your podcast. It really helped me to expand my understanding of this existence while floating in this moist rock called home.

I really hated reading back then. But as of now, I have already finished 180+ blinks and 9 books on my Kindle. And that’s something I’m really proud of. Keep up the good work guys! Bye!

BSS: Thanks, Kyle!

And we’d love to hear from more of you. Let us know what you’ve learned, or how you learn, or something you learned was easier or simpler than you initially thought it was. Send us your voice! Just record a voice memo and email it to us at [email protected].

OK. Let’s get back to the interview with Caitlin and Ryan Holiday.

Interview Contd.

CS: I was reading a blog post of yours this morning about, well, it starts with Churchill. Can you talk a little bit about what a personal platform is and why it’s important?

RH: Yeah. If you think about how the media environment used to work it was that there were a handful of outlets who had distribution, or access to the public. So, if you wanted to reach an audience, you had to get access to that distribution. Well, to a large degree that has fallen away. There’s unlimited points of access to the Internet, mobile phones, social media – all these different things.

So, what I talk about is that everyone wants to have a platform when they have something they want to say or release, but they don’t do the work to develop that platform in advance.

So the story I tell about Churchill is that, and most people don’t know this but, Churchill was driven from political advice after the first world war. And as Nazism begins to rise in Germany, he’s a marginal political figure. He has no access to the levers of power inside Britain.

And so he builds basically an international platform as a speaker and as a writer. He takes to radio. He’s actually more popular in America than he is in his own country. You know, you can go back and you can read these articles that Winston Churchill wrote in, like, Ladies’ Home Journal and all these different outlets, and he built up an enormous fan base, a platform.

And I think this is increasingly valuable in our own time. Let’s say, you’re a rock band right now. You know, you’re not going to get played on the radio, you’re not going to be played on MTV. How are you going to get your music out? You have to have access to rock music fans because everything is so fractured that if you didn’t do the work to develop an e-mail list or to develop relationships with influencers – you’re not going to have any way to tell people, “Hey, I made this thing and I want you to hear about it.”

And so I think this is true across all different industries. If you don’t have access to people, your message will die of starvation because you can’t get your message out.

CS: So, how do people build a platform if you are writing a book or releasing an album? What’s your recommendation? Where do people start?

RH: Well, you know, obviously the easiest way is social media. But I tend to find that these are the most fragile of platforms. You know, it’s like you think about the people who built huge audiences on MySpace, where is that now? Or, you know, Twitter used to have very high engagement and now has a very low engagement. I think ideally you want to build your audience as direct as possible, right?

Like, we’re talking on this podcast right now and probably the vast majority of people are going to listen to it through iTunes. But what if Apple decides to stop supporting podcasts. And then how do you have access to those same people?

So it’s, I think the first step of a platform is capturing as direct a link as possible between you and the people who like what you do. At the end of the day it’s about making a list of people who you can contact. And you know 50 years ago that would have been a literal mailing list and then more recently it was an email list and now it’s subscribers or followers or fans, you know, the words are always going to be changing. But you’ve got to have access to people or you don’t have a platform.

CS: What do you think is the relationship between having a personal platform and being a personality? Is there a connection there?

RH: I suppose. I mean, I don’t necessarily know – do you use the word personality in a positive sense or in a negative sense? What do you mean by that?

CS: I don’t think it matters. I mean I was specifically thinking about Tucker Max just now actually and I wouldn’t say positive or negative. I used to read him in college and think he was terrible but funny. Do you think that in order to have a successful personal platform, does a creator have to be a big, huge personality? Or can they just produce decent work?

RH: I don’t think so. I would say producing decent work is a hard sell in 2017. I don’t mean decent as in decent/indecent. I mean decent as in middle of the road. To build a platform or a brand I think you have to be excellent. And excellent is going to be relative in different fields to different audiences. But it’s really hard to make a living being just pretty good.

So, I think we tend to care about the personalities of the people who are consistently making good enough stuff for us to care about these things.

