WHOOP Podcast - Best-selling author Ryan Holiday shares his thoughts on stillness, ego, and defining success

Episode Date: May 27, 2020

Ryan Holiday is one of the most popular writers in the world and has authored bestsellers such as The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key. His books have become wildly successful among high-performing people and teams, including Rory McIlroy and the New England Patriots. Ryan discusses finding his calling as an author (3:15), dropping out of college to pursue writing (4:22), writing his first book (9:33), managing ego (12:34), the difference between confidence and arrogance (13:33), The Last Dance (15:00), defining stillness (21:35), trusting WHOOP to tell him to rest (26:23), practicing patience (30:03), weighing different points of view (37:18), using autonomy to measure success (41:48), his goals (43:39), why greatness shouldn’t be determined by external factors (46:38), and how WHOOP helps him optimize his life (48:32). Plus, Will answers your questions in this week's mailbag (50:40). Support the showFollow WHOOP: www.whoop.com Trial WHOOP for Free Instagram TikTok YouTube X Facebook LinkedIn Follow Will Ahmed: Instagram X LinkedIn Follow Kristen Holmes: Instagram LinkedIn Follow Emily Capodilupo: LinkedIn

Hello, folks. Welcome to the WOOP podcast. I'm your host, Will Ahmed, the founder and CEO of WOOP, and we are on a mission to unlock human performance. If you're unfamiliar with our technology, we build hardware, software, and analytics to better understand the human body. That is a membership. And if you use code Will Ahmed, W-I-L-L-A-H-M-E-D, you can get 15% off a W-W-P membership. If you're curious about how WOOP is helping combat COVID-19, I would encourage you to check out all the research that we've done around respiratory rate and how an elevated respiratory rate may be a precursor to COVID-19. You can find that at the locker at WOOP.com. My guest today is the brilliant and deeply philosophical Ryan Holiday. Ryan is a New York Times bestselling author.

He has written 10 books, including Obstacle is the Way and stillness is the key. Stillness of the key came out more recently, and I've devoured it, and we spent a lot of time talking about this idea of stillness. He talked about it in his own life. I talked about it in the context of building a business. And, you know, we explored what does it mean to be still, what is ambition, what is ego, what is confidence. It was a really insightful conversation. I think Ryan has a ton of insight around, frankly, the meaning of life and what it means to live a fulfilled and still life and what is stillness.

And Ryan also talks about his whoop data, his habits and things that he does in his routine to be as balanced and I would say as optimal as possible. and overall, I think you're going to find him fascinated. So without further ado, here is Ryan. Ryan, welcome to the Woof podcast. Yeah, thanks for having me. I just devoured your book, Stillness is the key. And congratulations to you on being a really thoughtful guy and a terrific author. Thank you.

Thank you. I appreciate that. Was it always obvious to you that you were going to be, you know, a New York Times best-selling author? Well, I guess it depends on how you mean by that question. I don't think I always knew I was going to be an author. Definitely not. And then this is, I think Stillness was my ninth book. And the first eight, even though they sold very well,

sort of mysteriously, did not appear on the New York Times Best Sell list. So even in that sense, it was unexpected that Stillness would debut at number one, just having sort of been snubbed so many times in a row. we weren't sure what was happening or why, but I'd sort of, I don't want to say I'd given up hope, but I'd stopped, I'd stopped with that as a goal just because it seemed like it wasn't in the cards for me. So, Ryan, you're 32 years old, I'm 30, so we're roughly the same age, and it seems like writing 10 books by the age of 32 is quite a lot. So did you fall in love with writing along that way?

Yeah, I mean, you definitely have to be in love with it to do it. I think writing is a bit like sports or sort of the startup world. You know, there can be totally sort of disproportionate and outsized rewards for it, but the risk is so high and so few people are able to do it that if you're sort of motivated by the outcome, I think, I think you're in a, you're in a bad spot. So at some point, early in life, I fell in love with books. I fell in love with the idea that there were these authors, these people who had wisdom or ideas, and they communicated them through books. It was a longer journey for me to get to a place where I thought I could do that. So it wasn't

like, you know, at age seven, I was like, I'm going to be a writer. That came much later. more towards sort of towards college. I had a high school English teacher that sort of maybe opened my eyes to it at first, but it was more of a gradual process. Now, you dropped out of college, right? Yeah, I dropped out the end of my sophomore year to be basically a research assistant for a great writer and then to work with some other writers. So even then it wasn't like, oh, I am, you know, dropping out to write this novel that, you know, I have bouncing around in my head. It was, it was more like, oh, I could just be, I could sweep the floors of this recording studio and that's at least getting me closer to the music. It was more like that.

