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John Jantsch: This episode of The Duct Tape Marketing Podcast is brought to you by Klaviyo. Klaviyo is a platform that helps growth-focused eCommerce brands drive more sales with super-targeted, highly relevant email, Facebook and Instagram marketing.

John Jantsch: Hello, and welcome to another episode of the Duct Tape Marketing podcast. This is John Jantsch, and my guest today is Ryan Holiday. He is, today, one of the world’s foremost thinkers and writers on ancient philosophy, and its place in everyday life. You’re probably familiar with The Daily Stoic, Obstacle is the Way, Ego is the Enemy, and his latest book we’re going to talk about today, Stillness is the Key.

John Jantsch: Ryan, thanks for joining me.

Ryan Holiday: Yeah, thank you for having me. I was thinking as I was getting ready to come on this, I think you were, like, the first or the second podcast I ever did, way back in 2012. You have been at this a long time, and so have I.

John Jantsch: That was with Trust Me, I’m Lying, I’m thinking?

Ryan Holiday: I think so, yeah.

John Jantsch: Yeah. Well, I have been at that a long time. It’s been really fun to watch the arc of your career, it’s taken you some pretty amazing places.

John Jantsch: So, I’m sure you get tired of this question, but I’d like to hear from you, the answer to this from you. I could look it up, and there’d be lots of Wikipedia entries on this, but how would you define stoicism?

Ryan Holiday: So, I give two definitions to people.

Ryan Holiday: If I’m giving the really, really simple definition, I just say stoicism is not emotionlessness, it’s not resignation, it’s the belief that we don’t control what happens to us, we only control how we respond. Right? The stoic just says, “Look, the vast majority of the things in the world are not up to me, but I control my thoughts, my opinions, my attitudes. That’s what I’m going to focus on.” That’s one really simple definition.

Ryan Holiday: If I was going to go a bit more advanced, I’d just say, look, stoicism really worships four virtues. It’s an ancient philosophy that dates back to Greece, and to Rome. The four virtues of stoicism, they sound familiar because they also happen to be the four virtues of Christianity, and a lot of Western thought. It’s just courage. Temperance, that means moderation. Justice, that means doing the right thing. Then, wisdom, that’s intelligence, education, learning, understanding. It’s a pretty straightforward philosophy, with not a lot … That’s not as controversial as people might think. It’s all in the execution, right?

Ryan Holiday: It’s easy to say, justice, wisdom, temperance, courage. It’s hard to do those four things, and to do them regularly, when the stakes are high.

John Jantsch: So, this book, Stillness is the Key, I’ve heard you refer to as a trilogy to go with Obstacle is the Way, Ego is the Enemy. What do you hope the third book in the trilogy adds to the over-arching message?

Ryan Holiday: Well, to me, stillness is this thing that’s timeless, but also very, very urgent.

Ryan Holiday: 500 years ago, Blaise Pascal said that “All of humanity’s problems stem from our inability to sit quietly in a room alone.” It was true five centuries ago, but today it’s impossible. It’s not our inability, it’s that it’s impossible. We have a device that magically transports us away from that room, or from any feeling of discomfort, or worry, or whatever. We don’t have any of the clarity we need to make decisions, to know what’s important.

Ryan Holiday: Both the Stoics and the Buddhists were very fond of a metaphor. They said that it’s like … “The mind is like muddy water. You have to let it sit, you have to approach it calmly, for the dust and the silt to settle. Only then, can you see through it, do you know what’s really there.” That’s just so hard to do for entrepreneurs, and for executives, and for parents. They’re running a mile a minute, and they never have any slow time in which the things sift to the bottom.

John Jantsch: Your books have sold extremely well. I know Stillness is the Key will sell quite well. Is your publisher asking you for the fourth book in the trilogy yet?

Ryan Holiday: Well, no. I was just laughing about this with Steve, who is our mutual book agent, that I talk about in the book, this idea of there never … The problem is there’s never enough, we’re always doing. I think I’ve done nine books in seven years. Steve is out with a proposal for the next one right now. I do like to always be working.