I guess, not making a judgment on quality, but it’s very hard to be average and to build a platform because why would I subscribe or pay or request to receive everything that you do if I didn’t think you made really great stuff.

CS: Totally fair contention. Right. Why would you? It seems to me, though, that we have the attention economy now and, to get eyeballs on content, people, outlets, brands need to be ever more controversial.

RH: Yes.

CS: When you advise clients, do you have a moral North? Are there just things you won’t do?

RH: Yeah, of course. I wouldn’t necessarily go, like, “here’s the list of the 10 things I refuse to do.” But, you know, I wrote this book about media manipulation that was supposed to be a book about why media manipulation is bad and how it can be misused. I’ll tell you it’s very alarming to hear that most of the notorious people in the alt-right have not only read the book, but many of them sort of consider it a bible.

CS: Wow.

RH: The truth is these tools are indifferent; the tools are neither good nor bad. It’s how we use them. So, that’s obviously not something that I support, not something that I want to see happen.

But I think your point is a good one in that, when it’s so noisy it’s hard to break through that noise, especially if what you do is quiet.

So, when I do sit down and I look at someone’s work or someone’s trying to develop a personality, or brand, or whatever, what I try to go is, “OK, what’s the most interesting thing here or what’s the most unusual or unique part of what you do? And let’s lean into that at least at the beginning so we can stand out. And then once we’ve stood out then we can round out the offering a little bit more.”

I think probably one of the bestselling business books of all time, there’s this wonderful book called Blue Ocean Strategy. And it’s basically saying, “Look, you want to avoid competition, you want to go where there’s like sort of fresh blue water.” And that’s how I would think about it with a brand or a personality or whatever you’re doing. Curves, which is one of the examples in that book, didn’t try to compete with 24 Hour Fitness or Planet Fitness or any of these other gyms. They said, what’s a market that’s not being served? It’s little old ladies. You know, let’s go there! And so carving out a unique space for yourself is really important.

CS: Have you worked with brands or personalities who have carved out that niche and then want to, I don’t know, claim some other niches or go a little bit broader? What do you do once you’ve developed a brand around one niche?

RH: I mean, look, my own career went this way, right. My first book was a marketing book. Obviously that’s a very sort of established market in the book space with a lot of prospective readers, and, you know, I’ve got a pretty big advance for my first book. And it did OK. And then for my next book when I said to my publisher, “Look, I don’t want to be a marketing guru. That’s not what I’m interested in. I want to write about, you know, an obscure school of ancient philosophy. They were not exactly excited.

But to a certain degree I had already developed fans for that kind of writing. So I knew I wasn’t totally guessing, that people might like this. I did know that, and I built up a big enough fan base on the marketing side that I knew, “Hey, at least a percentage of these people are going to like what I’m doing. So, I know it is possible to round that out.” I think what you find is, if you make really good stuff and you have that distribution, you should be able to make it work.

And then it’s not that hard to have multiple tracks. You know, I think that was a thing that surprised me a little bit, it’s like, “Oh, I can write marketing books and my marketing fans will buy them. And I can write philosophy books and my more general fans can buy those.”

I think what one of the things you want to be cognizant of is that you’re not trying to push the wrong product on the wrong person. So as long as I’m not trying to get my philosophy fans to buy this marketing book and I’m not trying to get the marketing people to buy a philosophy book that they’re not interested in, and I’m just focusing on where those two overlap – then I’m good.

CS: I have also worked in marketing for a while just in various roles and I always said that the core competency at the heart of somebody who can be good at marketing is that you have to kind of be an optimist and be willing to look for the good in whatever you’re trying to sell or spin.

RH: Yes.

CS: What is the core competency for someone who can be good at strategy?

RH: That’s a good question. I would definitely agree with your assessment of marketing. If you don’t believe in the product it’s very hard to be a good marketer of it. And I would say my biggest successes as a marketer were on the best products and probably where I did the least amount of work.

When a person has written an amazing book that fills a very real and compelling need to a very obvious audience, my job as a marketer is almost just to get out of the way. It’s to go, “Hey, check this out!”

