Are You Afraid to Start? | 10 Years Of Lessons From The Obstacle Is The Way

We have to be strong enough to will ourselves to do what needs to be done. Don’t be afraid to start. Don’t put it off any longer. The Daily Stoic New Year, New You Challenge is 3 weeks of ALL-NEW, actionable challenges, presented in an email per day, built around the best, most timeless wisdom in Stoic philosophy, to help you create a better life, and a new you in 2025. Why 3 weeks? Because it takes human beings 21 days to build new habits and skills, to create the muscle memory of making beautiful choices each and every day. Head over to dailystoic.com/challenge today to sign up.📕 Get a signed, numbered first-edition of the 10th Anniversary Edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each day we read a passage of ancient wisdom designed to help you in your everyday life. On Tuesdays, we take a closer look at these Stoic ideas, how we can apply them in our actual lives. Thanks for listening and I hope you enjoy.

• 0:29Ryan Holiday?

  Are you afraid to start? It could fail. It could go badly. It could be harder than you expected. It could. But how will you know? How will you know until you start? "That's the one thing all fools do," Seneca said. "They delay to start. They put it off. They let their fears or their laziness win." And this is where two essential Stoic virtues come in: courage and discipline. We have to be brave enough to push past our fears. We have to be strong enough to will ourselves to do what needs to be done. Perhaps this is where the third virtue comes in: justice. What you're doing might be important. It could make a real difference. It could fail, but it could also help people. And here you are, putting it off. Here you are, taking counsel of your fears, letting the resistance

• 1:14Ryan Holiday?

  win. And this is not without costs to yourself and to others. Don't be afraid to start. Don't put it off any longer. Do it. Do what you can. Do good. That's the whole goal behind the Daily Stoic New Year, New You Challenge. It's designed to push you to get started, to get the ball rolling, to build momentum, to help you make 2025 the year you realize just how strong you are, to challenge you to do what you are capable of doing in this life. And if you're worried that it's all too much, that it might be hard, that it's this or that, well, let's remember what Seneca said, "No man is more unhappy than he who

• 1:54Ryan Holiday?

  never faces adversity, for he is never permitted to prove himself." And for the last six months, we've been working on the Daily Stoic New Year, New You Challenge. We redo it every year. We come up with a bunch of Stoic-inspired challenges and practices that will help you become what you are capable of becoming. And it's designed to meet the unique year that is 2025. And you know, it's gearing up to be a crazy year. But just imagine starting every day of this new year with a clear, actionable challenge, one you can't procrastinate, one you can't get out of, just a powerful push to help propel you closer to the life you want. And I want to see you in there. I do the challenge every year, thousands of other Stoics all over the world do it.

• 2:39Ryan Holiday?

  And I'm pumped to see you in there. It starts on January 1st. Don't delay, don't put it off. Sign up. I'll see you in there. DailyStoic.com/challenge. It's always funny to hear the people who did put it off, because our customer service rep actually goes, I got so many emails on the first and the second and the third, people asking if they still sign up, can we let them in? Well, yes, I want to see you in there. DailyStoic.com/challenge. Don't delay. Let's have an awesome new year.

• 3:17Ryan Holiday?

  Almost 10 years ago, in a very different office than this, it was this small nook under a loft bed in an apartment in New York City. I started working on this book called The Obstacle is the Way. Flash forward now, that book has sold millions of copies. It's in 40 languages. I'm also a very different person than I was when I wrote it. And I'm having this unique experience of the publisher asked me to write a new foreword and to go in and kind of correct things, change things, tweak things, update. The obstacle is the way.

• 4:05Ryan Holiday?

  Here are my note cards.

• 4:10Ryan Holiday?

  I have a stack of note cards that I've accumulated since the book came out. Of just little things that I definitely want to add, so I have these. And then, this is the box, this is the book. As I wrote it, I'm gonna have to go back through these cards. Like, this is an email. An email I sent myself as I was writing the intro of The Obstacle is the Way. Let's see when I did that.

• 4:35Ryan Holiday?

