STOIC SECRETS To Destroy Negative Thoughts & MASTER YOUR LIFE! | Ryan Holiday & Lewis Howes

It's funny, if you should be afraid of anything, you should be afraid of betraying your principles, of falling short, of not doing what you know is the right but hard thing at the time.

I think you gotta have a dream. The School of Greatness. Really?

Yeah.

Please welcome Lewis Howes.

You can't just become a master of your craft. You have to learn how to promote yourself, put yourself out there, create content. Yeah. Be in relationship with managers, do deals, and not rub people around, show up on time. Like all these other things.

Yeah.

You gotta learn. in order to get your craft out there?

When you talk to writers or anyone, like creatives, I just love doing this stuff. It's good, it should just find its audience. Right. Never works. I see it as like two consecutive marathons. So like, you run the marathon, you win, you think they're like, oh, great job, Louis, here's your medal. And you think they're like leading you over to the podium to like, you know, stand in front of everyone. And they're actually just leading you over to like the second marathon that starts right now.

Right now, start running.

Yes, just back to back marathons, like making it, you put everything you had into it, you put your whole life on pause, you know, you gave everything, you have nothing left. And if you do have something left, then you cheated, you know, like you didn't put everything into it. And then they're like, now you have to go on the road, now you have to write articles, now you have to go talk to people, now you have to make all these decisions about the COVID or the title or release date, you know, all the stuff that goes into creative work. And then probably like the third marathon is just like, And now you wait. Like now, because it never happens as soon as you want. Like I started my first blog in 2006. I sold my first book in 2011.

Wow.

My first new... And then my first book about philosophy, the Obstacles Away came out in 2014 and it didn't hit a best seller list until 2019.

Crazy.

So it's on top of all that, then you just have to-- Master your.

Craft or acquire a skill and become really great at it. Then learn how to promote and market it and get it out there in the world. Then wait another five to 10 years for it to actually get the results you wanted to get.

Yeah, it's like investing. First you have to make capital, like earn wages, you have capital. Then you have to find the opportunity, the thing you invest in. Then you have to wait.

To wait five, ten years till you make some money.

Yeah, compounding returns, interest, you just have to let time do its work.

And I don't know if you're like me, 10 years ago I invested in a lot of things that never made money, that I lost all the money. So you have to make a lot of mistakes through the lessons of promoting, marketing, or putting yourself out in the second marathon. And the third marathon of just waiting around for time to pass.

And then what if your thing is really ahead of its time?

Right?

Then you'd know even longer. Then no one cares.

Yeah.

You have to wait longer. I kind of feel like masculinity for me was a little ahead of its time. It came out like right when MeToo was happening. They're like, oh, we don't want to listen to a guy talking about vulnerability. We just want to yell at men.

Yeah.

Or expose the men who have actually done the really hard things, the really bad things. And men weren't looking to find the answers or seek within. And so now I see it happening like a second wave four years later where people are like binding it, buying it, sharing it. They're like, wow, this is really powerful. understand this.

Well, there's this expression that nothing is more powerful than an idea whose time has come. And so the difference I found, yeah, like you work really hard, you make something, it's objectively good, but then timing is not perfectly right. It doesn't fail. It's like a single. But then when you have something and it's exactly timed to the moment, then it's a home run. Or your thing is just kind of floating there waiting for the moment. So like I saw this during the, I've been writing about, stoicism and so resiliency and obstacles and also stillness. These things they worked but then, you know, March 2020 they take on a different relevance to people and so- Six.

Years ago they weren't as powerful.

Yeah, and now also suddenly people have time.

Right. To do a daily meditation.

Yeah, so then it's like then yeah, you can either get a second life or a third life and so I think the the important part is like you do the work, you put yourself out there, you have to trust that it's going to work. Sometimes it does, sometimes it doesn't. But yeah, it's a grind.

I have a thesis that if you want to overcome your fears, you have to go all in on it. I don't think you can out-think your fear. You have to go all in on your fear in order for the fear to start to disappear.

Okay.

