Ryan Holiday

Lewis Howes:              This is 5-Minute Friday!!

Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at nineteen, he went on to advise many bestselling authors and mult-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 Neels were also a key component in the strategy and 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 New York Times Bestseller list, so I’m super grateful for his strategy and I believe he’s just a brilliant mind.

Ryan Holiday:               Aristotle says that it’s a spectrum, so he would say, like, recklessness and cowardice are the extremes, and courage is in the middle. 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.”

Lewis Howes:               “I’ve got no flaws.”

Ryan Holiday:               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 positions, right? You’re just always thinking about yourself.

Lewis Howes:               Denial on the either…

Ryan Holiday:               Yeah, and you’re just over here not thinking well of yourself, and over here, thinking too well of yourself. So confidence is in the middle. But I think it’s interesting, confidence has to be based… Frank Shamrock an MMA fighter, he was saying confidence is earned.

If your confidence is on, “I did the work,” or, “I’m a fast learner,” or, “I’m a fast learner so I’m going to be able to figure this out,” or, “I studied harder than anyone else,” or, “I know I can do this because…” Like, you know about how much weight you can lift, because you go to the gym and you’ve done it before. You might have 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 confidence is. It’s like, “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.” It’s not like, “Oh, sure! I should have a book!” 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 a little bit of a wake up call.” And so, sometimes that’s why failure can be good. Not catastrophic failure, but little things, right?

Like, you’re confident, so 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 when you do fail, it’s really painful.

Lewis Howes:               Yeah. Interesting.

Ryan Holiday:               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 that.

Lewis Howes:               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. Even if they’ll say it, they don’t want to hear it, right?

Ryan Holiday:               Yes. Right. You have to make sure you don’t punish people for telling you the truth, by not talking to them, or fighting them. Even if you disagree, you have to hear them. But it’s like, you can realise that, “Man, I only talk to people who work for me today.” 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 realise, “The only way I could deliver the truth to this person, would be a kamakazi mission.” We would not be friends after. They’ve gotten so far that I’m going to have to go in and say all this unpleasant stuff, and that’s going to be the end of it. And then you usually don’t do it.

If I’d gotten to a point where you follow me on social media and you knew what my life was 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 that I’d paid to meet that person.

You know, all the things, and you might want to say, “Hey Ryan, people are starting to think you’re full of it. You’re not coming off well. You should change,” but you might not do it, because you might be worried that I’m going to shoot the messenger, essentially, right?

And so, that’s the difficult thing. 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 people realise that it’s not in their interest to tell you the truth. If everyone else is lying. If everyone else in that organisation 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.

Lewis Howes:               So they can trust your opinion more.

Ryan Holiday:               Yes. So the big thing that 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’ve still got 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… I not only don’t want to do, “I told you so,” I want to like…

Lewis Howes:               Well, your ego wants to say that.

Ryan Holiday:               Sure. Sure, yeah. But I’m saying politically and relationship wise you not only don’t say, “I told you so,” you don’t even mention it, right?

Lewis Howes:               Let it go. Let them say.

Ryan Holiday:               Let it go and 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.”

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