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Ryan Holiday on Philosophy and Modern Life

By October 2, 2019 October 16th, 2019 No Comments

“Whether you’re experiencing massive success, or rock-bottom failure, ego is not something that will improve your situation.” – Ryan Holiday

Mark has a new book coming out in 2020 about the seven commitments of leadership. It is called “Staring Down the Wolf: 7 Leadership Commitments That Forge Elite Teams,” and is available now for pre-order. Commander Divine writes about many of the great leaders he met in SpecOps to give examples of the commitments that one has to make to the 7 key principles of  Courage, Trust, Respect, Growth, Excellence, Resiliency and Alignment. Check it out at Amazon to order yours right away.

Ryan Holiday (@RyanHoliday) is a well-known author of several books about using Stoic philosophy in the modern world, including “Ego is the Enemy: The Fight to Master Our Greatest Opponent,” “The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph,” and “Stillness Is the Key” which has just been released. Commander Divine talks to Ryan Holiday about his books, his writing process and what he has learned through his study of the Stoics and other philosophers.

Hear how:

  • Life is as much about the things we DON’T do as it is about our actions and deeds.
  • Journaling is an essential component of understanding and reflecting on what we actually know and understand.
  • A huge difficulty in the modern world is making the time for the stillness that we need.

Listen to this episode for insights and greater understanding of ancient philosophy, and how it is essential for modern life.

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Hi folks. This is Mark Divine. Welcome back to the Unbeatable Mind podcast. Thanks so much for being here today. I super-appreciate it. As you know and I say before every show – I do not take it for granted – there are 10,000 podcasts or more vying for your attention. There’s a billion other things you could be doing. The fact that you’re here learning to improve yourself, and wanting to listen it means a lot. So, thank you so much.

Before I introduce my guest, Ryan Holiday, who I’ve spoken to before… What an amazing author, writer… You know, leader – we’re gonna have a tremendous conversation – I can’t wait.

But before I get into that, I want to tell you a little bit more about the book that I’ve been working on that I’ve recently submitted. Kind of finalizing with my publisher. It’s called “Staring Down the Wolf.”

It’ll be out… Not actually out until March of 2020. But it’s available at amazon for pre-order right now. And I will be podcasting – I’ve already started, so I’ve already done solo podcasts on the first three chapters and I’ll be doing all the rest. So you can kind of get it here first in audio format, before it’s launched.

But it is about developing emotionally aware leadership by staring down your own fear wolf and what I mean by that, is those things that are the subconscious negative reactionary patterns that hold us all back. And I use yours truly and all my disasters as a way to kind of expose that. And then I contrast that with other seals… SpecOps leaders who have stared down their wolf. And have done some pretty extraordinary things.

So it’s different, it’s pretty cool, and I hope you’ll find it valuable.

Okay, as I mentioned, my guest today is my friend Ryan Holiday. He’s like a super prolific author and what he writes is really succinct, very impactful and powerful and totally in alignment with everything we talk about here at Unbeatable Mind.

You may recognize some of his other books… One was called the “Obstacle is the Way,” where he really gets into the whole essence of Stoicism and how challenge is your… The grist for growth.

And then “Ego is the Enemy.” which is about developing selflessness and getting out of that egoic state of mind, where it’s all about you. And really turning your eyes and putting themselves on others… Something that we teach our teams at SEALFIT and Unbeatable Mind.

And now one of the things we’re going to talk about – amongst a lot of things today, I’m sure – is his new book called “Stillness is the Key.” where he goes beyond Stoicism to look at some of the other, eastern philosophies of Buddhism and yoga, where the essence is to try to find the stillness that… The still water that runs deep inside of us, so that we can live better, be better, and make better decisions.

Wow, how’s that for an introduction Ryan?

Ryan Holiday. That’s great. I love that expression “the still water that runs in each of us.” I’ve not heard that before, but I wish I’d heard it when I was writing the book.

Mark: (laughing) Yeah, in the first lesson of Unbeatable Mind, I have a visualization and I call it still water runs deep. And that phrase came… I’m sure it’s been bounced around in different traditions, but it came from my Zen teacher. My Zen master-teacher. And I first heard it I think in 1987 after a 45-minute Zen sit with him. And he wrote it on the board in kanji characters. I had no idea what it was.

And then he started describing it. And he said “this is still water runs deep.” and he went into how the metaphor is… Your mind is like the turbulent choppy river. Anyone who’s been rafting or kayaking, oftentimes you’ll go around a corner and the river gets deeper. And the water gets very still.

He said “that’s what you want to find in your mind. The still water that runs deep.”

It’s kind of a metaphor for what you’re what you’re writing about right?

Ryan: Totally. I mean, one of the things that inspired the book was noticing as I read very deeply across sort of western and eastern philosophy – is that this same metaphor kept popping up. This idea of letting muddy or disturbed water settle, so you can see through it.

And you see Confucius, and the Buddhists, and the Christians, and the Stoics all use this same idea. And from what we understand they did this without influencing each other. These are sort of independent discoveries of the same eternal truth.

