EPISODE 375
Ryan Holiday
Control Your Destiny

Mark speaks with Ryan Holiday, an author, modern Stoic, public-relations strategist, bookstore owner and host of the podcast The Daily Stoic. Ryan became fascinated with Stoicism in college and dropped out at age 19 to apprentice under Robert Greene, author of The 48 Laws of Power. One illustrious marketing career and 11 books later, Ryan lives on a ranch outside Austin, Texas where he writes, works, and raises cattle, donkeys and goats. His newest book Discipline is Destiny comes out in September 2022.

Ryan Holiday
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Show Notes

Commander Divine speaks with Ryan Holiday, Stoic author, PR strategist, and host of The Daily Stoic podcast. In this episode, Ryan shares his passion for how Stoic philosophy can be practical and useful in real life, and how discipline is key to destiny.

Key Takeaways:

  • Discipline is a practice of moderation. As Seneca would say, “Live immediately.” Yet, also know the importance of planning and investing as though tomorrow may happen. Furthermore, discipline does not need to be sacrificial. You can enjoy the fruits of the present without that enjoyment impacting your future enjoyment.
  • The high performance paradox. It’s a fantasy to think there is such a thing as balance. Finding balance is like jumping into the music of life. And while many aspirers believe that more work will get them where they want to go, in fact stillness and calmness and security are what paradoxically allow you to do whatever it is that you do so much better.
  • Zen and Stoicism, cut from the same cloth. It’s said in Zen that sometimes the best action is inaction. And the best inaction is action. Yin and Yang. Ryan and I discuss in depth the paradoxes of equal opposites and the beauty of living in the tension between the poles of life. 
  • Real philosophy takes practice. Ryan shares candidly about the West’s version of Zen monasteries… academia. There has never been a more needed time to bring the practice of leadership to fruition in our world and our nation. 
  • Discipline (temperance), one of the four cardinal virtues. The others are prudence, justice, and fortitude – all of which counterbalance and interweave themselves into each other. One cannot be truly just without proper wisdom (prudence). One cannot be well temperate without proper fortitude.

Quotes:

“This is philosophy, but it’s not abstract ideas. It’s a code for the individual to live by.” Ryan Holiday

“I think what I’ve loved about Stoicism, and what gets me so excited about teaching it is you have 1000’s of years of tradition of people just like you and I, that was struggling to be their best self sort of thinking through how to live, how to be happy how to not be a slave to things, how to deal with adversity. I just love the idea that philosophy can be practical and usable in real life.” Ryan Holiday

“And what I love about the Stoics is that they’re all multi hyphenated. Right? Seneca was a playwright. He was a senator, he was the advisor to the Emperor, and he was a philosopher. And I don’t think he would have been as good at any of those things had he dropped one of those things, right? It’s the whole package. So I’ve always just tried to do other stuff for that reason.” Ryan Holiday

“You talk about this perspective that the Zen master gets to the state where he doesn’t feel like anything matters, and that’s actually not accurate. He gets to the state where we realizes that everything matters, because everything, absolutely everything, is interconnected. And everything comes together to create this moment.” Mark Divine 

“I’m trying to make a slightly bigger argument, which is that discipline will determine who you are, right? It determines whether you’re free or not, whether you’re great or not, whether you’re decent or not, right? Whether you’re in control of your emotions, or your emotions are in control of you. When we say that discipline is destiny, it’s in the sense that they used to say that character is fate, that your character determines who you are, what you’re going to be able to do. And so not only does discipline determine your destiny, but it can make whatever it is that you end up doing great or not great. At the end of the day discipline is the thing that sort of separates the pros, from the amateurs, the greats from the not so great. I agree. Discipline is definitely freedom. It’s also even more than that.” Ryan Holiday

“The discipline to know your why is actually the highest discipline, it’s the hardest. It’s the most challenging and it should all start there. That’s why the inner work of the stoic or the inner work of the Zen Master or the yogi was the most important because that’s where the why is found, right?” Mark Divine

“So the idea of what is the main thing like what do I do? What can only I do? This requires an immense amount of discipline, because people are going to say, Well, why aren’t you being involved in this? Why aren’t you doing this? What about this? What about this, there’s an infinite number of things that can consume your time in the world, if you don’t have the discipline to go, like, I agree, all those things are important. But my main thing is protecting this, and that’s what I’m going to do to the best of my ability.” Ryan Holiday

Mark Divine 1:05
Coming up on the Mark Divine Show.

Ryan Holiday 1:08
I think what I’ve loved about stoicism and what gets me so excited about teaching it is you have 1000’s of years of tradition of people just like you and I, that were struggling to be their best self sort of thinking through how to live, how to be happy, how to not be a slave to things, how to deal with adversity. I just love the idea that philosophy can be practical and usable in real life.

Mark Divine 1:38
I’m Mark Divine, welcome to the Mark Divine Show. On the Show, I explore what it means to be fearless through the lens of the world’s most inspirational, compassionate and virtuous leaders. My guests include notable folks from all walks of life, including Stoic philosophers, martial arts grandmasters, military leaders, high powered CEOs, and more. In each episode, I helped distill their remarkable experiences into actionable insights for you so you can create a more compassionate, courageous life yourself. My guest today is Ryan Holliday, author, media strategist, great communicator, Stoic philosopher. When Ryan was 19, he dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power, phenomenal author, inspiring leader. Ryan had a successful Marketing career at American Apparel, went on to found a creative agency called Brass Check, which has helped advise clients like Google Taser, Complex, as well as many prominent best selling authors, including Neil Strauss, Tony Robbins and Tim Ferriss. He’s the author of 11 books, including his Stoic series, starting with The Obstacle Is The Way and Ego Is The Enemy, The Daily Stoic, Stillness Is The Key, Courage Is Calling. And now his latest coming out in September, Discipline is Destiny, a second in the series of the Four Cardinal Virtues. Ryan lives in Austin, Texas, where he writes and works, raising cattle, donkeys and goats. Ryan, so great to see you again. Thanks for joining me today on the Mark Divine Show.