And what made you think that you were going to get better, I guess better exposure to writing outside of school? I do remember in college, I was in this sort of like honors program thing and And they had, they had, like, we had to read this book. I'm forgetting the title of it. I think Susan Strait is the author. And they had us read this book for, like, you sort of, your starting of your freshman year. And then the author came and talked because she was a professor at the school I was

going to. And I remember that was very eye-opening to me. It was like, oh, like, these writers are like real people and that, like, they, are at this university that I'm that I'm going to. So that was, I think, like, the first author that I ever met. And although there were other authors, clearly, at my school, it was an opportunity for me to work with Robert Green, who sold millions of books, who was sort of like, you know,

one of the great nonfiction writers of our time. It was, am I going to learn more about writing and life from this person who's doing it over here in the real world, or am I going to learn more about it from these professors, some of whom are writers, but the vast majority are not? And so it was, you know, an opportunity for me to sort of go learn directly from the source of things. Yeah, and look, I think that's, it was a bit of a gamble, right? But obviously one that's completely paid off for you. What did you see in Robert, and what did you learn from him? Well, so Robert writes the kind of books that maybe I thought I could write.

They were certainly the ones I was obsessed with reading. You know, he's not talking about himself in his books. He's sort of taking stories and ideas from history and organizing them and retelling them and packaging them and making them accessible. And Robert's also just a, you know, a wonderful person. He's sort of kind and generous and calm. and wise. So, I mean, I think what I really learned from him was the craft of making and producing

and creating a book. And that's a thing, weirdly, that not a lot of writers actually get much training in. So even if you, you know, let's say you went to University of Iowa, you got accepted their sort of prestigious writing program, you would have a lot of experience, you know, sort of writing the things in your head, you'd get good at stringing words together. But the actual process of publishing is its own thing. And in the way that, you know, being good at shooting a basketball is not the same as being a, you know, a professional NBA player.

You have to learn the ins and outs of the game. You have to learn, like, how a season works. You have to learn. And you want to learn from people who have done that before. And so with Robert, I mean, I worked on two. books with him. I worked on his book, The 50th Law and his book mastery. So before I wrote my first book, I'd work on those two books, plus several other books in a marketing capacity for other authors. So I'd sort of demystified the whole process. I deconstructed it to a great degree.

So then when it was time for me to put out my first book, the whole thing was a lot less mysterious and intimidating. So it sounds like, you know, for you, and spending so much time with him, you really got to understand the process and understand even the structure that goes into putting a book out into the world. And it then sounds like it took a number of books for you to find what was that content that made it the perfect result in the market. Or is that not a fair characterization? Would you say that some of your earlier books were just as good as some of your later books, but you just had a smaller platform at the time, so they were less well known?

I think it's a fair characterization in some sense, in others, maybe less so. I mean, my first two books did very well, and actually sort of when I decided to write these books about ancient philosophy, it was more like I had to get a lot of buy-in from the publisher because they weren't quite sure about it. It was like sort of switching sports, I guess, going from marketing to philosophy and then sort of more towards self-help. But I think what I learned in part of it, it's like doing your first book is kind of like running your first marathon. It doesn't really matter how you end up doing, even if you did quite well. A big part of

that is just learning how you do it. Right. It's like part of it is just like at the outset of doing any difficult thing, you don't actually know if you can do it. You think you can, but you don't. And so getting all the way through, you know, you're going to be making mistakes as far as pacing, as far as decisions. And like, you're just going to be making a bunch of decisions that in light of the fact that you actually don't know what it's like from start to finish are not going to be perfect. And so by the time you start book two or book three or project two or project three or marathon, you know, 50, you are getting better as you go because now you know you can make it. and now it's it's about what is the best way to make it what's the best way to do it and so with each one of my books it's still intimidating and scary because you know your last book doesn't write your first one but but you are much more confident you know you are much more confident when you sit down

that like hey if I put in a certain number of hours and I don't quit and I follow the process I will get to the finish line I don't know how pretty it is but I will get to the finish line And then you sort of having that belief lets you, you know, be a bit more flexible and creative and play at the margins and do different things that, you know, perhaps when you were a little bit less steady and a little bit less sure, you just didn't have the wherewithal to do. I imagine it's like starting your second company, your third company, you know, you're just, you have some sense of all the things that you need to do, the obstacles, the difficulties, you know that there's going to be moments where it feels like it's not going to happen, but if you just push through it, it will work. First of all, I think you described the process of creating anything really brilliantly,

and that comes through in both the way you speak about it and in your writing. And, you know, for me and just listening to you, I do think there's a lot of commonalities and what you described in creating a book and publishing a book as there are with building a business and leading a team. And even, you know, I've only started one business, but even in, you know, managing it for the last eight years, it's almost like, you know, over that time frame, it's learning how to lead different businesses because the business grows and evolves and the number of people that you have are different. And so in some ways, you know, each one of those sort of periods of time becomes its own book to sort of use your analogy here.

