Speakers

Greg McKeown, Ryan Holiday  


Transcript

Greg McKeown

Much of what has been written about success focuses on how to become successful in the first place. Almost nothing has been written about what to do once you are. And as it turns out, that may be a nicer problem to have, but it doesn’t make it less of a problem. We can sometimes find ourselves stretched too thin, busy but not productive. Where all of the opportunities, the outside noise is hijacking our day. It is what I have called the paradox of success. What got us to be successful is not the same strategy, the same set of behaviors that will help us to continue to be successful, to break through to a higher point of contribution. And in this conversation with Ryan Holiday, a modern student, and teacher, and best-selling author of the Stoics, we get to really explore this thing. It’s a great conversation. In fact, anybody who has achieved a certain level of success, but feel sometimes that they’re plateauing in their progress, or even starting to fail all together, this conversation is relevant. Sometimes it’s not harder work that’s needed. It’s not more ambition. It’s to bridle that ambition, it’s to bridle those passions. Here’s the conversation with Ryan Holiday.

Greg McKeown

Ryan it’s an absolute pleasure to have you as part of our conversation today.

Ryan Holiday 

Thank you. Yeah, I appreciate it.

Greg McKeown 

I want to start at the end.

Ryan Holiday 

Okay.

Greg McKeown 

One of my favorite things to do when I’m reading a book is to read any afterward or acknowledgments first.

Ryan Holiday

I’m the exact opposite by the way, I hate acknowledgments and I don’t like anytime the author puts them at the front of the book.

Greg McKeown 

It’s for me, I feel like I get the insight into the person.

Ryan Holiday    

Okay.

Greg McKeown 

And I, I’m curious about that. I want to just sort of understand a little about what’s going on. I love the afterword, I love the forward, not forward the preface that because these are the things that were written last these are the things that were written after all the work is done the research the versions, this is the moment the author pauses and says okay, here’s what it is that I really know having one this. But it’s not like that for you.

Ryan Holiday 

No, I guess that’s I guess that’s true it as far as how process goes, I would also argue the preface, or the afterword is usually the thing that got the most attention in the whole project. Because, you know, it’s the most important. So I certainly, I guess my point is, like, when I’m designing a book, I never I, I think about the process by which a reader is opening a book. And so I want to get them into the book as quickly as possible. So whenever I see the acknowledgement upfront, I always think that’s a user interface mistake because you should be sucking me into the book.

Greg McKeown 

I completely agree with that. I love the idea of just starting with the readers mind in mind and designing it in that way. It sounds like I’m not the average. Yeah, don’t come at this in the normal, probably sensible way. But I loved your final note, I don’t remember what you call it. And actually, I want you just to read it because I think it’s a story worth sharing.

Ryan Holiday 

All right. Well, so a note on it, I think what is different about this book. So in my book, the obstacle is the way I don’t appear in the book at all. It was very deliberate attempt, I wanted it to be about the philosophy. Then after that, I wrote this book about ego. And there was a long back and forth between my editor and I also did not want to be in the book about ego. And I ended up sort of losing the argument. That sort of forceful but polite request was that there had to be a preface in which I appeared in it. And so for this one, I had a little more leverage. And I did want to explain where I was coming from on the book, but I did not want to start the book about me. And so the afterword is the only place where the word I like referring to me Ryan appears in the whole book.

Greg McKeown 

There I am ruining that intent by putting it first in this conversation.