And ultimately that idea of stillness… Like, what happens when you slow down, when you let things settle…? What kind of better decisions you can make? What kind of happiness or strength can you access inside yourself? I found that to be deeply inspiring, and very interesting.

And ultimately that’s sort of what the book is about.

Mark: Right. I think it’s fascinating… I reflected upon this… About how much water as a metaphor is used to describe what we’re talking about. Like we had this still water run deep, which is kind of the pond-slash-river metaphor. And then many spiritual additions will use the ocean and waves as a metaphor.

So the ocean… The depth of the ocean… The expansiveness of the ocean kind of represents that depth inside of you. And the waves is the surface chop of your daily thinking mind.

And then I’ve also seen my Ninjutsu tenth degree master used to use the fish bowl. And so I’ve kind of co-opted that as a visualization as well. Where your mind is like a muddy fish bowl, which is what you just referenced… And through stillness or sitting in silence, slowly it becomes clearer and clearer.

I wonder why the water metaphor is so powerful. Maybe because we’re 80% water and… Who knows?

Ryan: Yeah, look, I think there’s certainly something very special about water. The metaphor aside – I find like I was telling you before we started recording – like what I did before this, I actually spent all morning recording the audio book for “stillness.” so I was exhausted, and instead of sort of throwing myself right back into work, I went swimming in Barton Springs, which I think is probably the greatest freshwater pool in all of Austin. It’s 70 degrees whether it’s snowing outside or 110. It’s fresh water pouring millions of gallons an hour or week or I don’t know… But millions of gallons of water are just pouring from the earth.

And you can swim in this eighth of a mile long pool. And so I love it as a swimmer. You can do a mile in eight laps – I mean the worst part of swimming is just the back and forth. And to do this mile, it was 30 minutes… But it was probably the most meditative and peace-inducing and clarifying thing I’ll do all day. One reason is no screens work underwater, which I think is a huge advantage. You’re somewhat sensory deprived, right? You can’t really hear anything. You’re looking straight down so your vision is limited.

And what I like about Barton Springs, is that I’m also not even thinking about my laps, right? Because I’m not like you know my laps…

Mark: Like swimming in the ocean is very different for me than swimming in a pool. Because you don’t have to count, you’re not constantly flip turning. You’re just going…

Ryan: Yeah. And so the mind slows down in a way that gives it… I found I’ve done so much of my best writing, I’ve worked all day then I’ve gotten in the pool, or I’ve gotten in a lake, and the inspiration just comes. That problem that I couldn’t solve, just kind of magically solves itself. The solution just appears in my mind.

And so I’ve long been a believer that there’s just something magical about water. That it is the most underrated form of exercise, and just has something special…

It’s almost like being back in the womb or something. I wonder if that’s why it has that effect.

Mark: I think that’s part of it. And I think there’s this new kind of movement toward grounding. They say “go outside, and walk barefoot.” well, why not actually expose your entire body to the earth? That’s what you’re doing in fresh water.

And so there’s that amazing grounding effect. Anyways, we could talk a long time… I think we could create a whole training program just around this…

Ryan: Sure. And I like how low resistance it is too. Of all the exercises, it’s the one you’re probably hurting yourself the least to get the most benefit. And so I try to do it as much as I can. And I probably wrote a large chunk of this book in water in some way or another. And look I think – and you’ve talked about this, and other people have popularized it – but also the other benefit of water is that you actually don’t want to get in it, right?

It’s cold, or it’s wet, and so…

Mark: Face our fear and challenge our self.

Ryan: Yes. Exactly.

Mark: I love that.

ego is the enemy


Mark: I want to talk about your book, but not just yet. Let’s talk a little bit about how did you kind of develop a passion for writing? Where did that come from?

And then I’d love to kind of review some of the key elements in the egos the way… I know we did a podcast a while ago for “Ego is the Enemy.” we talked about the “Obstacle is the Way.”

But I don’t think we’ve talked about “Ego is the Enemy,” and I’d love to talk a little bit about that.

Ryan: So I grew up as someone who loved books… I just loved reading. The idea that you could access all these different worlds and learn these things. I think I took a special interest in them, in that books were always so much more interesting than whatever my teachers were talking about.

So I remember in school getting in trouble for reading under my desk. You know, like I wasn’t paying attention, but I was reading a book in my lap…

Mark: Isn’t that amazing that you could get in trouble for reading in school?

Ryan: Of course. Because it will harm your scores on a standardized test. And so I loved books, but growing up, both my parents were civil servants. Certainly we did not know anyone that made books, or had probably even met someone who had made a book.

So I think the big you know piece of resistance for me was just like “is that a job? Like people can do that?”

And so when I was in college, I was writing for the college newspaper and I met the first couple authors, through interviewing them for the paper. And it was super exciting for me to do that, but also super revealing that these were just kind of regular people who had learned a skill.

And so one of the authors that I ended up meeting was this guy Robert Greene – who I think it’s probably one of our greatest living nonfiction authors – “48 Laws of Power,” “Laws of Human Nature,” “Mastery” – and I ended up becoming his apprentice. And so he sort of taught me the craft of writing over several years. And then when I had my first book idea -I think this was in 2011-2012 – I could then put those two pieces together.