You've gained confidence from overcoming the previous obstacles of building, of getting that far. But then all of a sudden, you've got this sort of new challenge that builds on itself. Anyway, it's, you know, it's a fun process. That's, I think, why we're both doing the things that we're doing. Yeah, and I wrote about this in my, in my, in my book, Ego is the enemy. You know, I think a lot of people think ego is this sort of asset. And it can be, like, on the first product or the first time, like if you're sort of delusional, that can like, by not looking down, you don't realize how scary the thing you're doing is. But I actually am much more a proponent of and I've tried to, I think confidence is something you earn and you earn it from the work. You

earn it from the results. And you know, as opposed to like you're, you know, you're lying to yourself, even if you believe the lie. And so I just, I think, If you're not getting more confident as you go, something's probably wrong. It probably means that either you're not looking at the evidence that you're compiling and getting the confidence that you've earned, or it means you were way overconfident and delusional when you started. I mean, how would you define the difference between confidence and arrogance? Yeah.

So confidence to me is based on something you earn. It's based on the work. It's based on the evidence. but that there also has to be a sense of the weaknesses, of the flaws, of the realities and the difficulty of what you're doing. And when we get into ego and we get into arrogance, we sort of veer away from that and we get towards, you know, a sense of superiority, a sense of invincibility, a sense of entitlement.

You know, and even if in some cases these things are warranted, I just haven't seen any evidence that they're helpful, you know, I think, to me, the story of David and Goliath is the story of confidence versus ego. You know, Goliath thinks he's invincible. David knows he's quite small. He knows his weaknesses, but he also knows that he has some strengths. And it's in leveraging those strengths against the weaknesses that Goliath, you know, fails to realize he has that little is able to defeat big.

It's such an interesting phenomenon where these people, and you write a lot, you write a lot about very interesting people in your book's stillness is the key. But this phenomenon of from an outside observer looking at someone who is seemingly doing impossible things, there becomes this gray, at least from my perception, of whether the person is operating with supreme confidence or some level of ego and arrogance. And often there has to be some level of overlap. So, for example, I just watched the documentary, the last dance on Michael Jordan. Yeah.

Right. And here's a guy who you could argue was probably the best at his job of really like anyone's ever been at their job, just in terms of the results delivered. And he had this air of such supreme confidence. But then you also listen to him still talking about, you know, past successes and past slights that people have had against him. And there's an anger there and there is an ego there. And so it's sort of this great paradox of success in some ways. What do you make of that? I think it's a couple things. So I think you look at these people and you seem like, it seems like,

oh, that must be fun. It must be wonderful. And then, yeah, you realize Michael Jordan is still hanging on to things that have accumulated through the course of his life. And is that really why he's great or is he great because he puts in the work, right? I think usually egotistical people are not the kinds of workers that Jordan was. To me, the illustrative moment of ego in that in that documentary is actually the season when Jordan is gone and they're in the playoffs and Phil Jackson draws up a play. There's a few seconds left in the game. The Pipp and play. Yeah, it goes to Tony Cuckooke, instead of Scotty Pippen, and Scotty Pippen says, like, I'm out. He quits on the team, basically, because he thinks he's earned a thought.

And it's this shameful moment, and I don't think he's a bad person. I think he's a great person. And clearly was a player who had managed his ego quite well to be the number two on that team for so long. And yet, what I thought was most illustrative is not even that moment. it's that when he was asked about it in the documentary, he's still so sensitive about it and unable to look in the mirror about it that it goes, you know, if you gave me the choice, I'd probably do it again.

So that's what ego does. It just makes us our own worst enemy. We mistake ego for confidence, but they are very different things. One is strong and the other is incredibly fragile. If not, you know, I think in some cases it has like a death wish. for us. It's the source of so much failure and unnecessary conflict and pain. If someone meets a successful person and sort of their first reaction to something that the person says is, oh, this guy's arrogant, and the other person, the speaker, the person

who's, you know, demonstrating some level of success and some level of confidence believes what he or she's saying is actually a display of confidence, how do you actually look back on that moment objectively and determine whether or not someone was being confident or being arrogant. You know, when Elon Musk says he's going to put people on Mars, you know, doesn't the question end up being, well, was he right? Because it's a super arrogant thing in some ways to say that this person is going to drive a whole company to be able to build something that no one's ever done before in the history of humanity. But if he ends up doing it, doesn't it then appear that it was a sign of confidence? Yeah, I think these are complicated.

things, but in some ways to me, that's sort of like a false construct. What I would look at is go, hey, you know, is Elon Musk's inability to regulate what he says or, you know, the proclamations or the assurances that he makes, on the whole, does it hurt him or help him? Right. And so maybe in some sense, it sets these really ambitious goals that, because he is so talented and, and brilliant, that he's able to achieve. Okay, so maybe there it helps. But then, you know, funding secured. Was that a positive development in Tesla's history? Yes or no. It's calling some guy a pedophile for no reason, you know, helpful or detracting. You know, is this sort of weird tweets he's been doing about COVID-19 and the lockdowns and stuff? Is that helpful or hurtful? I think typically what happens is

people are so talented. I actually just wrote about this for Daily Stoke a couple weeks ago. People, if you read William Manchester's biography of Douglas MacArthur, which is a brilliant biography of an incredibly talented but also deeply egotistical man, people, like, because MacArthur was so egotistical and so successful, people thought the two things were very related. And what Manchester says is actually know that he was so talented and so brilliant, and he so surrounded himself for so long with the right people

