How Stoicism Can Help You Persevere and Succeed

​​On today’s podcast Ryan speaks to a group of entrepreneurs about one of the biggest threats they will face in pursuing their goals: themselves. Our egos can stunt us, alienate us, tarnish our successes and deepen our failures, which is why it is so maligned by the Stoics. Watch the video: https://www.youtube.com/watch?v=WOvvZBPcF_IThe Jordan Harbinger Show is one of the most interesting podcasts on the web, with guests like Kobe Bryant, Mark Manson, Eric Schmidt, and more. Listen to one of Ryan's episodes right now (1, 2), and subscribe to the Jordan Harbinger Show today. Sign up for the Daily Stoic email: https://DailyStoic.com/signupFollow us: Instagram, Twitter, YouTube, TikTok, 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.

• 0:03Ryan Holiday?

  Welcome to the Weekend Edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:53Ryan Holiday?

  Hey, it's Ryan. Welcome to another Weekend episode of the Daily Stoic Podcast. You might not think of me as a business owner, but of course, that's what I am. Every author is an entrepreneur. You work for yourself. You have to eat what you kill. You have all these collaborators and people who work with and for you, but at the end of the day, you work for yourself. But also, Daily Stoic, as it's grown and grown and grown, has become its own business. And now, for almost 10 years, I've had my own marketing business, Brass Check, as well. And Stoicism has been a philosophy that's guided me in that. I've, you know, even one of my first articles was Stoicism 101, Stoicism for Entrepreneurs.

• 1:36Ryan Holiday?

  But Stoicism is great for a small business owner because you're responsible. And there's so much that you don't control. And all you really control is how you respond. And I think you see companies fall apart because of the CEO or leadership. They don't know, as we say, ego is the enemy. You see people put their lives in to something, but they don't actually prize what's important. And so, that success is meaningless. Really, I think what Stoicism is, is a sort of set of principles, a guiding philosophy that helps you as a... Business owner and executive that helps you in the real world. And I don't think it's a coincidence, of course, that Zeno himself began his pursuit

• 2:21Ryan Holiday?

  of philosophy coming after the collapse of his small business. He was a die merchant. And so today's episode is about how Stoicism can help you perse-- is about how Stoicism can help you persevere and succeed specifically, I think, in business. So I hope you like these lessons and I'll talk to you soon.

• 2:45Ryan Holiday?

  What happens as an entrepreneur when at the early stages, everyone tells you your idea is crazy, it's not going to work, you absolutely shouldn't do it, do not quit your job, do not invest this money, do not go down this road, it will only lead to ruin. And then it turns out that you're right and they're wrong, right? This is what every successful entrepreneur's story looks like. So what a lot of people do, if you're motivated by ego, if you don't have a good check on your ego, is you learn from this, never listen to other people, right? It takes everyone who's giving you feedback, everyone who's expressing doubt, and it tells you that they're haters and you absolutely shouldn't listen to them, right? And sometimes when people are telling you, "Stop, don't do this," they're preventing you from driving right off of a cliff. So I watched ego destroy this company that I loved, and I think everyone has seen ego

• 3:30Ryan Holiday?

  tear apart people in their lives, businesses that they're a fan of, bands that they're a fan of. We're pretty good at spotting other people's egos, we're much less good at identifying where ego is causing problems in our own lives. Just as an example, right, I write this book about ego and probably the most common question I get is, "How can I do something about my boss's ego?" It's never, "How can I do something about my own ego?" Which of course ironically is ego. So ego is this force, I argue, that sucks us down like gravity. Cyril Connolly, a British writer, he said that. And look, if ego was a problem, it sucks us down like gravity. If you're never getting off the couch, it's not really a big problem, you're already down there. The problem is all of you have employees who count on you, investors who count on

• 4:15Ryan Holiday?

  you, families who count on you. When you're out doing big things in the real world, ego has some real world And so that's what we're going to talk about today. Ego is a timeless element in the story of catastrophic collapses. This is John Delorean, the inventor of the Delorean Motor Company, super talented executive at GM, brilliant inventor, brilliant engineer. His playbook for Delorean is essentially the playbook that Elon Musk has now run with Tesla, but it didn't work out. And why didn't it work out? Someone once described Delorean's leadership style as chasing colored balloons. He would go to whatever the fancy, sexy, exciting thing was. He was an extreme micromanager and then ironically not interested in solving the really tough,

• 5:00Ryan Holiday?

  complicated problems that didn't have easy solutions. He loved the marketing side of things because that's where the validation and the fun is, but actually delivering on the promises of the of the marketing was another. He actually collaborated on a book called On a Clear Day You Can See General Motors. He wasn't even close to General Motors, but that's what ego sort of puffs us up. And then as the wheels start to come off, literally, of the Delorean Motor Company, instead of deciding, hey, I'm going to get really serious about this. Hey, I've got to fix these problems. Hey, I've got to look in the mirror and see, you know, what the root of these problems is. He decided that a $50 million cocaine deal was the way to secure some much-needed bridge financing. Not a good idea for anyone fundraising, and it ends ultimately in handcuffs.

