Daily Stoic Sundays: If You’re Not Seeking Out Challenges, How Are You Going to Get Better?

In today's Daily Stoic Sunday episode, Ryan talks about the importance of taking on new challenges so that you are pushed to greater and greater heights. He discusses it in the context of writing his book Conspiracy: A True Story of Power, Sex, and a Billionaire’s Secret Plot to Destroy a Media Empire. Get Conspiracy: https://geni.us/bCz57NtRead the original article: https://ryanholiday.net/seek-challenge/This episode is brought to you by Trends. Trends is the ultimate online community for entrepreneurs and business aficionados who want to know the latest news about business trends and analysis. It features articles from the most knowledgeable people, interviews with movers and shakers, and a private community of like-minded people with whom you can discuss the latest insights from Trends. Visit trends.co/stoic to start your two-week trial for just one dollar. ***If you enjoyed this week’s podcast, we’d love for you to leave a review on Apple Podcasts. It helps with our visibility, and the more people listen to the podcast, the more we can invest into it and make it even better. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicSee 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.

• 0:04Ryan Holiday?

  Welcome to the Weekend Edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something that can help you live up to those four Stoic virtues of courage, justice, wisdom, and temperance. And here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We reflect. We prepare. We think deeply about the challenging issues of our time. And we work through this philosophy in a way that's more possible here when we're not rushing to work or to get the kids to school, when we have the time to think, to go for a walk,

• 0:46Ryan Holiday?

  to sit with our journals, and to prepare for what the future will bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan. Welcome to another Weekend episode of The Daily Stoic. I hope everyone's doing well. I hope everyone's wearing a mask. If you hear me say that and you find that to be a political or a frustrating statement, if you don't mind, just hang up the podcast. We don't need to talk or be friends anymore. We are talking about taking care of each other. We're talking about taking care of ourselves. We're talking about being smart. So I just wanted to say that. And then I was going to read an article I've been working on, something I've been thinking about for a long time here. The good news is, this was partly inspired by the fact that I got the unexpected news early this week that my publisher had discounted my book Conspiracy,

• 1:39Ryan Holiday?

  which is the true story of the billionaire Peter Thiel's 10-year secret quest, conspiracy, if you will, to destroy a media empire that had outed him as gay. To me, it is this sort of strange Shakespearean epic story. It's actually being turned into a movie. They're casting it right now. I actually think it's my best book. It's the one I'm most proud of. But anyways, it's discounted on Amazon Kindle in the US right now for $1.99, which is as cheap as basically it's ever been. You can check that out in the show notes, but I wanted to write sort of about why I would take on a challenge like writing that book. And so my idea is like, look, if you're not seeking

• 2:20Ryan Holiday?

  out challenges, how are you going to get better? My point is, if what you're doing is easy, you're not growing. It's like lifting weights. If you can do it without trying, you're not going to get any stronger. The whole point of life of working out and of work is to push yourself and to grow as a result of pushing against and through the resistance. A couple of years ago, I was at a book signing. This is actually the book signing for Ego is the Enemy. And a friend came to the signing and afterwards we were talking and he said, you know, hey, I think you should write a book about Peter Thiel and Gawker. And I said, get out of here. I have no interest in doing that. That sounds extremely hard. That seems like a great way to get my life destroyed and get sued. And by the way, I don't write those

• 3:05Ryan Holiday?

  kinds of books. So, you know, there were way more reasons to say no than yes. It was outside my wheelhouse. It would be a ton of work. It would be the kind of project that would upset a lot of people. And frankly, it was personally quite risky to be writing about a powerful gossip merchant and a right wing billionaire who had just shut down a media outlet that he didn't like. I was just about to have my first kid and it seemed like it would be terribly difficult to manage a newborn and a new kind of book, particularly one that in the case of conspiracy, required that I read something like 20,000 pages of legal documents just to get started. So you can imagine what I said. I said, yes. I don't know why I said yes, but I said yes. I

• 3:48Ryan Holiday?