that he was able to survive or outweigh the cost of his ego. But eventually this puts him in a position towards the end of the Korean War, the middle of the Korean War, where that balance is no longer in place. And this is when he sort of spins off the planet and ends up sort of getting unceremoniously fired. It's all about, you know, to me, on the whole, this, you know, is this a good trait or a bad trait? Are you playing with fire or not? And I think ultimately what ego does, sometimes it makes for good marketing. Sometimes it inspires people. Sometimes

it's entertaining. You know, sometimes it puts you in a position to be successful. But on a long enough timeline, it eventually brings us down. I have a coin that I made that says ego is the enemy on the front. On the back, it has a quote from Cyril Connolly, the British writer. He says, ego sucks us down like the law of gravity. And so I think it's in that sense on a long enough timeline, eventually gravity wins. And I think that's sort of where it goes with ego. Well, I completely agree with you in the way that you've described ego and I enjoyed reading more about it. And ego is the enemy.

And I encourage people to read that. I want to play with a different tension. So we just talked about confidence versus arrogance and ego. There's a really interesting tension in. in the book, stillness is the key, which is around this concept of stillness versus what all sort of loosely defined as a restlessness, this sort of like ever abundance of ambition and drive. And let's just, we'll get to that and have a second. Let's just start by just, how would you define stillness? So stillness is, again, another hard word to define. I seem to tackle that in

my books quite often like sort of words that even even I sort of admit have an ineffability to them but to me stillness is when when things slow down when you get into a zone when when things are clear when you're not sort of distracted by external or internal things it's it's the ability to concentrate the ability to focus it's the ability to be at peace with oneself so stillness comes in a lot of forms I guess I think we can more clearly define it by what it's not it's not inactivity, but it's also not needless activity, right? So it's when we get centered, when we get clear, when we get focused, and that can come in many forms for many people. One of the things that I found very interesting in thinking about, and you do a good job,

really, just like looking at stillness through all these different people's lives. And one thing that I enjoy just thinking about personally is if I think about moments in my life where I feel like I've felt this stillness that you're describing. There's sort of, there were two sort of separate, but also completely opposite moments that came to mind. The first is the fact that I practice transital meditation. And so as a meditator, and I've been doing it for, I don't know, about six, six years now, I do it every day. The stillness that I get from that is quite profound, and I would argue has really changed my life for the better. And I was thinking about that, But then I was also thinking about these other moments in my life where I feel like I've been under this unbelievable amount of stress, like an unbelievable weight of something.

And that could be, you know, some of these sort of excessive athletic moments or exercise. I used to overtrain in college and sort of remembering so that pain when you're really deep in this moment, but also recognizing that when you're deep in that moment, there is nothing else. there's a clarity of it. Yeah. And I even remember this with building, with specific moments of building whoop where it felt like everything was falling down and we were running out of money

and the technology wasn't working, et cetera, et cetera, sort of your, and I remember being so incredibly present in some of those moments. And it's sort of like everything else disappeared and I was just so focused in that moment. And yet when I reflect on this

and even saying it out loud, to you, those are so different in some ways, like sitting on my couch meditating versus being under an enormous amount of stress. And so help me unpack that. What am I describing here? Yeah, I very much relate to what you're describing. I mean, there's been moments in my writing career and in building my business where, or just in your personal life where you just sort of over commit or you overdo and you sort of hit this wall. And it's interesting. You might think if the book is about stillness or what I'm talking about, that my response would be always in those moments, that's a sign that you should stop, that it's too far. You've got to sort of remove

things. In fact, it's sometimes in those moments that in pushing through that you get to a place of stillness or clarity, that it's a moment of adversity that's that the resistance that you're overcoming is making you ultimately stronger. So I do think it's a tension, it's a paradox. Look, sometimes in, sometimes we have to clear the mind, but sometimes you have to focus very deeply and think very deeply. I think that's actually sort of one of the, I think the myths or maybe the misappropriations of Eastern philosophy that we've taken, which is that it's somehow like having an empty mind that these people are never consciously thinking about anything, that it's just about, you know, becoming like blank in your, in your brain. You know, a Zen

Cohen is the deliberate focus on a very complicated, if not. impossible to solve problems. So I think some situations call for one aspect, some of which call for another. And I don't know if that's a paradox or if it's just the reality that life is complicated. But, you know, sometimes, like for me, the struggle is, you know, getting up and working out or getting to work. And sometimes the struggle is, I want to get up and get to work and work out, but it's actually not the prudent, smart, or safe thing to do. Sometimes you're forcing, you know, fields that need to be left to rest for a minute. That's a very whoop phenomenon that you just described.

Totally. That's what I was just going to say. It's like you pull up your whoop. I think some people, I would like it always to be saying, like, you have to work out super hard today. And, like, I'm in the middle of a 62 day streak because of the quarantine. I've just worked out every day. I've hit my exercise goal every day.