• 5:45Ryan Holiday?

  Howard Hughes, another sort of brilliant mind, but becomes increasingly untethered from reality as fewer and fewer people can tell him no. Richard Nixon, people forget Richard Nixon was re-elected in the largest landslide in American history, but he would talk about how he'd always seen himself as the underdog. He sort of was stuck in this vision of himself as the little guy because that's what he was his whole life. He remembered being bullied. He remembered being kicked around. And so he brought this kind of paranoia to the White House that made him constantly lash out and pick fights with people, which ultimately proved to be his undoing. So if ego is so destructive, why is it so common? Well, I would argue, one, we don't have a lot of good examples, but also doing things

• 6:28Ryan Holiday?

  is scary, and so we we sort of take the edge off in the ...form of ego. This is Billy McFarlane, the creator of Fire Fest, right? Selling a festival is fun. Delivering on an island festival, not so fun. He actually called me before he went to prison. He wanted me to talk to him about writing a book. So again, not learning the lesson of his failure in any way. Again, we love the social media. The image of being an entrepreneur, selling the brand of being an entrepreneur, but actually delivering it is something else. Steve Jobs, right? Steve Jobs should have been fired from Apple. They absolutely made the right decision firing him from Apple. He was totally unmanageable. He was way behind, way over budget. He would burst into tears at the slightest provocation.

• 7:13Ryan Holiday?

  I think we can often take the wrong lesson from someone like Steve Jobs. There's all sorts of way less talented people that sort of see themselves as a Steve Jobs-esque figure. But like, the second chance that Steve got, that was extra. That was a stroke of good fortune. Most stories don't have a redemption like that. So, we have to look at the opportunities that ego is closing off for us. Kanye West, of course. I would argue that in the studio Kanye has to be humble and obsessed with craft. You couldn't make the music that he makes if he wasn't. The problem is, he can't, once he leaves the studio, contain the ego and it sort of constantly gets him into trouble. Elizabeth Holmes, she loved, again, the idea of seeming like Steve Jobs.

• 7:57Ryan Holiday?

  She even mimics the turtleneck sweater. The problem with faking it till you make it is that's just another way of saying fraud. And the Elizabeth Holmes story, again, is a story of a person who marketed their way to the top but didn't like the actual delivery of a product that worked. This is 6'9", Takashi 6'9", now facing life in prison. A strange story in hip-hop, decides to join a gang and commit armed robberies after he became a successful rapper, because he liked the street cred of it, I guess, right? But now he will not record another song. And then, of course, it's impossible to talk about ego without mentioning this guy. Trump is a great example, wherever you sit politically, of how ego takes a really hard job being president.

• 8:42Ryan Holiday?

  And makes it harder and harder and harder every single day, right? He is constantly making enemies that he doesn't need to make. He's bringing on investigations that don't even need to happen. What ego does is it sort of picks fights. It makes us the center of things we don't need to be the center of. And it's just, again, the enemy that we're going to talk about today. So my argument is, look, building and leading things are scary and ego is kind of a defense mechanism from dealing with the reality of that fear and that terror. Elon Musk described starting companies as eating glass and staring into the abyss of death. Maybe you guys can relate to that a little bit. I know I can't. But he keeps starting companies, right? And so ego is kind of like a defense mechanism against that, but it ultimately makes that

• 9:26Ryan Holiday?

  thing scarier and harder and less likely to succeed in the long run. So my argument is that doing anything important is scary. Steven Pressfield calls that that fear the resistance. And instead of facing the resistance, instead of facing it with our eyes wide open, ego creeps in to kind of numb us in the way that, you know, really talented, sensitive people are attracted to drugs or alcohol. Ego is like a numbing agent. And actually, in Alcoholics Anonymous, they describe ego as a conscious separation from. And what they mean is it's kind of a buffer, a bubble that we put around ourselves. And while that might feel good in the short term, the problem is what that separates us from are the most important things, both in business and in life.

• 10:10Ryan Holiday?

  So I would argue that it's a conscious separation from our employees, from our customers, from our friends, from our family, most of all from truth, right? As entrepreneurs, we have to, we need truth. We need real feedback. We need real data on what's happening and how things are working. And if ego is there corrupting that or misleading it, that's when you end up making really bad decisions that lead your business astray or lead your personal life astray. Remember Courage is Calling: Fortune Favors the Brave is now available everywhere. You can go to your local bookstore and pick it up. You can come to the painted porch and pick it up. We are still offering the preorder bonuses. We've extended it to the end of this week. So you can get that at dailystoic.com/preorder. But you can also get Audible, you can get eBooks, you can get whatever you want from

• 10:54Ryan Holiday?

  wherever you want it. But I would very much like you to support the new book Courage is Calling: Fortune Favors the Brave.