Let’s talk about Ryan for a moment. Okay, how did you become, like, so fascinated about Stoicism because now, you know, I could give you literally the mantle, if I were to give a Pulitzer Prize today, I’d say this is the man who brought stoicism alive to Western culture. So thank you very much.

Ryan Holiday 3:23
That means a lot to me. I got introduced to it when I was in college. But it was so different than what I was learning about in college. This is philosophy, but it’s not abstract ideas. It’s a code for the individual to live by. And that just hit me so hard, because it’s not something we really talked about. I mean, if you’re not a religious person, where do you get a code to live by? I mean, maybe you join the military. Maybe you’re drafted by the New England Patriots. It’s like, if you’re not part of an organization that has that code, you’re kind of S.O.L.. I think what I’ve loved about Stoicism, and what gets me so excited about teaching it is you have 1000’s of years of tradition of people just like you and I, that was struggling to be their best self sort of thinking through how to live, how to be happy how to not be a slave to things, how to deal with adversity. I just love the idea that philosophy can be practical and usable in real life.

Mark Divine 4:25
I love that, too. So at what point, did you decide that this was the main thing for you? What was your early work?

Ryan Holiday 4:33
My first book was called Trust Me, I’m Lying. And it was an exposition of the marketing and media system. I did my first three books while I had a full time job in the sort of corporate marketing world. And I struggled with keeping it the main thing, I don’t know if I was afraid of it. I don’t know if I just had more energy than I knew what to do with. But it took me a while. I do think part of me was and remains a little worried about just being a writer, because I worry that that’s not real. That’s not a real life. Right? Like, I’m somewhat suspicious of people who only talk about things for a living.

Mark Divine 5:14
But also I would challenge that I don’t think, I mean, there might be people who are just writers, but you’re certainly not just a writer. I mean, look at what we’re doing right now. We’re communicating through a digital media platform. So you are a communicator, you are a thought leader. You’re a philosopher, you are a business leader. I mean, look at what you’ve created, or you and your partners have created, with The Daily Stoic. I mean, that’s extraordinary. Started out with a book that became kind of a movement. So you’re way more than an author, you know what I mean?

Ryan Holiday 5:42
Like, I don’t just want to be talking about this stuff. I also want to have opportunities in my life. As you said, we’re all householders. So having kids challenges you to be Stoic, being in traffic challenges you to be Stoic, right? Doing your taxes challenges you to be Stoic. But I wanted to have other things that I do. I like what I loved about the Stoics. And what I love about the Stoics is that they’re all multi hyphenated. Right? Seneca was a playwright. He was a senator, he was the advisor to the Emperor, and he was a philosopher. And I don’t think he would have been as good at any of those things had he dropped one of those things, right? It’s the whole package. So I’ve always just tried to do other stuff for that reason. And I think that’s why I stayed in marketing longer than maybe I needed to, I liked it not being my full time thing. But I think there was also a part of me that was held back by that.

Mark Divine 6:40
I think the bigger theme here that you’re talking about is to not necessarily identify yourself with any particular role.

Ryan Holiday
Yes.

Mark Divine
Have an identity that is much bigger, more expansive, you know, that can be your calling, right, in life? Or the Eastern idea of dharma, right? You’re calling. And so you have a calling. And it’s not wrapped up in an identity of being an author or a business person, or even a Stoic philosopher, this or that. I mean, Ryan Holiday has a much bigger why. And then so the Discipline Equals Destiny piece iis for you to be true to that why every day and to make decisions, disciplined decisions that are going to allow you to align with that and to bring that to life in a variety of different roles, to include being a father and a husband, and etc., right? Because those are just as important as being an author and inspiring millions of people.

Ryan Holiday 7:28
Totally. And in some ways, those are the most challenging things of all right? I heard a Zen expression where it’s like, Oh, you think you’re Zen go spend a week with your family?

Mark Divine 7:38
(laughing) I just did, by the way, my family of origin totally destroyed my Zen, you know, appearance, and I was like, “Oh, my God.” It doesn’t take long when you head back to spend some time with your parents.

Ryan Holiday 7:48
It sure does not. And you realize, man, there are no two people on the planet more uniquely suited to push all of your buttons.

Mark Divine 7:58
So zeroing in on this new book.

Ryan Holiday
Yeah

Mark Divine
Do you have, like, a few practices or principles that are like must have takeaways that are maybe appropriate for a listener who’s driving their car right now, or you know, is going to give it the attention of a podcast.

Ryan Holiday 8:14
I sort of break the book up into a couple of different kinds of disciplines. So there’s obviously the physical discipline, I think anyone listening to this probably already has some kind of physical practice. But I do feel like the physical practice is a great metaphor, a great training ground for the other practices, right? And like, I’ll give you an example. It’s not just like, “hey, I got to work out because that’s what discipline is about,.” Like, I’m working on this book now, and it’s a little like all over the place. When I look at my desk, like if I could pick this camera up and show you my desk, like my desk is a mess. And so as I was sitting down, I made a note to myself, I was like, before I get back to the book, after I finish this, I’m going to clean up this desk, because this mess is contributing to the intellectual mess.