It's actually like the decision, the decision to, to break that streak is actually harder for me than the decision to go run six miles when it's 90 degrees outside today. I have much less problem working out than getting myself to not work out. A lot of that phenomenon goes back to the earliest days of whoop in my mind as an undergrad and as a college athlete and just being someone who, you know, I would describe myself as pretty driven, but sort of overdrive, you know, and just burning it on all ends and being someone who would crash incredibly hard. And so realizing that the way I was training or the way I was approaching life was, you know, too excessive. And I needed to understand balance. I needed to understand

that actually the amount of strain that you put on your body requires the appropriate amount of recovery to match such strain. And sort of the more research I did around physiology, the more I became fascinated by this idea of balancing strain and recovery. Yeah, and it's hard because, you know, working out is active. It's a thing that you do. And recovery is often the opposite of doing. So it's less clear, less straightforward. It's like, I think we're seeing this with the coronavirus right now. You know, people are like, well, what's the magical vaccine you can give me? What's the, what's the medicine I can take to fight the virus? And it's like, actually right now we're in a preventative war. I tell the story and stillness is the key of, you know, the great Roman general Fabius. Fabius was famous and achieves ultimately the critical victories over Hannibal by having the discipline to not attack. And that this was, this is not only difficult as a general, but it's even more difficult

in a general being a general when you are subject to public opinion. And so how can one say, okay, everything I know. know is telling me that the best military strategy is to not engage the enemy here, that they're far from home, that they're short on resources, that every day we wait is better for us and worse for them when everyone's calling me a coward, right? And everyone's, you know, lobbying for my job and people are, you know, saying I should be fired. So that what we call a Fabian strategy and military history is weirdly the easiest to do and the least dangerous in that it means you don't have to fight in a battle, but it's actually the hardest and the most rare because it is

the most misunderstood by people who are not there and people who control the other layers of power, be it, you know, decision makers or the public opinion or newspapers or whatever it is. I love how you describe that. And if we think about the stillness and that it's having the wherewithal to recognize the moment and stand up against the opposition or criticism that this person's receiving for not attacking, right? Or, you know, like, let's say you run a restaurant and now everyone, you know, there's some fad, now everyone's doing food trucks or now everyone's doing fusion or now everyone's, like, can you go, hey, look, my thing is not the flavor of the moment, but I think it's,

it's rooted in the right principles. And I'm going to stick to, you know, sort of why I do this or who I am. Like, you know, even with my books, right, when the obstacle is the way came out, it did not sell particularly well at first. You know, it's all okay when it came out and didn't hit any bestseller list, but it came out and it sold consistently, you know, but it wasn't until nine or ten months later that the sort of growth began to accelerate. And it's been on an upward trajectory sort of ever since then, almost, you know, five years. years now. But, but, you know, there was a temptation to call it a failure, right? To say, oh, that was a mistake. I should go in a different direction, right? Or to, to hear that sort of

feedback as evidence that I didn't succeed. And so you have to have, this is where that confidence comes in. You know, did you do what you set out to do, you know, do you know that the product is good? And then do you have the patience? Like, I'm thinking about this. again, let's go to confidence and this moment that we're in right now. It's like the principles of how to respond to something like this pandemic are pretty straightforward. But then when things start to look safe again, when the first wave of the emergency crashes, you start to question things. You start to go, oh, well, maybe I could do this or maybe I could get away with that. And so, you know, I'm watching this with people that I know and neighbors that I have

and stuff. You know, you're watching people go sort of, they were prudent and smart, but there was an expiration date on their ability to be prudent or smart because they don't actually have the confidence in the researcher and themselves or in their ability to make decisions. So we look around and go, well, what's everyone else doing? I'll just do that. Everyone else must be right or they wouldn't be doing it, right? And this is where we get in trouble as creatives, as business owners, and then just as regular people, you know, people chase the fads of the moment. And really, the sort of things that stand the test of time are much less sexy, usually less exponential, but linearly sort of add up over time to be the right call.

You know, as you were describing the confidence you had in sticking with your book launch, I was thinking about these decisions that we've made along the way with whoop, which at the time, I think, were somewhat contrarian or maybe a lot of people disagreed with. We got a lot of pressure, for example, to put a screen on the whoop strap, which was something that I thought would actually distract people from its true intention. We got a lot of pressure to calculate steps, which we, you know, based on our research viewed, was a sort of irrelevant metric to what we were trying to accomplish. And I think, like, if I were to summarize other people's points of view of those decisions

at the time, they would, you know, from the outside in, they might view those decisions as coming from a place of ego. and yet, I think now looking back on them, you could view it as confidence in that we were, you know, we were largely right to our identity. How do you think about that? Look, as a writer, you struggle with this all the time because unlike, say, a business, it's your business, right? As an author, you're publishing a book with a publisher, so all these decisions end up bumping up into other people's opinions, right? What should the intro look like? What should the cover be? What should the title be?

even like I'm in the middle of selling a book right now. And so I don't think it's about ego. So ego is, how dare you tell me what the cover should look like? Don't you know who I am? Look at what I've done, right? Or like, like you don't get to tell me what to do, you know, blah, blah, blah, right? This is when we have the emotional reactions and usually it's about our identity being challenged in some way. What I always have to work on, because I have that part of myself too.