  knew it would be hard and I also knew that it might not work, but I also knew that it might be the most interesting thing I ever did. And if it did work, it would be a book unlike any of the others that I had written or might write in the future. And mostly I said yes, because I have always believed that a writer betrays their craft if they don't push themselves. In fact, I think this is true of all crafts. If you're not seeking out challenges and getting better through them, what are you doing? And what are you doing it for? One of my favorite passages in meditations is this one. From Marcus Aurelius, he says, "Practice even what seems impossible. The left hand is useless at almost everything from lack of practice,

• 4:29Ryan Holiday?

  but it guides the reins better than the right from practice." Not everything that's hard is good, of course, but most everything good is hard. Think about all the things that you're good at. There was a time when you weren't good at them, right? They were hard, but you worked at it. And despite feeling deficient and frustrated and fighting the urge to quit, you saw a glimpse of goodness. You clawed out a bit of progress. You felt a glimmer of confidence and you chose to keep at it, to keep pushing. And you grew from the fight against resistance. Even more, you found something on the other side of it all, a you that you realized you didn't entirely know and had possibly never met.

• 5:11Ryan Holiday?

  You learned something incredibly valuable about yourself that you're capable of more than you know. And that's why we have to fight those urges to quit. That's why we have to keep at it. That's why we have to seek out challenges. Because would we know anything about ourselves if we never did? In my own writing career, I've grown from each of the challenges I took up. I was asked to write a piece about Stoicism for Tim Ferriss's website in 2009, one of the first times my work would be in front of a large audience. Tim was a tough editor, but I grew from that experience. The things I wrote and researched for Robert Greene were so beyond my depths that I was constantly worried I'd be exposed as a fool.

• 5:51Ryan Holiday?

  But with time, I grew because of the material and ideas I was exposed to. My first book was like flying off a cliff without a parachute and trying to build a plane on the way down. I made it with, trust me, I'm lying, but just barely. And in 2016, having reaped the benefits of those decisions, I was sitting in a nice, comfortable spot. I had two books under contract, nearly finished. I had a backlist that was selling. I had this niche applying ancient philosophy, you know, what we talk about here. So when I got two surprise emails after that conversation I had at that book signing, first from the billionaire Peter Thiel and later from the founder of Gocker Media, Nick Denton, "The decision to write a book about them was to essentially

• 6:34Ryan Holiday?

  gamble the gains of the progress and comfort I had gathered. If it didn't work, wouldn't it set me back in the business? Wasn't it very likely that I would fail on this project? Isn't narrative nonfiction a totally different genre than what I know how to do? Isn't it insane to compete with other people better than me?" And yeah, I thought, "Probably." But there was also, I felt, almost no chance that I wouldn't emerge from the challenge a better writer. That's why I jumped at the chance. I was forgetting the business logic, and I figured it would make me better at my calling, and that was reason enough to do it. And I started writing. It was harder than I thought. It kicked my ass. It made me feel stupid. I doubted myself almost every day. But when I emerged, to paraphrase

• 7:19Ryan Holiday?

  Mark Cirelius, "My left hand was now stronger," although technically, I'm right-handed, so I guess we'd have to flip this. "My practice had seen to my growth." And look, when the book came out, it was crazy. It got great reviews. New York Times called it a "masterwork" and genius and a hell of a page-turner, which, of course, I'm gonna take. And the movie rights were optioned, as I said, and I can't say who will play Peter, but it's supposed to be really cool. And that was good. But the reality is, from a sales perspective, it actually struggled because it was outside my wheelhouse. I would have thought that people just read anything that I wrote because I wrote it. That's sort of how I think about it. But that wasn't the response. And it came out of the gate slow. And the publisher was a little disappointed. And it was weird. It didn't feel like a failure, but it felt

• 8:04Ryan Holiday?

  like a disappointment. It felt like maybe the risk hadn't paid off. And honestly, these were all the things that the people who told me not to do the project had predicted. It all came true. Yet neither the success or the struggle of the project is why I look at that book now with some distance as a win. Defining it early on as an opportunity for growth meant that I controlled the outcome. So if it had sold another 100,000 copies or it had sold zero copies, it would have not made it more successful or less successful to me. Because to me, the success is on the page. It's in my mind. It's in my toolkit, Using right now to talk to you. I got better because it was hard. I took a risk because there was so much resistance.

