Heading up marketing for American Apparel, Ryan Holiday had—at age 25—success most only dream of. Now 32, he's a best-selling author influencing Silicon Valley moguls and NFL stars. Learn how he found his calling, juggled 2 careers, and let go of idealized success for happiness. To get a free 7-day trial and 25% off, visit blinkist.com/som
[Ryan]: I remember, one day I was out for a run… and then I get an alert on my phone, ...you have a calendar appointment… I realize I have to be across town at a meeting in 15 minutes....
[Niklas]: Ryan Holiday became chief marketing officer of American Apparel and reached the peak of marketing in his early twenties. That’s a remarkable feat that most of us wouldn't even accomplish within the span of an entire lifetime. But as this driven young man kept climbing the Everest of the corporate world, he realized more and more that this was not his idea of a successful life. Especially since his true passion was writing and to keep working on his books.
[Ryan]: It occured to me, i had done this really hard thing, I developed myself as a writer that afforded financial success, could decide what I wanted to do... and how many people would kill for that… and here I was, having to cut short what i wanted to do to go to a staff meeting, and no one had put a gun to my head and force me to do this… I've climbed to the top of this mountain, and someone said “hey we’ll pay you some money to be over on this other mountain”, and I would like to have both…
[Niklas]: After the success of his first book, he realized that he had to make a choice.
[Ryan]: it was a wake up call, you can’t have everything… You have to know what's important to you…
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[Niklas]: Like me, Ryan became a professional in the era of tech entrepreneurs and business disruptors.
[Ryan]: I was the director of marketing at a company called American Apparel and started a marketing company that's worked with all sorts of awesome brands and public figures and done a lot of really cool I think provocative interesting stuff.
[Nikki]: he left college without graduating to become the director of marketing at American Apparel. And he was like absurdly young. I think he was 19.
[Nikki]: My name is Niki Papadopoulos. I am the editorial director at portfolio which is an imprint of Penguin Random House USA and I'm also Ryan's editor for all of his books
[Nikki]: And and he was you know have a taking a job that someone twice his age would have trouble doing. And so he's had more experience in the business world. You know by the time he was in his mid 20s than most people get. By the time they're 40. I think that's had a profound influence on him.
[Niklas]: Ryan single-handedly built the marketing department of American Apparel from the ground up.
[Niklas]: Then in 2012, he became a “media manipulation” guru after releasing his first book: “Trust me, I’m lying.”
[Ryan]: it was, it was very exciting. It was very interesting I learned a lot.
[Niklas]: Being at the peak of his career at such a young age, Ryan had a very bright future in marketing.
[Niklas]: But then…Ryan started to realize... he was climbing that mountain for the wrong reasons… and in doing so, he was becoming another wheel inside the corporate clockwork.
[Ryan]: that's not what I want. That's not what I want to wake up and do every day
[Ryan]:To me success is freedom… more things that I don't want to do. And me being told more and more what I can and can't do because I have you know employees to answer to or have this to manage or that fire to put out that doesn't feel like success to me
[Ryan]: I think it's very hard to be happy if your life is back to back meetings, if you wake up in the morning, you walk in and somebody has a clipboard and they tell you “here’s what every minute of the next 24 hours is for you”... and you have no saying on it?... that doesn't sound like success to me…”
[Ryan]: The point is you have to know what success looks like.
[Nikki]: He left American Apparel to write books full time a few years ago after we published his second book a book called The “obstacle is the way” which was a breakout hit. And it was it was clear from the success of that book that that he could really have a full time life and career writing books and talking about them.
[Niklas]: “The Obstacle is the way”, was Ryan’s third book, but it was the first time he wrote about a subject he was truly passionate about. And it was a topic that couldn’t be further away from media or marketing.
[Ryan]: I read the Meditations of Marcus Aurelius that I saw what philosophy is actually supposed to be which is you know practical it's supposed to be like, used in the real world by real people.
[Ryan]: This is a recipe for living here real people talking about real things in a real way and in language that me as a 19 year old actually understands there's not they're not using words I've never heard of. I actually get this
[Ryan]: It just hit me like a ton of bricks. It was just like wow this is exactly what I was looking for. This is a recipe for living.
[Ryan]: And then I went into writing about ancient philosophy and those books have been I think to a to everyone's surprise including my own had an enormous amount of resonance with, with all sorts of interesting people in different niches from the military to you know heads of state to professional athletes to entrepreneurs. And I think that the it's the books have worked for the same reasons that the philosophy worked for me which is like people are trying to figure out how to live what to do what not to do.
[Ryan]: I don't think there's anything in any of my books that I don't personally struggle with on a daily basis.