Ryan Holiday 

No, no, but I’m happy to read it. Alright, so it’s called afterwards, and it says it’s getting to be early evening now and about time for me to get up from the computer having made some progress on the pages you’ve just read. Years ago, I got myself out of the busy city and set up my family here on a little spread outside of town with a picture of Oliver Sacks in his nose sign hanging above my desk. Now that my writing is done, I’ve got work to do on the farm, chickens to feed some donkeys to sneak carrots to and fences to inspect. Not unlike the plot of that Zen poem about the taming of the bull. My neighbor’s long horn has gotten onto my property and I need to go find him. My young son helps me load some tools into the back of the ATV, the tractor, the twactor, he calls it I hug him and head down the levee through the middle pasture and back down by the creek. The fence there has started to weaken from the elements and the explorations of the wayward bull and I spend the next hour grabbing and pinching t-post clips. You take the clip and wrap it around the back of the post, grab the end with the pliers hooking it over the wire and twisting it tight so it can’t come loose. Wrap grab hook, twist, wrap, grab hook twist, no thinking, just doing. The sweat gets going quickly in Texas and my leather gloves are shades darker almost as soon as I start, but by the end the fence is tight. I tell myself it will hold or so I hope and next up is moving the hay backing the buggy up to the round bale letting the arm fall over top of it. Then gunning the engine of the ATV. It catches teeters flips and falls over 2000 pounds of food now lying flat on the trailer. By the time I’ve driven to where I need to drop it, the cows have gotten wise to the sound and are coming to investigate. I line it up with the hay rained back up again and watch it come tumbling off the back. With the knife in my pocket I cut off the netting and drop the heavy steel hay ran over to prevent waste. The cows begin to eat yelling in appreciation jostling with each other for their place at the bale. With them properly distracted, it’s time for me to go find this bowl. I heard him when I was working in suspect he’s over in the back corner of the front pasture. I find him there a ton or more of muscle in horns. I’m a little frustrated. This is not my problem. Though, my neighbor seems not to mind that this keeps happening. I’d be hold him there, as the poem says, but keep my distance not just because I don’t want to be gored, but because in rushing this process before in getting him worked up, I’ve run the bull right through a barbed wire fence a costly reminder of the cost of impatience. The key is to nudge him in the direction you want to go to eliminate the other options and then get him moving. It’s got to feel like it’s his idea. Otherwise he’ll panic and get angry. And the problem goes from bad to worse. So I stand there resting against some cedar, looking up at the first croppings of the violet crown, the Texas sunset that settles over Austin, that is coming toward the horizon. In this moment, I am at peace. It doesn’t matter how tough things have been lately. It doesn’t matter what’s going on in the world. My breathing is slowing down. There is no social media here. The outrage factory that has become the news cycle can’t reach me, neither can my clients or business partners. There’s no reception in these woods. I am far from this manuscript I have been working on, far from my research in my notes from my comfortable office and the craft that I love and here far from my work the story of Shawn Green, which I read a few months ago, and what he was teaching slips from my subconscious and into the front of my mind. I get it now. I get what he was after chop wood carry water fix fences load, hay seize the bull, my mind is empty. My heart is full. My body is busy. Adam and tranquilles.

Greg McKeown  

That’s beautiful.

Ryan Holiday 

Thank you.

Greg McKeown 

As you read that again. Now, what’s your reflection on it?

Ryan Holiday 

One of the things that struck me is because of this quarantine, how similar that has been to my days for the last, you know, going on two months now. You know, I’ve spent probably more time in a row at my house than that I have in several years. I think what I’m trying to describe in that section, something I’ve talked about before but sort of like what is a good day look like? What does a good day feel like? And you know, what is sort of necessary to actually be happy? And how often that’s kind of fleeting. And we don’t have it often enough. And so I was just kind of describing this idea of stillness, not necessarily actually being the thing without activity. It’s just a thing without the wrong activities and it gives you time to do the things that you enjoy that make you present that make you satisfied that get you outside that, you know, make you feel at peace.

Greg McKeown 

Was that an essential moment for you? Are you describing something that was essential?

Ryan Holiday 

Yeah, absolutely. To me that feeling that to me is happiness. That’s what it’s all about. I mean, I get that feeling pretty often. I went for a long walk this morning with my two sons, and we watched the sun come up and we picked blackberries and I was just feeling really good like this is what life is. I find that to be particularly poignant to experience that given, you know, just how bleak some of the things in the world are right now.