Ryan Holiday: In my defense, what I would say is the reason I like to have the next book, is that I find that the stillness of work to be better than the anxiety of, what am I going to do next? Or, look how successful I am? Or, how is it selling? As much as I want this book to sell well, and I’ve wanted the other books to sell well … I’ve gotten very lucky. When Obstacles … They way it came out, I had sold what became Ego is the Enemy before it came out. When Obstacle is the Way came out, and it did okay, but it didn’t blow the doors off, I didn’t care because I had deadlines to meet. Then, when Obstacle is the Way really started to take off, I also didn’t care, because I had deadlines to meet.

Ryan Holiday: I think it’s important to have good things to focus on, rather than to have just space for our mind and our ego to do their dirty work.

John Jantsch: Yeah.

John Jantsch: You and I were laughing a bit before we started recording this that, you know, when you write a book like this, or a series of books that suggest a way to live, you probably yourself get held to a higher standard, right or wrong. How has that impacted you, or do you feel that sense of, oh, I can’t let anybody see me freak out? I’m the one that’s telling them you can’t do that.

Ryan Holiday: I mean, you can imagine writing a book about stoicism, and wring a book about ego and stillness, and then I go home to my wife, who does not allow me to get away with any of not having those things. It’s like, there is a downside to writing a book about ego, as you can never … You’ve got to be constantly on guard that you’re not being a hypocrite.

Ryan Holiday: I do think about that. It’s really hard. When you are out doing and making things, it’s busy, your active. You’ve got anxieties, you’ve got fears, you’ve got frustrations. It’s never as good as you want it to be. People are never doing it the way you want them to do it. I’ve dealt with enough monstrous people in my life to know I don’t want to be those people. I’m always trying to catch myself before it spins out of control.

John Jantsch: Well, I think a lot of what you’re suggesting in this work is that we’re all a work in progress. You’re working towards something, you haven’t arrived at anything, right? Would you suggest that’s right?

Ryan Holiday: Oh, completely. Ego is not this thing that you magically get rid of once. What’s so insidious about ego is that it’s always creeping in. What’s so both demoralizing and refreshing about obstacles is that there’s always another one up around the curve.

Ryan Holiday: I think with stillness, you have this moment of stillness, maybe it’s early in the morning. You wake up before the kids, you don’t check your email, and you go straight into this project you’ve been working on, or you go for an awesome run or a swim. You just experience, you’re just present, and you’re killing it. It’s just awesome. Then, you pick up your phone and you’ve got to start from scratch.

Ryan Holiday: It’s not only we’re a work in progress, but this state we’re trying to get to is inherently ephemeral. It’s like success. Success isn’t something you have, success is something a bit more elusive, [inaudible] with, but you don’t own it, for sure.

John Jantsch: Yeah, it’s funny, but I think you’re, in some ways, the work that you’re doing is helping people redefine how they even talk about success, or think about success.

John Jantsch: I read between the lines, that you’re writing that success in a lot of ways, is realizing that you can’t control everything, and you need to trust yourself enough to know that you’re hopefully doing what you’re supposed to be doing, but that you need to let go of trying to control every aspect of how it’s going to get done. I think when we come to that ability to have some level of letting go, to me, that’s like stage one, or the starting gate for success.

Ryan Holiday: Yeah, totally. What I try to do a lot of work on in my own life, and when people ask me for advice about it, I talk to them about this, too. Particularly in something as unpredictable as the book world, which you know very well. You have to find a way to root your idea of what success is, as much as possible in the parts of the process you control.

Ryan Holiday: So, we’re talking here. My book comes out tomorrow. I feel … I’m not at 100%, I don’t think it’s possible to get to 100%. I feel like 90% of the success of the project, I’ve already gotten all of that. It came from enjoying the writing, it came from expressing what I wanted to say. It comes from knowing I put as much of myself into it as possible, that I grew in the process, that I didn’t cut corners. That I got even the opportunity to do it, so on and so forth.