So you know, this is why in the military, they make you shine your shoes and tuck in your uniform. It’s about the presentation, I think about this, like as a writer, I work from home, I can do whatever I want. But I shower and shave every day before I write. I don’t write in my pajamas, you know, sitting on the couch, I get up, I get dressed, I go to work. No one asked me to do this thing, but it’s part of the ritual. It’s part of the discipline that allows me to take what I do seriously, or to use Steven Pressfield’ thing, as a pro, right? A pro shows up dressed for work.

Mark Divine 9:35
I love that. And I’ve often said that your outer environment is a reflection of your inner, so if everything’s cluttered outside of you, then it’s likely you have a cluttered internal life. And you can reverse engineer that by decluttering your external which will then lead to more peace of mind or clarity in the internal.

Ryan Holiday
Yes.

Mark Divine
And then that becomes a little bit of a discipline, right? So anytime you feel a little bit cluttered inside, it’s probably… look around you and you see your desk is a mess or your closet’s, you know, shoes are spilling out. So reverse engineer your way back into clarity.

Ryan Holiday 10:03
The next discipline would be like your temperament, right? So as a young man, George Washington saw a play. That play was called Cadeaux by Joseph Addison. And it’s sort of the Hamilton of its day, ironically. It was a huge play, like the biggest thing in the world. And in fact, in the American Revolution, a lot of the famous lines like give me liberty and give me death, or I regret I have but one life to lose from my country. These are lines from that play. Everyone would have gotten that they were references from that play. But Washington’s favorite line from that play is, “to look at everything in the cool light of mild philosophy.” Right?

So when we think of discipline, we think of someone who’s strong, who works hard, but I also think of the discipline of someone who doesn’t lose their temper, who’s difficult to provoke, who’s calm. You know, grace under pressure. When we think of discipline, it’s that coolness in the moment. That’s not just happening.

One of the sculptors of Washington spends, like, you know, seven or eight days just studying the man in person. And he realized that Washington had like, quite a temper, and was a very passionate man. But, that Washington kept all this on a leash. It wasn’t that he was just naturally calm, and naturally Stoic. It was that he worked at it, it was a discipline for him. And I think we have to apply that standard to ourselves. It’s easy to get provoked. It takes discipline to say, I’m not going to let that get to me.

Mark Divine 11:35
I love that. That’s kind of mindfulness in action, right? Yes, it’s creating that separation so that you don’t react but you can respond, respond with discipline.

Ryan Holiday
Yes.

Mark Divine
So that’s a discipline in itself.

Ryan Holiday 11:46
I tell the story in the book about Sam Casell, the basketball player, he’s playing for the Timberwolves, and he hits this shot. I think it’s in game six, it might have been in game seven, he hits this corner three, it’s an incredible shot. And as he’s running back on defense, he does what they call the big ball dance, or the big balls dance. He acts like he’s having to cradle his enormous testicles.

Mark Divine
Oh, my God. (laughing)

Ryan Holiday
Like as he’s running back, it’s this like, you know, it’s a touchdown dance. That’s what he’s doing.

Mark Divine 12:17
Yeah it’s like spiking the football and doing the dance.

Ryan Holiday 12:19
Yeah, as he does this, he fractures his hip

Mark Divine
Oh, my God.

Ryan Holiday
And they go to the NBA finals next, and lose. And he’s a nonfactor. He plays two of the games, basically, takes himself out of a championship, cost his team the championship, because of one moment of a lack of discipline, right? That one celebration, that one bout of enthusiasm that wasn’t necessary, that didn’t do anything. It was a devastating career altering injury. And so when we think about temperament and self control, it’s not just the control to show up and work or to run an extra mile. It’s to keep those emotions in check, because they very rarely lead to a good place.

I heard a General Mattis story about doing interesting things while you have time, someone told me they were at a dinner with General Mattis. And he got up and he went straight to the dessert table, and got dessert and so and said, “Oh, you’re getting dessert first?” And he said, “Dessert is not guaranteed. Life is short.” I love that. The idea is, like, do the thing that you want to do. While you’re sure you can do it, because you have no idea what the future holds.

Mark Divine 13:30
Yeah, the caveat to that is, if you live that way, without discipline, then your destiny will be a little different than if you live that way with discipline.

Ryan Holiday 13:39
No, that’s true. There is this sense of Memento Mori, from the stoics that we have to live while we can, you know, the future is uncertain. As Seneca says, “Live immediately.” But also how do you plan for a future that may happen? I kind of think about it, it’s not that you will die tomorrow, or next week or next year, and live accordingly. It’s that you could say you have to balance both the moment, now, that’s in front of you with the fact that the future could happen also. And if you have not invested in or been disciplined enough, that will be miserable.

Mark Divine 14:17
That’s right. And I think at the highest level, the mastery level, those two come together, in an effortless choice. For instance, you can enjoy the dessert with great awareness, and have it still be a practice that supports your long term evolution and growth. And with great awareness, you probably would eat just a very small fraction of that dessert, as opposed to eating without unawareness, you know, because you’re just joining it for the hedonistic pleasure of it, or you’re eating because of you want to be distracted from something else that’s causing you suffering in your life. You don’t need to sacrifice in order to have great discipline.