Versus, if someone has made an offering that’s complicated or hard to understand, or maybe that has a great promise but doesn’t fully deliver on that promise, then as a marketer that’s where I have to really sort of go to bat and, you know, sort of beg, and plead, and borrow, and steal to get people on board with it.

I feel like there are very few new strategies. Most strategies are just repurposed old strategies in a new context. So, I think an understanding of history is very important, an ability to see a bigger picture is really important.

And then, you know, knowing the right strategy and then convincing people to get on board with said strategy are very different things, so I think the strategist has to be a good communicator as well.

So, I mean I can’t really talk about the specifics but I had a session with a client on Friday and we sort of talked about this idea and we’re all very excited about it. I think it’s a great idea. But then actually convincing this person to do it and to do it right is much harder than brainstorming the idea in a conference room.

CS: Oh totally.

RH: And that’s true with marketing as well. You know, it’s like, you could have this great idea, and then by the time that the lawyers have gotten to it it’s been stripped of any of the reason for doing the idea at all. So that’s the depressing part.

CS: So depressing. Before you were good at what you do. What did you screw up doing? This comes from, I watched you on a London Real interview and you said that one of the things that we need to get better at is saying, “I don’t know about that.” And how do you live with that? What do you do when you don’t know about something?

RH: Yeah, that’s a good question. You know, one of the interesting things about being you know a somewhat public figure at whatever level I’m doing it at is like, you’re at in this exchange, for instance, you’re asking me questions and I’m expected to answer that. That’s how an interview goes.

But what I just noticed you can pick up a nasty habit from that which is that even if you don’t have an answer you just make one up. And really the “I don’t know” or “I’m not sure” or “I’m going to try to figure that out,” that’s something I deliberately try to practice now is like, refraining from having a conclusion just yet. Like, I want to wait and see. That’s something I don’t think comes naturally to me. I’m not sure if it comes naturally to other people, but it’s something that I’ve certainly tried to work on more. And I think that as I’ve become successful I’ve noticed it’s actually harder to do. So that’s why I work on it.

CS: Yeah, I don’t think that in general people do well with uncertainty, especially not when you’re supposed to be the expert and you’re put on the spot. You want to have a facile answer.

How have you cultivated it for yourself? Like, are you in a conversation, and you go, “OK, Ryan, slow down”, and want to think about it more? Like, what have you been doing to make sure that you can you can nurture that habit in yourself?

RH: Yeah, that’s a big part of it. And being comfortable saying “I don’t know.” I think we tend to see it as a weakness but it’s not. And then I would say the other thing is like I’ve tried to just say less generally. There’s a line I like from William Tecumseh Sherman where he’s saying, “never give reasons for why you think what you think because the reasons can change.” And so it’s just like the less you say the more options you have. And so from a social media standpoint I think realizing that just made me go like, “Oh wait, there’s very little upside for me in doing my thinking out loud here.” Like, if there’s a chance that I’m going to change this opinion in a month, why would I put it on record now?

Midroll #2

Hey, I’m Holger. I’m the co-founder and CEO of Blinkist. I’m here at our headquarters in Berlin and one thing I learned that was easier than I initially thought it was, was to learn another language. To be specific, Spanish. When I was in school, in German schools a lot of times you only learn one language which is English, and then in university I said I want to study abroad in another country and I really want to learn another language but I was kind of afraid of doing so but then kind of faced my fears, started to learn Spanish, learned it quite well and moved to Mexico for one year and there I really got fluent in no time because when you’re surrounded by people who speak another language it’s really not as hard to grasp another language and speak fluently.

Interview Contd.

CS: I really did want to talk to you about books because you obviously have such a strong relationship with them. Can you just talk to me about your relationship with reading?

RH: Well, I do it a lot. That would probably be the first characterization of the relationship. I have a quote in my book Ego is the Enemy from Bismarck where he’s saying, “any fool can learn by experience. I prefer to learn by the experiences of others.” I think that’s sort of a motto that I’ve tried to live my life by. I think if I’ve had any early success it’s it’s been a result of that model.