Greg McKeown 

That even with all of the noise out there, not only can you be still in conceptual way, but you can be living what’s important now, fully and richly. You write you quote Epictetus, saying most of us would be seized with fear, if our bodies went numb, and would do everything possible to avoid it, yet we take no interest at all in the numbing of our souls. I love that. I love that you quote that, but then you go on to tell the story of Tiger Woods. Share that with me.

Ryan Holiday 

You know, Tiger Woods story is incredible, and that he is probably the greatest golfer of all time, and you know, incredibly disciplined, incredibly focused, you know, physically in incredible condition, and yet sort of spiritually he is adrift for many years, miserable. When you read biographies of Tiger Woods, you don’t get a sense that it’s fun to be Tiger Woods and I sort of liken it to the you know, the famous Bible verse of what use is it to gain the whole world if you should lose your soul, and so on. Talking about how often, you know, we go and get the success that we want. But it comes at an incredible cost spiritually, mentally and also just in terms of sort of our personal freedoms.

Greg McKeown 

And you outline and describe early on the experience that Tiger is having, from, you know, nine months old in his family loft. He’s supposed to climb down of his, you know, out of his charity, picks up the golf club and hits the first ball. This is how they tell that story. And then you describe what it is to be his father’s son. Tell us more about that.

Ryan Holiday 

Certainly not fun to be Earl woods, his son. It’s easy even for parents to sort of gloss over when they talk about, you know, Tiger Woods. Basically, Tiger Woods, his father was not particularly excited about being a father, you know, again, and so he would go in the garage, put Tiger Woods in a highchair and just hit golf balls for an hour, for hours. And so, they estimate that, you know, Tiger Woods got a good chunk of his 10,000 hours just watching his dad hit golf balls. Now on the one hand, you could see where that would might be advantageous from a training standpoint. But then anyone who’s had a nine-month-old, knows that they don’t like being locked in a chair for hours watching you do stuff. You know, on the one hand, Tiger Woods his upbringing prepared him or, you know, train them to be an incredible athlete, almost without precedent and achieve, you know, unthinkable feats on the golf course. But personally, came in an immense toll that I have to wonder if you know if you in a vulnerable moment, could get could ask Tiger Woods if you would, if you would trade it away. And I don’t think this is at all limited to Tiger Woods, I think have a chapter in the book about Jordan. And one of the people that I’ve become friends here in Austin with Lance Armstrong, who is another sort of athlete of that caliber. Obviously, he’s had some somewhat of an asterix there to some people about those accomplishments. But I don’t think anyone would question that he was as driven and motivated and cutthroat as Woods or Jordan. You can’t have done what he did if you weren’t. And that was one of the things I wanted to ask. I ended up asking him as I was writing those chapters is just, I wanted to make sure I was within bounds of the analysis that I was making. And, and he said that I was and he told me something illustrated, he said for him after he’d come out of his cancer diagnosis. Part of why he’d been able to survive cancer, he believed was that, you know, his desire to compete and win, motivated him to you know, crush this sort of internal foe, but he said that winning and losing became synonymous to him with life and death, and that that’s how he approached the world for many, many years. And so, when it became issues of, you know, do you do you use this substance which will help you win? Or do you not? And then you risk losing? It sort of clarified all those answers to him quite clearly. And I think that’s similar to what happened to Woods. It’s similar what happened to Jordan. I think it’s a tempting place for many of us to go. And ultimately, I think, even if it does get you to the medal stand, or win you have the trophy, it comes at an immense personal cost.

Greg McKeown

I mean you’re describing there an idea that losing his death. It’s not just you, we’ve heard the term of winning is everything and the costs associated with that, but, but that’s an extreme idea. But somehow, even if we don’t have it as strongly as Lance Armstrong, maybe we have some version of that. That leads us to make decision. ones that really don’t, you know, aren’t the right ones.

Ryan Holiday

And so yeah, there’s this tendency to associate success with life and you know, failure or loss with death is a place that ambitious, talented people end up going and, you know, it’s not based in reality, but it is certainly rooted in, you know, emotional and philosophical issues that we have.