Ryan Holiday 14:56
No, I think that’s right. And we forget that temperance, the virtue from which self discipline is derived. Another way to say that is moderation. Right? So you’re not putting off the dessert because you don’t deserve it, you think life should be without pleasure. You’re just saying, “I’m going to have it now while I still can.” But I’m not going to eat so much that this pleasure becomes…

Mark Divine
An obstacle.

Ryan Holiday
Yeah, I mean, think about this with drinking is such a good example. I don’t happen to drink. But if you drink so much tonight, that you have a hangover tomorrow and you’re miserable, the first several hours of the next day, was it really a pleasurable experience? You had pleasure at one moment, but that same pleasure was causing regret and pain in another moment?

And so I think the idea when we think about temperance or when we think about living now and living later it’s… Can you make a decision now that brings you joy and pleasure without the expense or costs of doing it later? A more common example would be like work. You’re working really hard, you’re invested, you’re building your business, etc. But by the time you get that success, if you’ve driven your spouse away, if you don’t have a relationship with your children, you know, you don’t have any friends, you don’t have any hobbies, your health is deteriorated, you know, how successful are you really, because you know, you have traded other valuable things to get this other valuable thing.

Mark Divine 16:24
And there’s a fine line here to Ryan, because especially when we’re beginning something new, whether it be a relationship or a book project or a business, oftentimes you have to sacrifice the short term balance and pleasure for you know, to get the inertia broken, to get the, you know, the spaceship through the atmosphere, so to speak, metaphorically. And so you can feel like you’re out of balance. But the reality is can you rebalance that, as the thing kind of gets up to speed and you’re in between book deals. And if you’re, if you’ve done this a number of times, you take time to recover, you go back into creativity mode, and it swings in the other direction. We swing between creativity and action. And sometimes it feels like we’re doing too much action, but it’s because it’s necessary.

Ryan Holiday 17:08
Yeah, a friend of mine was saying that early in your career, you have to say yes to everything, to hopefully get to a point where you can say no, to basically everything. I think what we’re talking about some people might say, Oh, is this a contradiction? No, it’s a balance, right? It’s, there’s a tension, the two different poles, keep it in tension, if you need it to be certain if you need it. To be clear, you’re probably not at that master level, as you said, that tension that balance is key. And you figure out as you go, what the balance is, in different times the balance is different. But I think Eastern philosophy is more comfortable with paradoxes. That’s when seeming contradictions where Western philosophy wants a specific thing,

Mark Divine 17:52
Right, because Westerners believe in the linear cause and effect reality in the Western, or the Eastern mind is more a holographic or, you know, simultaneity, which allows for synchronicity and possibility. The other thing that’s really interesting about this conversation is I think it’s a fantasy to think that actually there is such a thing as balance. I think there is always a fluctuation. And you said the more competent you get at challenging the notion, the it’s all effort, or it’s all play, right? It’s all hedonism, or it’s all sacrifice. You get more and more competent at balancing. And the metaphor I’ll use is like a teeter totter, right? The teeter totter is never ever actually imperfect balance over the center point. But the more depth the kids get, the arcs go smaller and smaller until it appears as if they’re balancing. But in reality, there’s a million little adjustments that are going on. And that’s similar to how we want to live our lives is like we want to get more and more skilled at this kind of juxtaposition, this flow between action and effort, and recovery and creativity until it appears as if there’s balance. But there’s always a little bit of dynamic tension between those two. And that tension is important because it creates a little bit of resistance, which creates us moving forward, as opposed to collapsing back into inertia.

Ryan Holiday 19:09
Yeah, the Stoics have talked about… Marcu Aurelius talks about this idea. There’s like the rhythm of the universe, the idea that there’s this rhythm, so balance, your right is tricky, because you’re never going to get exactly there. But the idea that there’s like a beat that there’s music going on, and you can come away from it and come back to it. But the idea that, like you’re trying to stay on the beat as much as possible, but because you’re a human being, you’re never perfectly going to be in sync with the music. But you can catch yourself, “Oh, I’ve come off of it. Now I’ve got to come back to it.” I like that idea. I like the idea of trying to approach balance. But if you think that the balance exists, or worse, this is what people do… They think that once they have gotten balance, they can then keep it there. It’s something you do one time as something you’re continuously doing and adjusting for. That’s also wrong.

Mark Divine 19:57
Right. I agree with that. Because that’s the similar to saying, I’ve made it and now I can kind of relax, which then spins you back into that inertia, where then you’re gonna have to overcompensate with action again, to get out of that. Your metaphor on music is fascinating. Because the more competent both a musician and a composer gets, the more they appreciate the silence between the notes. And the more often, I imagine, that they’re making their music from that silence as opposed to from “This is the sound I want to make.” I’m just making that up. But I really believe that’s probably true. And just like a poet, the better poets have fewer words, and they appreciate the space that it takes to settle into the words as opposed to just throwing more words at the reader.

Ryan Holiday 20:38
That makes sense that I would also say when I think about music, I think about early on, when you are playing music, you’re very conscious of all that you’re trying to do. This is the beat, this is the key. This is what this person’s doing. This is what I’m going to do. But as you get better and better, the whole process becomes much more intuitive, much more natural, much less conscious. And it just becomes something you’re just simply doing, you’re existing fully in it, the flow state is naturally there. So early on, like, when you’re talking to a writer, they’re like, “This is how many hours I do, this is the way that I…” you know, it’s very rigid. But as you get better at it, it’s not that you become less strict with yourself, it becomes more amorphous, you know, you’re just kind of flowing with it, and you go in and out of it. And you’re operating just on a deeper, more intuitive level, whether it’s balance or work life balance, or, you know, just all of it is just coming from a deeper, more masterful place.