Which is very different than I think most people… Most people have the sort of inspiration for a book where they go “you know, I heard that you know doing a book would be great for my speaking career,” or whatever it is.

Mark: They approach it from a business perspective or what’s in it for me. As opposed to wanting to share… Necessarily.

Ryan: Yeah, and they don’t necessarily have the chops to realize that vision. So the idea might be great, but the final product isn’t what it could be. And so I feel very fortunate having sort of learned it as a craft in the way that…

I could have met a great cabinet maker, and I’d be on a podcast right now talking about how I make cabinets. I just got lucky to meet a guy that made books. Or I could have met someone that made knives, or any other sort of old human product.

But it happened to be books for me. And that’s what I can sort of can’t stop making now. Mark: Right, well it sounds like Robert Greene was a huge influence on you. And I know that he recently passed away.

Ryan: No, no, no. He’s still alive. He had a stroke last October. But he is doing well.

Mark: Is he in recovery?

Ryan: Yes.

Mark: (laughing) Sorry, Robert. I didn’t mean to misspeak on that one. Put you in the grave, before you’re ready.

So, he’s doing okay.

Ryan: He’s doing better, yes.

Mark: Good. What were some of the like big “a-ha”s or ideas that he passed on to you that helped you become the writer you are today?

Ryan: The biggest one – and I can answer in two seconds, because it was so informative for me – he was like “Ryan, everything is material. It’s all material.” he was like “it doesn’t matter what happens to you. It doesn’t matter how bad you mess up. Some horrible thing that someone does to you. Some setback you have in your day job.”

He’s like “the great part about this profession, is that it’s all material. And you alluded to this when you were talking about your book earlier – that like, you’re the main examples in the lessons you’re teaching.

And so that was hugely freeing for me. And hugely inspiring. It’s like “oh, actually the best thing I can do to advance my writing career is to just go off and do things. And to experience things and keep my eyes open. And just be constantly gathering material whether I’m reading a book, or I’m in the middle of an argument or whatever it is that I’m doing…”

And so this idea of always being on the lookout, always being present, always observing, has probably shaped my writing more than any other piece of advice I’ve gotten.

Mark: That is really cool. And do you have a process for capturing material? Like you said if you’re in the middle and something interesting happens do you like pull out your phone, tap Evernote, and jot it down? Or what do you do?

Ryan: Yeah. So this is something I learned from Robert as well.

I was just laughing, thinking about it. I woke my wife up last night reaching across her. I don’t keep a phone in our bedroom, because I try to limit my access to phones as much as possible.

But I needed to send myself an email, because I had this idea of something I wanted to write about. But that’s sort of the exception that proves the rule for me. I would say 98% of the research, or writing, or sort of material gathering I do is on four by six note cards.

Mark: Really? Old school.

Ryan: Yeah, I have a big stack of them here. Actually, what I’ve started doing is now when I pick what the title for my next book is, I go and get note cards printed up with that. So I can like see the phrase over and over again.

But if I’m reading a book, I take notes on note cards. If I watch a really great documentary, I take notes on note cards. If something occurs to me while I’m on an airplane, I reach in my bag, and I get out a note card, and I write that down.

And the idea is that I’m always gathering and recording material, that then as I sit down to write the book, I’m organizing in a way. So like each… “Obstacle,” “Ego” and now “Stillness” are about roughly 30 chapters each, in three parts.

So that becomes a box that has basically 30 individual sections. In the three larger sections, I’m just moving the note cards around to fill in what I think I need to write that specific chapter, or that introduction, or conclusion, or whatever it is.

Mark: That’s fascinating. So you’re looking for… You’ve got ten cards per chapter that kind of profile or ascertain what the chapter’s about. And then do you have cards for different people you’re profiling? Or different ideas?

Ryan: Yeah, yeah. So it just starts as a random accumulation of cards. Like basically, let’s say, I remember when I found the first note card that went into the obstacle is the way. I’d read a book and this guy was talking about this Stoic idea of turning obstacles upside down.

And I thought “oh, that’s really interesting.” and as I wrote down this passage and then I’d put in the corner like “obstacles.”

And then over the next year or two I accumulated, let’s say, ten or fifteen cards of interesting obstacles that people overcame, and the sort of similarities that they all had and then I thought, “Oh man, there’s something here.”

And so I went in… Now I’m specifically researching for that idea. I’m gathering more and more cards. And then eventually… Now I’m committed to doing a book on this topic. And so I’m going “okay, here are some cards that would work for the intro. And that’s the intro section.”

And then I want to do a chapter on calming your nerves, let’s say. Well now I’m accumulating all the cards and I’m writing “nerves,” in the top corner instead of “obstacle.” and it becomes sort of subsections of subsections.

And then when I’m writing those specific chapters I only have the maybe 20 or 25 note cards for chapter 16, and that’s all I really need to be thinking about in that moment.

Mark: Wow. That’s pretty cool. I mean, we were talking briefly about my process which is I’m still trying to define…

But I imagine every author has a unique process, right? Because what works for one person, isn’t going to work for another.