You'Ve got to have a lot of courage in order to face the thing that you're insecure about, that you're afraid of, people judging you, that you're afraid of failing or falling down in your face. Sure. But once you overcome it, or at least you're able to face it in a comfortable stance, maybe you're never fully comfortable, but at least you're like, I can do the thing, that's when I feel like your greatest gift can come to the world, or that's where I feel like there's so much reward on the other side But it's extremely scary to face our fears. Why do you think it's so hard for people to face their insecurities, their shame, their fears, their doubts?

Well, if it wasn't scary, then courage wouldn't need to be there.

So.

It'S good that you're afraid, right? I guess one way to think about it is if there wasn't a risk, let's say it's starting a business. If all you had to do was have an idea for a business and then it was guaranteed that you'd be successful, then there'd be a lot more businesses. Right? Like everyone would do it. So the fact that it's scary is partly what makes it valuable.

Right.

Because most people are not going to get over the fear. So like when you think about things that are scary or challenging, it's like you could think about like a heavy weight. If the weight is easy to lift, you're not going to build any muscles. So like that you have that sensation of fear or hesitation or doubt, One way to think about it is that it's a positive sign. Like Steven Pressfield talks about that the resistance you feel is commensurate with the value. So you're not afraid to do things that don't matter. You're only afraid to do big things that matter.

So the harder or the scarier it is, the more valuable that thing is for you sometimes.

I think I would say a lot of the times, not all the time. Maybe it's scary because you're about to you know, implode or drive off a cliff for no reason. Like, it's not that fear has no place, but it could be a sign that you're on the cusp of something. And so when I think about it, I go like, okay, if I'm not pushing myself, if I'm not scared, that's probably a sign that I'm just doing something that I'm already really comfortable with and therefore not growing. So I think it's good. It's a good sign. But I think the reason it's scary, you said you can't out-think it. I don't know, I disagree a little bit. What I would say is that oftentimes the reason we're scared about it is because we haven't really thought about it. So we have these kind of vague fears, you know, like, well, I don't want to do it because... and then you're like, because why? Tell me what you're really thinking about.

The worst thing that would happen, because I could make fun of it, because I get, I lose my money.

It's actually not that big a deal. I talk in the book, there's this story about Pericles. He's this great Athenian general and he's leading these troops in a naval convoy and suddenly there's an eclipse. And imagine living- yeah, thousands of years ago, you don't know what an eclipse is. Just all of a sudden, in the middle of the day, it's dark. And so everyone's scared and they thought, is this like an omen? Is this the gods? Are they angry? There's a similar story where like thunder happens and they're like, what is that noise? What's going on? And it just goes like, so plunged into darkness and he grabs his cloak and he puts it over this guy's head and he goes like, are you scared of this? Like I goes, no. And he's like, but it's just darkness. He's like, what does it matter if the darkness is because the sun disappears or because like I put, you know, my cloak over your head. So I think some of the times we're scared because we haven't really thought about what it is. And so it's kind of this enormous boogeyman that if we actually took a minute and we broke it down and we thought about it, it wouldn't be as scary as it was. So I agree that you want to go head on, but part of head on is just like, what am I actually afraid of? You're like, what is this? And oh, it's not nearly as big as you think it is.

I hear you there. For me, I guess the thing that I'm thinking of is like, when I was a teenager, I was terrified of talking to girls. Sure. And I wasn't able to out-think it and be like, okay, they're just gonna laugh at you, then you're gonna be fine.

Yeah.

I almost needed to experience it and realize physically, I'm okay.

Yeah.

Same thing with salsa dancing. I was fascinated by watching salsa dancers, but I was terrified to get laughed at.

Sure.