Mark Divine 21:37
That’s fascinating. Yesterday, someone was interviewing me. And they asked me, said, you know, in between stuff, right, in between your writing your podcasts in your business meetings, and this and that, the other thing? What does your mind do? Like, what do you think about? And I paused for a moment, I said, Well, I think about what I decide to think about in those moments. And I was trying to make the point that at the level of, at least where I’m at, I don’t know, if you want to call that mastery or not, some might, my mind just doesn’t fill up with whatever, just because I’m in between the things that I decide to do. Right, I literally have an opportunity every moment to decide what’s next in the whitespace. Oftentimes, that is nothing, right? Or just listen to a great audio book, or allow for some recovery and spontaneity, which is very different than the answer I would have given 15 years ago would have been like, you know, what’s next? What’s next on my task list? Or, or I’ve got to fill that time up with learning, right? I’ve got to get my 20 minutes or half hour or hour of reading in or you know what I mean, I would have checked off the things I’m supposed to do to optimize myself as a human being, which is all doing.

Ryan Holiday 22:45
Yeah, I think as you become more confident in yourself and what you do, it turns down the volume on noise, but it also turns down that little engine inside of you that’s needing to constantly do and do and do.

Mark Divine
To protect itself.

Ryan Holiday
Yeah, that’s also very insecure. So you’re just kind of like, what are you doing next? I’m doing this, whatever I want, you know, I’m doing me, right. Like, you’re just sort of confident just being in whatever you’re in doing whatever you’re doing, there’s not this franticness I feel like as I’ve gotten older, and as I’ve gotten more successful, it’s not that I’m less intense. But I am less frantic.

Mark Divine 23:26
More relaxed, which is not the opposite of less intense. It’s a different quality altogether.

Ryan Holiday 23:30
That’s right. Like if you walked into a jiu jitsu gym, the highest ranked person would be the friendliest, the calmest, the most welcoming, the most secure. They know they can take anyone in the room. And they know that they don’t need to take anyone in the room. And they’re just comfortable with who they are and what they can do.

Mark Divine 23:54
Right. So I totally agree with that. And reminds me of Nakamura, my meditation and karate instructor. And that got me kind of down this whole path. I mean, the Zen path, like he was one of the most intense individuals I’ve ever seen in my life, or will ever see in my life. And people say that about me, but just what you described, he was also the most playful and relaxed, this idea of being coiled like a spring really tightly, so you can explode an explosive, you know, violent action if necessary. But within that coil gives you the freedom to operate, right, because the coils locked in tight, it’s not going to spring at the slightest trigger, it’s not going to go off and the wrong person for the wrong situation. It’s been trained and honed and refined through 40, 50 years, so that it’s completely in control. The trigger point is in control.

Mark Divine 24:44
Steven Pressfield was just downstairs. I was recording a podcast with him this morning. But he has a scene in his book, The Virtues of War, which is about a young Alexander the Great.

Mark Divine
Great book, right.

Ryan Holiday
I think he based his story on Diogenes, who Alexander the Great, and Diogenes, the philosopher and the conquerors have a number of really interesting interactions with each other. But Pressfield, as a fictional account in the book is Alexander the Great comes across this philosopher, and it says, “Get out of my way.” The philosopher says, “No, I’m not going to do that,” or something. And then Alexander the Great says, “I’m the most powerful conqueror in the world, who are you?” And the philosopher looks at him and he says, “I have conquered the need to conquer the world” To get totally to his zen place where you don’t feel like anything matters. I’m not sure that’s exactly what we’re talking about. But this idea of where you’ve gotten to a place where you’re like, I am good. I’ve done what I have done. I know who I am. I know I’m capable. I don’t need to prove anything to anyone. I don’t need to do anything that I don’t want to do. It allows you to operate on that plan. I think of stillness and calmness and security that paradoxically allows you to do whatever it is that you do so much better.

Mark Divine 25:51
Right? You talk about this perspective that the Zen master gets to the state where he doesn’t feel like anything matters, and that’s actually not accurate. He gets to the state where we realizes that everything matters, because everything, absolutely everything, is interconnected. And everything comes together to create this moment. Again, this is the Eastern reality and it starts out as philosophy, then it becomes reality through the experiential aspect of the practice and this is back to stoicism. Stoicism as a philosophy is a dead art. Stoicism as a practice brings the philosophy alive. Zen as a philosophy where you just study in a satsang, or, you know, and you’re not doing the daily practice, is just words. It’s just dogma. When you practice, and you have the lived experience, and you recognize that the fabric of humanity, fabric of this life, is this infinite interconnectedness. Then you recognize that everything matters, including this moment between the Emperor and the philosopher because it’s important for the Emperor’s enlightenment or his path. Very, very different than the view of the Zen monk hiding from the world in a monastery and thinking that nothing matters.