I don't like to get told what to do. We all have issues from our parents where, you know, we don't like being bossed around or maybe it was a teacher who was a bully or, you know, we all have different reactions to authority. But for me, it's it's the question of what am I actually trying to accomplish and is this feedback or note getting me closer to that yes or no, right? So a lot of times the criticism that you get or the feedback you get, whether it's about a book or a business or whatever, is not, it's, the people mean well, but what they are trying to do is make you more like things that are already successful or that they are already comfortable with. And so in some cases, this is the

right thing to do, right? If someone is saying like, hey, you know, maybe it's not good to have all your employees work in your house. This makes people uncomfortable and it leads to, you know, like difficult, tricky, you know, ethical or moral or, you know, issues, you go, okay, yeah, sure, I want to run a successful company where everyone feels safe and good, and I don't want to get into trouble. So I'm going to have an office instead of having everyone show up to my house, right? But if someone is saying, hey, put a screen on your device, and you're saying, well, the whole point of my company is to create a different kind of tracker, one that you're not looking at all

the time, that's tracking sort of longer trends that's not supposed to be, you know, in the way that an Apple Watch is, then that advice is making you more like your competitors when the whole point is to stand out from your competitors. And so with a book, for instance, it's like, what am I trying to say? What do I want to say? What do I think needs to be said? Not, what is this other person telling me, you know, is not right. And so the question I'm always having to measure my editor's notes against and the feedback from my publisher and feedback of friends is are they trying are they getting me closer to my vision or are they drawing to my attention concerns or issues that that benefit the reader that I'm not aware of or are they trying to make this more like

their thing and it's not egotistical for for for me to say I don't want this to be like your thing I want it to be like my thing because the whole point is you're paying me to do it because I have some skill or, you know, vision that I'm trying to fulfill. It's me putting the thing out there. If you can do it, if this is about your thing, then you should do it. Does that sort of make sense? Yeah, of course. Of course. I mean, I totally get what you're describing. And I think a lot of maturing as a creator, whatever that means to you, is finding that balance of having a really strong point of view on something and then letting other people tear it down and deciding how to react to that. I mean, I got kind of screwed up as like a young 20 year old starting a business

and that so many people I met told me I was going to fail that I built up a real wall, I think, to outside feedback and sort of a stubbornness to it. And so it actually took, it took a few years for me to learn how to hear opposing feedback without necessarily feeling an obligation to listen to it, if that makes sense. No, that is a profound danger in entrepreneurship. I've written about that before. You know, I was the director of marketing and American Apparel for a long time, and I watched a guy who everyone said was crazy, who they said ideas, his ideas would never work, sort of prove people wrong time and time again. And what he took from that was like, don't listen to other people, everyone is a hater.

And so as he veered into more sensitive issues, as the stakes got higher and higher, he was, in a sense, a ticking time bomb. And I think that, to me, that's what I see happen with a Kanye West or an Elon Musk, which is when you escape, you know, consequences for your actions, for your arrogance time and time again, you're not actually blessed.

It's setting you up for a much more pan. painful fall, right? Because you are learning, you are telling yourself the rules do not apply. And then you are getting evidence that the rules do not apply, but they do apply. You know, gravity is an equal opportunity, you know, killer and at you. I like the way you describe that. So can, and you talk about this in the book, but describe it for audience. Can, and can a person have stillness in one aspect of their life, but not in others? yeah sure i mean look there are plenty of people who meditate all the time they get a few minutes of stillness but like if you were to sort of check in in their mind on a random point in a random day you'd be like oh man uh i don't want to be that person at all meanwhile there might be someone who's never meditated once in their life but it's sort of operating on a sort of on a day-to-day stillness that we really admire uh that that that's worthy of emulation so yeah look i think you can I think some people can compartmentalize.

I think some people have a natural disposition. For me, it's about cultivating habits and systems that create stillness, that allow you to access stillness in the course of your day, in the course of your life. So for me, you know, the first thing I do in the morning is something I don't do. I don't check my phone. I do not want to start the day on my back foot. So this morning I woke up at 6.30 and I touched my phone probably 8.30. I took a long walk with my two kids

and then I sat down with the journal and then I drove to my office right and it wasn't until then that you know the phone came into play and the first thing I did was right you know I someone texted me there was a news article that was coming out about one of my books that I was like really looking forward to

and it was like even then it's like no okay I'm not going to look at this I'm going to do the work that I have to do I'm going to stay in this place of stillness. I'm not going to be reactive because the mornings are, I think, the most important time. And I want to do what I need to do before I get jerked off of the path. What other habits do you have for cultivating stillness? I mean, I think exercise is a huge part of it. So I do some form of strenuous exercise almost every day, whether it's running or swimming or biking.