And to look out of place and not in the right cultural fit. And for months, I was paralyzed of the idea of looking silly, making someone else look bad, getting laughed at, not fitting in, not belonging, all these things, just not understanding the language of salsa dancing. And finally, I did it for the first time in the middle of, I don't know, probably a hundred dancers, and I was shaking, trembling, terrified. And I remember after about 10 minutes, I looked up and no one cared. No one was watching me, no one was looking at me, but I don't think I'd have been out-think it because the fear was in my body, it was almost like I needed to physically do the action and feel it until I was like, okay, I'm still not comfortable in this situation. But like Batman, he had to live in the cave. He didn't just say, well, let me just think I'm a bat. He was like, I need to become the bat. I need to live with the bats and let them swarm around me and realize, like, I'm not that afraid, or it's okay. I can learn to embrace this discomfort as opposed to. Outthink the fear.

I remember one time I was sitting in a cafe on Houston Street and you walked by and you-- In New York?

Yeah.

It was like it had like a glass wall and all of a sudden I heard this knocking on the door. It was you. And you were like, Hey, I'm going salsa dancing. Do you want to come?

And I just remember thinking like, I.

Would literally rather die than do that.

Right.

Because that's terrifying. But I do think physically experiencing it can be really valuable because you realize, yeah, it wasn't what you thought it was. But it is interesting, so like you, you're afraid of salsa dancing or tango girls. At the same time, you were playing football at an elite level. You were going up for passes, getting smacked by someone running full.

You could literally die.

You were not afraid to be hit basically by a car, and yet you were scared of what people thought. So it's funny, because when we think about courage, we tend to think of physical courage. as being like the end all be all.

I almost feel like it's easier to run into a building that's on fire than it is to like go up and talk to your crush when you're like terrified of the rejection. Because maybe physical instincts would be like, I'm gonna go rescue this person out of a car, out of a crash. Like I would just get up and go, but I would be like, as a teenager, this girl's gonna laugh at me and all my friends are gonna laugh at me and I'm not gonna be accepted and no one's gonna love.

Me and I'm gonna die alone. Well, there's war heroes that run for political office that then are afraid to vote against their party because people will be mad at them or they can't get a job.

Exactly. So different types of courage, right?

Yeah, so we often think of physical courage as the end all be all, but I would actually argue that moral.

Courage is the hardest.

It's the hardest and more rare. And the tricky thing is that people will have one and not the other and it could go in either direction, but that's really the tricky thing.

What has been the heart before you wrote this book? Because I feel like every book you write, there's always something in you of like, I gotta write this because I know I haven't been fully mastered this thing yet.

Of course.

So where were you lacking courage in your life before or during writing this book? Was there parts, or maybe it was years ago that you've mastered now, but what was the thing maybe that was the hardest for you to have courage around?

So I mean, I've gone through scary things in my life, whether it was dropping out of college, the decision to leave the corporate world to become a writer, these are all scary things. Even the decision to go from the marketing track I was on to writing books about an obscure school of ancient philosophy. That was, I took a major hit in the advances. It didn't work right away. I was worried whether people were gonna like it or not. But one of the last stories in the book I talk about when I was at American Apparel, and I think one of the scariest things that people face is, if I do this, I could lose my job, right? Even though this might be a job they're thinking about quitting, like at that very moment, we had this huge mental block between quitting and being fired, right? And I was thinking, the story I tell is I was thinking about leaving American Apparel to become a writer, and then I get asked to do this sort of unethical thing at work, and I say, I'm not gonna do it. I don't do it. But that was as far as I took it. I didn't want to stop, I didn't want to go toe to toe to stop it from happening.

You just did it, said, I'm not gonna do this, but you knew it was still happening.

I said, that's a bad idea. I'm not gonna do it. Find somebody else. But I could have said, that's not right. Don't do that. And I didn't have to watch as it happened. And I think back, I go, why? And it was like, well, you didn't want to lose your job. A job that I left shortly thereafter anyway. And I think what I think about in retrospect is like, why did I want to keep a job that you could get fired from for doing the right thing? And so when we, I think the reason I told the story is that I wanted to make an important point, which is The excuse, I was worried about X or I was afraid of Y does not age well. Like when you look back, you're never glad that you chickened out. Like you never are.

That's the truth.