[Ryan]: When I sit down to write about something, it's because I'm struggling with it and I need help and I'm looking at the best sort of strategies and thinking and wisdom from other people. So you know it goes something I struggle with you know overcoming obstacles difficulties just dealing with all the things that go wrong in the course of a day and not taking them personally not getting upset by them sort of mastering our emotions these are all things that I struggle with..
[Nikki]: His books have been translated into over 30 languages and read by more than 2 million people worldwide
[Nikki]: one of the first things he ever said to me when we first met he said I want to write books. That's what I want to do. And. And he hasn't wavered from that at all…
[Niklas]: Becoming a writer didn't mean that he would retreat and fall back into a bohemian lifestyle. He still had the same drive and hunger that turned him into a top marketing master.
[Nikki]: Ryan is incredibly driven and holds himself to a very high standard…
[Nikki]: He never ever misses a deadline with anything like not page proof or no manuscript nothing. And that makes him very different from ninety nine percent of the authors I work with…
[Nikki]: He is relentlessly focused on writing great books and from my point of view that is how he should be spending his time
[Ryan]: I mean primarily why I want autonomy is because I really love writing and I really love reading. these are my sort of two loves and my two passions. And the more people are telling me to go do this or that the less time I have to do those things that I think you know not easy artistically that I think I'm good at I think I have talent that And so what. Why am I attending meetings if that's not what I'm good at and why am I not writing If that is what I'm good at.
[Niklas]: After the break. we’ll find out how Ryan became one of the most successful authors of recent times.
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[Niklas]: For many years, Ryan had been juggling his life as a marketing strategist while also writing his own books. But eventually he realized that he couldn't have it all.
[Ryan]: One of the things I struggle with on a very regular basis and I talk about a little bit in this still in this book is this idea of like what do you say no to versus what do you say yes to...
[Ryan]: I think you can sometimes only figure out what your limitations are by saying yes to a lot of things and going Oh like you know there's been times where I've I've done a bunch of things that all that I wanted to do that I thought were good and then I realized OK I'm bumping up against like my outer limits here. Like it's not humanly possible for me to do all these things simultaneously… and then you've got to scale it back
[Ryan]: It's this balance of like how do you say how do you how do you feel grateful for and appreciate and take advantage of all the opportunities that you have. But then how do you make sure that you're not saying yes to so many things that your work suffers your personal life suffers
[Ryan]: I'm constantly struggling to to figure out you know what pitches to swing at an end.
[Nikki]: Some of the best conversations we've ever had have been about about being protective of time with your family. And finding that space for the things that really matter in your life. And I respect a lot that he is aggressive about protecting that he knows what's important to him and he's not willing to compromise on it. And you know so many people kind of slide into saying yes to things that they don't want to do or they feel like they're obligated to do. And he's very clear about what he's about.
[Ryan]: Fuck yes or fuck no. If you wouldn't say fuck yes to it then you should say no to it.
[Ryan]: What's so insidious about it is that your mind is always telling you that there's an exception that this thing is so important that it's definitely worth it. And so you end up constantly as kind of in a battle with yourself about these things
[Ryan]: I mean there's there's little rules I like you know like you know if you wouldn't do it in in in six days don't say yes to it in six months. You know if if if you're gonna be glad you did it 50 years from now these are good tests…
[Ryan]: One of the rules I have for myself is I try to do the things that only you can do the things that you won't be replaced on…
[Ryan]: What's the thing only you can do? What's your one thing? What's the thing you were put on the planet to do? Spend as much time as possible on that thing... knowing that gives a lot of clarity and helps make a lot of decisions for us
[Ryan]: If I stopped writing you know at least a few people would be sad about that right? I've just tried to get better at on OK. I don't need to do all these things. I need to do the thing only I can do
[Ryan]: I think deciding where you're going to live is also really important along these same lines. A lot of people live where they think they're supposed to live where they live where they think it's sort of sexy and cool to live or high status to live and they don't optimize like their day to day like habitat around being conducive to having this sort of stillness or clarity or productivity.
[Niklas]: After having worked in L.A for a few years, Ryan knew the impact that the loud city life can have on productivity. He knew that he needed to avoid distractions if he wanted to fully focus on his writing career. And he managed to do that by moving to the beautiful countryside of Texas.
[Ryan]: I spend most of my time, we have a small farm outside Austin, Texas. And I look one of the benefits of like living out in the country or spending a lot of time out in the country is that you have a really good excuse. You know people go oh like do you want to come out for coffee later and you go sorry it's like a two hour drive for me or whatever. One of that one of the benefits of living in Texas instead of living in Los Angeles or New York City is that I just get invited to do less stuff…
[Niklas]: Living on a farm gave Ryan more time and freedom to write 10 books in less than 7 years.
[Nikki]: I think that that single minded focus has been the reason for his success… And also you know the reason why he's been able to be so prolific. He's incredibly disciplined.