Greg McKeown 

Yeah, I think it’s one of the real, non-essentialist traps in the world, success traps. As a friend of mine said, success traps are harder to get out of them failure traps, because at least in failure traps you’re incentivized to change with success traps are incentivized to keep going and keep going. And it can become, I mean, in this case, life and death in your mind, a fabrication but nevertheless, one that feels really real. In my own life, accomplishing goals matters. I want to achieve things. But there are other elements that cool those calls, that that are so much more important to keep things in perspective. And so, I forget that there are people who don’t have those checks and balances. And so, they can cross sort of fully over into the non-essentialist dark side. And just embrace this as this really is what it’s about.

Ryan Holiday 

You know, I think about that all the time and at different points in my life, I’ve gone sort of back and forth on it. And that actually, that is a liability, right? One of the things that that’s been interesting for me and I’m sure you’ve gotten to meet some, some different athletes in the course of your, you know, writing career, I know Essentialisms popular in sports, but a couple years ago, I met Manu Ginobili and here’s a guy who has four rings, right, which is more NBA championship rings, then, pretty much anyone ever. You know, it’s definitely in the point 0001% of players you’ve ever played the game. Here’s a guy who, who up until you know, the season he retired was the, you know, oldest player in the league, one of the longest running players in the league. You know, revolutionized the game in a whole bunch of ways. And certainly, driven certainly motivated certainly wants it really bad. You couldn’t have the accomplishments with it, but I would argue that isn’t looking at it as matters of life and death and is a more well-rounded, normal person. So, all of which is to say, I feel like one of the things I struggle with I think about in my life is how can you be really great at what you do? How can you be elite at what you do without taking it so far that you become like a monster, or you become utterly one dimensional, or you become, you know, something that ultimately you’ll look back on with some regret? Because there is no amount of accomplishment that actually justifies those things.

Greg McKeown 

I feel that, is that sort of the test you’re describing here? Is yes, you want to do excellence. Yes, you want to achieve, but where is the tension? Where is the line that you won’t cross in order to pursue that?

Ryan Holiday 

Yeah, that’s exactly right. And I hope in talking about it that I’m in no way implying that I that I successfully managed this tension. it’s often something that you realize only in retrospect.

I don’t know if you’ve watched any of the last dance documentary about Michael Jordan. But, you know, Jordan talks quite openly about how he really felt like his father loved and was prouder of his older brother and favored him. And that a large part of Michael Jordan’s competitive drive, his desire to achieve his desire to prove was about trying to get something from his father that he should never have had to, to feel like he needed to earn. And I had a dynamic that’s similar to that in my family. And that the subtext of all of that work and effort was probably, maybe now if I do this, they will see me they will give me this thing that I wanted as a very young child, that that I shouldn’t have had to want for that I was, you know, I think that all kids are sort of biologically entitled to. And so on the one hand, this drive has served me well. It’s been financially lucrative. It’s helped me do cool things. It’s helped me, you know, achieve my dreams. But the other the bittersweet part of it, is how, you know, ultimately, there’s a tinge of disappointment in it. Because you realize, Oh, actually, you didn’t want to win an Olympic gold medal. You wanted your parents to finally be proud of you, or you didn’t want to become president, you just wanted to not feel poor and stupid, or, you know, whatever that that happened to be for you.

Greg McKeown 

And what you’re saying is that there’s two simultaneous experiences. One is the pursuit of these goals, these accomplishments, these gold medals, and then internally, there’s this second thing running which says, this isn’t getting any better. This doesn’t feel any better than it did before the gold medals. I just feel the same sum total emptiness, but that other track isn’t being touched by the accomplishment track.