Ryan Holiday 27:01
It’s funny, I’m just thinking about this, I wrote it down. I’m gonna write about this because it’s really interesting. I’ve often been skeptical of the Zen tradition of like, yes, retreat to a monastery, exit the world, give up all your material possessions, give up relationships, give up material success, etc, Contrasting that with stoicism, which I’ve always loved. Marcus Aurelius is an Emperor. Seneca is a writer. Kato’s a soldier. I’ve always loved that. But Western philosophy did the exact same thing, instead of retreating to the monastery, the philosophers retreated to the academy. They exist in academic life, they’ve removed it from the practice of day to day existence, and turned it into a theoretical exercise. When really, it’s Musashi, the samurai warrior, studying Zen. And Marcus Aurelius is studying it to be emperor. That’s what philosophy is, to me, whether it’s East or West, it’s to be used in life.

Mark Divine 27:57
Or the benevolent leaders of ancient India, who ruled these vast civilizations as a benevolent leader who were practitioner, scholar leaders, right, they were integrated, they were whole.

Ryan Holiday
Totally.

Mark Divine
The Stoics were pointing to that the real juice is in not hiding from the world, although, you know, again, at the same time, there are certain people where that’s their path, so to speak, right. So it’s not like it’s wrong for them. But it’s not right for everybody. And it’s also a mistake to think that Zen or stoicism is this way. The Stoics and the Zen Masters of the past were pointing to this need to go back to what we were talking about earlier to find that center point between action and inaction. And there’s the saying in the martial arts, you find the inaction in action, and you find the action in inaction. And this is like the Yin Yang symbol, right? Sometimes you just see it with black and white. And it’s kind of like a merge. And if you were to stretch those apart, it looks like an infinity loop. So you collapse it back together, you get the Yin Yang. And now that was kind of an insight I had. I’ve never seen that written anywhere. Oftentimes, you also see a white in the black region and a black in a white region that represents the contrast we’re talking about. You’re looking for the Yin and the Yang and the Yang in the Yin.

And so that is what we mean by living Zen in everyday life or being what the yogi’s would call a householder. It was considered the highest path, to be able to practice yoga to attain enlightenment, as a husband, father, wife, son, mother, business person, lawyer, academic. And so that’s the path that I’ve been teaching. And I believe that’s the path that the Stoics were talking about. Because again, Marcus Aurelius makes it very clear that Stoicism isn’t just about thinking about these ideals, it’s about getting out, getting your hands dirty, and your heart dirty and figuring out in real life experientially proving it as a study of N equals one. And that’s the experiential nature of stoicism that is so beautiful.

I think that you make a big attempt to bring that alive in your writing, starting with The Obstacle Is The Way, because that was eye opening for a lot of people. Like, wait a minute, Mark has been saying failure is not an option. What does he mean by that? No. Ryan comes out and says the obstacle is the way. Actually, it’s not even an obstacle. It’s a blessing, because it’s going to be where you find your greatest learning and your lessons in life. So embrace the suck of those, learn how to navigate them. That’s called resilience with joy and bliss and learning. And then guess what the obstacles appear to diminish in your life because you get more and more adept at overcoming them.

Ryan Holiday 30:24
Yeah, I mean, if you learn from it, if you become better for it, if you take something away from it, that improves you, it wasn’t a failure. If you decide that it was a failure, an unalloyed pure, complete failure, then it was, right? And so when you’re saying that failure is not an option, and when I’m saying the obstacle is the way, we are, in fact saying the same thing, which is that you have to choose to see this as a way to move forward even if it’s a situation you didn’t want to be in and no one reasonably would choose to be in.

Mark Divine 30:59
That’s why this is unreasonable. Stoicism and Zen and Navy SEAL training are unreasonable, but they’re necessary if you want to perfect yourself or have a life of freedom. I’m going to invoke Jocko, but discipline equals freedom. I was thinking about that when I thought about the title of your book. That was his saying, like trademark Jocko discipline equals freedom, discipline equals destiny, destiny should be freedom.

Ryan Holiday
Yes, of course.

Mark Divine
If you don’t have total autonomy over your mind, and your movements and your finances and your relationships, then in some way you’re under the control or spell or, you know, even if it’s just childhood trauma, you’re under the spell of your parents trauma, right? And you haven’t freed yourself from that. Ultimate freedom is a difficult thing to attain.

Ryan Holiday 31:39
Jocko is totally right, that discipline is freedom. There’s a great Eisenhower quote, he says, “Freedom is really the opportunity for self discipline,” right? Which I love. I’m doing this series now on the cardinal virtues of courage, temperance, justice, wisdom. So as I sat down to write about temperance, or self discipline, I wanted to think about what I had to say on the topic. And while I would totally agree that discipline creates a kind of freedom, and that someone who has no discipline is not only not free, they are a slave, right? Because you’re a slave to your impulses to your urges to what other people do.

I’m trying to make a slightly bigger argument, which is that discipline will determine who you are, right? It determines whether you’re free or not, whether you’re great or not, whether you’re decent or not, right? Whether you’re in control of your emotions, or your emotions are in control of you. When we say that discipline is destiny, it’s in the sense that they used to say that character is fate, that your character determines who you are, what you’re going to be able to do. And so not only does discipline determine your destiny, but it can make whatever it is that you end up doing great or not great. At the end of the day discipline is the thing that sort of separates the pros, from the amateurs, the greats from the not so great. I agree. Discipline is definitely freedom. It’s also even more than that.