[Ryan]: A lot of people tell themselves you know like I'm my work's too important, I'm too busy I don't have room for a relationship in my life...
[Ryan]: I think for successful people and ambitious people so much of their identity is tied up in to ing and working. I mean I think one of the reasons that someone would say like put in the insane amount of hours required to be a comedian or a writer or an artist is this sense that your personal worth is is wrapped up in it and that if you don't do it if you're not good enough you're somehow worthless.
[Niklas]: After having been part of a noisy and hectic world, Ryan slowed down and freed himself from disturbance. Or as he would call it, he was able to cultivate stillness.
[Ryan]: One of the reasons we we cultivate stillness is so we can see where ego is causing us pain and trouble. And and one of the one of the way we master our emotions are we see the big picture or we overcome where we have the insights of the creativity or the the the you know breakthrough necessary to overcome some really difficult vexing problem or obstacle that also requires stillness… Like when you remove when you remove ego you have more stillness and then also stillness is a wonderful way to get rid of ego and sort of they're all related in that sense.
[Niklas] For Ryan, developing stillness was to climb his own personal mountain, away from social expectations and the burden of his success-driven ego. Climbing that new mountain meant understanding there was more to life than just becoming one of the youngest marketing executives.. Like enjoying life on the farm, in the company of his family.
[Ryan]: I think you can you can find that person that helps you see yourself with a little bit of objectivity that sort of a support system for you that that appreciates and loves you for who you are not because of your accomplishments… And this is all essential in the sort of pursuit of stillness and happiness.
[Niklas]: Ryan figured out building his road to happiness involved sharing the love, complicity and companionship of Samantha, his wife. He consciously designed a lifestyle around having the time and freedom to joyfully spend time with her. And a few years later, when they had their first child together, it was in his own words, a life changing experience. the last ingredient to find stillness, and to discover through parenthood, the simplicity of life.
[Ryan]: But when you see you know a defenseless 2 year old sad because you're not there because you went to do something that you didn't really need to do it allows you to sort of externalize the costs of this sort of disease. If you really want to you know call it what it is.
[Ryan]: I think the other thing that kids give you is a sense of just how simple and easy how simple and straightforward life actually is like my son Will wants to go outside to play dirt bike that's literally what he says he doesn't want to play in the dirt. He wants to play dirt like dirt like you buy them all these expensive toys you want to take them to do these activities and what he really wants to do. We have like we have 40 acres of land and he likes this patch of dirt you know by the back door and so you just realize that so much of what we tell ourselves we need to be happy.
[Ryan]: So much of what we tell ourselves is is the best or the most exciting or the coolest. Is it this is all artifice and that what it takes to be happy is quite simple
[Ryan]: I didn't realize just how much sitting around there would be that like an infant just falls asleep on your chest and you can't move until they wake up… because sleep is so rare you're definitely not going to wake them up. And so like the time of your appointment is not 10 o'clock it's whenever you're your kid decides to wake up. And this is a powerlessness that that you're not naturally used to that doesn't that doesn't occur readily and you certainly don't choose but it's adding It's very humbling. It's refreshing and it teaches you how to be present. And ultimately it's quite wonderful
[Niklas]: Being present, enjoying the moment. This is one of Ryan’s key takeaways from his experience of shifting careers, of radically changing his lifestyle to achieve freedom and stillness of mind, becoming truly grateful for what he’s got.
[Ryan]: the Buddhist would say you know we we we seek the way in what is distant when really the way is what is in close and and you know we we travel all over the world to find these prettier and prettier sunsets or sunrises or scenes and they're all the same it's the same sun no matter what angle you're looking at it from it and you can have the same sort of moment of peace and reflection anywhere you want to get it you might have to work a little bit harder for it but but it's there and I try to I try to cultivate that in my life I try to catch myself and stop and go This is just wonderful. This is this. This moment is wonderful this moment is enough I don't need it to be anything more I just need to to soak it in I just need to enjoy it.
[Nikki]: He's a really inspiring guy… And you know one of the pleasures of and the privilege of getting to do a job like mine is that you get to publish people like Ryan who are who are exceptional and who are were very singular and who inspire you and will then go on and inspire many minute readers too.
[Niklas]: According to Ryan, we all have that one thing we’ve been put on this planet to do. All we need is to slow down and focus on what is really important to us.
[Ryan]: when we have these moments where we're out in nature we're really doing what we know we're supposed to be doing and there's no interruptions and there's quiet and it's natural and it's peaceful… We have this sort of sense of stillness and when that stillness comes over us we're happy we're grateful we're present and we love those moments and yet they're so rare in our lives. And, and I think they’re mostly rare because we make decisions that don't provide a lot of room for it.
[Ryan]: And to me those are the moments that make life worth living.