Ryan Holiday 

No, absolutely. And that is a pivotal moment in one’s life. I’ve written about this before, I think a piece, I think it was called, like how it feels to get everything you ever wanted. And, again, first world problem of first world problems. But that aside, we have two reactions to getting that, right, you become a multi-platinum musician, you become a best-selling author, you sell a company for, you know enough money that you never have to work again, you know, you get elected to your public office or whatever. So one moment, you get that, and it feels great for a second, and then you realize, Oh, actually, this didn’t give me what I wanted. That, you know, what I really wanted was dad to be proud of me, or what I really wanted was for, you know, the kids to stop picking on me. What I really wanted was to feel safe, you know, whatever the sort of subtext inner child motivation is. And so that can either be an immense wake up call for you that, oh, there’s other forces operating in the background and maybe I need some therapy, maybe I need to process. Doesn’t mean you have to stop doing what you’re doing at all. It just means you’ve got to do some real introspection as to what is swirling on inside you.  That’s one reaction. But the more common reaction and the easier reaction is to say, oh, the reason it doesn’t feel great to be senator, is that being a senator is not enough. I actually have to be president, or, you know, whatever. It wasn’t enough to hit number one. It was I have to sell a million copies, or I have to do it again to prove that it wasn’t a fluke, right? And so, a lot of times, what we end up doing is, instead of seeing that the unpleasant reality in front of us that you can’t fix internal problems with external accomplishments. We say, oh, this is simply an issue of quantity. And I need to go get more.

Greg McKeown 

Where are you on that journey? Are you like how I’ve done the work, or I am right now beginning that work?

Ryan Holiday 

I would say if that’s a spectrum, probably in the middle, you know better in some ways, progress in some ways, other ways still stuck. For me, it’s kind of an ongoing process, but it’s certainly something I struggle with. It’s certainly a dialogue I’m constantly trying to have, I would say one of the things that’s had the biggest impact on me, it hasn’t been any conscious work I’ve done. It’s having my own kids, and then getting the chance to see my kids interact with my parents. And that gave me a lot of understanding of how things that maybe I thought were normal would have been interpreted by me as a six-year-old or whatever.

Greg McKeown 

Like what?

Greg McKeown 

I don’t know, you were a kid. So you don’t remember how your parents really were. And it’s impossible to put yourself back in the mind of a child, right? And so you don’t, as a kid, you don’t know what’s normal and not normal. And so you’re not able to sort of go, this is what’s happening, but I don’t have to let this affect me. And so as, as I watch my parents, sort of be grandparents and I watch, it just gives me a new perspective on how knowing how I think and act, how I must have interpreted and felt, you know, things that I don’t think is intentional for them, but, but I can just see how I can imagine better how things would have affected a, you know, a child.

Greg McKeown 

I think what you’re saying is that there are ways that they may still parent a certain way, but you interpret it differently because you’re more mature because you’re not so dependent, because you’re not so vulnerable.

Ryan Holiday 

Yes. And I’m able to have more empathy now that I understand how like I talked about in Stillness. I talked about the idea of reparenting the inner child, which is sort of how you have to heal from this stuff. Now that I see how, say, this attitude or this, you know, tendency affects a three year old, I have a son who’s a three year old, I can now have a little bit more empathy and kindness towards myself, knowing that I was once a three year old, and I didn’t have someone who could do that for me.

Greg McKeown 

There’s a poem that one of my daughters read at school that says, whatever age you are, you are also all of your other ages.

Ryan Holiday 

Oh, that’s beautiful.

Greg McKeown   

Even though you’re a 10-year-old, you’re also a nine-year-old, an eight-year-old, a seven year old and so on the that all of us have within us like to use the massive for the rings of a tree that all of those rings still within us. And so there’s something not just liberating about that I think there’s something that’s produces empathy.

Ryan Holiday 

I think that’s right.

Greg McKeown 

And compassion for ourselves and how we might be sometimes reacting, kind of like we did as three and four and five-year olds. And same with other people around is that that vulnerable in those same ways they look confident I mean, especially with teenagers now they look confident that big on the outside, you know, that that really they’re adults on the outside, but really inside this still, they can still be at times very young, and, and a needing of that kind of gentleness, that might not be obvious from their external behavior.