And so yeah, I don't want the book to come across as like, you know, I'm super brave. This is my story. The story is, the book is, Here are inspiring people throughout history whose courage is calling to us to be better. And like, I actually end the book not with a story of courage, but a story of sort of a failure of courage. Because I think that's really, like, it's funny. If you should be afraid of anything, it should be afraid of, like, you should be afraid of betraying your principles, of falling short, of not doing what you know is the right but hard thing at the time.

How does someone develop their principles or their values if they're not clear on them? Or if they were taught different values by their parents, by society, by friends in high school, college, how did they get clear on those core things?

I think you develop them as you go, and that's why you can't be too hard on yourself when you fall short, because that's one of the ways you are learning. I can learn, yeah.

By being a coward.

Yes, you're right.

By making the mistake of being a coward, you learn through pain.

Yes.

You should have done it differently.

Well, and you learn, oh, the thing you, the self-preservation that you were trying.

To.

That you were following, it's not a guarantee anyway. You know what I mean? You're like, oh, I don't want to mess this up. I don't want to piss off this or that. And it's like, you're assuming that it's yours anyway, that you have control of it, and you don't. And so it's kind of like, It's like the stoics talk about momento Mori, right? One of the benefits of momento Mori is like actually life is too short to try to hang on to it too tight anyway. Yeah, but I think you develop your compass one of the ways I think you do it is is like who are your heroes? Like who do you look up to the models? Yeah, what would they do in this situation? What is the code that they lived by? That could be your grandparents could be your spouse. It could be Jesus. It could be Marcus Aurelius, it could be anyone from history, could be a character from your favorite book. Like, what would they do? I think that's a really key way to do it.

But interesting.

What the book, this book and then the series of books is built around what's called the cardinal virtues, which are actually the virtues in Christianity and Stoicism, actually appear in a bunch of different philosophical schools. But the idea is courage, self-discipline, justice, wisdom. So to me, that's kind of what I, those are the principles that I try to live by. And I think every situation that we face calls for one or all of those things.

Where do you think people lack courage the most? In what parts of their life? Is it in just being honest with themselves? Is it in how they lie to other people? Is it in how they don't stand up for what's right, or at least what they believe is right. Is it physical courage, emotional courage, you know?

I think it's all of the above. And I think it's important, it's like no one is fully brave or fully a coward, right? It's more like day in and day out, what do you do? Right, I see. But I think one of the places we struggle with the most is, if courage is rare, Courage in pursuit of the right thing is rarer still. So the virtues are interrelated, right? Like one of the stories I tell in the book is, okay, think about Michael Jordan. The decision for Michael Jordan to walk away from basketball. And play baseball.

Immense courage, right?

Think of the amount of people who told him it's a bad idea, told him he couldn't make it, wasn't gonna work. Think of the money he left behind, right? Real courage. But I contrast that with Maya Moore leaving equally dominant in the WNBA. She leaves at the height of her career, not to go play a different sport, not to go on some spiritual pursuit, not to spend time with her family, but to free a man wrongly convicted who's spending his life in jail. So courage is important, right? The courage to like, oh, I'm gonna quit my job and start a company. Great, very courageous. But the person who quits a job to dedicate themselves to some meaningful cause, that's to me the level above. So I think it's courage, but courage in pursuit of what? We all know people who are savvy investors, they're great at taking risks, managing risks, they're bold, they're making cool But is it in service of their bank account or is it in service of doing something that matters?

Right. Where do you feel like you struggle the most with courage still?

I think that's a good example. The story I'm telling is where I continue to struggle. It's really hard to say or do things that you know.

Will.

Have financial or career repercussions for you.

Right.

Right? So, like, I think early in my career, I was like, oh, I don't, I guess I've said this to people where it's like, I was just too, I was like, happy to be here or happy to be wanted. So, like, I would go like, oh, this is the opportunity. I'm excited, grateful. Let's do it. Not like, does this align with my values? Do I feel like this makes the world a better place? Right. So, but so it wasn't greed so much that was motivating me, but a fear of what would happen if I said no. So, like, I often find myself saying yes or not objecting or being like fully articulating what I think and feel because, like, I don't want to be on the outside or I don't want to rock the boat, right? So I think what I've been working on is just like, this is what I think, this is what I feel needs to be done, like come what may. I'm trying to get to a place where that is consistently who I am and what I do, but it's scary because like, first off, what if the opportunities dry up because of it, right? And then I think as I've gotten older and you have more responsibilities, you realize like, It doesn't just affect you. It affects the people who work for you.