Ryan: Yeah. Well, I think that goes into a very Zen idea – which I talked a little bit about in the “Stillness” book – which is like ritual. So I don’t actually know if my method is superior or inferior to any other method. I don’t know if it makes me a better writer, or worse writer. But what it actually is about, is about going through that specific process. And it’s the time that I’m spending sitting down, working on the note cards… I could just as easily be recording audio messages to myself, or having conversations with a collaborator…

You know, there’s so many different ways to do it. But for me, it’s that ritualistic process and now that I’ve done it almost 10 times, I really love that. So I’m not even thinking about what the finished book is, I’m just thinking about how I gather material. How I organize material. How I write based on the material.

And then on the other side books sort of appear.

Mark: Books come out of that. That’s pretty cool. They reveal themselves.

Ryan: Totally.

Mark: That is really neat.

ego is the enemy


Mark: So as you were developing “obstacle,” then you must have seen some patterns that led to “ego” evolving out of that. Is that…?

So what were those patterns? And what are the primary themes for “ego is the enemy.”

Ryan: Well the primary motivation on “Ego” was this idea… This sort of counter-intuitive idea that many of the most successful people – especially like in things like martial arts… I think I think I was reading Sam Sheridan’s book “A Fighter’s Heart,” and “A Fighter’s Mind” – which are great books – and he had a quote from maybe it was Renzo Gracie who was talking about how, because you stay a student, you actually get more humble the better you get, because you’re realizing all that’s left to learn.

And so I really was fascinated with this idea of humility, and I was researching about it. So I kept gathering this material, but what I noticed was most interesting about the material that I was gathering – and this also jibed with my personal experience – that as important as humility is, it’s really ego that is the biggest variable that we have to avoid.

So it’s like when you eliminate ego, humility ensues.

There are humble people who are also kind of egotistical, right? So I think that the book became more about the perils of ego, than the virtues of humility. But I think that’s two ways to make the same point – which is very few situations are improved by the introduction of ego. Whether you’re experiencing massive success or you’re at rock-bottom failure – ego is not something that will improve your situation. And it will almost invariably make it harder and worse.

Mark: Right. And how do you define ego in the book?

Ryan: Yeah – look I am not a psychologist, I’m not a doctor, I’m not a Freudian – so I don’t have a definition like “this is ego. This is not ego.”

To me it’s kind of a “you know it when you see it,” kind of thing. You know the ego that got Steve Jobs fired from Apple the first time. The ego that gets Donald Trump in trouble all the time. The ego that prevents Kanye West from keeping his mouth shut. The ego that tears apart the partnership of Kyrie Irving and LeBron James. That makes it impossible for Kyrie Irving to succeed in Boston…

You know, the ego is this force that can manifest itself very differently in different kinds of people and in different situations. But it’s this kind of voice in our ear that’s preventing us from… It’s making us think we’re better than we are. That’s preventing us from learning. Preventing us from forming connections with other people.

You know, in alcoholics anonymous they say ego stands for “edging God out.” I would argue that it really just edges everything valuable out. It edges out relationships, collaboration, allies, insights, realism… All the important things that we need, ego is like the antidote for…

Mark: Yeah. Interesting. I love that. It’s a personality flaw, right? As opposed to a psychological construct of the mind. That’s what you’re kind of presenting.

Ryan: Yeah, and I make a big distinction between ego and confidence. And I talk about this in the stillness book a little bit too.

I think confidence is very important. Confidence – and actually this appears in that Sam Sheridan book… But, you know, I think Frank Shamrock was talking about it, he’s like “confidence is earned. Ego is stolen.” like he says ego is garbage, but confidence is something that you earn from the work.

And so I think if we can make that distinction, it becomes a little easier to know kind of where the line is. You got to know what you’re capable of, because if you don’t think you can do something, you’re probably not going to be able to do it.

But the problem with ego is ego thinks, “because I think I can do it, obviously I can do it.” and whether it’s Napoleon invading Russia, or Hitler invading Russia – making the same mistake twice, because you think the rules don’t apply to you – that is responsible for catastrophic failure after catastrophic failure.

Mark: Mm. that’s fascinating. And so what were some of the key individuals? You reference Steve Jobs. You’ve referenced Hitler and Napoleon. Did you profile them in the book?

Ryan: Yeah. I try to mostly lead my books by stories. I mean, one of the main sort of heroes of the book… Someone I think you know illustrates what egolessness looks like, but is still extremely successful is George Marshall. Who I think may be one of the greatest Americans to ever live. There’s a fantastic new biography about him by George Roll that I suggest everyone read.

But the idea with Marshall… Like the famous story for Marshall that I love is that he passes… FDR is choosing who is going to lead the invasion at Normandy, and Marshall is chief of staff. He has probably the most important job in the armed forces, but the least glamorous and the least well-known. And FDR goes to him, and goes “look, I know that your reputation depends on what you do in battle. And I have to choose who’s going to have this job.”

And he’s like “I know you probably want this. So if you do want it, all you have to do is ask for it and I’ll give it to you.

And Marshall says “you know, I don’t want my personal feelings to influence this decision at all. I want you to choose who you think is best for the country, that you think will give us the greatest chance of success.”

