Stoicism’s Lessons on Becoming Wise - Ryan Holiday - #1001 artwork

Stoicism’s Lessons on Becoming Wise - Ryan Holiday - #1001

Modern Wisdom

October 2, 2025

Ryan Holiday is a podcaster, marketer and an author. If intelligence were enough, the smartest among us would also be the wisest. Yet time and again, they stumble over life’s simplest lessons. Wisdom isn’t about knowing more; it’s about seeing deeper.
Speakers: Chris Williamson, Ryan Holiday

Topics: Society & Culture, Health & Fitness

**Chris Williamson** (0:00)
How did the live shows go? The last time we were talking, we were discussing upcoming live shows.

**Ryan Holiday** (0:05)
Yeah, I think I was doing two in Australia, and you gave me this advice. You were like, well, you told me that you'd done it with no notes. And usually when you do talks at events, they don't want you to just go up and give a speech, they want a presentation. But this was different. So yeah, I had to figure out how to do it with no notes. Which was, it's good to pick arbitrary challenges and take something that you're good at, that you've done a lot of times, and just figure out a way to do it the hard way.

**Chris Williamson** (0:35)
Yeah, what's new.

**Ryan Holiday** (0:36)
Yeah. And so I had to sort of reinvent it from scratch. It was challenging, but good. It's actually funny, in Mark's Realistic Meditations, he talks about practicing holding the reins with your non-dominant hand. And so just like, what's the way that you're comfortable doing it, what's the way you normally do it, and then how do you force yourself to do it not the way that you like to do it? And to force yourself to do it in front of, the way you're not comfortable doing it in front of 2,000 people.

**Chris Williamson** (1:04)
A huge fucking audience.

**Ryan Holiday** (1:05)
Is it, you know, it's a whole thing.

**Chris Williamson** (1:07)
Difficulty plus.

**Ryan Holiday** (1:08)
Yeah.

**Chris Williamson** (1:09)
I've always thought about doing a podcast episode with a guest that somebody had organized for me and sat down opposite me, and I didn't know who it was. And I had to try and do an episode without breaking the fourth wall that I didn't know who they were, and see if I could excavate what the fuck is going on here. Who is this psych-colo-gist, athlete, coach, trainer, like you, what the fuck are you? And do it without like destroying the episode. I always thought that would be like a fun challenge.

**Ryan Holiday** (1:37)
Well, and the reason you challenge yourself artificially is that life doesn't really care about your plans.

**Chris Williamson** (1:44)
It doesn't play by your rules.

**Ryan Holiday** (1:45)
So I had a talk I was supposed to do in Kentucky, like a couple of weeks ago. And so I was supposed to fly in. I had all day and then I would do the talk at night. And then, you know, I get to the airport at nine and it's like 30 minutes to late, 30 minutes to late, 30 minutes. It's starting to get crazy and some incredibly complicated and very expensive travel adjustments later, I land and I'm in the car. Like I'm already late. So they've pushed it, they've been stalling.
Everyone's there and I'm the last speaker and I'm, you know, I'm texting them and I go, okay, like I just landed. I'm 12 minutes away. I will be there. I will run up and go on and they go, okay, that's awesome. We're waiting for you. Where are your slides? And I go, what do you mean? Like I know for a fact they came in yesterday. So you should definitely have them. But I'm like, here they are again. I'm like texting, here's the link to the, here's the dropout link to the slides again. And they're like, okay, awesome. And then so, you know, they get there.

**Chris Williamson** (2:46)
Seven minutes to go.

**Ryan Holiday** (2:47)
Yes, seven. I open the door, the car and I'm running upstairs. I'm carrying my suitcase up to the thing. I'm getting there. And then as they're miking me up, they go, and you don't have slides, right? It's like, is no one talking to each other? But like, now I know for a fact that you've had the slides for at least seven minutes, you know?
So, and there's like a band on stage performing that's stalling, cause it's like, it's unusual. And the guy goes, okay, so the band's going to play the first 20 seconds of Two Minutes to Midnight by Iron Maiden, and then you're up. And I go, okay, so we got that. Like we had a live band performing a song that I like, but no slides. And then the guy's like, I'll try to figure out the slides. And I go, in the next 20 seconds, what are you talking about? I was like, this is, you know, this is done, man. I was like, I'll just, you know, but I walk and so I start to talk and I'm, you know, now I've got, you know, 45 minutes of time to fill with no slides. And you can't just do the talk you were gonna give without slides because it's, you can't be like, normally there'd be a slide.

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