The Fearless Stoic with Ryan Holiday

 

Chapter 1: Ryan’s Mamba Work Ethic

 

FRED: Ryan Holiday, welcome.

 

RYAN: Yeah, thanks for having me.

 

FRED: Thanks for being here. So you’re the best-selling author of ten books now, many of them on the wisdom of Stoic philosophy, including The Obstacle Is the Way, Ego Is The Enemy, and your latest book, Courage is Calling. You started your career as the first marketing director for American Apparel, where you were the strategist behind some of the most provocative and successful campaigns ever in retail fashion. Over the years, you’ve worked with several Mavericks, thought leaders, and best-selling authors, including Tucker Max, Tim Ferris, and of course, the great Robert Green. A lesser-known fact is that you’ve actually won a Grammy Award for producing a jazz album in 2017. Just pretty awesome. You’re very active.

 

RYAN: I was a producer. Not the producer, but yes, it was a weird experience.

 

FRED: That’s great. I want to talk about that. You’re very active on social and traditional media, spreading the wisdom of Stoicism to a new generation. Your Instagram account, Daily Stoic, is a source of daily wisdom tidbits for over a million people. I love it. It’s one of my favourite Instagram accounts. I’ve been enjoying your books and insights for years now. Ryan Holiday, it’s a pleasure and honour to have you here with me today.

 

RYAN: Yeah, thanks for having me.

 

FRED: Awesome. So, I want to start by talking a little bit about your mindset at work. Okay, first of all, I look at everything you’ve achieved, and I can’t believe you’re only 34 years old. It’s kind of crazy. I mean, you’ve achieved more than people do an entire lifetimes, and not just in one area, but in, like, multiple areas like marketing, consulting, book publishing, music production, and all at world-class award-winning levels. At the same time, you seem to also have this very humble philosophy about work. On your Grammy trophy, the caption you chose to write on it was, “When you die, this will go in the trash along with the rest of your accomplishments.” In your book, Ego Is The Enemy, you write about how dangerous it is to be invested in the story you tell about your own specialness and how this can actually hold you back from achieving great things. A lot of people today were raised on ideas from the self-esteem movement in education, where they’re told they’re special and unique just the way they are. And it’s funny because you’re technically part of the millennial generation, and the cliché is, we hear a lot of people are entitled in the millennial generation, but you seem to be the opposite of that cliché when it comes to work. I read stories about when you started working with Robert Green. You transcribed hundreds of pages for him. You’d read all the books he doesn’t want to read. If you needed something in seven days, you get it done in three days. There’s something very old school about your work ethic and self-discipline and your high standards. Tell us a little bit about your mindset when it comes to work, how you approach what you do and where does this come from?

 

RYAN: Yeah, I don’t know exactly where it comes from, and I have been described that way before. I don’t know what generation I would, I would assign myself, like, which one I would identify with, but I’ve always just been focused on, like, doing stuff. So not talking about stuff but doing stuff. And especially early on in my career, that meant there was a lot of things I had to learn first. And so by… when I was working for Robert… It’s funny- I was just in Los Angeles very briefly, and I went to see Robert, and it struck me how many, as I was driving, it was like how many times I’d done this drive late at night to go drop off a manuscript or a page or a book that he’d had me read or something. And I thought I recalled it very fondly because as sort of gruelling as it was and sort of unsexy as it was, at the same time, I was just beyond excited. Like, I really wanted to be a writer. And here was one of the greatest living writers in the genre that I wanted to be in. And this person was letting me, not just like, know them, and not just paying me money, but letting me work on something they were making that I would have been excited just to read as a fan. And so I think when you, when you find something that matters to you a great deal, like that money is not important, status is important, you just actually love and are interested in that thing, you’re sort of willing to do anything and everything else kind of falls away. So I kind of- I just really love, like, the work that I do. And I know that sounds very simple. You know, “Find- Do what you love and you’ll never work a day in your life.” I’m not saying that. What I’m saying is that, like, my publishing output is not because I was, like, consciously I need to write this many books. It’s that it’s more fun and enjoyable for me to be writing a book than not writing a book. And so I always am doing it. And in fact, the hardest part, as I’ve got, I think early in my career I was… Obviously, I wanted to be successful at what I did, and there’s a certain amount of sort of ego and validation that you chase as well. But like, as I’ve gotten on this track now, the one thing I don’t like about the process, and I’m going through it now on the new book, is like media, like, press is not only like, not that fun, but the hardest part is like, how do I fit it into the schedule when what I really want to be doing is writing? Like, this morning I had to do a bunch of interviews, and it was like, I wasn’t thinking like, “Oh, this is so fun and validating and cool. I’m important.” It was like, “This is really getting in the way of the writing that I wanted to do.” And so I think at the core, it’s about, like, genuinely finding the process enjoyable. If that, if you can nail that down, pretty much everything else follows from it.

 

FRED: So it sounds like you’re really invested in the craft. So you found this thing that you love, writing books, and then you immersed yourself in the craft so much that even the things that may not be the most enjoyable parts of it because they’re connected to that thing that you love, you learn to love them over time. Is that fair to say?