Ryan Holiday 

That’s exactly right. And, and I think like to go back to this Tiger Woods example, it’s like, you understand. You see him as the most successful golfer of all time with millions of dollars, a beautiful wife. But you know, he sees himself as a, you know, maybe a pimply 11 year old, whose dad is taunting and torturing and, you know, an alcoholic and, you know, cheating on his mother and doing all these things that, you know, he had no way to process that, no understanding of what it meant. And they talked about this with, particularly with abuse victims, that it often kind of freezes you at the age that the trauma you had happen and, and again, I feel on the one hand, my pain is my pain and my frustrations are my frustrations. But I of course, I feel very fortunate also that this is the first world again version of some of these problems that I wanted for very little and was otherwise very well treated, but there’s still a part of you that can get frozen or trapped in, you know, just to an unhealthy situation. And as you get older and as you try to do this work, what you’re hopefully trying to do is just free yourself a little bit?

Greg McKeown 

Well, I think it’s such an important amount of work to do. And to be willing to be vulnerable. I remember waking up in my sort of mid 30s, and really wondering why a particular thing was affecting me so much disproportionately. And so I went down on this journey, you know, over the next two, three years of exploration of trying to understand this, and it is courageous work, which I’m not trying to be self-congratulatory, I what I mean to say is, it’s vulnerable work. Therefore, it takes courage to even go down there. And I was amazed what I learned, I found, among other things, there were certain subjects in my family of origin that not only we couldn’t talk about, but that we couldn’t even talk about not being able to talk about.

Ryan Holiday 

Yes, that that’s exactly right.

Greg McKeown 

And so, in that, what I discovered was the reality of intergenerational trauma. That was one of the paths of research and an exploration that I was able to go down. And even now I’m still curious about and still study and try to understand is because often the drivers of this kind of let’s call it ultra-success, the undisciplined pursuit of more, yes, that has its roots not just in well, I happen to be super driven, or I happen to be obsessed about this goal, or it’s just about ego. You know, all of these kinds of surface explanations, some of those have some of the faults in the stars. Come from things that were unspoken, unresolved, wordless experiences that we had when we were young, and it’s not the same as you don’t have to have been explicitly abused or anything like that. Maybe one’s parents were abused, you know, or even grandparents were abused. But it can still create all sorts of interesting dynamics and even dysfunctions that then have a manifest later. And so, doing this exploration, I think is key to actually discovering this calmer, better, well, more essentialist way of living.

Ryan Holiday 

Yeah. The Buddhist talk about sort of samsara are the sort of the generational sort of repetition of things and trauma is certainly part of that, right. It’s, you know, alcoholism is passed on this way. It’s both biological and behavioral, and so are a lot of the habits or patterns or behaviors that we get trapped in. And if we talk about you sort of described it as heroic, and that might seem, you know, a bit exaggerated to some people or self-indulgent, but I don’t I don’t think that’s the case. Provided you know, look at It’s only about you sure, but actually, the heroism in it is how these things get passed on generationally. So, the cycle of suffering can stop. But it requires each individual to sort of do their part to not pass it on to your kids were to pass on only a much milder form of the same disease at the very best, right? And so, doing that work is important.  

Greg McKeown 

Oh, and another thing that I think is, you know, so vital in this is to recognize that this positive obsession, these gold medals of success being precisely what they are, they don’t get either as much or any negative attention, right? They just applauded. Where actually, if they are manifestations of these internal weaknesses, then then you can pass on both threads, you’re passing on the cult of achievement, the rise of accomplishment and the fall of everything else.

Ryan Holiday 

And I think look, this is the role that literature is really supposed to play in people’s lives and particularly ancient classical literature, the plays of Shakespeare, the poems of Homer, you know, these were these are immensely complex, sort of psychological profiles that are designed to that one is designed to read and reread over the course of your life to get you to question and think about things. And the Great Gatsby is supposed to hit you a certain way in high school, and then it should hit you a certain way and in your 20s, in a certain way in your 30s, in a certain way at 80. Actually, literature is a way that we’re supposed to learn truths about ourselves and the human condition.