I think reading is a big part of it. journaling is a big part of it, you know, limiting the amount of distractions or inputs that you have. You know, like I don't watch the news. I don't read the news as much as possible. You know, I don't check my social media a ton. It's about sort of creating a space where you're able to be focused, where you're in control of the environment, to me is really, really important. Now, if you find yourself on, I don't know, a book tour or something, and the day is kind of completely out of your usual norm. Those are the worst days.

So will you find that you cannot be still in that type of an environment? Well, look, I think sometimes we have to, sometimes life demands sort of less than ideal circumstances, and that's why we have adrenaline, and that's why we have the capacity to adapt and be flexible. So, look, sometimes the job or life requires certain things. I don't want to spend all day at the airport, but if my flight is delayed, like, that's what I have to do, right? I think sometimes you have to surrender to the energy of the moment or to what the moment is calling for. But I think generally, I try to avoid, I think I could also be in that space all the time deliberately if I want it, right?

I could set up my life differently. I could accept things differently. You know, I could say yes to certain opportunities, yes or no. That can happen also. So, like, to me, my definition of success is autonomy. Do I have autonomy over my day, over my body, over my habits, over how things are done? If I'm moving towards autonomy, then I'm becoming more successful. If I'm moving away from autonomy, I'm becoming less successful, even if, depending on the direction, I'm making more or less money,

or, or, you know, achieving more or less recognition for my work or selling more or less books. To me, autonomy is where I'm trying to move toward. But it's also been interesting for me having, you know, met many, many successful people in many fields, including, you know, some of the best athletes of all time. There are the outliers who are extraordinarily successful and sort of addicted to winning or a slave to the thing. But then there's also plenty of people that I've met, you know,

that have four or five rings in some cases, some cases or have set all-time records, and I would define their life and their existence and their personality as being one of pretty high autonomy. They're not miserable, and so I don't, this idea of stillness, this idea of being ego-free, I don't think it's antithetical to achievement, to success, or to great, you know, great feats of prowess, whether it's in art or sports or business or whatever. I just think, I actually think it's more impressive to be successful and good at something and not a slave to it. To be, like, you know, for the stoics, one of the primary virtues is this idea of temperance, moderation, to have balance, to be, have real self-discipline, including over your self-discipline.

And so that's, like, I want to be a great writer. I want to be as good as I can possibly be as a writer. But to me, that's a distinct goal from being the most famous writer or selling the most books of any writer or, you know, making the most money of any writer. Those are goals that are outside of my control. But to fulfill the potential that I've been given to say all the things I want to say, the way that I want to say them, that is much more my, you know, field to plow. Yeah, this reminds me of.

of the tension that you write about in the book of, or I think of it as a tension, but this idea of enough, right? Like, you make a compelling case for why the greats need to recognize that they've made it. And you talk about how Tiger Woods had this word with his father enough that he would never utter because it was like this sign of almost of defeat. Yeah. And in fact, you frame enough, I think, and, you know, recategorize it, but you frame enough as actually being an important, I think, recognition of greatness and sort of unpack that. In a way, I think actually getting to enough is freeing, right? Because especially in the creative fields, like I feel like I've proved what I need to prove.

And so everything here is gravy. So that allows me to take risks. That allows me to experiment. That allows me to think longer term. So, you know, in the last answer is that scene where we, he wins that first championship, or it might have been the first three, but he's just, he's kind of holding the trophy and he's sitting and all these people want things from him. And he just says, can I just sit here for a minute?

You know, can I just sit with it? Yeah. And I think that's really powerful. And I'm not sure how much he was able to sit with it. But I don't think, I'm not singling him out. I think a lot of us aren't able to sit with it. Because if we were, like, look, when obstacles away hit number one for the first time, It was actually five years after the book came out.

I was mowing the lawn and I got a text and I pulled it up and it had happened. That's so cool. And congratulations. Thank you. But you know what it felt like? It didn't feel like fucking anything because it's nothing. You know what I mean? I had already written the book five years ago, right?

Like the book has not changed. It was not a result of what I was doing in that moment. Me mowing the lawn was not what got it over the edge, right? it would and and it and it's not really meaning meaningful because it's not an accomplishment it's it's that a random bestseller list decided to give me their stamp of approval after having previously not given me said stamp of approval it's it doesn't mean anything it doesn't mean anything um i don't know i just i just i just think defining greatness by external things is a dangerous position to be in. I'm not saying that external things aren't

impressive, but what I'm saying is, is that what is truly impressive is to get there and then go beyond it and realize that there's some other thing that's motivating. To me, it's like the love of the game that's pure in a Michael Jordan. It's the desire in a comedian to just get to what is funny and what is true more than the comedian who wants to sell them most amount of seats or or you know have the the the most famous special. I think it's like Zen and the art of archery. You're putting, eventually you get to a place where you can put the target out of your mind. And to me, that's like the sort of the higher level realm to sort of get towards. A couple last questions here on how you're using whoop, because of course it's fascinating

to me that you're on whoop. What have you gotten out of it? Well, the recovery thing has been great. I like the journaling feature that's been interesting for me, just sort of tracking trends over a long period of time. What are you looking at in your journal? What are you trying to A, B, test, if you will? Yeah, it's actually something I don't do a lot of stuff.

