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RH Ryan Holiday Ryan Holiday Author focused on marketing, culture and Stoic philosophy.

“Very few military figures have ever actually been successful politicians, because they're totally different forms of leadership. One, you have authority, and the other you have to basically use the bully pulpit of persuasion and public opinion.”

The Daily Stoic · Ideas & Essays · November 2026

“Very few military figures have ever actually been successful politicians, because they're totally different forms of leadership. One, you have authority, and the other you have to basically use the bully pulpit of persuasion and public opinion.” — Ryan Holiday, The Daily Stoic

Context

Generalizing from the coaching example, he argues a win in one field tempts people into another that needs a completely different kind of leadership.

Transcript

The Daily Stoic Around 08:38 into the episode
Ryan Holiday

Yeah.

Seth Wickersham

And giving examples of the things that probably have the best chance to prove wise. You know? Well, I think I'm good

Ryan Holiday

at writing. Like on another, I'm good at putting it in writing, which is like the thing I actually like doing. Right. If you told me I had to show up for work every day at, you know, a locker room for a sports team, like that might seem cool, but I would actually hate it. I would hate it so much, like, because I would not be in charge of my schedule. I would be in meetings all day and I would be not operating in the medium that I am most comfortable in, which is the written word. So like it is really important. I think that's, we can deceive ourselves with our own outcomes. Like I actually talk about this in the ego book. Like it's very common, for instance, like someone makes a great general and then somebody says you should run for office. And like very few military figures have ever actually been successful politicians because they're totally different forms of leadership, right? One, you have authority and the other you have to basically use the bully pulpit of persuasion and public opinion. And they're just different…

Seth Wickersham

And no more so than in sports, I think, because you see it all the time where you have a good assistant coach who becomes a head coach.

Ryan Holiday

Yeah.

Seth Wickersham

And they had an expertise for calling plays or coaching pitchers or whatever it might be. But like to be a good head coach, you need to have a completely different skill set, a completely different ego and gall and, you know, fragile self-belief to stand in front of people and get them to follow…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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