And so FDR ends up choosing Eisenhower. And he chooses Eisenhower, not because Eisenhower is better than Marshall. In fact, Marshall is the one who discovered Eisenhower and had advocated for him and sort of promoted him as a protégé.

But Eisenhower was already in Europe. And FDR felt like he couldn’t afford to lose Marshall.

And so here you have Marshall basically losing the opportunity of a lifetime… The thing he’d worked his entire career for… He’s putting the team over himself. And this is where I think he cements his reputation in my eyes as a truly great man – FDR chooses Eisenhower, is completely indifferent to how this must feel to Marshall, and he actually has Marshall write out the orders giving the job to Eisenhower. And when Marshall does this he keeps the original copy, and he writes a note on it.

And he says, “Dear, Ike. Congratulations. I assume you would want this original as a memento of your great accomplishment.”

So here he is not only passing on the opportunity, giving it to a protégé, ensuring he will not be president, not be such a famous man, but then actually rooting for and thinking about the feelings of the person on the other side. And so I just find that to be so wonderful.

And yet you can’t argue that Marshall didn’t accomplish an incredible amount. That he didn’t get to the top of his profession. This didn’t hold him back. In fact, his egolessness is why we won the Second World War. And I think that’s what he took great pride and motivation in.

Mark: Hmm. What a great story. So the biographer he said was George Roll?

Ryan: Yeah, I just realized it’s David Roll. He’s actually Rich Roll’s father.

Mark: No kidding?

Ryan: Yeah, it is a fantastic book. It gives you like the whole picture of Marshall. I strongly recommend it.

Mark: I’m gonna get it, when we’re done here. Very cool, I don’t usually read autobiographies, but I know that I need to do more. There’s so much learning from them.

So Ryan, continuing kind of that theme – while you’re writing “Ego,” interesting things are coming out about stillness right? And so I know that you’re a big fan of Stoicism and stillness as part of that whole philosophy, so let’s talk about the evolution of this idea. And your most recent work.

Ryan: Yeah, I mean one of the things that I found when I was studying all these egotistical people is just how unfun it seemed to be to them. That it didn’t seem like… I wouldn’t want to trade places with them.

Mark: (laughing) it’s hard to be egotistical.

Lived Philosophy and Stillness


Ryan: Totally. And that’s what I love about Stoicism, and what I love about ancient philosophies – religion tends to make the argument it’s like “don’t do this or that, because God doesn’t want you to.” or worse “don’t do this, because if you do, it’s a sin and you will go to Hell.”

What I love about philosophy is philosophy says like “don’t be egotistical, because egotism will make you miserable. And it will disturb your inner peace and your satisfaction and prevent you from experiencing joy.”

And so as I started to research, “what does greatness have in common? What are the people I really admire? What do all the schools of philosophy see…? What are they aiming towards? What are they trying to get to?”

Its virtue, but it’s also this sort of sage like wisdom. This perspective. This ability. You know when we say someone is very philosophical, we don’t mean they quote big words. We mean they have a kind of a sense of the bigger picture. So they’re not easily riled up. They know just what to do. They have wisdom.

And so stillness for me became kind of this obsession. Like when I think about my best moments – when I’ve done my best work, when I’ve experienced happiness – it’s never been at the height of accomplishing something. It’s been on a walk with my son, it’s been standing looking out over the ocean like we talked about. Or maybe it’s just a quiet drive in the car looking out the window. Or it’s sitting there with a book that is just telling me something I’ve never heard before.

And so to me that’s all what stillness is. If “ego” is hard to define, “stillness” is even more difficult. But again we know it when we see it, or rather we feel it. I feel like there isn’t anyone who when I say the word “stillness,” doesn’t have some sense of what that is. And hasn’t experienced it in their life.

Mark: Mm-hmm. Yeah, what I think is really neat about stillness, is because – it’s like, back to the philosophers – these philosophers that you study weren’t reading books. They were being still, and tapping into some information, some knowledge, some energy field. Which then led them to think deeply about these things. And then they were articulating their experiences.

So the philosophy back then with the Stoics and with the eastern philosophies of Buddhism or yoga or the Vedanta kind of traditions – was like a lived experience, right? It wasn’t so important to study the text – even though later – as the texts became available, and more readily available, of course you want to do that for reference.

But it was mostly about the lived experience. And being able to discern your version of that truth, right? And you can’t do that unless you’re still.

Ryan: Totally. And I think also realizing that these philosophers weren’t monks, right? They weren’t like living in these temples. Like Socrates was a soldier, you know Musashi was the greatest swordsman of his time. Confucius was an advisor to princes and kings and emperors. And Marcus Aurelius was the emperor. So when these men – and unfortunately it was mostly men – when they are talking about stillness, they don’t mean like stillness – as you’re saying – so you could read more books. Or they’re not talking…

It’s interesting – like Buddha*a renounces his kingship to become a philosopher. And that’s almost the exception to the rule. Marcus Aurelius is using philosophy to be a better emperor. And so realizing that these exercises, this stillness, this isn’t like soft stuff. This isn’t academic stuff.