 

RYAN: Yeah. And so like a book, for example, a book is a very big problem. What is it about? How will it be set up? Who are the characters, etc? But then it’s also a number of many smaller problems, right? What will chapter three be? Who will you open chapter three with? How will you arrange the thoughts? What are you going to include? What are you not going to include? Should chapter three be cut? Because actually, it’s redundant with chapter seven, right? It’s all the little pieces. And I think what I really love is, I love the problem-solving. So I love, first off, the big problem “What should this be? What’s the angle on it? Why is it important? Why do I care about it?” But then I break each big problem up into lots of smaller problems, and I focus on those and then so day to day, I’m not even really thinking about writing a book. I’m thinking about this little thing that I have to do, like, and so I’m always zoomed way in on a pretty engaging, compelling problem that if I do that enough times, cumulatively, a book comes out of the other side of that.

 

FRED: Very interesting. It sounds, really spoken like a true craftsman and, you know, we may look at it from the outside as self-discipline and like pushing yourself to do things, but like the passion and the love for what you’ve chosen to do is very, very clear and evident.

 

 

Chapter 2: The Dark Arts of Marketing

 

FRED: When I look at your career as a whole, I see sort of two big themes. The first one that you started your career with, let’s call it “The Dark Arts of Digital Marketing”. Ok? You practically wrote the book on manipulating digital media to spark publicity. I mean, you also actually wrote a book on that topic, Trust me, I’m Lying, which is really, really fun read and very educational too. Your campaigns for American Apparel are epic. When you started helping Tucker Max with his infamous classic I Hope They Sell Beer in Hell, which sold millions of copies, you guys did some pretty hilarious stuff to drive publicity. Some examples: you created a Facebook boycott of your own product; you vandalized your own billboards; you’d make formal complaints about your own offensive ads, get them banned, and then put out a press release denouncing the ban and… Really hilarious stuff. And it was also very effective at driving publicity and awareness about the book. That’s why I say that I call it “The Dark Arts of Marketing and Publicity”. The second theme, though, is the one you developed later on. And it’s about as far from this world as possible. It’s about taking Stoicism, this really deep, introspective philosophy that was pretty obscure from public view for a very long time, that you’ve done a great job popularizing and democratizing and bringing it to a new generation, to the Facebook, Instagram generation. And almost to the contrary of digital marketing, Stoicism isn’t about selling or manipulating emotions. It’s about developing inner fortitude and not giving into, you know, superficial passion and overcoming adversity and not worrying about what you can’t control and all that good stuff. How did you transition from the one to the other in your life? What led to that switch for you? Was it an experience, a realization? How did this come about?

 

RYAN: Well, it’s weird because actually the former, or the latter precedes the former. So, I was introduced to Stoicism when I was in college, and I sort of was very interested in it as a philosophy, and I was exploring it. And then also professionally, I was sort of very interested in digital marketing. So I kind of had this… I think I say this in Trust Me, I’m Lying, we think of the word disintegrated, meaning that it fell apart, right? But actually disintegrated means not integrated, right? And so I sort of had these two spheres. So I was very interested in marketing and what one had to do to be successful in this world and how one mastered it, how one understood the logic of that world… And then personally, I was very interested in philosophy for my own development. I was interested in writing about philosophical ideas. And I admired great writers like Robert Green who were able to communicate those ideas to people. And so, I sort of kept them separate, and I, but I grew increasingly disillusioned with, not just the marketing world that I was in, but where that would inevitably take me and what it would mean if everyone was acting the way that I was acting, right? I think one of the things that really struck me as I was sort of doing these pranks and these stunts is like, look, this is relatively harmless stuff in that I am promoting a T-shirt company or an author or an interesting brand. But what I really became suspicious and alarmed about was what might someone with worse intentions or motivations be able to do with these same ideas? And that’s in part what motivated the book, which was also an opportunity to transition from one world to the other, or at least to integrate them more closely together. So I always had this idea that I wanted to be a writer. And then it was really a question of what the first book might be. And so for me, the idea the first book could be this thing that I was professionally known for, that I had an interesting perspective on, and that by writing about it, I was also, in a sense, burning the boats behind me and would have to go do something else. So, you know, the week that Trust Me, I’m Lying came out, I had sold, I went out with and sold the proposal for what became The Obstacle Is The Way. So the transition was pretty abrupt. But the irony was when I came out with Trust Me, I’m Lying, a lot of my readers were like, “I thought you wrote about ancient philosophy.” And then when Trust Me, I’m Lying came out and did well, and then my second book came out about philosophy, they were like, “Oh, wait, I thought you wrote about marketing.” So there was kind of these weird parallel tracks, and then they kind of merged and then one stopped, you know, altogether.

 

FRED: I wonder if… I know that you’re not super political, but you do have political consciousness in some of your writings and some of your posts.

 

RYAN: Sure.

 

FRED: And I’m curious to know if your fear that some of the dark arts that you studied and published, that you see them manifested in the political landscape today? I’m thinking of, like, Roger Stone-like tactics. Have you seen some of the…

 

RYAN: I’ll give you a terrible example. I’ll give you a terrible example. There’s a guy named Sam Nunberg who was an aide to Trump, who, he claims, and there’s some verification of it… So his favourite book is Trust Me, I’m Lying, this guy’s. And his claim to fame is that he gave Donald Trump the idea for the border wall. And so, yeah, it’s heavy shit, and not exactly… it’s exactly the opposite of the intention of the book. To me, the idea was, I wanted to expose how media manipulation work, hopefully, to make it less effective, right? And then to watch, not just political operatives inside the United States, but you could also argue a lot of the disinformation and misinformation tactics of sort of foreign actors, whether you’re talking about Russia or China, relies on some of the same stuff that I was talking about in the book. I’m not saying they got it from me. But these are the ideas that I was trying to wake people up about in 2011 when I was writing that book. And so the other terrifying part is, you know, that book is now ten years old. I thought I was late, like, when I was writing about this stuff, I was like, there was a part of me that was like, everyone knows this or if I don’t get this out right away, it’s going to be irrelevant. And so for that book to continue to be relevant is not exactly my definition of success. I would like to, it to have been proven wrong or to have done its job, which is that, you know, people put up some relatively obvious defences against these sorts of loopholes.