CS: Have you run into any problems because you thought you knew something from reading about it and then you didn’t?

RH: I mean I’m sure there has been instances where I thought I had an understanding and it turned out my understanding was only partial or it was superficial. But I guess I just mean, we have about 5,000 years of stories and myths. And so it’s like, why would you not avail yourself of that? You know, you read something like The History of the Peloponnesian War, and it’s like this epic… It’s the first or the second basically history book ever written. And contained within it is essentially everything that is happening right now and everything that will be happening in 100 years, and maybe instead of using you know wooden ships we’ll be using spaceships. You know, the names and the places and that the things change, but the fundamental themes never do. And so I think as a reader my goal is to learn – either to learn or be exposed to as many things as possible to eliminate as much painful trial and error as possible.

CS: So you kind of go in knowing that that’s your sort of philosophical reading goal?

RH: Yeah.

CS: What I notice about your books is that you do a tremendous amount of historical research and you cite plenty of examples; there are quotes everywhere. But what is uniquely yours? What do you want to be remembered for in your writing?

RH: I think what I’m interested in, and why my books have worked, is that I’m making connections between things that save people a lot of time.

So, I think one of the things that I’m sort of doing with my books is taking a huge swath of history or literature or philosophy or whatever it is and reducing it to a set of principles or lessons about a very specific topic. And so, I think I’m really good at research. I think I’m really good at making connections and I think I’m providing a service for people.

CS: Yeah and that’s like the essence of creativity too, I guess it’s finding new ways to make connections between old things that are novel and impactful.

RH: Yeah, there’s this quote I’m forgetting what it is exactly but it’s sort of like “the job of a great new book is to make you love old truths.” And I sort of feel like my job is to capture some of these timeless lessons maybe in some of the ones we were talking about earlier in this podcast and illustrate them in a way that makes people consider them and hopefully makes it stick with them.

CS: What old truth do you love?

RH: I love many, many, many, many old truths.

CS: What’s one that comes to mind? I’m just curious.

RH: In a more religious time and in a more uncertain time we thought about death all the time, right? There’s a whole genre of art called Vanitas which is just like pictures of skulls, basically.

So, an old truth I’ve been thinking a lot about and talking about and even made, like, a physical reminder that I carry around with me. But just this idea of memento mori like remembering that you’re mortal and that you have a very small amount of time on this planet and that, instead of that being scary, it’s actually liberating, and it should give you a sense of urgency about what you do.

That’s such an obvious truth. But I don’t think anyone could argue that it’s overly discussed.

CS: Yeah.

RH: You know, we have that exercise you go, “Oh, did you hear so-and-so got cancer. You know, what would I do if I got cancer?” And it’s like, you already do have a fatal diagnosis, like –

CS: Living!

RH: Yeah. When you were born the doctor could have said with 100 percent certainty that this child is going to die. It could die tomorrow, it could die 87 years from that moment. But we’re all going to die.

And yet this central – arguably the most important – fact about our existence is regularly, if not forgotten, deliberately suppressed.

CS: On that note, what are you reading lately?

RH: I’m reading this book called The General In His Labyrinth by Gabriel Garcia –

CS: Ah, Marquez, yeah.

RH: Yeah. Which I thought was really interesting. I was in Colombia, maybe like, two weeks ago and I ran in this park called Simon Bolivar Park and I’ve obviously seen statues of him. I think there’s one in New York City. And I realize I’ve no idea who this human being is. One of the most famous people in the continent directly below ours. And I know nothing about him. I never learned about him in school, I’ve never read an article about him. So, I started there and then it’ll be sort of the hopefully the beginning of a long journey into finding out who this extraordinary individual was.

CS: Hm. I like how curious you are about everything that you decide that you’re going to follow up on it when you get curious about something that seems like an important thing to cultivate too.

RH: Well, I think one of the ways you make connections is that, like, if I just read this book and then I moved on to a different fiction book about a different topic, I don’t think you’re – you’re not understanding the essence of what happened or who was involved. So I like to, you know, if I read one book about the Civil War five or six years ago and now I’m probably on 20 or 30. And so it’s – I understand the people, I understand this author’s take. I think one of the things that I try to cultivate as a reader is to ultimately know so much about a topic that I can tell whether the author is right or not.

