The School of Greatness - 633 Let Go of Ego with Ryan Holiday

Episode Date: April 27, 2018

“CULTIVATE PEOPLE AROUND YOU WHO ARE NOT AFRAID TO TELL YOU YOU THE TRUTH.” Whether you want to admit it or not, you have an ego. Everyone does. We tend to put a bad connotation on it, but in truth a little ego is healthy. Ego can be confidence about yourself and what you do. It can be a challenge if you become successful, because people become afraid of telling you the truth and pointing out your flaws. To keep growing, however, you must surround yourself with people who aren’t afraid to tell you the uncomfortable truths in a polite way. And if you truly respect someone with power over you, you’ll do the same. To go deeper into this, I am bringing back a strong segment from a previous episode with Ryan Holiday. Ryan is a writer and media strategist. When he was 19 years old, he dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power. He went on to become the director of marketing for American Apparel. His creative agency, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors, including Neil Strauss, Tony Robbins and Tim Ferriss (and me). He has worked with huge egos in his career, but what I love about Ryan is his willingness to take on his own ego as well. Learn how to control your ego and help those around you on Episode 633. In This Episode You Will Learn: The spectrum of Ego (00:54) Where confidence comes from (1:33) How to continue your growth (3:02) When people stop listening to the truth they need to hear (3:32) How to tell powerful people the truth (5:18) What to do when you’re right (5:48) Plus much more...

This is 5-Minute Friday! And Ryan Holiday is a media strategist and prominent writer on strategy and business. And after dropping out of college at 19, he went on to advise many best-selling authors and multi-platinum musicians. He served as director of marketing at American Apparel for many years, and he is also a bestselling author of The Obstacle is the Way. Ryan and his partner, Niels, were also a key component in the strategy and the success of the School of Greatness book. They were a huge part of it for me, and it wouldn't have been a huge success, sold over 55,000 copies by now, and also hit the New York

Times bestseller list. So I'm super grateful for his strategy. And I believe he's just a brilliant mind. Aristotle says that it's a spectrum. So he would say recklessness and cowardice are the extremes and my courage is in the middle, right? Or it's above, so it's like a triangle. And I think it's like that. So confidence, like ego is I'm the greatest who ever lived. I'm perfect. I've got it all handled.

Nobody knows better than me. Yeah. And then like I'm worthless. I don't know anything. Why would anyone listen to me? In a weird way, those are both sort of self-absorbed yes positions right you're just all you're just thinking about yourself denial on the either yeah right yeah and you're just over here just not thinking well of yourself and over here you're thinking too well of yourself so confidence is in the middle but i think it's interesting

like confidence has to be based frank shamrock an MMA fighter. He was saying like confidence is earned. If your confidence is on, I did the work or that I'm a fast learner or that I'm like, I'm a fast learner. So I'm going to be able to figure this out. Or like, um, I studied harder than anyone else. Or, you know, I've like, I know I can do this because like, you know know about how much weight you can lift because you go to the gym and you've done it before you might have a an inkling that you're capable of a lot more but you're confident based on what you've done or done in a sort of a reasonable circle

so i think that's where the confidence is it's's like, okay, I know that I can write a book because I've studied harder. I've written long things before. I've worked with other authors. You know, those, it's not like, oh, sure, I should have a book. You know, like that, that's the difference. If ego is being confident in things that you shouldn't be confident in, reality is like, oh, wait, okay. I got too far over my skis. I went too far in the other direction. I needed like a little bit of a wake up call. And so sometimes that's why failure can be good or not catastrophic failure, but like little things, right? Like

you're confident. So, you know, you put something out there and someone's like, Hey, this is wrong for the following reasons. You got to listen to that stuff or you keep investing and you go further and further. And then when you do fall and you go further and further and then when you do fall and when you do fail it's like really painful yeah interesting so i think you got to cultivate people around you who are not afraid to tell you the truth that's the hard part especially as you become successful i'm sure you've seen this i think you've got to be willing to have people tell you the truth because most people don't want to hear the truth yes right even if they say it they're like they don't want to hear it right right you have to make sure

you don't punish people for telling you the truth like by not talking to them or fighting them even if you disagree you have to hear them but it's like it's like you can realize like man i only talk to people who worked for me today right like who are in some sense not super motivated to tell me the truth like i've been around a lot of really really successful wealthy people and you realize like the only way i could deliver the truth to this person would be like a kamikaze mission like like they we would not be friends after like they've gotten so far that like i'm gonna have to i'm gonna have to go in and say all this unpleasant stuff and that's going to be the end of it and then you realize like and then you usually don't do it if i've gotten to a point where like

you follow me on social media and you like you knew you know what my life is like but the pictures i was posting were not at all representative you knew maybe i was inflating numbers about what i've done or look at this photo with me and this celebrity, but you knew like I paid to meet that person, you know, all the things. And you might know like, hey, Ryan, like you might want to say like, hey, Ryan, like people are starting to think you're full of it. Like you're not, you don't, you're not coming off well, you should change. But like you might not do it because you would be worried that I'm going to, I'm going to shoot the messenger essentially. Right. And so that's the difficult thing is like if you don't have that realism in your life and you don't cultivate it, you're not checking in all the time, you get to a point where it's like people realize that it's not in their interest to tell you the truth. If everyone else is lying, like if everyone else in that organization is not telling the truth, oftentimes being the person that tells the uncomfortable truths is a position of power because you're the only one that's not like everyone else.

You'll start to trust your opinion more. And I think, so the big thing I found is that it's not about showing that you're smarter and it's not about making them feel stupid. It's often, I find it's, hey, here's my opinion about this thing. Like, let's say someone's making some important business decision and you think they're making the wrong decision. You say, look, I think this is the wrong decision for these reasons. But you're the boss, so you've got to make the call. And then whatever they decide, if they decide not to go with you, you still have to support them in whatever they're doing.

And then you have to let the results speak for themselves. If they're not insane, they'll remember, hey, Lewis told me when I was thinking about investing in this company, and Lewis said, that's a bad idea. And I did it anyway. And then I lost all my money. As long as you weren't a jerk to them, and you didn't rub it in along the way. And then I like to even pretend that I didn't do it. I not only don't want to do I told you so. I want to like. Well, your ego wants to say that.

Sure, sure. Yeah. But I'm saying like politically and relationship wise, you not only don't say you told you so, you don't even mention it, right? Let it go. Let it go and let them say – let them remember, hey, at that critical moment, Lewis was right and he was big enough about being right that he didn't rub it in. he's the kind of person that I should go to for advice in the future. Or he's a voice that I know is reasonable and speaking the truth and not selfish and just not about him. It's about the truth.