 

FRED: It’s almost a sort of like Frankenstein phenomenon where it’s like you create this thing… And clearly in the book, anybody who reads the book, you’re trying to sound some alarm bells, right? And you’re trying to say, like, “Hey, guys, look at how the state of journalism and media has deteriorated to the point that we can do these things and they work.” Yes, of course there was the tactical goals that you had for particular projects, but there was also this larger point of like, raising

some red flags about journalism ethics and about how easy it is to manipulate the system. And low and behold, we’re like ten years later, and if anything, the media apparatus looks like it’s deterred even more and even more prone to this kind of manipulation.

 

RYAN: That’s exactly right. I sort of likened it even then, sometimes people who are really good computer hackers will like, seek something out for the challenge of it, like an FBI database or a major corporation. But there’s a difference between black hat and white hat. And white hat hackers will hack into something and then sort of explain how they did it and alert the people to the vulnerabilities in the system. To me, that’s what I was doing with that book. And I think the fact that I published it in a book instead of, you know, profiting from it personally is evidence of that. But unfortunately, by ignoring that, we’re now in a position where people who are much more of the black hat variety are still able to take advantage of these same vulnerabilities and do so on a regular basis. And that’s why we’re in this divided, dysfunctional, frankly delusional media environment that we’re in, where it’s impossible to discern fact from fiction. It’s weaponized against vulnerable communities, and basically, everyone is unhappy.

 

 

Chapter 3: Overcoming Fear

 

FRED: It’s very interesting. I find a potential running thread between your two passions or your two large endeavours is maybe about controlling fear. You’ve written about how, in your consulting work, when you go to people about, you know, different things they can do with their ads and, you know, ask whether you could deploy this for other fashion companies, you said, “No, most of them are too afraid to do this.” Right?

 

RYAN: Sure.

 

FRED: So there’s a fearlessness that is implied in everything you do. And there’s this approach to fear- overcoming fear to achieve your outcomes seems to be, seems to be one of the running threads I find in your work.

 

RYAN: Yeah, I guess that’s true. I mean, to me, what I have always just found from a marketing perspective, whatever you’re doing, whatever industry you’re in, that there’s a premium attached to being boring. So if you’re boring, if you’re afraid, if you’re timid, everything costs more. Everything is harder. When you’re interesting, when you’re unique, when you’re the only one doing a thing, it stands out. Like, when I proposed my first book about Stoicism, my publisher was not very excited. You know, it’s an obscure school of ancient philosophy. They were not like, “Let’s back up the Brinks truck and just throw money at you.” In fact, they offered me considerably less money than I got from my first book. The irony now is that, on a regular basis, I’m pitched for my podcast and such, I’m pitched other people who are writing about Stoicism, right? And so their deals are all easier for higher amounts of money based on, you know, the track record that I have and the media attention that I have brought to this space. Now, I’m not, like, jealous of it. That’s not what I’m putting out. What I’m saying is, the irony is, it was easier for them in some ways, right? But it will ultimately actually be much harder for them to be successful because people don’t actually have that much room for that many different flavours of one thing. So, you see this in all different kind… You know, most markets are winner-take-all markets, right? And so, people will see that someone’s successful in a market and think, “Oh, I could be successful there, too.” And the irony is, the fact that someone is already there and successful makes it safer, but also less likely that you will be significantly successful. So, I’m always interested in what are other people not doing. That’s what I want to do. Or what are other people doing? Let’s not do that. And that’s how you stand out. Fearlessness kind of feels like a strong word to describe that. But I am always interested in being different or unique because, ironically, it’s scarier to be like everyone else. It’s just a riskier proposition.

 

FRED: So let’s talk about the inner phenomenon of fear a little bit. I think you started working with Robert Green on the book The 50th Law that he wrote with 50 Cent on the importance of being fearless. And your latest book, which I’ve just preordered, by the way, is called Courage is Calling, on one of the great four Stoic virtues of courage. And in a lot of ways, we seem to be living in a climate of fear today, almost panic. I mean, people are scared of everything. They’re scared of, whether it’s COVID or big government or big corporations or grand global conspiracy or the evil people on the other side of the political aisle, or the rise of China or just, like, being judged on social media and being hated on. And for sure, there are real challenges out there, but there’s an emotional climate, it seems, almost drenched in the energy of fear and negativity. And you write this in The Obstacle is the Way, which is a fantastic book, probably my favourite one of yours: “Don’t let the negativity in. Don’t let those emotions even get started. Just say, no, thank you. I can’t afford to panic. This is the skill that must be cultivated: freedom from disturbance and perturbation, so you can focus your energy exclusively on solving problems rather than reacting to them.” How do you train yourself to tune out all the noise and negativity coming from every direction it seems, and those emotions and the fear that it can give rise to and just stay on task and stay on your path and keep executing at such a high level?