Greg McKeown

One of the things that David McCullough writes about that I love I one of his rules of writing history, of course, he wrote, John Adams and in 1776, and many other, you know, great historical pieces now, when the Pulitzer twice, is that we got to remember that none of these characters and people from history lived in the past. And he says, whenever we try to evaluate them, as if they did somehow live in the past, we missed the point. When they were living, they just were dealing with their reality every day. They didn’t know what was going to end. You know, it’s so easy to read about Churchill, of course, he was an imperfect character. Of course, he was what else would we expect from anyone, but to then just dismiss it all feels like not learning from history. That, you know, to me, we have to look at the amount of courage that had to be demonstrated in the reality that they had not in our reality they didn’t live in our reality they didn’t live now. I’m not keen to, to judge historical characters based upon now I want to get into their situation so that I can learn the real lessons, for example, for example, there’s this I just came across the most extraordinary story of Churchill from when he was, I think, I think younger than 16. And he and he writes to one of his classmates at the time, maybe you’ve already seen this but I’m going to read it here he says, This is Churchill speaking younger than 16. I can see vast changes coming over now peaceful world, great upheavals, terrible struggles, was such as one cannot imagine. And I tell you, London will be in danger, London will be attacked, and I shall be very prominent in the defense of London. I see further ahead than you do. I see into the future; this country will be subjected somehow to a tremendous invasion. By what means I do not know but I tell you I shall be in command of the defenses of London, and I shall save London in England from disaster. Dreams of the future are blurred. But the main objective is clear. I repeat, London will be in danger. And in the high position I shall occupy it will fall to me to save the capital and save the Empire. I mean.

Ryan Holiday

Oh man, that’s insane.

Greg McKeown 

That’s insane.

Ryan Holiday 

I was just reading McCullough’s biography of Truman and talking to someone about it. And I think it’s in his book on Roosevelt there, I guess the observation of Theodore Roosevelt from a biographer. If it wasn’t McCullough, I apologize. But something like Theodore Roosevelt grew up reading about the great men of history and decided that he could be one of them. And I think ultimately, that’s what history education is supposed to do. That’s a pure and wonderful motivation, I think and that’s certainly that’s certainly what I try to talk about in my books is just what are those stories? What are the lessons we can learn from them? How can they help us in what we do? And you know, psychological childhood trauma side, how can we all sort of reach a little bit and try to try to be better and do better and, you know, sort of keep this whole thing going.

Greg McKeown 

There’s a distinction, here right? Before he passed away, Stephen Covey was someone that I spent some time with. And one of the distinctions he made in conversations with me was that there’s primary greatness and secondary greatness. He’s saying, look, secondary greatness is all that we’ve just been talking about around success is the gold medals is the public victories. The, the applause, but the primary greatness is the character. It’s the humility, it’s the it’s the patience, it’s the virtue. It’s the compassion, it’s the love, it’s all of those primary greatness elements. And when you divorce the two, then you you’re just on such a slippery slope. Because then then then of course, it doesn’t matter how you get your success as long as you get your secondary success. It doesn’t matter secondary grades fine. Whereas if you can celebrate and that’s what I see. You seem to be on this mission to do is to try to bring people back to principles around primary greatness that I think often do lead to secondary greatness. But to do it in a way that doesn’t make those successes such a liability.

One of the writings that I love the most. And I just couldn’t have this conversation without asking you about it is Seneca’s on the shortness of life.

Ryan Holiday 

Yes, a beautiful essay.