Mark Divine 33:00
And it’s also important that we expand the concept for people what discipline means, because most people automatically think it has to do with either hard physical work or hard work in general, often to an extreme, like a Navy SEAL training, right? Or the discipline of the stick, right? But to me, like when I break that word down, it means you know, its root word is disciple, it means to be a disciple to something bigger than yourself, or to some future vision of what’s possible for your life or for humanity. Like we as a country lack discipline, largely because we lack of vision for our future. So we’ve got, we really don’t know what we’re working toward. So it’s very hard to mobilize efforts if you don’t know what you’re working toward. So discipline, being a disciple to, you know, hey, we are kind of all in the same spaceship Earth together. So wouldn’t it make sense to create a collective vision for where we’re going, and then create some disciplines around making sure that we can get there and don’t like, blow ourselves up or destroy ourselves in the process? Right?

Ryan Holiday
Yeah.

Mark Divine
Now, I went really broad with that. But discipline to me is to be a disciple to something bigger than your ego. Like, in this case, the Ego is the Enemy, because the ego will always contract to the simpler, the lowest or the easiest path. And discipline requires us to move beyond that and take the harder route of determining what’s better for the higher good, either our higher good or your sense of God, right? Because many people say, I’ll be a discipline or disciple to God, or my sense of a universal power. And that’s absolutely fine as well, right?

Ryan Holiday 34:30
Well, I think if you think about where you’re trying to go, or who you want to be, it makes discipline easier. So Seneca says, If you don’t know what port you’re sailing to, no wind is favorable. If you don’t know who you want to be, or what kind of country you’re trying to make, or what kind of business you’re trying to build. Or if you don’t know what you’re trying to end up as, it makes it extraordinarily hard to make these individual decisions, right? Do I eat the cake or not eat the cake? Do I show up and work today? Or not? Do I get my best or not? Right? Am I kind or not? If you don’t know what your code is, what the ideal, the standard what you’re a disciple of and you’re right, that’s where the word discipline comes from. If you don’t know what you’re a disciple of, how can you know what to do in these individual micro decisions? But when you have that clarity, then it makes it much easier, and much simpler and more black and white, about what to do and what not to do.

Mark Divine 35:30
Right. But we’ll invoke Simon Sinek here the reason his work it all starts with why was so powerful, is so powerful, continues to be, and it’s so radically simple that when you listen to him, his TED talk or read his book, you’re like, “Duh, yes.” How come I didn’t think about this? Right? Right. It’s because the discipline to know your why is actually the highest discipline, it’s the hardest. It’s the most challenging and it should all start there. That’s why the inner work of the Stoic or the inner work of the Zen master or the yogi was the most important because that’s where the why is found, right? It’s not found through more action by creating more businesses by writing more books, you know, unless you have a deep internal practice as part of those external initiatives, those outer initiatives.

Ryan Holiday 36:13
I have a chapter in the book that was inspired by the GM of the Los Angeles Rams, Les Snead, who have gotten to know, I went and saw them a couple of years ago. And he said, “the main thing is to keep the main thing, the main thing,” right? Like sort of what is your core value, your core mission. So when we think about discipline, it’s not even, “Hey, this is what I have to do to be who I want to be. But also, here’s all the things that I can’t do, right?” That I have to say no to that I have to ignore that I have to tune out, right. So you’re the disciple of x? Well, there’s going to be all this other stuff that you like, or that distracts you or that you have opportunities to do when Simon Sinek says you start with why, that’s obviously a huge part of the discipline, the strength, and clarity and focus to sit down and go, “Why am I doing this? What am I trying to accomplish, etc.” But then there’s the day to day discipline of sticking with that why. Not getting distracted with all the other things you could do or that other people want you to do? Or that are also happening? Not to get too political. But I was reading an article a few months ago about the ACLU, which started as an organization designed to defend free speech, right?

Mark Divine 37:20
Where have they been in the last couple of years? (laughing)

Ryan Holiday 37:23
Particularly unpopular free speech. But the problem is, as an organization, they got distracted by all these other political causes. And sometimes those causes are not only not related to protecting free speech, but might have contradictory values, right? So the idea of what is the main thing like what do I do? What can only I do? This requires an immense amount of discipline, because people are going to say, Well, why aren’t you being involved in this? Why aren’t you doing this? What about this? What about this, there’s an infinite number of things that can consume your time in the world, if you don’t have the discipline to go, like, I agree, all those things are important. But my main thing is protecting this. And that’s what I’m going to do to the best of my ability.

Mark Divine
Wow, what just came to me is that was the original why for this country not to stay on the political and I don’t want to go down the political rabbit hole. But it was freedom. The Founding Fathers, so to speak, created the founding documents built upon this idea of freedom. And so it’d be nice to go back and remember that, re-invoke that why.

Ryan Holiday
It’s tricky, though, right? Because freedom…

Mark Divine
Means different things to different people, maybe.

Ryan Holiday
Yes, but this is an interesting thing that the founders talk about. And I talked about this in at the end of the book. Like I agree, the founders said, “Hey, we’re not going to legally mandate you do this, or that.” Almost all the founders said something to the equivalent of, “This system will not work without virtue in the people,” right? Basically, you can say whatever you want. But there’s a lot of things that you should not say, because it’s rude because it’s wrong, because it hurts people because it’s stupid. So free speech is a good example. Just because I can walk down the street, insulting everyone I meet doesn’t mean that I should. Oftentimes people talk a lot about freedom, which is important. But to me, discipline is also about obligation. It’s also about a set of standards that you set for yourself that says I don’t care what’s allowed. Here’s what’s acceptable, per my code, and my duties as a human being. I wrote a piece a couple months ago about the Statue of Liberty. Viktor Frankl famously suggested on the West Coast, there’d be a Statue of Responsibility to counterbalance the Statue of Liberty,

Mark Divine
Love it.