 

RYAN: Well, one of the things I tell myself is that the thing I’m trying to do is very hard, right? Whether it’s giving a talk or it’s writing a book, or it’s starting a business or whatever- it’s very hard. And most people don’t succeed at it, right? And so, if it’s hard and the margin of error is low, then time spent worrying, listening to doubters, being anxious, focusing on these things that you don’t really control, is only taking away from a finite amount of cognitive ability or resources that you have to focus on the problem. I actually have a quote here on the side of my wall that I’ve been thinking about as I’ve been writing this new series, and it’s a quote from Martha Graham, and she says, “Never be afraid of the material. The material knows when you’re frightened, and it will not help.” And what I like about that is the idea of like, you should be tackling really ambitious, challenging things, things that are a reach for you, that it’s harder than something you’ve done before, it’s something maybe you don’t quite understand. It’s a big leap, right? So you should be doing that. But then the irony is, if you are afraid, if you were doing it now out of timidity or doubt or you’re coming at it from a place of uncertainty, you will likely… it will be harder. You will not be successful. So, like, when I’m writing this series of books, I’m not going, “This is so hard. You’ve never done a four-book series before. What if it doesn’t work?” I’m just thinking “It’s a four-book series. You’ve already written four books before. You know, thinking about the totality of the problem is going to be overwhelming. What do you have to do today? Let’s just do that, and then we’ll take it from there.”

 

FRED: So you’re very practical in how you break down these philosophical rocks. I almost think, like, in Aristotle’s tradition, like, the emphasis on practical wisdom, right? It’s not like this crazy construction. It’s just like, “Look, I have limited bandwidth. What I’m doing is difficult.” If I… And then it just logically, sort of coheres with that, that if you spend energy and time focusing on, you know, what other people are saying, what other people… You’re just removing that… It’s a very practical consideration. I find it very, very interesting and very helpful, actually, to just break it down in very simple pragmatic terms like this. Just attempting big things. You need every ounce of energy, makes a ton of sense.

 

RYAN: Yeah. I think it’s just about- it’s a resource allocation issue to me.

 

FRED: Interesting. So what would be a great fear that you’d say you’ve overcome in your life that has actually helped you become who you’ve become today? What was a great- an example of a fear that you had, maybe at one point, where you feel that your ability to overcome that contributed to, you know, turning into who you are today?

 

RYAN: Well, I’ve got a bunch of them, but sort of two that were related. There are sort of two big transition points in my life. First, when I dropped out of college to work for Robert, and then second, when after I had gone on and had a career in marketing, to leave the marketing world, to leave, like the sure thing of a salary to become a writer. Then you could argue maybe the decision to go from one kind of writing to the other kind of writing. But the three things all have in common, the idea of sort of leaving the status quo or the comfort of the present moment behind for a riskier

but potentially more lucrative or exciting or fulfilling future, right, the decision to transition from one thing to another, to change courses. And the first time I did it, I was, like, just beyond terrified. Like, I thought I’d end up under a bridge somewhere. You know, my family was terrified. My parents basically, like, disowned me. It was like the biggest thing that I had done in my life at that point, right? I wasn’t just, like, trying some new thing. I was blowing up, you know, twenty years of work and direction and safety to do an uncertain thing. But the interesting thing that I found almost immediately thereafter was that it was a lot less scary than I thought. I remember walking in to drop out and thinking like, it was this sort of irrevocable, life-altering decision, and I was like, “I’m here to drop out of College” or whatever. And I remember the woman in the office was like, “That’s not a thing.” She was like, “You can take a semester off and then just not re-enroll.” And I was like, “Oh, okay, I’ll do that.” And so I thought I was, like, jumping off this cliff, and I get there, and it’s like, “Dude, there’s like, stairs. Just walk down the stairs, and then you can come back up if you don’t like what you see at the bottom.” Right? And so realizing very quickly that it was a lot less scary than you think, it’s only scary because you haven’t done it, was really helpful to me. And then to see, as I went through that, I was stronger than I knew, I was more talented than I perhaps thought, that I had more control over my life than I thought, then allowed me the other sort of pivot moments. It was like, oh, I’ve been at a juncture like this before, right? If you never have and you avoid it each time, it gets scarier. If you go towards it, if you explore it, then it gets less scary as you go. So, like, if you told me tomorrow, let’s say tomorrow, it was like, “Hey, do you want to sell everything you own and move to South America to start a llama farm or something?” If I actually wanted to do that, I’d be like, “Sure, I could do that. Like, I could figure that out, right?” That’s not… there are a lot scarier things in the world than that, right? And I imagine, you know, the first time you run into a building as a firefighter, the first time you’re under fire as a special forces operator, you have a similar understanding of, oh, okay, part of why this was so intimidating and scary to me was my lack of familiarity with it. And now that I’m familiar with it, I understand it, and I understand there’s a process. If I follow that process, I’ll be successful more often than not.

 

FRED: So it’s almost like not jumping to the extreme conclusion or the extreme scenario of what might happen when I do this and just kind of focusing on, like, the next step and then the next step and then investing yourself in that process, giving yourself a chance, telling yourself, you know what? We can always pivot, we can always move, we can always counter-move. It’s not the end of the story, right? Not staying at that freeze frame moment in the distant future of all the catastrophic things that may happen.

 

RYAN: Yes.

 

FRED: And again, just going back down to the practicality of the next step- sounds like that’s the process that you’ve gone through.