  This is the intro, this is a chunk of the intro of The Obstacle is the Way, which I sent myself as a note in June of that year, I think. So I was already working on the intro, and then this made it into the book. So, I'm just going back through and tweaking stuff, I'm already making some changes. That's my next little project, the 10th anniversary edition of The Obstacle is the Way.

• 5:02Ryan Holiday?

  Almost 10 years ago, exactly, I was in this exact spot. I was going for a run along the East River in Manhattan, and this idea popped into my head. When something like, "In the year 170, in this tent on the front line, in the war in Germania, Marcus Aurelius sat down to write." That's the first line in The Obstacle is the Way. I was on my run, and it just popped into my head. That book has gone on to sell millions of copies. It reintroduced Stoicism to millions of people. It's been this incredible journey that I could not have anticipated. But I sort of take two quick lessons from that. One, it's always a good idea to go for a run. When you get your body moving, you have no idea what can pop in your head. And two, there's this Stoic idea that we never step in the same river twice.

• 5:46Ryan Holiday?

  The river's different, I'm different, I'm standing in the exact spot, but so much has transpired. How I would even think about that line, how I think about the Stoics, has changed. We are always changing, the world is always changing, even though things stay the same, and that's the lesson.

• 6:05Ryan Holiday?

  Seneca wasn't just a philosopher, he was a writer. And so he knew this very acutely, the mortification you feel when you go back and read or edit something, not just that you did, but that you put out in the world. He says, "When I think of all the things I have said, I envy the mute." This process of going back through and updating The Obstacle is the Way 10 years later, of listening to my voice on the audiobook, having to redo the audiobook, changing sentences, seeing sentences that not just like I put out in the world, but literally millions of people saw, you envy the mute. It's a very humbling thing to go back and look at what you did and what you thought was your best work, and maybe indeed was your best work at that time. And you see what does or doesn't age well.

• 6:50Ryan Holiday?

  I think what doesn't age well is certainty, simplification, judgment. And so hopefully, as I've gone back through The Obstacle is the Way, I've softened some of those things. I've been kinder, more empathetic, more nuanced. Mostly, I'm trying to take that forward on the next project. Like, if you think about that unpleasant feeling, I get to adjust it, fix it here. I can't undo that it happened in the past. What I can do, though, is on my next project, be a little wiser, be a little kinder, be a little bit more open-minded, do a little bit more work. So in a way, that's the real lesson. That's like the way I'm getting better for having gone through this, that sometimes this sometimes agonizing process.

• 7:32Ryan Holiday?

  I'm seeing all the ways that I have changed and become better in the last 10 years, but I want to become better so that when I look at this edition in 10 years, there's still going to be some mortification, still going to be some changes I want to make, but hopefully fewer of them still.

• 8:05Ryan Holiday?

  I haven't written the new preface yet, but you can see all the red stuff. So here's just some tweaks. There's a whole, like, I'm adding stuff. Like, I have this chapter about Rockefeller in the book. And, like, obviously Rockefeller was not the greatest dude, so I'm sort of qualifying that. There's a paragraph there.

• 8:26Ryan Holiday?

  Cutting, there's a section on Rommel that I'm cutting. This is a piece about the Canadian astronaut Chris Hadfield. He's saying that, I've done this in like a million talks. So, and I found it after I finished the book. And I would talk about it, when I would talk about The Obstacle is the Way, the audience has always loved it. So I'm adding that in the book. But he has this great line, he says that in space, when you run into a problem, there's a bunch of things you can do to make a situation better. And then he says, "There's no problem so bad that you cannot make it worse also." So that's going in there. For instance, I've already messed with, let's see, I did a lot on one of my favorite stories in the book, which is how Marcus, at the end of his life, so I'm adding, this is a deeper story.

• 9:10Ryan Holiday?

  That the end of the book, as I wrote it 10-plus years ago, was only about Marcus and the fight against Avidius Cassius. But I'm taking this more, fuller picture of Marcus, which is the plague that he faces, the floods that he faces, his stomach ailment, the years of war, burying children, just like a life of pain and struggle. There's this ancient historian that says that Marcus doesn't meet with the good fortune that he deserves, and his whole reign is involved in a series of troubles. And so I'm sort of talking about how Marcus's life embodies this idea of The Obstacle is the Way, that he doesn't just coin the phrase, that his life really illustrates how he lived it. So anyways, these are all the stuff, the things that I'm adding.