I mean, I realize at some point it was very rare that I ever disagreed with the people I was reading about. You know, like I never disagreed with the author and that made me think that maybe my understanding of the topic was too superficial and that I wasn’t challenging myself.

So, yeah, I try to…I call it swarming, I sort of try to swarm around a general topic and sort of read everything about it and then, once you understand it really deeply then you can sort of analogize from that topic and you can know what’s important or not. You know, you can know when you’re watching the news and you know they go, “Oh, this is just like right before World War 2.” You can know if that’s true or not.

CS: Right, yeah. It seems like one of the things that we keep coming back to in the course of this conversation is is the importance of looking deeper and getting comfortable asking the big questions. Do you have books that you would recommend someone read if they wanted to get better at asking the big questions or better at being comfortable with that process?

RH: Yeah, that is a good question. One of my favorite books is by a French philosopher named Pierre Hadot. It’s called Philosophy as a Way of Life. And his basic contention is that we think of Aristotle or you know, Marcus Aurelius or Epicurus as these philosophers who are trying to create this systemic explanation of the universe, because that’s what we sort of see philosophers at you know Harvard or Yale doing. It’s like, “Oh, this person has this complicated explanation for this or that” when really they were – self-help sounds sort of dismissive– but really they were just trying to help people with problems.

If you take the stoics, if you take Seneca or Epictetus, often a student asked so-and-so a question and then here was their answer, they were basically bits of advice on how to live. And ancient philosophy was in the past mostly designed about answering that question, like, “How do I live?” and “How do I live well”?

And so I think focusing on books that guide you towards that is very, very important.

CS: Sort of on the note of how do I live and how do I live well, I was also looking at your Instagram, I did a thorough search on all of your social media profiles. I saw this lovely new letterpress print from The Daily Stoic that you posted and it says “Waste no more time arguing what a good man should be. Be one.”

RH: Yes.

CS: What does that mean to you? How do you enact that? And I mean does it have to be about being a “man,” it means being a good person. What does that look like?

RH: I think what the Stoics were saying is that the philosophy wasn’t this thing that you do in a classroom, it’s supposed to be what you do in life. So it was interesting, right, that’s the quote “waste no more time arguing what a good man is like, be one.” And then, you know, I got an email, and they’d go, “Oh my God, why does it say man, why not…” You know, I was like, this is actually exactly what he’s talking about, that, like, we would rather in our culture have sort of semantic debates about what does this word mean or is this the fairest way to say that instead of understanding what the obvious point was when he was making it two thousand years ago and then acting on said point.

CS: Well, I think there’s something to be said for semantics, in fairness, as well.

RH: Of course. But my point is that you could not pick a more ironic instance to do that than in this specific one which is saying that we tend to spend far too much of our lives arguing and talking about things theoretically rather than actually doing them.

So you know the most important discipline in Stoicism is the discipline of action. So what are you doing with this thing that you’re studying? What is the person that you ultimately end up being? What are you doing in in the moment?

There was just I think a month and a half ago a French philosopher, her field of study was risk, she was saying that taking risks is what makes life worth living. And she was on vacation on the beach and she saw a child drowning. I think it was a child of a friend and she ran out into the water to save the child. I think she did save the child, but she ended up drowning and dying.

And I don’t mean to be flip about it, but that’s the ultimate philosophical act, right? Writing her books about risk-taking is only the first step. And the second step – and I think she would have agreed with this – is, do you put the philosophy into action. Hey, there’s a child who needs me. Am I going to act on my principles in this moment or not?

CS: Again, to go back to how do I live and how do I live well: given all of the research you’ve done, given your vast amount of reading, given what you try to put into practice every day, what would you tell someone if they wanted to live better?

RH: Wow. I’d probably point them to writing, you know, much better than my own or that I could articulate. But I think this idea of the present moment is all that you’re at least guaranteed in life.