• 8:47Ryan Holiday?

  And this is the essence of what the obstacle is the way means. That idea from the Stoics. Each obstacle, everything that goes wrong each time we're out of our depths, is an opportunity to practice virtue, to give you a chance to work with your non-dominant hand. One obstacle gives you a chance to practice controlling your temper. Another, a chance to take a long walk through the park. There is always something you can do, including right now, today. We're all going to come to crossroads in life. Decisions about how to do things and what things to do. Should you walk 15 minutes to your meeting or take an Uber? Should you pick up the phone and have that difficult conversation? Or leave it to an email? Should you apologize and take responsibility or hope it goes unnoticed?

• 9:30Ryan Holiday?

  Should you swim in the outdoor pool or enjoy the warmth of the indoor one? As you weigh these competing options, I say lean towards the hard one. Let it steer you away from the drift of least resistance. Seneca talked about how a person who skates through life without being tested and challenged is actually depriving themselves of opportunities to grow and improve. Jump in the colder pool. Have the tougher conversation. Walk instead of drive. Accept the responsibility you've never done before. Take ownership while you can. Choose the more difficult option. Seek out the challenge. Lean into it. Iron sharpens iron. Resistance builds muscle. You'll be better for it, not only for the improvement that comes from the challenge itself,

• 10:15Ryan Holiday?

  but for the willpower you are developing by choosing that option on purpose. When you have two choices, choose the one that challenges you the most. Choose the one, as Marcus would agree, that allows you to take the reins in any situation. And so, look, will I ever do a book like this again? I don't know. Maybe if I ever found a story as good as this one, that I remain as obsessed with to this day, as I remain with this one possibly. But overall, it was just this, you know, it was a great experience. I got to spend time with two of the most provocative, you know, sort of unique figures of our Nick Denton and Peter Thiel, I got to meet Hulk Hogan. He showed up to our meeting in a shirt with his own face on it.

• 10:57Ryan Holiday?

  I got to study what a conspiracy is. I got to study history. I got to study strategy. You know, I got to connect with Robert Greene. He gave me a bunch of advice on the book. It was actually his idea to connect it to the Machiavellian chapter on conspiracies, which I happened to also find a copy of in Peter Thiel's apartment. So it was just, I don't know, it just felt right. And it was this cool, strange experience. And again, if it had sold zero copies or if it had been the success that it has been, if the movie comes out and as good as they're thinking it will be, I've read the script. It's really great. You know, maybe I'll think about it even differently, but I'm trying to go, I accepted a challenge and I grew better for the challenge. I don't need a trophy at the end of it.

• 11:40Ryan Holiday?

  The trophy is that I'm better at writing. And the books that you may have read from me, if you haven't read Conspiracy, that I've published since 2018 have been better because of the sort of crucible I went through in doing this in that book. And so that's how I try to think about it. I seek out challenges and I hope that you'll walk away from this idea that you can learn from that example as well, which is, you know, Eleanor Roosevelt says, do the thing you cannot do. Do the hard thing. You're better for it. Push yourself. Don't get comfortable. Actively seek out that discomfort and you'll be better for it. So anyways, look, Conspiracy is 199 on Amazon Kindle right now. I guess probably anywhere eBooks are sold.

• 12:25Ryan Holiday?

  I think it's my best book. As I said, it's got rave reviews. If you don't agree with everything, I think you'll still admit it's a hell of a story. Check it out. This is as cheap as it gets. If you have read it and liked it, I'd appreciate an Amazon review. It makes a difference. Or just tell someone about it. That's how books spread and stay tuned for the movie. Charles Randolph, who wrote the script for The Big Short and then Bombshell, the movie about Roger Ailes, is the one who wrote the script of it. And there's a great director attached. And so you and I both remain in the dark as to when that will happen, but maybe it will. And I will look forward to watching the story on the big screen as well. If you like the podcast that we do here and you want to get it via email every morning,

• 13:09Ryan Holiday?

  you can sign up at dailystoic.com/email.