• 9:51Ryan Holiday?

  And I have to turn it in by beginning of January to get it out for the 10th anniversary. So that's what I'm working on.

• 10:16Ryan Holiday?

  As crazy as this week has been, I feel like I will spin off the planet if I don't get at least one small look at the manuscript I'm supposed to be working on, which is the 10-year anniversary of Obstacle. My rule, this is like a discipline thing too. It's like, you don't have to be perfect all the time. You don't have to make enormous contributions. You just have to make lots of little contributions. And so if I can just go, hey, did I do one or two good things to the manuscript this week? That's enough. That's what I'm doing now. So I'm literally, it's literally, it might seem like this isn't what a writer does. You know, it's like spinning a globe and just pointing out where to go. I'm literally just kind of like rolling the dice and pulling up a random spot and just kind of spot checking and seeing what I want to fix.

• 11:12Ryan Holiday?

  Go ahead. Yes?

• 11:17Ryan Holiday?

  Probably the biggest change between writing it the first time and working on it now is just came in my, my life or my lifestyle. I was with my wife when I was writing The Obstacle's Away, but we lived in this tiny apartment in New York City. We had a dog, but we didn't have kids. We weren't married. And as I'm working on it now, I, I have two kids. And my, my son is turning eight this fall. So he's almost as old as, as the book. But you know, my life is noisier. My life is more unpredictable. My life is more chaotic. I have more responsibilities. It's not right to say that, that having kids is an obstacle. It's not, but it is a challenge. It is a constant trial. It challenges you in so many ways.

• 12:00Ryan Holiday?

  And as I have been working on the book, that's one of the things I thought a lot about is how do these ideas inform me as a parent? How do you apply these ideas to the unpredictable, crazy, exhausting, overwhelming 24/7 job that is raising human beings? Where do I find the time to work on this book in addition to all the things that I have going on?

• 12:28Ryan Holiday?

  It was a lot. The last 10 years have been a lot.

• 12:32Ryan Holiday?

  It is Thanksgiving.

• 12:36Ryan Holiday?

  It is Thanksgiving 2023. My kids are watching SpongeBob on the TV there. And I am in Florida on vacation down by the beach. And I am working on the preface of the new intro.

• 12:51Ryan Holiday?

  I've been chugging away on this. And it's just gonna be like maybe one, two pages at the beginning of the book to mark the fact that 10 plus years ago, I sat down to write this book. I'm talking about the fact that this one person who predicted it would sell 5,000 copies. The Obstacle is the Way sold more like 2 million copies. There was probably a couple thousand people who cared about Stoicism on the internet at that time. And now, every morning, the Daily Stoic reaches a million people by like 9:00 AM. So that's sort of what I'm talking about, how I've come to interact and understand the material since so much has happened since it came out. There was the pandemic. There was the books doing well. There was hundreds of thousands of miles on the road. There was getting married. There was having kids.

• 13:35Ryan Holiday?

  Just a lot of life. And that's what the new intro is about. And then we're gonna go have Thanksgiving together as family.

• 14:01Ryan Holiday?

  We are heading to the Breakfast Club. Did you write thing right now? And then my publisher is like right here and I have to drop off the 10 year anniversary manuscript of Obstacle. So we'll get it by car.

• 14:35Ryan Holiday?

  It's crazy to me that 10 years ago, almost exactly, this book was being released, my first book on stoicism. And now I'm editing the 10-year anniversary in the green room of The Breakfast Club. I gotta drop this off on my publisher, who, when I wrote it the first time, was way downtown,

• 14:55Ryan Holiday?

  on Barrick Street. And now is all the way up here, near the park, because Penguin merged with Random House. But now I'm just tightening up. This is the second pass, which I guess now is like my fifth or sixth pass, because I've done it so many times.

• 15:23Ryan Holiday?