 

RYAN: We sort of have these vague ideas of what we’re worried about. We have these fears, but we don’t actually understand them. And so when you explore them or you experience them, you do have that familiarity. And so the Stoics talk about how what’s foreseen lands less heavily than what is unforeseen. So, like, on a book, it could fail. It could be, not just a failure, it could be an embarrassing failure. So what? You know what I mean? I’ve now explored that thought about it, touched it enough that, again there’s worse things that could happen, right? And so I think when you, instead of like, “I don’t want to talk about that. That’s scary” or “I don’t want it to be a bad omen or bad luck or whatever”, you almost make it scarier because it’s undefined.

 

 

Chapter 4: The Obstacle Is The Way

 

FRED: Right. So focusing on the way, okay, and The Obstacle is the Way, fantastic book, again, that I highly recommend to anybody, builds on this great insight by the Stoic Emperor Marcus Aurelius, when he writes: “The mind adapts and converts to its own purposes the obstacle to our acting. The impediment to action advances action. What stands in the way becomes the way.” And it’s a piece of wisdom that I find, it’s aged very well, in this crazy twenty-first century where life is changing so fast and the pandemic and technology and constant change, people are facing obstacles that no one ever predicted that they might face. But a lot of people I speak to today question how much agency they really have, little hold them, to overcome the obstacles in their lives. I mean, what do you do when COVID has wiped out your business, when you’ve lost a loved one or you’re struggling with depression or addiction, when you’re not even sure that your career path even exists anymore? A lot of them have very compelling stories, when you listen to them and the adversity they speak of is real… What would you respond to those who say, “OK, the obstacle is the way is good advice if the obstacle is somewhat manageable or when you have the resources to deal with it, but when it’s too big or overwhelming, it’s not so simple and, like, the obstacle is the obstacle.”

 

RYAN: It’s still- it’s almost more true in those extreme cases than the minor cases, right? So when we say the obstacles is the way, we’re not… Is it also true that flippantly like, “Hey, you can use this for good, that, hey, maybe there’s a little bit… we’re going to turn this into the best thing that ever happened.” Yes, that’s true. But I’m actually… I think the Stoics, when they’re talking about this idea of the obstacle is the way, they’re talking primarily about these major things that are outside of our control. So let’s say your business has been destroyed by COVID. First off, I’m sorry, that sucks. It’s not your fault. I wish that it hadn’t happened to you, right? But it did happen to you. So the obstacle is still the way. Give me another way, right? Like, you’re going to magically make this unhappen? You’re going to blame someone else? You’re going to expect someone else to solve it for you? No, like, it’s still there. And the fact that it’s bigger and that it’s been as catastrophic as it was, almost makes it more of an imperative that you have to figure out what you’re going to do with this. So when the Stoics say we don’t control what happens, we control how we respond, right? Which is basic, but also very brilliant and complex. So, a lot of the world is just outside of our control. We don’t control the pandemic, but we control what we learn from and to change because of the pandemic. So you hear people go, “I can’t wait for things to go back to normal.” Normal would cause this, right? So, you know, you lose someone, you lose someone you love in a pandemic or in an accident or something. Again, tragic, unfortunate, you wouldn’t have chosen it. But are you going to make that event more tragic by becoming paralyzed by it, by declining to remember them fondly? Because… are you going to torture yourself because something sad happened? Like, no, you have to figure out how to move on and move forward and integrate the memory and the good things about that relationship into your life going forward. So what the Stoics are saying is not that everything bad is good if you just flip it upside down. That would be very insensitive and naive. What the Stoics are saying is that everything that happens is an opportunity to practice one of the Stoic virtues, right? Everything is an opportunity to prove yourself, to prove what you believe in, to prove what you’re capable of. That’s what that idea means.

 

FRED: That’s great. That’s what I’ve always believed is that, it’s almost like with those biggest obstacles that, there’s this notion that we read up sometimes in psychology, it’s not your fault, but it’s your responsibility how you respond to whatever happens to you. It’s not your fault, right? I mean, if your business…

 

RYAN: Even if it was by the way…

 

FRED: A lot of the businesses that we see, never was. Right. And it’s like, a lot of businesses…

 

RYAN: Even if it was your fault… Even if it was your fault, it still happened. So what are you going to do now? Yeah.

 

FRED: Still happened. Right.

 

RYAN: So you start with the fact, you start with the fact that this is going on whether you like it or not, whether you predicted that it would happen or not. And a lot of people that go through a lot of ups and downs during COVID, it’s like, in a sense, their business was exposed to that risk or that fragility, right? COVID highlighted it, unfortunately, ruthlessly. And so now, in a sense, it’s an opportunity to build something that perhaps is not as fragile to these kinds of changes. Easy to say. But at the same time, these are the facts. What are you going to do about it, right?

 

RYAN: Or to change direction in your life. It’s a chance to rebuild. It’s a chance to grow. It’s a chance to exit something that you should have needed, you should have already exited, right? That there’s an infinite amount of ways you can look at it. But the point is, it happened. And whether it was your fault or not, whether you could have done it differently or not, is now irrelevant because it did happen. So now what, right? And I was thinking about this the other day, sort of like, I think the really superficial level is, you’d be like “Here, this bad thing happened to me” and then the Stoics would be like, “So, so what? So what are you going to do about it?” Right? That’s where- that’s what we’re trying to figure out. What am I going to do about this?

 

FRED: It’s almost really like, like stressing and emphasizing the agency piece of this. So between stimulus and response, there’s an opportunity to make a choice and sort of expand in that space.

 

RYAN: Exactly.