Yeah, your kids, your family.

Exactly, exactly. So people will go along to get along, right? And that's like, so one of the things that's done is given me some empathy. I have a chapter in the book about like, basically never question, the title of the chapter is Never Question Another Man's Courage. Meaning, like, we watch for like, why are these bums in Washington? Like, why is the mayor doing this? Or like, why isn't LeBron James speaking up about, you know, his indo-- like, why is it LeBron James speaking up about what's going on in China?

Right?

And it's like, why don't you speak up about what's wrong in your industry?

Right?

So it's like, it's very easy to get in this trap where you're criticizing other people's courage or lack thereof, instead of doing what we should be doing, what we should take from these examples is like, what am I putting on the line? What deals am I torching?

How am I stepping up?

Exactly. We look at a politician, we go, why won't they vote for this or that? Who cares if they don't get reelected? And it's like, well, they care. And so it's like, what When have you gambled your career? What stands have you taken where you're like, this is unpopular, but I feel morally obligated to do it, and I'm willing to accept the consequences of that.

What happens if the consequences are really bad, and you are broke for years, and you don't have opportunities for years, even if you want to self-start and just no one's, you're just so, excommunicated from whatever society or community or families that you were a part of that now, okay, I stood up for what was courageous, but what did I get for it? My own personal pride and loneliness?

I mean. Well, there's a tension there. So at American Apparel, so I didn't do that, right? And, but by not doing that.

You kept your job.

I kept my job, which didn't just benefit me. I was then later in a position.

When.

When the company had more leverage over the founder and the owner to actually make it right in a way that worked. Noble failure, what good is that? If you take your stand too early, if you're the person who, you and I both have an audience. If we had earlier on in our career, maybe taken certain stances that audience wouldn't be there to then talk about whatever the important thing is. The problem, the trap is we say, oh, I'll do it later. I'll do it later. I'm still building. I'm still working. And then you never do it because now it's actually more expensive.

Right.

Now we have more to... We think like, oh, that guy's a senator. He should be able to... Or this woman's the governor of the third most popular state. She should, but actually the hard part is as you get bigger, it's more to lose.

Right?

Like you go, oh, this decision could cost me a billion dollars.

A lot.

Not that I ever had a similar cost. But actually it doesn't get easier as you get more successful. It can get harder. So you actually need more courage as you go. It's easy to be the guy on the sidelines saying how things should go. But then when you have, again, when you have people dependent on you, you have influence, you have something you've worked your whole career for, it's scarier. So you need more.

So what is something from the Stoics that everyone should learn right now to help them have more courage and live a greater life? If there are three things that everyone could take away from the Stoics to improve the quality of their life right now, first, what would that be?

I got some good ones. So one of the questions we ask ourselves when we're like afraid of something, when we're thinking about, we go, but what about me? What would I do if?

Right?

Like we're worried and Marcus Aurelius goes, you,'ll meet that with the same weapons you've met all your other problems. So remembering that like, hey, you've been scared before and you're still here.

Right?

So we often, often what our fear is really doing is underestimating or under counting how good we actually are at what we do. Like you're not suddenly tomorrow gonna be a helpless loser. you're the same person you are today. And what will you do? You'll figure it out. Just like if you quit your job, you'd be like, I'm quitting and I'm gonna go find a new job. But if you got fired, that suddenly feels like disempowered, whereas the other one feels very empowered. So remembering what you're capable of to me is really important.

Okay, that's one.

Number two, the Stoics say that we should always be training. So one of the reasons I think it's important to have a physical practice, one of the reasons it's good to seek out adversity and difficulty, is so when stuff happens, you're ready. Epicetus, one of the early Stoics.