Ryan Holiday: Look, if it sells zero copies tomorrow, or if it sells 10 million copies, obviously that’s going to have some impact on how I feel, but I’m not going to live and die by it. If I woke up tomorrow, and this happened two books ago. I went out for a run with a friend, and while I was running my phone blew up. I got a bunch of text and emails that it had been positively reviewed in the New York Times, which I had no idea was coming. It was really wonderful that had almost no impact on me. I don’t feel like, this isn’t a weird humble brag. I had already knew that I had done what I was best capable of doing. If the review had been negative, I don’t think it would have rocked me. Had the review not happened, I wouldn’t have missed it. The fact that it was positive was just like, oh, that’s a wonderful surprise rather than, oh my God, I hope this comes back. Please come back good, please come back good.

Ryan Holiday: You’re trying to set yourself up in a position where you’re as invulnerable as possible, to things that are outside of your control.

John Jantsch: What’s interesting is, and I could find the [Seneca] quote, here. “When no noise reaches you, when no word shakes you out of your self, whether it be flattery or a threat, or merely an empty sound buzzing about you, with unmeaning din.”

John Jantsch: I think what a lot of us miss this idea that, you have to stay … Not just worry about the things that you see as a threat, but also forget about the things that you see as flattery. Don’t judge either of those as right or wrong.

Ryan Holiday: Yeah. Marcus [inaudible] talks, he says one of my favorite lines from him. He says, “To accept it without arrogance, and to let it go with indifference.”

Ryan Holiday: So, you shrug off the bad stuff, and you shrug off the good stuff, too. I just love the idea that Bob Dylan didn’t go accept his Nobel Prize, he was too busy working. You know what I mean? I love that. That’s a whole other level, and I have no idea … I’m very sure that if I was ever given a Nobel Prize, I would accept it, but I respect the amount of confidence, and stillness, and just focus on the craft that it must take to be like, “I don’t want to go to Sweden. I’m busy.”

John Jantsch: That may have just been him being on brand, too, but yeah.

Ryan Holiday: Sure, sure, sure, sure.

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John Jantsch: So, you quote 500000 year old text and writers. I’m wondering if there’s some contemporary writers that you think are getting this right, right now?

Ryan Holiday: I think Cal Newport is one of the great, non-fiction self-help writers of our time. I think Mark Manson, another friend of mine, really great. [inaudible] people out there that are touching on it. How do you minimize your exposure to things that disrupt your stillness? How do you make sure that you’re caring about only the things that matter?

Ryan Holiday: When Mark Manson talks about the subtle art of not giving an F, he means don’t care about the things that you don’t need to care about, so you can care more deeply about the things that you should care about.

Ryan Holiday: Yeah, I think there’s lots of great writers out there that are touching on it. I think that’s what’s so wonderful about this topic is that we’ve been struggling with it a really long time. There’s lots of insights and wisdom about it.

John Jantsch: Yeah. You quote Robert Green quite often. I would throw him in that category I suppose, huh?

Ryan Holiday: Of course, yeah! Robert Green is, I think, probably the greatest writer, non-fiction writer of our time. I think he’s just spectacular. He talks about … In Mastery, he talks about just how transformative it is, mentally, spiritually and physically, to just fall in love with just every aspect of what you’re doing, and to so deeply love that process.

John Jantsch: Yeah. I think there’s a lot of people that preach this idea, you’ve got to find what you love. Then, that’ll be your purpose. I think it throws aside the idea that, get good at something, and you’re probably going to love it.

Ryan Holiday: Yes! Yeah, of course. If you’re not good at it, it’s hard to love it. Yeah, of course.

John Jantsch: All right, a big part of your work, and certainly it shows up in Stillness, is this idea of letting go. I think that, no matter how many times … I talk to a lot of entrepreneurs. No matter how many times they hear that, I say that, it still seems to be one of the hardest things to do.