This is really hard work you do because the stakes of your profession. Or of the situation that you’re in are life and death. And so that’s what I… It’s like oh, okay, stillness isn’t meditating in a beautiful mountain stronghold far away from the cares of the world. It’s meditating to improve your archery, right? Or it’s meditating because you have to make a decision that the fate of millions of people depend on.

So like when I talk about stillness, one of the examples – one of the stories I tell in the book, is Kennedy during the Cuban missile crisis. You know, here’s a guy who’s is faced with this terrible predicament, and if he can’t access that still, deep water inside of himself – and not be distracted by the provocations, by the bad advice he’s getting, by the fact that it’s an election year – he could make a decision that could destroy life on this planet forever.

And so to me that’s what stillness is about.

Mark: And do you have any examples of how Kennedy cultivated that?

Ryan: Yeah it’s a fascinating story. I mean, my favorite part of the Cuban missile crisis when I was researching it – you find this letter that Kennedy wrote after the crisis to the gardener of the white house thanking her for her important contributions to world peace. Because he had spent so much time standing out in the rose garden, trying to slow things down, trying to center himself that it had provided incredible insights to him.

He also – going on what we were talking about – he goes swimming several times during the crisis, he’s doodling…

Mark: (laughing) Probably freaking out his generals, right? Like, “what are you doing in the pool? We got a crisis here!”

Ryan: Totally. He’s doodling on this piece of paper. He’s writing over and over again like “consensus, consensus, consensus.” because the temptation was like “I’ll just do what I want,” right? Like, “how dare these people? I’m in charge of the strongest military on the planet. You think you can come in here and put missiles ninety miles from the coast of Florida? I don’t think so.”

But what Kennedy was realizing is, it’s not just about who’s stronger, it’s about who has public opinion on their side. It’s about who’s thought this all the way through. It’s about who has the most allies.

And so yeah, you see him just slowing it down. I think one of the great quotes from the missile crisis he goes “look, I don’t care about step two.” he’s like, “I care about step six.” he’s like “I care what they are gonna do in response to what we’re gonna do and what we’re gonna do in response to that.” because he’s like “by the sixth step, we’re gonna all be dead.”

And he was realizing that the more time he could give his opponent… If he could give them a way to back down without being humiliated, he could prevent horrible bloodshed. And again all of this comes from accessing something that I think we all possess which is stillness. Because if you are going with your gut, if you are reacting emotionally – if you’re reacting out of ego – you’re going to make a bad decision.

And frankly – not to get into our current politics, but that’s what’s so alarming about our sort of social media-driven world right now. Presidents, and congressmen, and senators, and world leaders are like hammering these things out in 140 characters. And these things are very complicated, and should not be tweeted from a telephone.

Mark: Agree. Yeah. Well said. This type of stillness and the ability to slow things down we just showed with Kennedy – or you show with Kennedy – is kind of cultivated. So he cultivated in one way.

What are some of the other examples of how leaders who’ve made an impact, cultivated stillness in their lives.

Ryan: Yeah, look I think… Some of the tools I talk about in the book… I think journaling is a huge one. If you can take time to sit there and reflect on your thoughts, you are going to be a better person, right?

And so Anne Frank is… Here you have a 13 year old girl being subjected to one of the worst things humanity has ever done. And at a time when hormones are making most teenagers more selfish, she is sitting there and evaluating herself at the end of each day. And finding things to be grateful for.

You know, there’s these beautiful passages in her diaries about a tiny tree that she can see from the top window of the attic where they are hiding from the Nazis. And she’s saying you know, even in great tragedy, beauty remains. And she says “paper is more patient than people.”

And so I think journaling is a huge part in my own ritual for cultivating stillness. And actually, I like to go for a long walk in the morning, and then I journal. And I don’t touch my phone until the end of that process. And so to me that’s a way to cultivate…

Like, I think, cultivating stillness in the way that Kennedy did is obviously extremely important, and extremely difficult. But on a much more practical level like, “hey, can you just try to get up early in the morning? Can you just try not to go straight to your phone, or your computer, or whatever work you have to do for the day? Can you sit down and just put some of your thoughts on paper so you can see them from a distance? On the various ends of the spectrum – these are both ways to develop a little bit more stillness in whatever you’re doing.

Mark: Mm-hmm. You know, I started when I was a teenager. I would spend hours and hours, especially during the summer – when it was summer break – in the Adirondack Mountains. And I enjoyed it most when I was alone. Great appreciation for that, because it taught me just to be quiet and to love nature.

So just being out in nature – like you said. Going for a long walk in the morning… And journaling didn’t come to me until later. That’s a more disciplined practice actually than just getting up and walking. But both are really powerful and combined is powerful.

Zen and the art of everything


Then when I was 21, I was exposed to Zen. I mentioned that before – that’s like the eastern kind of Buddhist discipline of cultivating stillness. You have a story about the baseball player… Is it Sodaro?

Ryan: Sadaharu Oh. Yes.

Mark: Tell us about that. That guy is fascinating to me.

Ryan: I mean arguably the greatest home run hitter of all time. Better than Babe Ruth. Better than Hank Aaron. He happened to play in Japan, so his record doesn’t register with most Americans. But hit way more home runs than either of them did. And people aren’t familiar with the fact that he got there training basically as a Zen master. Along the lines of how someone like Musashi trained.