So in the sense, like, I don't drink, I don't really do coffee. I sort of stick to the same. I'm pretty sort of regimented in my habit. So I don't have a ton of stuff. stuff to experiment with, and especially with quarantine, it's kind of made all the days blend into each other. So there's less travel. You know, it's, I am sleeping in my bed, same bed every night. So there's stuff like that. So I'm not getting the full value out of it the way that, you know, I probably would under ordinary circumstances. But for me, I think that the recovery thing

is that the recovery almost has to be as conscious and deliberate as a workout. And so being able to measure that's been really great. And then the sleep is obviously a big part of recovery, but it's like it's easy to tell yourself, you know, I went to bed at this time, therefore I got this amount of sleep, but that, you know, the data is much less forgiving. It's quite impactful, obviously, seeing that, you know, when you don't get enough sleep. And you write about sleep as being an important, you know, like kind of a fundamental core

of stillness, right? Yeah, of course. Of course. I mean, I think it's a key part of balance. And so if you're trading sleep, you are heading down a dangerous imbalance road. I like the story you told about the CEO of American Apparel giving his phone number out to everyone and then like slowly not getting any sleep ever. No, I think he descended into sort of a sleep deprived insanity to be perfectly honest. Yeah, it's amazing. Well, what's next for you and where can people find you? Just always more writing. So more books on the way. But, you know, you can, I'm at Ryan Holiday. I'm pretty much all platforms. And then at DailyStoic. And then DailyStock.com is sort of a

stoic-inspired meditation every day that goes out for free to millions of people all over the world. Well, Ryan, I really enjoy your writing. Keep with it. I think it's amazing. And I'm proud to have you on Woop, man. This was a pleasure. Yeah, thanks, man. I'll keep using my Woop. Thank you, Genda Ryan, for coming on the WOOP podcast. I would encourage everyone to check him out and check out his books. I think they're really good, really thoughtful. I will do a quick mailbag here in a second, but I want to remind you first that you can get 15% off a W-WP membership if you use the code Will Ahmed. That's W-I-L-L-H-M-E-D at checkout.

and you can find us on social networks at Whoop, at Will Ahmed. We're out there and ready to answer your questions and tell you more about Whoop. Okay, over to member questions. What do we got here? Tim asks, how do I get in the green more constantly? Gosh, that's like answering what is success with Ryan Holiday. So I would say, Tim, first of all, there's a few habits that we see that generally speaking, put you in the green more often.

So one is sleep consistency. So going to bed and waking up at a similar time every night. That's hopefully a little easier in the world of lockdowns. Two is good behaviors. So whereas drinking alcohol decreases heart rate variability decreases recovery, things like, again, good sleep, meditation. You know, those are the types of things that will increase recovery. And a lot of this is figuring out what's right for you, too.

So that's where the Whoop Journal can be a powerful tool. And you can see how different behaviors, lifestyle decisions, you name it, diet even, affect your body. The last thing I'll say is that balancing recovery with strain properly can also lead to more green recoveries. So if you have a red recovery, but you put a lot of strain on your body, you're probably not going to have a green recovery the next day after that. You know, so a lot of this is appropriately putting stress on your body for how recovered your body actually is.

David asks, what were some of the technical challenges in designing whoop? Gosh, a lot of comes to mind there. So, first of all, anything that you have to wear on your body, even for 15 minutes, introduces an enormous number of challenges. The fact that you have to wear whoop 24-7 really amplifies that. And so we've needed to be able to develop something that is part technology, really part fabric, part material, where the technology needs to be able to collect enough data to justify you wearing it all the time. And the fabric needs to be able to make it comfortable for you to wear. And then the combination of those two things also need to create an environment in which you're wearing it properly so that it all works in harmony. So, for example, if the sensor were too loose on your body, you wouldn't be getting good data.

If the sensor, if the fabric were uncomfortable, you wouldn't be wearing it on your body. If you're hairy or you have lighter skin or darker skin or different wrist sizes, all of those things affect the data quality that you're actually getting from the whoop strap. The other thing that's fascinating is this question of, well, why doesn't it have a screen on it? I talked about this a little bit with Ryan. The fact of the matter is we build technology at Woop to improve your life, not invade your life. And so we believe that if you have a screen on your hardware, you're actually then being absorbed by that feedback all the time. And it's not actually making the experience as reflective as it should be. We also believe that there's plenty of screens in the world.

So we don't need to create another one. But that's the type of example that goes into designing. something to be worn 24-7. And look, we're constantly evolving. We believe also that wearable technology should either be cool or invisible and not something in the middle. So we work very hard to straddle at those two edges at those two ends of the spectrum and not get caught in the middle, which, in my opinion, is no man's land. So there you have it. Those were some of the technical challenges and some of the ways we think about designing the whoop strap. Thank you to everyone for listening. I hope all of our listeners are healthy and in the green. Be safe out there.

And thank you again.