John Jantsch: First off, why is that, and how do we do it?

Ryan Holiday: Well, it’s really hard because what made you who you are is that you care. You become a champion, or you become a successful entrepreneur, or you become a leader because you always want to get better, and you’re not satisfied with the status quo.

Ryan Holiday: Obviously, I think that’s better than not caring at all. There are plenty of people that are like, “I want to be successful.” It’s like, do you really? Because it doesn’t seem like you’re putting in the effort or the commitment. It’s just realizing that on the other side of that gift, is a consequence. That consequence is it makes it very hard for you to accept when you don’t have control over things. It makes it very hard for you to enjoy what you’re doing, as you’re doing it. It makes it hard for you to ever feel satisfied.

Ryan Holiday: I think you just … Every virtue has to be balanced out, just like every vice. I think what we’re talking about is how to do you take some of your natural inclinations and make sure that you them on a leash, rather than the other way around.

John Jantsch: One of the things you talk about a lot is this idea of staying in wonder, and having wonder still for many of the things you’re doing. As you start a business particularly, a lot of things become un-wonderful over time, because they’re routine, or because you just don’t like doing them. What do you do to stay in that state of wonder?

Ryan Holiday: One of the things I always just remind myself is how absurd existence is. We’re these monkey spinning around on a rock in space. How lucky we are to be where we are, how lucky we are to be here right now. As scary and bad as things might seem, I’d much rather be alive now than 100 years ago, or 1000 years ago.

Ryan Holiday: I always go, this is so frustrating, this is so annoying, but it’s so much better and so much unbelievably better than what many people could have ever even imagined. I would be an idiot to take this too seriously. That’s something I do.

Ryan Holiday: The other thing is just make sure you’re not … I remember early on in my career, I was working in Hollywood. I realized that I had not seen outside during the daytime during the week for months. I would leave my apartment early, and I would get to work right as it was starting to get light. Then, I’d go, I’d be leaving the office after dark. It’s just crazy! That’s just not a healthy way to live.

Ryan Holiday: It might seem irresponsible to say, you know what? I’m going to go outside for an hour and read a book on this picnic table, or I’m going to go for a walk. Or, you know what? I’m working from home tomorrow, and I’m going to do it at a café, where I sit out on the porch. That might seem irresponsible, but if it’s about preventing burnout, it might be the very … Think about athletes. They’re the most driving, ambitious people in their field. They don’t practice on Monday if they played on Sunday, because that’s how you get hurt. The coaches know you have to have rest days because the muscles will snap. The mind is a muscle like any other, and you’ve got to be giving it rest.

John Jantsch: I know the Stoics wrote about this, and I’ve, as you know, have embarked on a workout where I’m really curating a lot of the work from a body of literature a lot of people call The Transcendentalists. Thoreau being in that, Emerson being in that.

John Jantsch: For them, nature was such a perfect example of how to live, and how to stay in wonder. That, to me … I happen to be sitting in the Rocky Mountains right at the moment, and have pine trees out my back and out my front. For me, going and sitting under one of those is the most refreshing thing I can do.

Ryan Holiday: Yeah. There’s even a term for that, they call it forest bathing. You’re just bathing in the forest. If you’re not doing that, I think you’re accumulating a lot of gunk, and goo, and nasty stuff. You’ve just got to go out and wash yourself in nature from time to time.

Ryan Holiday: In Austin, there’s a pool close to my house, at a gym that I like. There’s two outdoor pools that are spring-fed, right along the river.

John Jantsch: Is that Barton Springs?

Ryan Holiday: Barton Springs and [Deep Eddy 00:21:01]. It takes longer, it’s more expensive. Sometimes I’ve got to wait for a lane. Every time I do it, I’m just so glad that I did it. I feel like it roots me in something in a way that a chlorine filled pool in a windowless room just does not do.

John Jantsch: So, you write about this, the Stoics wrote about this. I think there’s lots of contemporary literature that suggests this is a good practice, and that is the practice of solitude, or seeking some level of solitude.

