The Obstacle Is the Way, 10 Years Later

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1:05Welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like here or recommend here at Daily Stoic, and other long form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy. And most importantly, that you're able to apply it to your actual life. Thank you for listening.

1:45So 2014, actually go back even further. 2012, 2013. What's going on in the world? What's going on in my life? Who am I? I'm not married. I don't have kids. I don't have a house. I live in LA and New York and New Orleans. I'm still working at American Apparel. The world doesn't seem quite so insane. TikTok does not exist. Political parties, at least in America, had a very different set of beliefs. Artificial intelligence was a pipe dream. We had no idea a global pandemic was coming. Stoicism is this kind of obscure school of ancient philosophy that's not particularly popular. The idea that there was a series of potential books in there seemed nonsensical.

2:37And then even in my own life, just what has transpired in the 10 years, the places I've traveled, people I've met, mistakes I've made, injuries I've had. A lot has happened, right? Professional obstacles, personal obstacles. That's what life is. There's that Chinese curse, may you live in interesting times. The last 10 years have been pretty interesting, to say the least, personally, for both me and for you, I can imagine. So when my publisher said, hey, hey, do you want to do an update on The Obstacle's Way? It's coming up on 10 years. I was excited slash nervous. You know, how does the book stand up?

3:15What would I change? What needs to be changed? What could I add to it? You don't want to break something that's working, but I ended up doing it. And that book is out now. You can grab copies at dailystoic.com slash obstacle. What I did was I added a new forward. I sort of told the 10 years that we're just talking about. I walked you through what I've learned, how I think differently about the ideas and the obstacles away, what those ideas mean to me, what my understanding of stoicism is. I've been working on that edition and I just re-recorded the audio book. The idea that I'd be recording, I recorded the first audio book for the obstacles away.

3:49Tim Ferriss had bought the rights. I recorded it in this studio in Austin that 10 plus years later, I'm recording it in Bastrop, Texas in my own studio, a converted barbershop. seems crazy to me that the Daily Soak podcast would exist. All of this seemed, you know, unreal. But here we are. And I wanted to bring you the forward. So my favorite part of the new book is this forward that I wrote, where I'm thinking about what the book means, sort of explaining what I've done in the book. So that's what I wanted to bring you in today's episode. You can grab the audio book. I think it should be up everywhere.

4:28Audio books are sold here very, very shortly. And if you want signed numbered first edition, you can grab that at dailystoic.com slash obstacle. So when I was recording the audio book, I was still making changes. That's just how it works. I'm still making changes. And as I was doing that, I kept all those pages and then I signed them. So you can get a signed page from the audio book reading, like the actual manuscript of the book. And that's pretty cool. And anyways, I'll get into it. Here we go. here is The Obstacle is the Way, Reflections, 10 Years Later.

5:04Reflections, 10 Years Later. It's not that the last decade, 10 years and counting since the publication of this book, was hard for me. It'd probably be bad form to admit that in a book about overcoming obstacles, but I think I'm safe to say it was a lot. There were natural disasters, floods and fires, a freeze that broke the power grid in most of our pipes. There was a long drought that was murder on our livestock and land. There was a devastating, tragic pandemic that stretched on for years, dashing so many plans to dust, nearly killing the independent bookstore we opened in the teeth of that virus.

5:45There were disputes with business partners and employee caught embezzling. There were funerals and late-night phone calls with news you never want to get. The company where I made my bones went bankrupt, taking with it not just much of my resume, but what was supposed to be several years' salary worth of stock options. May you live in interesting times, goes the ancient curse. Well, it's been interesting. There was a global logistics and supply chain crisis. a paper and a printer shortage in publishing. There was a falling out with family, hundreds of thousands of miles on the road. There was getting skunked on the bestseller lists, creative differences, daily battles with procrastination.

6:33There was the steady drift towards fascism, unrest in the streets, the failure of institutions. It was a lot in a much more welcome direction to 10 years of marriage, having kids, running businesses, sunsets and sunrises, beautiful sights and new discoveries, friendships rekindled, breakthroughs in therapy. Word that this book had made its way into the locker rooms of professional sports teams and the offices of heads of state. Signs that it and my other books had started to sell, like really sell. There was the flood of attention and offers, the financial rewards, the fame, the platform, the expectations that followed.

7:15Listening back to the audiobook, which I'm re-recording actually for you right now, I hardly recognize the voice of that younger person, that person who had been through so much less, who knew so much less. Because what happened in those intervening years is life. Modern life, yes, but also life as it's always been. Life not altogether unrecognizable from someone on Zeno's stoa back in the third century BC, or nearly 500 years later, in the Rome of Marcus Aurelius. The simplest idea at the center of this book is that there are hidden advantages in every situation. That businesses and teams and people can take seemingly impossible situations and find ways to triumph over them.

8:04Hard times can be softened, Seneca writes in one of his essays. Tight squeezes widened and heavy loads made lighter for those who can apply the right pressure. While this is true and more essential than ever in difficult times, in experiencing life and all its interestingness in the intervening years, I have come to more fully understand what the Stoics were getting at. The suffering and struggle of centuries of existence taught them something more profound than the fact that every downside has an upside. How glib it is to talk of silver linings to someone with a cancer diagnosis, someone who has buried a child, someone in the grips of a crippling addiction, someone who has been bombed, someone who has lost their livelihood.