Greg McKeown

Talk to me about that. What reflections do you have? I mean, it’s just one of the best things I’ve ever read. You know, it says it’s not that life is short, it’s that we waste a lot of it. And, you know, Seneca talks about time and that essay and a lot of his essays. I mean, when he talks about the shortness of life, I think the most profound thing I’ve taken from Seneca and I gave it a TED talk in Budapest in the fall of last year, and I walked the audience through this, and it’s often it usually just draws silence. But I think it’s worth thinking about, you know, Seneca goes, we’re wrong to think of death as something we’re moving towards that it’s something that lays in the future. You know, he says, actually, all time that has passed belongs to death. If death is a state of non being, or you know, the end, then every second that passes is a form of death. And so actually, we’re dying, not in the future once, but that we’re dying constantly. We’re dying every minute. And when you realize this, it profoundly changes what you say yes to what you say no to, and how you spend your time.

Greg McKeown

And when you take that philosophy, what does that mean for you? What is someone listening to that right now wants to be more of an essentialist? What does it What does it mean for them?

Ryan Holiday

Well, I think first off, it’s that Oh, you don’t pay for things with time you pay for things with life, life that you cannot get back. And so, I hope it makes people a little less afraid to hurt people’s feelings a little quicker to say no, you know, a little quicker to make decisions, period. It’s to realize, oh, life is not this thing that is happening in the future, but it’s happening right now. So again, it’s not that if I’m lucky, I’ll live to be 75. It’s that I’ve already died 32 years. And so the question is, have I lived 32 years? Or have I simply been alive for 32 years? And I’m not sure. I certainly haven’t. I certainly can’t say I’ve lived all those 32 years. I’ve wasted a lot of time and you know, some of that was because I was a kid and you know, some of that was because I didn’t know things. Some of it because I wasn’t didn’t have enough fortitude or strength. I’ve done all the things that I’ve wanted to do and more. And I feel like I’m in a position to treat each day as bonus.

Greg McKeown 

I appreciate so much your conversation today, the life work that you’ve taken on your pursuit of that mission. Or maybe it’s not just a mission. I was having a conversation just this week where somebody said no a mission is they think of a mission as being something they go after, and grateful that you’ve spent your life and are still pursuing, you know, being funneled into that coin. I want to maybe my final word would be a quote from on the shortness of life. We are told that life is short and the art is long. Hence to the grievance most improper to a wise man which Aristotle expressed when he was taking nature to task and dodging animals with such long existences that they can live through five or 10 human lifetimes. While a far shorter limit is set for men who are born to a great and extensive destiny. It is not that we have a short time to live, but that we waste a lot of it. Life is long enough and a sufficiently generous amount of has been given to us for the highest achievements, if it were all well invested, when it is wasted in the heedless luxury and spend on no good activity, we are forced at last by deaths final constraint to realize that it is passed away before we knew it was passing. So it is we are not given a short life, but we make it short. We are not ill supplied but wasteful of it. Justice when ample and princely wealth falls to a bad owner, it is squandered in a moment, but wealth however modest is entrusted to a good custodian increases with use. So our lifetime extends employee, if you manage it properly.

Ryan Holiday 

It’s amazing to think that that was written 2000 years ago, and what he was experiencing as he wrote it and what he went through in his life. I have a quote from Seneca, which maybe I’ll close with, he says, some lack the fickleness to live as they wish and live simply as they have begun, which to be titled into that, quote, it may be from the same as I don’t recall exactly, but its point is, you know, it’s never too late to change. It’s never too late to realign your priority. It’s never too late to do it right.

Greg McKeown 

Thank you again. Ryan Holiday. Stillness is the key, but more than that, a person bringing the wisdom of the ancients from various philosophies, religious and non into a world tilted, who knows where, but is definitely desperately in need of more of that. Thank you for joining me for this conversation.

Ryan Holiday 

Thank you very much.


Essentialism Podcast

Greg McKeown

Wheelhouse Entertainment

Credits:

  • Hosted by Greg McKeown
  • Produced by Greg McKeown and Wheelhouse Entertainment
  • Executive Produced by Greg McKeown, Avi Gandhi, Brent Montgomery, Eric Wattenberg, and Ed Simpson
  • Edited by Emma Gladstone and Deanna Markoff