  Keeping our word does cost us. But it's not free to break your word, because the next time, that person's not gonna trust someone else. And so we all think about it as like, "What's good for me?" But what we're doing is we're stealing from the public trust, from our ability to collaborate and count on each other, because everyone's saying, "You know, your word isn't worth anything." And collectively, unfortunately, in a lot of cases, it's not. I pride myself on being honest and truthful at all times. I love chapter three in the book, "Tell the Truth." But I think sometimes when we say, "I'm gonna be honest with you," it's a buffer to this whammy, "I'm about to leave." "I'm actually gonna be a dick," is what I'm saying. Yeah, yeah, yeah.

• 16:24Ryan Holiday?

  So I'm still pretty old-school about it. Not only do I write the books with physical note cards, having read physical books, but then I do all my notes. I have the publisher print them, like print me out a bound manuscript. I wanna see what it's gonna look like, and the size that it's gonna be. And then I do all my notes. This is the second pass, but...

• 16:49Ryan Holiday?

  So I realized something crazy. I realized that I sent the first draft of this from like one year ago on a plane flying across Australia and then here. It doesn't feel like it's any of this.

• 17:04Ryan Holiday?

  Am I in here? Where?

• 17:17Ryan Holiday?

  There's been lines up there? That's incredible.

• 17:24Ryan Holiday?

  And that one? Oh, they're not behind us. Wow. Good.

• 17:33Speaker 01

  Yeah, try to keep your hands still.

• 17:35Ryan Holiday?

  Do I, how do I get all six?

• 17:36Speaker 01

  Oh, there's an obstacle.

• 17:37Ryan Holiday?

  Oh, where?

• 17:40Ryan Holiday?

  Okay, that's insane. So then we'll have to we'll have to replace it.

• 17:47Ryan Holiday?

  Do you think it's a first edition?

• 17:49Speaker 01

  It might be.

• 17:51Ryan Holiday?

  How do you decide which one's going?

• 17:54Speaker 01

  I can find out.

• 17:56Ryan Holiday?

  Like, do you ever demo a pop?

• 17:58Speaker 01

  I don't think we've ever taken anyone away.

• 18:00Ryan Holiday?

  I am now having to do the new audiobook. It's a Saturday. I got up early. I came here before my kid's soccer game. Supposed to be a 20, 25 minute drive. Took 50 minutes. Just getting frustrated about the traffic. Then I came upon the source of the traffic and it was a fatal car accident. There was a body out in the road covered in a tarp and it sort of put some things in perspective. And I was trying to think, okay, what did I do with the extra 25 minutes? Was I as in control of my emotions as I'd like to be? I don't think so, but I listened to a nice podcast in the road. I learned something. It gave me an excuse to text a friend about that podcast. So I'm gonna, I'm gonna see it as a positive.

• 18:44Ryan Holiday?

  And then I, I get to come here and do what I love. I, I noticed something here that I need to fix already. That's the other thing about audiobooks. What they are is a chance for you to read the draft all the way through very slowly, sort of performatively. And you, you catch some stuff that you want to fix.

• 19:08Speaker 01

  When you go through the book, how do you determine what you want to change and what stays?

• 19:13Ryan Holiday?

  There's a bunch of very specific things that I had notes that I wanted to change. And then I kind of, I would just, you know, every day I was working on it, I would just open it, flip to a random spot and then just kind of reread it and ask myself, hey, is this how I would say this now? How could this be said better? What is this missing? So a lot of times it was stuff like that. And then on the, even during the audiobook, which I just did, and in this chair, having to say every word of it out loud was like an excruciating experience because I hadn't done that for 11 years.

• 19:53Speaker 01

  Yeah.

• 19:53Ryan Holiday?

  And to go through and have to say things that you put into print a decade ago, there's a Seneca thing, he says, when I think of all the things that I have said, I envy the mute. And the experience of editing something you've already published or rerecording the audiobook of something that millions of people have listened to, you're like, I mean, it's horrifying because you go, I said that? Like, I allowed myself to leave it at that? And I mean, not everywhere, there's lots and lots and lots of parts of the obstacles

• 20:37Ryan Holiday?

  where I'm very proud of. But if you can reread something you wrote or worked on a long time ago, and you think it's perfect? I mean, to me, that's a sign that you haven't gotten any better since you've done it. Like, the idea that you don't have improvements to make, to me, would imply that that was the peak, which I definitely don't think is true, and I definitely don't want to be true. I mean, what was the point of continuing to do it if you're not getting any better?