In fact, he trained a lot of his swing using a sword. And the idea was, you know, could he slice a piece of paper in half with a sword. If you could do that, you could hit a ball.

And I think one of the interesting things from Sadaharu is he’s talking about the idea of wu-wei, non-action.

And we tend to think of baseball and all sports as action, right? Like you think “oh, you hit a lot of home runs. That’s what you did.”

But if you actually think about how many pitches a guy like that did not swing at, you actually realize that his real genius was not swinging a bat. Like, the act of hitting a baseball is almost physically impossible. I don’t mean like with your muscles – I mean like physics – straight physics. Like, it takes 400 milliseconds for a ball to leave the pitchers hand and arrive in the catcher’s glove. The batter almost has to begin swinging before the ball has left the pitcher’s hand.

Mark: (laughing) Right, there’s no AI that’s gonna be able to replicate that…

Ryan: Right. And so what it is it’s the batter’s ability to sense all these sort of subconscious cues and subtle pieces of information to determine what is going to be a good pitch or not. And to be in such control and connection with themselves that they can make this thing happen.

And so you actually what a great pitcher like that is, is someone who knows what pitches to swing at. And I think that’s a great metaphor for the rest of us. We think that our life is defined by the books that we write, or the businesses that we invest in, or the meetings that we take.

But just as much it’s defined by the things that we say “no” to. By the space that we carve out, by the non-action, by the void that we create. Our success is as much a product of the emptiness, as it is the actions that we take.

Mark: That’s fascinating and I agree with you hundred percent. But it kind of seems to conflict with one of the popular theories of success and that is just keep doing. You know, do more, do more – just don’t ever give up and all that. And so people just keep on doing and trying to do their way to the pinnacle of success. And I think they’re missing the key element here. The other side of the coin, right? The non-doing.

Ryan: They are because they’re missing the point. I think someone like Sadaharu or there’s another baseball player named Sean Green who is a big practitioner of Zen. Probably had the single greatest game in the history of baseball in 2002. I think he hit six home runs in the same game.

But they were both fond of that Zen idea of chop wood, carry water. So you are supposed to keep doing, but you’re supposed to keep doing the process. Like, the smallest, least sexy part of it.

So you are supposed to keep going. It’s not that you do nothing. But you’re not swinging for the fences. You are showing up for practice and working hard, even when you’re in the middle of a slump. It’s giving your best, even when the coach doesn’t believe in you. It’s training even in the offseason. It’s working hard, even when you’re tired.

In my case, it’s doing the notecards even though it would be easier to copy and paste. Or to have a research assistant do it for me. It’s that chop wood, carry water – do the work, detach from the results. Don’t think about what other people are thinking about you. Don’t think about the sexy stuff. Just keep your head down and carry the water.

That, I think, is what people are missing.

Mark: Yeah, I agree. There’s so many references to this kind of idea that you find in the different cultures through the different traditions… You know, the martial arts tradition wax on, wax off – chop wood, carry water… The Buddhist tradition of 10,000 preparations, right? So everyone wants – like you said – to swing for the fence in meditation. That’s why most people – in my opinion – find meditation so frustrating. Because they’re going straight for the gold or the brass ring, or the gold medal, right?

And really, the Buddhists taught that there’s a lot of preparatory work. So let’s just first learn how to sit comfortably, you know?

Ryan: Yeah.

Mark: And let’s dial in our exercise and nutrition, so that your body can sit for long periods of time. So let’s do these over a number of years.

And the yoga had the yamas and the niyamas which were the ethical principles, and the discipline, right? And Stoicism had philosophy as a practice. It wasn’t meant to be just something that you just talked about – that Socrates talked about, or Aristotle talked about with his their students. It was meant to be something you go out and practice, right?

Ryan: No, that’s what you realize when… The more I’ve read about Stoicism, it’s given me a greater context let’s say Marcus Aurelius’ work. Because I thought “Meditations,” which is his only book, but I think one of the greatest philosophical texts of all time – I thought that this was a singular work of genius, by a great human being.

But as I’ve read all of the predecessors to Marcus Aurelius – and I’ve read the history of Stoicism – I’ve realized how few of the ideas in that book are his. Or are new.

And then you realize that “oh actually, here’s the most powerful man in the world, leading troops in battle, and then he’s spending a few hours at night writing in a journal. Just almost like repetition. Just writing the ideas out.”

So he’s reading a book and then he’s putting his own spin on it. And he’s writing it and rewriting it. You know, even in “Meditations” he repeats himself quite a lot. And it’s like “oh, he’s not talking philosophy to you or to me. He’s talking… He’s practicing philosophy to himself. Almost like in a mirror.”

Mark: He was journaling

Ryan: Totally. And I remember reading about Musashi. It was Musashi or one of the other great swordsmen had practiced in a mirror drawing his sword out ten thousand times. And you’re like “oh, I see. This is you putting in the hours – doing the tiniest possible thing. Detaching from the outcome and knowing that if you trust the process, you get the results.

Mark: Mm-hmm. So let’s take this to a real practical matter, and then we probably have to wrap up, cause we’ve been going for a while here…

Ryan: Okay.