 

FRED: Great. So in a lot of ways, I also find that Stoicism can be one of, if not the perfect antidote to developing inner peace at a time when the culture tells us it’s always about chasing more, right? More money, more success, more attention, more fame. We get almost emotionally addicted to and dependent on external validation and rewards. You’ve written quite a bit about the life of Seneca, who lived in very tumultuous times, and he responded to this by striving to develop inner peace- apatheia he calls it- so that even if the world is going crazy and is at war and whatever’s going on on the outside, you can still be at peace on the inside and thrive even. And on this point, you have this great line, and stillness is the key, where you write: “It’s ironic that stillness is rare and fleeting in our busy lives because the world creates an inexhaustible supply of it. It’s just that nobody’s looking.” So this sounds like a really attractive idea for a lot of us today. How do we develop this in motion? So while juggling a million things, working, paying the bills, changing jobs, managing friendships, some of us raising kids, you give a lot of great historical examples on this, but how do you manage to consistently find and cultivate this inner peace and stillness in these crazy times?

 

RYAN: Well, one of the things that’s been interesting about the pandemic, if we want to talk about the idea of the obstacle being the way, is that I think it really challenged a lot of assumptions that we had about how our lives had to be set up. Like, oh, I have to commute into the office every day. Oh, I have to travel a lot for work. Oh, I have to do a lot of in-person meetings. Oh, I have to make X amount of dollars, or I have to do this, that or the other. And then COVID came along and said, “No, you don’t. And in fact, you can’t.” Right? And then we had to figure out what does life look like with a whole bunch of things off the table. Now for me, I found that, actually, being forced to stop a lot of things helped me be better at what I actually should have been doing and actually like doing. So I kind of see it as this forced lifestyle experiment, right? What is a lot less look like?

What does it look like when nobody’s doing anything all at the same time? And so when we think about stillness, we often think like, oh, I want to go on a ten-day silent meditation retreat. Or, oh, I’m going to go on a one-month vacation, or I’m going to quit my job and then in some form of retirement, finally have sort of peace and quiet. And the reality is you can have those things right now, right? And you need them right now actually to do what it is that you do. And so I think for me, it’s just been interesting to sort of have, in a sense, to have redesigned my life from the ground up a year and a half ago and find that all of a sudden the things that I can’t do that I thought I had to do, I actually don’t want to do and I don’t need to do. And that I do the things that I do need to do and that I do want to do better when I am only focusing on them. So, to me, stillness is not like the absence of activity. It can be very active. It’s just the absence of inessential activity, frivolous activity, frantic activity. So then the things you are doing are coming, you’re coming at them from a place of stillness and self-control.

 

FRED: That’s a fantastic distinction. And it reminds me, you had this great post on Daily Stoic, a little conversation between Joseph Heller and Kurt Vonnegut, where they were at a party together hosted by a billionaire, and Vonnegut tells Heller: “This billionaire has made more this week than your book ever will.” And Heller responds: “Yes, but I have something that he doesn’t, and that’s enough.” And that’s a super powerful message because, enough of what, right? Enough frantic activity, enough friends, followers, enough… all of this stuff that doesn’t really matter? It’s a moving target, right? If we stay unfocused and undirected, in a sense, there’s never enough. I mean, we just keep chasing one pleasure after the other. So I think that distinction that you just brought between essential, really core important activity and frantic activity is probably a great clue. But in your life, how do you get to that point of enough of satiation, but yet still have this tremendous drive to keep going and keep doing great work over and over again?

 

RYAN: Well, you mentioned Seneca, and I think that’s one of the tragedies of Seneca’s life is that he was so busy, so ambitious, that it sort of ends up taking him, it takes him to a very illustrious place, but ultimately a very dark place. And I guess for me, it goes back to where we started, which is, like, I’m not frantic or busy. I like doing this one thing, and I do that thing steadily, day in and day out. And the byproduct of that is productivity, or so publishable output, if you will. So again, I’m not like, I have to do a book a year. I’m not like, I have to write a certain number of books. They all have to be best- I go, what do I need to do today, right? What’s my job today? And I do that. And you stack enough of those days on top of each other, and you get the output that people will think is impressive. But again, the output is not the goal. The process is the goal. The daily routine is the goal, the making, the small daily contribution is the goal. The rest is extra.

 

FRED: It’s so interesting how they’re almost like these crisscrossing paths of like, the way you talk, when we look at your achievements, it almost looks like crazy, frantic activity. It’s like all of these things that you stack up right at your age. And then there’s people also that are, like, super busy all day, like 15 hours a day running around, running around. And then you look at what they’re actually achieving, and it’s like, not very much, right? It’s almost like the impression we get in the immediate moment is almost like the opposite of what we’re actually doing when you spread it out over time.

 

RYAN: Well, and I think one of the things I talk about when I talk to sports teams is, as I sort of say, “Well, what are you going to say “no” to this year?” Because everything that we say “yes” to means saying “no” to something else. And everything we say “no” to means the opportunity to say “yes” to something else. So a big part of it is like, what do you say “no” to? And I think that has been a helpful lesson to me is like, oh, there’s a lot more things that when they suddenly became illegal or suddenly became impossible, my productivity and my satisfaction both at home and at work went up. And so, as the world does return to some semblance of normal where these things are possible again, now I’m going to have to be more active and actively saying “no” to them as opposed to them just sort of being not up for discussion.

 

FRED: So that was one of the blessings of the pandemic, right? It stopped all this extraneous activity and forced people to stay focused, stay in their zone. What are the relationships that really matter? What are the things that really matter in my life? I found that that’s really been one of the great, in a sense, hidden blessings of the pandemic.