• 21:06Speaker 01

  I always think you have a, you have a unique relationship to your work in that it's like a lot of your favorite stuff as a reader that you're bringing together.

• 21:13Ryan Holiday?

  Sure.

• 21:14Speaker 01

  And the experience of going back and looking at a lot of those stories, I imagine, was like, I actually think the lesson embedded in that story is different than I initially thought.

• 21:25Ryan Holiday?

  Yeah, well, that's the idea that when they say, no, you don't step in the same river twice, that's the other part of it is that what stands out at you in a specific story is different. And yeah, the meaning of it can be different. So yeah, like, when I talked about Rockefeller at 24, I'm just thinking of him and I'm only thinking about him in the context of how did this guy overcome obstacles? I'm only thinking of the heroic aspects. But then the book I wrote immediately afterwards about ego. And then I wrote a book about stillness. And then I've written a book about discipline. And then I wrote

• 22:05Ryan Holiday?

  a book about justice. And so if those subsequent deep dives into topics don't inform your worldview going forward, what does that say? And so now, and of course, I understood these things about Rockefeller, but that wasn't what I was focused on. Those weren't like the salient things that were jumping out of me. But now, looking back at this person and my own writing, and what I want the book to mean to people, you're adding on these additional layers. And I think the portrait that I present of him is more nuanced. And then also, just on top of this, I've had a decade more of reading. So I've read more,

• 22:48Ryan Holiday?

  like my stuff on Ulysses S. Grant, my stuff on Lincoln in this book, I think are much better now, because I've read literally thousands of pages about their lives and the time that they lived. And all the while, I was making, oh, that's a perfect obstacle's way thing that I want to add in there. And so I just, yeah, have these like, it's like comedians talk about tags. There was like, which is like a thing at the end of a joke. There's just like a lot of little tags or little extra layers or an additional detail that I wanted to put in there.

• 23:24Speaker 01

  How did, so I remember in the prologue or the intro of this book, you specifically talk about, or sort of anticipating a lot of people's, how they associated the word stoicism 10 years ago.

• 23:38Ryan Holiday?

  Yes.

• 23:38Speaker 01

  And the work you've done since then to make that word mean something very different to a lot of people now.

• 23:44Ryan Holiday?

  Yeah.

• 23:44Speaker 01

  And did that?

• 23:47Ryan Holiday?

  I remember when, I remember when I was writing the book, the Stoicism subreddit on Reddit had like 9,000 subscribers. And I think it has like a half a million now, some crazy number. And so, yeah, when I was writing The Obstacles Away, it was, hey, let me tell you about this thing called Stoicism. And the task was much more along the lines of popularizing and making interesting a thing that a lot of people did not think was interesting. And then one of the tricky things about success is,

• 24:29Ryan Holiday?

  if you succeed, the original context in which you were operating is obliterated. And so, the idea that Stoicism was this unattractive or uninteresting thing to people no longer exists. And so, I think that's something else I wanted to very much address in the book. I'm not, I'm now obligated and able to give a fuller picture of the philosophy that I think is more urgently needed than it was then, if that makes sense.

• 25:08Ryan Holiday?

  The feeling I feel most strongest from this experience, though, is just gratitude. The idea when I was writing The Obstacle is the Way, that I would still be writing 10 years later, that it would sell millions of copies, that it would be in all these different languages, that I would have this platform, that Stoicism would be as popular as it is, that was incomprehensible to me. I feel incredibly fortunate. And that's possible because every one of you that watched one of these videos, that followed us on social media, that read the book, I wouldn't be here, the book wouldn't be here, Stoicism wouldn't be here without the collective. And also, just the sheer amount of emails and feedback, and sometimes not-so-nice criticism, but criticism that was not incorrect. All of that shaped and informed who I am as a person

• 25:52Ryan Holiday?

  and also shaped and informed this new edition of the book. And I'm better for all of that, and I appreciate it.