8:52What I understand today is that when the Stoics said that there was an opportunity in every obstacle, what they meant was the opportunity to practice virtue, to be a good person despite the bad things that have happened, to do good in the world despite the bad that has befallen you. They were speaking of the idea of erite, excellence in all forms, finding professional advantage, possibly, but this was not their primary concern, what they meant when they said the obstacle is the way is that the hardest, most heartbreaking moments of life can be transformed by endurance, by selflessness, by courage, by kindness, by decency.

9:35And they also had more in mind than just adversity. Success, too, is an opportunity to practice virtue. Indeed, it demands it. Because with success comes temptations, comes distractions, comes stress, comes responsibility and obligations and obstacles. How great it is then in the face of abundance to be humble, to be disciplined, to be decent, to be generous, to hold true to your values. Great, but challenging.

10:13Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work, stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in.

10:58We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course. Because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you.

11:38Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours.

11:50One of the great gifts of my life was discovering stoicism, which I came to at the end of my teens, purely by chance. I desperately needed guidance, some sort of compass for life. Around the same time, I began to hear the first soft sounds of my calling to be a writer. And eventually, I was able to combine these two loves into my career. When I first approached what is now Penguin Random House with the idea for The Obstacle is the Way in the summer of 2012, I can't say that they were exactly ecstatic. I was slightly offended, but in retrospect, it was an extreme act of open-mindedness and trust that they were interested in a book about an obscure school of ancient philosophy at all, let alone from a 25-year-old college dropout.

12:36This open-mindedness had its limits, naturally, and their offer was less than half what I had received from my first book, which was then on the bestseller list and generating headlines. My editor, long after this book found its audience, would tell me that her hope was that I'd get this philosophy stuff out of my system and go back to marketing and business books. She was probably right. The idea was crazy, and I'm grateful that they let me try. Someone else that I thought was a friend and a patron was privately telling people that the book would sell no more than 5 ,000 copies. Being underestimated is usually an advantage, however frustrating it can feel in the moment.

13:13The expectations from everyone were low. The concept was so absurd as a business book that it effectively worked as counter-programming. It generated a bit of attention. The Obstacle is the Way did okay its first week and then sales tapered off. They never went to zero. Amazon discounted the ebook as some kind of loss leader and the algorithm blessed me. A year and a half or so later, after news that the New England Patriots had read the book on their way to the Super Bowl and that the Seahawks read it after their gut-wrenching loss, suddenly the publisher couldn't keep it in stock. Here we are a decade later and the obstacle is the way it's been published in 40 languages and sold over 2 million copies in English alone.

14:00Sales are great, but what's far more exciting to me is that this obscure school of ancient philosophy is no longer quite so obscure. In 2012, there were a few thousand people interested in Epictetus, Seneca, or Marcus Aurelius spread out across the internet. Today, the Daily Stoic, which I started in 2016, reaches a million people before 9 a.m. each morning. There are more Stoics walking the earth today than ever before in history. You'll notice that in this book and in the Daily Stoic emails, I don't talk about myself. The word I appeared in the body text of the first edition of Obstacle only once or twice and even then only by accident.

14:42It's been corrected in the version you're listening to now. But that doesn't mean my own experiences have not informed my writing and understanding of Stoicism. Of course they have. In fact, that itself is yet another confirmation of how the obstacle can always be the way. A writer, and I believe generally all persons must think that whatever happens to him or her is a resource, the great Jorge Luis Borges once explained. All things have been given to us for a purpose, and an artist must feel this more intensely. All that happens, including our humiliations, our misfortunes, our embarrassments, all is given to us as raw material, as clay, so that we may shape our art.

15:32Our experiences become the fuel for what we create. The crucible of experience informs and instructs. It doesn't matter how awful, how unfair, how expensive an experience is. I've come to understand that I have the greatest job in the world because I can take what happens to me, even heartbreak, and turn it into material. In this way, nothing is ever truly a waste. Nothing is totally irredeemably bad. There is always some cold comfort in every experience, some way to move forward from it and use it productively. I'm not alone in this. The same is true for leaders, for comedians, for athletes, for military officers, and for parents alike.

16:14It doesn't matter what happens to us. It can be for the best if we use it to be better for ourselves and others. So the pages before you, rooted as they are in history and philosophy, are also the product of my own history, successes and failures, high points and low ones, failures and breakthroughs. Would I write the book differently if I was starting over? Of course. And certainly there are changes and corrections I have made in this new anniversary edition. If I were updating it again 10 years from now, I would hope I would make changes still that I would be wiser and understand philosophy more deeply.

16:55But everything in here was something that I needed to hear when I wrote it, a lesson I myself needed to learn most of all, that they have been of value to readers around the world is, as Marcus Aurelius would say, a bit of nature's inadvertence, a pleasing byproduct of a timeless process. For that's what Stoicism is, a great conversation that stretches back thousands of years. Men and women talking to themselves, talking themselves through obstacles and opportunities, big moments and small ones, reminding themselves to be excellent, to follow virtue, to do what is demanded of them. It's my honor to invite you to join it.

17:50Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.

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