Right? So, many of us are either dwelling on the past or anticipating and thinking about the future. Meanwhile the present moment – what are you going to do right now, how could you live better right this second or do the thing that you know is right in the second – would obviously be a big part.

I would probably urge them to think about the sort of Stoic concept of making a big distinction between what you control and what you don’t control. And when you make that distinction and you focus your energy entirely on the things that you do control, you find that you have incredible amounts of energy that you were previously wasting.

And then, you know, sort of how can you see beyond, past or through the sort of petty either squabbles, or temptations, or obsessions of other people. You know, the people that want to be famous, or the people that want to be you know extraordinarily wealthy, or the people that are chasing this high or that high. I think one of the ways that you live better is by sort of making the distinction between what’s essential and what’s inessential. And then again focusing on those things that really matter to you and I think obviously more universally.

CS: Great. Thank you so much. This has been such a great conversation. Have a good day!

RH: Alright. Awesome

CS: Take care.

The Bookend

Ben Schuman-Stoler: Welcome to The Bookend, where we end… with books.

Caitlin Schiller: Hi there from Bookend #2 for Season 2 of Simplify.

BSS: Cool! That was a really surprising interview with Ryan Holiday.

CS: Yeah.

BSS: I’m really impressed, the guy’s awesome.

CS: He really was, we had a great conversation! He and I had a lot of fun and he was great to talk to. I mean, you know, I was kind of nervous about this one. It was a challenge to prepare for.

BSS: So, it was a couple of weeks back, but what really stuck out to you. I mean, what do you remember now about that conversation with Ryan?

CS: Yeah. Well, I think that, really—and this sounds very obvious, I know, but bear with me. It’s this idea that we can bring our passions alongside our profession and it doesn’t dilute a personal brand or personal integrity. I had, as I just said, I had a challenging time preparing for this interview, because I wasn’t sure if I wanted to talk with Ryan as a marketer, or as a student of philosophy, or something else entirely. And it turns out that we did both, because he is both—and I think that’s really important.

BSS: You mean like to have a personal philosophy in your marketing, or?

CS: Well, I mean, I think integrity is important, yes, but I mean that we get caught up sometimes in believing that we have to be ONE thing, that we must focus on ONE thing, that we have to consistently distribute only ONE message or it means that we lack integrity.

Yeah. And it’s not necessarily true, you can be somebody who does marketing for a living and also believes very, very passionately in the importance of something as esoteric as Stoic philosophy.

BSS: Right.

CS: And bring, you know, some unity to that in your professional life.

BSS: I mean, yeah. And I also just like how deeply he thought about how to read.

CS: Yeah.

BSS: So, speaking of reading, I’m curious to hear what kind of booklist we can make for people.

CS: Indeed. Yeah, I’ve got a couple for you. Ready?

BSS: Hit me!

CS: First one is Bird by Bird by Anne Lamott.
This one is actually on Ryan’s List of Books To Base Your Life On, which is on his blog. Bird by Bird is about the art of writing, but it’s also about life in general: how to deal with problems, temptations, opportunities, etc. etc. And Lamott writes it from her own perspective, so it’s her own advice on writing on her life and her own approaches, but there are also some nice anecdotes. So it’s mostly that appreciating life’s larger obstacles and small gifts.

BSS: That’s interesting that’s on his list, I would have thought that he would pick something like military history.

CS: Oh, but Ben, there’s more!

BSS: OK, so what’s the second one?

CS: The second one is The 48 Laws of Power by Robert Greene.
So this one is a classic. And it’s also by one of Ryan’s mentors. Ryan met Greene when he was 19 and Greene really shaped his trajectory. This book is on power and strategy. And Ryan says, “It is required reading for anybody who’s trying to accomplish pretty much anything in life.” This is the primer on what power is, how to get it, and how to keep it.

BSS: I also like Robert Greene. I can see them being connected, because Greene is really into these deep research projects. I did my own little bit of research, I went onto Wikipedia…

CS: What did you find, Ben? Tell the class!