 

RYAN: For sure. And when we talk about the obstacle being the way, it’s not that, oh, that made the pandemic worth it, but it was the good you managed to derive from the pandemic, right? Because that’s all we can focus on. I’m not saying that 700,000 American deaths was worth me being slightly more productive as a writer and happier at home. That would be insane. What I’m saying is that the only thing I was able to focus on was that, and so that’s what I’ve managed to derive from it.

 

 

Chapter 5: The Stoic Virtues

 

FRED: That’s great. If there’s one, maybe not criticism, but something a lot of people say is missing from Stoicism, it’s that it’s too serious, it’s too internally focused, and that it doesn’t emphasize positive emotions like empathy, love, joy, or positive relationships, at least not as much as other philosophies do. Even in ancient Greece, people used to call the Stoics “the men of stone”. I know your book on courage is the first of four that you’re writing on the four great Stoic virtues: courage, temperance, justice, and wisdom. What I find really interesting is that these virtues intersect perfectly with the six great virtues that Martin Seligman, the father of positive psychology, talks about. So the four virtues are the same, then he adds two more. He adds empathy or love and then beauty or transcendence. And it’s kind of similar to the thought that, I read recently that Jonathan Haidt had when he wrote The Happiness Hypothesis, he says that when he started writing the book, he believed, like the Stoics, that happiness comes from within. But by the time he finished writing the book, he changed his mind to happiness comes from between, from getting the right relationships and living for something greater than yourself. I know you’re a family man. I know that you give advice that helps millions of people. What’s your view on the importance of empathy, love, positive relationships, and their role in living the good life?

 

RYAN: So I would say that those two things you said about sort of beauty and transcendence, and then about relationships and empathy and love, I would just, I would say they’re very important. I would agree they are not talked about enough in Stoicism, but I would say that they clearly fall under the buckets of justice and wisdom. Wisdom is not simply the study of books, but also the study of nature, the understanding of nature, the understanding that some things are inevitable and cannot be articulated, but can only be experienced, right? So, to me, that all falls into the bucket of wisdom. And I think the Stoics actually talk about beauty quite a great deal. Not sort of superficial beauty of like a woman’s face, but the beauty of, you know, a sunset or the way doves fly together or whatever. As far as love and empathy, to me, this fits very clearly under justice. Not justice in the legal sense, but justice in the sense of like- what are our obligations? What produces meaning? What is our true purpose on this planet? It’s other people, right? It’s the good we’re able to do for and through other people. So I agree they’re very important, and there are certainly major priorities in my life. You know, as I first started writing about Stoicism, I was more interested in courage and self-discipline, the sort of independent sort of, of the world virtues. But I think as you study it and you learn more about it, eventually these other doors open and you come to understand them as being equally important and fulfilling.

 

FRED: Amazing. Yeah. That’s often the case, right? You’ve got the sort of, the general understanding of a certain school of thought. And when you get deeper into the ideas, you find that those thinkers have actually talked about a lot of the things that, you know, might not seem obvious when you think of Stoicism, you think of this really, like stern, self-control, self-discipline. But then you get a little bit deeper into the writings, and you realize that they do talk about a lot of these other themes.

 

RYAN: And when you really look at who the Stoics were as people, they were husbands and fathers and sons and daughters, they held public office, they fought for causes, they wrote poetry, you know, they tended gardens… So the idea that these were these, like, unfeeling beasts disconnected from the world, it’s just not borne out by the facts. And they weren’t monks, right? They didn’t live in monasteries. They were, of all the philosophical schools, the most, like, of this Earth, like the most connected and involved in participatory of all of the, all of the philosophical schools. And actually, this is the fundamental contrast between Stoicism and Epicurianism. It’s not that the Stoics didn’t like pleasure and the Epicureans did, it’s that the Epicurians pursued those interests at the expense of participation in public life. And the Stoics said, “No, we are obligated to each other and that relationships are important and that you can’t run away to your little garden and live in a fantasy world.” And so I see Stoicism as a philosophy that’s engaged with other people, and there primarily for other people.

 

FRED: Interesting. So also looking at the way these philosophers live their lives, not just like the first reading that you might get off of their readings, that’s a great distinction as well. I know that you recently just opened up an independent bookstore in Bastrop, Texas. I’m curious to know, what do you feel the future of the bookstore is in an age of Amazon.

 

RYAN: So it’s been interesting. First off, probably the worst possible business that you could try to open during a pandemic. Probably the worst possible business you could open, period, in a world where most people don’t read and most people that do read buy online or read audiobooks or whatever. But it was just something important to me. It was something I felt like would do some good in this little community that I’m in. And then, something I felt like could be additive to what I was already doing without much additional work. Like I needed office space, and then I had this sort of storefront beneath the office, and I was sort of, what would I do with it? And it’s actually integrated in nicely with the stuff that I was already doing. The only part that makes me sad about it is that, part of it was I wanted to really interact with people. I wanted to do events, I wanted to meet fans, I wanted to interact with human beings. And the pandemic still makes that a little bit difficult.

 

FRED: So, what I hear is it was a labour of love.

 

RYAN: Yes.

 

FRED: And what you’re trying to create- bless you-  is those experiences where humans connect to humans which is not something you get when you order something on Prime or Amazon.