Mark: There’s two things that I think are really salient for modern-day warriors, and everyone listening to this podcast.

You know, one is to declutter, right? And we call it the “keep it simple” principle. You got to get rid of the crap that doesn’t belong. Like you said – Ryan – to start saying “no” to the wrong things, and to open up the “yes” to the right things.

And then two is to find that narrow range of things that you can master. That are gonna be the wax on, wax off or the chop wood, carry water things that are gonna be something you love to do. That you can be really passionate and disciplined about. That’ll cultivate stillness.

What do you have to say about those two kind of points? And how do we be practical about this?

Ryan: I think that’s totally right. Like, if you’re trying to lose weight, the first thing you would do is throw away all the junk food in your house, right? If you’re trying to have more stillness, you gotta delete social media from your phone, you got to turn off the TV you have running in the background all the time, you’ve got to cut toxic people out of your life.

You got to do that.

And then you got to say “okay, now that I’ve freed up this time or space, how am I going to use that productively? What am I going to do with it? Am I going to read more, am I going to journal more, am I going to exercise more…? What am I going to do?”

And look – I think the interesting thing about this is that at the core level it’s like… Look, if you’ve been eating horrible junk food and you eliminate you’re gonna lose some weight.

But the truth is like I’m sure you deal with really great athletes or elite performers… Who for them it’s not like “you got to stop eating Cheetos,” because they stopped doing that a long time ago.

But even in their elite diet – there’s room to eliminate junk. Or refine the inputs. And so where I was at 19 trying to add stillness in my life, is very different than where I am at 32. Now I’m thinking “oh, okay, I spend too much time doing x.” or “I’m carrying this grudge around.” or “why do I keep working with this type of person, or get involved in this type of situation if it’s not contributing to my happiness?”

And then I go “and what is the thing that I’m really here to do? That I’m really working on? What’s the work I should be doing?

So the point is it doesn’t matter who you are, where you are, what level you’re at this process – and I think the great philosophy Zen especially – it’s so simple, because they want it to be universal and they want it to be able to be applied to someone who’s a king. Or someone who is a peasant.

And so knowing that what you just described is like the recipe for success whoever you are I think is really important.



Mark: What are…? Let’s just end with like… Let’s say people are doing a good job decluttering – they’ve shut off the TV – they don’t touch their iPhone until after breakfast say or whatever… They’ve done those certain things. And now they’re thinking “oh, what are some of the most effective ways of me to chop wood and carry water?” I mean I do it through aikido and yoga and breathing practices. You do it through reading and journaling and probably writing as well.

What are some ideas for people if they’re like “I don’t even know where to start?” in that category.

Ryan: Sure, sure, sure… Look, I think experiencing nature in some way or another. You don’t have to write it down, but also can you experience nature as if you are going out as a painter, or as a writer, or as a photographer.

Mark: So mindfully attending to nature, as opposed to just going out in it and playing or something.

Ryan: Exactly. I mean one of my favorite exercises is like work really hard to deconstruct things that are really important to us. So he’d go like this bountiful feast is just a bunch of dead animals and rotten grapes. He’s trying to reduce its importance.

And then you see him describing quite beautifully and poetically really mundane things. So he’s talking about how you put a ball of dough in the oven, and it cooks and it becomes bread. And he’s talking about how the bread just cracks open at the top. And we don’t know why it does this, but it stirs our appetites.

And I just love so what I think he’s doing, is he’s practicing looking at the world like a poet or like an artist. And he’s trying to notice the things that ordinarily, he would completely take for granted. I think that’s really important.

The last one, I would say – and you hinted at this earlier when you were talking about the trips you took to the mountains. I think we need more solitude. James Mattis gave a great quote in a book called “Lead Yourself First” a few years ago where he said “you know, the major fear I have for this generation of military leaders, is a lack of solitude.” they don’t have time in their life where they are alone. Where they are reflecting. Where they are thinking big picture.

And so someone like bill gates – who takes a “think week” every year, where he just goes off into a cabin and he just thinks – I think adding some practice like that to your life is really important as well.

Mark: Yeah. I agree. That’s awesome. Ryan, thanks so much for your time. This has been fascinating story – or discussion – and super looking forward to reading the book. “Stillness is the Key.” appreciate what you’re doing.

Ryan: Thanks. This was so cool. I really appreciate it.

Mark: Yeah, we’ll stay in touch and hooyah. Good luck with everything. Stay still. We’ll talk to you soon.

All right folks. Ryan Holiday. Check out his book “Stillness is the Key.” Ryan what’s your website or what is all the other stuff?

Ryan: and I’m @ryanholiday pretty much everywhere. And then also the, if people want to find out more about Stoicism.

Mark: Another great resource. I love that. And then “The Daily Stoic” book, we didn’t talk about… What a great book, what a great tool to wake up in the morning or for your own reflection and journaling. Very cool.

Alright folks. Thanks again for listening. This has been the Unbeatable Mind podcast. I’m your host Mark Divine. I appreciate your time as I mentioned earlier, and until next time stay focused, declutter, and find some stillness.


Divine out.

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