BSS: Robert Greene wrote a book with the rapper 50 Cent. Remember him?

CS: What?

BSS: Yeah, and it’s called “The 50th Law”.

CS: Wait, where is 49?

BSS: It’s a semi-autobiographical account of 50 Cent’s rise through, like as a hustler and as a musician. But what I really like about it is that it features anecdotes, according to the website, with people like Abraham Lincoln –check out this list– Abraham Lincoln, Sun Tzu, Socrates, Napoleon, Malcolm X, and James Baldwin.

CS: Wow.

BSS: Yeah. It’s a diverse list. But that also tires into Ryan’s thing of, like, read broadly and, you know, extract truth…

CS: Read broadly and look at history. Yeah. And like, read broadly, extract truth.

BSS: Ok, so we have Anne Lamott, Robert Greene… We have another one?

CS: Yeah, last one is actually Ryan’s book – The Obstacle is The Way.
So this is a really nice light intro to Stoic philosophy basically, and it does exactly what Ryan talks about in the interview. It brings the main tenets of Stoic teachings to the fore through sharing stories of historical figures. There are also lots of great quotes from Stoic thinkers in here, so it’s a nice book to read to reorient yourself in terms of what it means to be impeded, what it means to set yourself free, and how to treat obstacles as your friends, not your enemies.

BSS: Yeah. We didn’t go into that much about Stoicism in this episode. But a little teaser about the kind of modern Stoicism that Holiday is into, is it’s a lot about dealing with obstacles and a lot about the logic of perseverance.

CS: Yeah. And about how perspective shifts are everything.

BSS: That’s a great book list.

CS: Thanks, Ben!

BSS: Alright, let’s give credits to the people who made this podcast. It’s always more than just me and you.

CS: Definitely.

BSS: First, thanks to everybody for listening to another episode of Simplify. This episode was produced by me, Ben Schuman-Stoler, Caitlin Schiller… Hi Caitlin!

CS: Hi!

BSS: And Ody Constantinou, who doesn’t carry a wallet.

CS: Oh, more fun facts. All right. Well, if you enjoyed this episode or feel that you learned something, consider sending it on to someone else who you think might like it too. Thanks to everyone who’s given us rating and reviews on Apple podcast, Overcast, etc., Pocket Casts, everybody who has ever said a nice thing about Simplify. Thank you guys, it means a lot to us! And if you haven’t done that yet, maybe take a second to do it. We really appreciate it.

BSS: Right. And another quick reminder that we’re on Twitter. I’m @bsto.

CS: I’m @caitlinschiller

BSS: That was really good! And Caitlin and I work at Blinkist, and Simplify is made by the in-house audio team who make the Blinkist audio also. So, we just want to remind you guys, Blinkist is a learning app that takes the world’s best selling nonfiction books and condenses them into focused little capsules of audio and texts that you can listen to or read in just 15 minutes.

CS: Awesome.

BSS: Right. And we made another voucher code, so you can try it out for 14 days.

CS: So you can go to and type in this episode’s very special voucher code, which is…

BSS: “vanitas”.

CS: Indeed.


CS: You can email me and Ben at [email protected]. If you want to let us know about your personal philosophy or anything else really.

BSS: Right. And you heard probably in these episodes that we are including your voices in the middle of some of the interviews, which has been really fun to hear from you. So you can record yourself answering Caitlin’s favourite question.

CS: Which is…

BSS: Which is… I’m going to try it.

CS: Do it!

BSS: What have you learned was easier than you initially thought it was?

CS: Yes, perfect!

BSS: It could be about anything. It doesn’t have to relate to this episode or marketing, or Stoicism, could be about anything. And just email the audio file to us at [email protected] and we’ll try to get your voice into the podcast.

CS: Yeah, it’s as simple as firing up your Voice Memo app on your phone and just recording us a quick message.

BSS: Cool! Then we are back next week again with another episode of the second season of Simplify. So, in the meantime, stay awesome! This is Ben and Caitlin checking out.

CS: Checking out.

BSS: See ya!

Read the show notes for this episode here!

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