 

RYAN: Yeah, it’s certainly not a get-rich-quick scheme- opening an independent bookstore in 2021. I think, you know, there’s something special about bookstores. Stoicism is actually founded in a bookstore. So I sort of loved the continuity of that, and that’s where the name comes from. It’s called The Painted Porch, which is the name of what the ancient Stoics translates from into English from Greek. But I felt like, I have a podcast that reaches millions of people. I have insta- social media that reaches millions of people. My books have sold all over the world, but all of that is digital. I think at this point something like 60% of my sales are in e-book or audio form. So, but we exist in a physical world, right? The digital world is wonderful, but we exist in a physical world and so it just felt sort of special and important to do something like, real, and that’s what was excited to do.

 

 

Chapter 6: Ryan’s Mission In Life

 

FRED: Ryan, you got a lot of projects going on, obviously. You’ve got the four books on the great Stoic virtues. You’ve open up the bookstore in Bastrop, Texas. Who knows? I think you’re maybe even cooking up another Grammy Award-winning rap album this time.

 

RYAN: Hopefully not.

 

FRED: I know you’re a student of Victor Frankl’s, the concentration camp survivor who founded logotherapy, a form of therapy where you try to find meaning in life. And you’ve also written about this, about how Frankl used to hate the question, “What’s the meaning of life?” As if somebody could just tell you, right? Instead, he says that life itself is a question and it’s your job to answer with your actions. In one of his stories, he also talks about the analogy of a chess game. People- he goes, asking what the meaning of life is is almost like asking, what’s the best chess move? It’s a meaningless question in a vacuum. It depends on where you are in the game, who you’re playing, what your level of skills are, so on and so forth. My question to you is, having achieved everything you’ve achieved already at your young age, having earned the freedom, the independence, the platform, the options that you have in front of you, what do you see as your most important or meaningful work and mission in life stretching into the future?

 

RYAN: Well, I guess first off, you would say as a parent, your greatest shot at sort of multi-generational impact is at home, right? So working on yourself, working on your abilities as a parent, is probably the most important contribution you make. Certainly the most direct contribution you will make to anyone. So I take that very seriously, and certainly, the pandemic has helped with that. But I guess as a professional, I see my contribution in taking ancient ideas and making them applicable to modern life. And that is something I’m doing for both myself and for the audience. So I take a lot of satisfaction, but also get a lot of joy and fulfillment and excitement out of taking stories that I found, ideas that I found, and communicating them in a way that’s compelling and interesting to people. To me, one of the highest bits of praise you can get as an author is someone will go, “I haven’t read a book in years, you know, and I read your book.” I like to take… I am particularly proud that my books have- are primarily popular with people who are not interested in philosophy, right? Because that’s how you know you’re actually introducing people to new ideas as opposed to just retreading the same tired things to the same small group of people.

 

FRED: Yeah. Your approach is almost the opposite of, like, philosophy in the classroom, right? Super, highly technical, jargon, verbose, complicated, difficult to understand, kind of confusing complexity of argument with intelligence. You try to cut through all of that and try to find ways to deliver that direct insight, that direct impact to the reader. I think that’s one of the reasons your books have been so successful.

 

RYAN: Well, I learned that from Robert Green, that the best way to teach and to illustrate is through story, that you show rather than tell. And so from the beginning, my books have been illustrations of philosophical ideas rather than explanations or discussions about philosophical ideas.

 

FRED: Yeah, that’s a great distinction as well. It just accelerates the learning process, accelerates the absorption of the insights by the reader. So you’re really kind of thinking of the reader first. It’s a great approach that you guys have. So, Ryan, I want to really thank you so much for this. You’re doing really important and valuable work, in my opinion, raising the collective consciousness, spreading useful knowledge to millions of people. I think there’s a great blend of, like, modern strategic thinking, like, very practical, very tactical, very immediate, and- but also blending that with deep wisdom in your work that always makes it really, really interesting and valuable, helping people develop more resiliency, more inner peace, more resolve, and focus on doing great work by controlling what they can control. I personally can’t wait to read your books on the four Stoic virtues. As a lawyer, especially the one on justice, but all the others as well. Obviously, wisdom is always a big one, and it’s a complex topic, and I can’t wait to see how you tackle that. Keep doing what you’re doing, man. It’s fantastic stuff. I look forward to what the future has in store for you, and I can’t wait to consume more of it.

 

RYAN: Well, thank you, and congratulations on this new path. I imagine it’s requiring a variety of different muscles and scratching a bunch of different itches than the corporate legal world.

 

FRED: Absolutely. It’s exactly what you said earlier about picking a new path. I mean, you picked a new path. It’s great. You’ve got this vision, you’ve got this ambition, but at the same time, you don’t necessarily yet have the skills, have the experience. You haven’t trained those muscles yet.

So, it’s a whole new challenge. And I think part of it, part of the joy also is picking a new challenge.

 

RYAN: Sure.

 

FRED: Going back with that beginner’s mind, where the Japanese talk about beginner’s mind. I forgot what the term is for that. I think it’s Shoshin or something. I don’t want to mess it up, but there’s that notion of approaching it with a beginner’s mindset. And if you’re a learner, you always get excited with that. And I resonated with what you said earlier, when you made those big transitions, that’s sort of like, part of what drives you forward is picking a new mountain to climb and see what you can make of it.

 

RYAN: Well at the very least, it’s not boring because you’ve never done it before.

 

FRED: That’s right. That’s right. Thanks a lot, Ryan.

 

RYAN: Appreciate it. Thank you for having me.