Ryan Holiday
And to me, that’s the difference, that when we think about these virtues, also, they’re in a tension with each other.

Mark Divine
That’s the yin and the yang, because liberty is truly, ultimately found within so that’s the Yin and responsibility is found through disciplined action and habituation and virtue building. That’s the external. Do you think temperance and humility are the same thing?

Ryan Holiday 40:02
I think they’re related. Ego is a form of intemperance. Ego is excess, like, confidence to me is also temperance, though, right? Confidence is, this is what I’ve earned. This is the right amount. To little is a problem. And too much is a problem. But you’ve got to have the right amount. And to me, the right amount is the amount you’ve earned.

Mark Divine 40:25
You’ve earned it but also you are aware of what the right amount is, through trial and error.

Ryan Holiday 40:30
Yes. I think there is a kind of level of self discipline above just regular self discipline, that kind of heroic self discipline. And so I kind of wrap the book up. I’m talking about Marcus Aurelius, it’s like, we have this expression, absolute power corrupts absolutely. And here you have Marcus Aurelius. He’s given absolute power. And the first thing he does is he makes his stepbrother co emperor, like he shares absolute power. Again to go to Washington, Washington repeatedly relinquished his his power. Right? He resigns his commission, he doesn’t seek a third term as presidency, setting an extra constitutional norm that stands for 200 years, Washington was all about that kind of heroic self sacrifice, that there’s normal discipline. And then there’s that heroic discipline. You know, Shackleton is heroic self discipline, it shouldn’t even be humanly possible to pull off what you just pulled off.

Mark Divine 41:30
Abraham Lincoln, right, stocking his cabinet with his enemies is a good example of that as well.

Ryan Holiday 41:36
Yeah, you think about how provoking and obnoxious and unpleasant that would have been. And he not only dealt with it, he chose it for himself. Right? If he had inherited the cabinet, you’re like, oh, that must have taken a lot of self discipline. He knew what that was going to be like and he chose it.

Mark Divine 41:53
Because he was a disciple to something bigger than himself, he did it because he knew it was in the best interest of the country. Wouldn’t that be nice if our politicians today did what was actually in the best interest of the country?

Ryan Holiday 42:03
I’m almost upset that you brought that example up, because that would have been the perfect thing to include in part three of the book, and I didn’t. And that’s exactly what I’m talking about.

Mark Divine 42:11
That’s awesome. So what’s next, you’ve now tackled two of the four virtues

Ryan Holiday 42:15
The cardinal virtues is this series that I’m doing… So I did courage, temperance, and now I’m starting justice, which is the third.

Mark Divine 42:22
And what’s the fourth, gonna be?

Ryan Holiday
Wisdom.

Mark Divine
It’s fascinating, because I could see the challenge in writing these because all these cardinal virtues kind of overlap or edges of them overlap. Right. So this story about Lincoln could fit in all four of them, there’s courage, there’s discipline, there’s wisdom.

Ryan Holiday 42:37
I think that’s the idea. Yeah. And none of the virtues work particularly well in isolation. Right. So courage in pursuit of the wrong cause, and unjust cause is not a virtue. And then how do you know what the right cause is? But now you need wisdom. And then how do you know how much courage, you know? Now you have self discipline. So yes, they’re all in a tension in a balance with each other. But justice is the one I’m most intimidated by.

Mark Divine 43:04
For this particular book, Discipline Equals Destiny. Anything to say on that? Do you have any pre-launch? Or when’s it come out? Or

Ryan Holiday 43:11
It comes out September 27th. Everywhere. And yeah, we have a bunch of pre order stuff at dailystoic.com/preorder. You can get signed copies. I’m even doing like pages that I cut out of the manuscript that I’ve signed, like all the pages that I wrote while editing.

Mark Divine 43:26
Ryan, thanks so much. I’ll let you go here. It’s been an honor. And you rock.

Ryan Holiday
Thanks for having me.

Mark Divine
You take care now. Thanks so much.

Ryan Holiday 43:33
All right. See you guys.

Mark Divine 43:37
Phenomenal episode in conversation with Ryan Holiday of The Daily Stoic and author of Discipline is Destiny coming out in September of 2022. Show notes and transcripts are up on the site of MarkDivine.com. A video of the episode is on our YouTube channel at MarkDivine.com/youtube. You can find me on Twitter, at MarkDivine and on Instagram and Facebook at RealMarkDivine and on my LinkedIn profile. If you are not a subscriber to Divine Inspiration, then I recommend you do so at MarkDivine.com. You can go sign up there, get on the distribution list. This is a weekly newsletter where I disseminate my most top of mind thinking, my blog, my podcast, show notes, and other interesting things that come across my desk that I think would be inspirational to you. So go check it out. MarkDivine.com and subscribe. Special shout out to my awesome team, Geoff Haskell and Jeff Torres, Melinda Hirschey and Jason Sanderson, who helped produce this incredible podcast and bring these amazing guests to you every week. Very helpful if you review and rate the show at Apple or wherever you listen to it. So thank you for doing that. And thank you for being a Stoic yourself and having the discipline to do the work to improve yourself every day to become more whole, more compassionate, more courageous, wiser, more temperate. It’s very important that we do that so that we can be the change we want to see in the world at scale. Till next time, this is your host Mark Divine. Be courageous and let this be your destiny.

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