John Jantsch: Why are we so deathly afraid of that? The worst punishment you can give somebody in prison is to put them in solitary confinement. I mean, on top of that being … Obviously, we’re talking about that being a positive thing, but why, as humans, are we so frightened by it?

Ryan Holiday: Look, I certainly wouldn’t want to spend 60 days in solitude.

Ryan Holiday: I think one of the big reasons is that, going off to a cabin in the woods to think doesn’t sound like work. Sitting at your computer at an office, where you’re actually just reading ESPN, and checking your Fantasy scores, that looks like work. A lot of people … If I walk into your office and you’re not there, I go, “Where’s John? He’s supposed to be working, he has a book deadline.” If I came into your office, and it looked like you were sitting there, but I couldn’t see what was on your computer, you’re actually watching YouTube videos, I’d be like, “That guy’s hard at work.”

Ryan Holiday: I think a lot of this is just the logistics and the appearances of how our modern world is set up. Even Silicon Valley had the idea that everyone should work in one large room, where they don’t have any doors. It’s like, have you ever met a human being? This is not how people thrive. People … What does every kid want? They want their own room. They want their own space where they can think, and reflect, and have quiet time. For whatever reasons, in terms of workplace culture, and society, we have just obliterated that. Then, we wonder why people are frantic, and nervous, and stressed, and overworked.

John Jantsch: I believe all human, living things are connected in whatever soup pot you want to call it. You’re right, we are one big collective organism engaged in one endless project together. We are one, we are the same. Still, too often, we forget it, and we forget ourselves in the process.

John Jantsch: How do you come to terms with this idea of us being all connected?

Ryan Holiday: Yeah, this is a really important stoic idea. They talk about this idea of [sympathea 00:23:44]. The stoics talk about the idea that we’re this large organism, that we’re made for each other, that the common good is the thing that matters. So many people, they’re not starting a business to make the world a better place, they’re starting a business because they want to get rich, or they want to get famous, or they want to get powerful. I talk to authors and they’re like, “Oh, I’m writing a book.” I go, oh, why? They’re like, “I want to be a best seller.” It’s like, aw, man, that’s such a crappy reason to do anything.

Ryan Holiday: The reason you should write a book is because you have something that you feel needs to be said that would help other people. The reason to make a business is because you feel like there’s a need that deserves to be met, and that would improve the world if it was met.

Ryan Holiday: I think it’s just like, when you’re selfish, it seems like a good strategy, but it’s a short-term strategy. Eventually, you burnout, or you overreach, or you become alienated from the people that you’re serving. You’ve got to figure out how to make this about more than just you, if you want to be happy and you want to thrive. At least, that’s my take.

John Jantsch: Yeah, absolutely.

John Jantsch: Speaking with Ryan Holiday. Out October 1st, 2019, everywhere that books are sold, Stillness is the Key. Ryan, you want to tell anybody where they might find out more about your work, and you?

Ryan Holiday: Yeah. The book’s available everywhere. You can go to, or @RyanHoliday.

Ryan Holiday: Then, if you’re interested in stoicism at all, or that idea of a page a day thing, we have a website called Daily Stoic. It sends you one email about stoic philosophy every single day. It’s my favorite thing to write. I think I’m on the fourth year of it now, it’s been just an awesome experience.

John Jantsch: It sounds like a lot of work, but you have built a heck of a community and following. Obviously, it’s reflected in the depth of your work, but also in the depth of your following. Go on you, Ryan.

John Jantsch: Thanks again for stopping by the Duct Tape Marketing podcast, and hopefully we’ll run into you soon, out there on the road.

Ryan Holiday: Yeah. Thanks for having me.

Order your copy of
The Self-Reliant Entrepreneur

by John Jantsch

“A book that deserves a spot in every entrepreneur’s morning routine.”
—Ryan Holiday, #1 Bestselling Author of The Daily Stoic and The Obstacle is the Way

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