SW

Seth Wickersham

Things Seth Says on Podcasts

Where to Find Them

Seth Wickersham has been a guest on The Daily Stoic (4 times) .

Recently: “3 Pieces of Advice Worth Keeping Close | Seth Wickersham” on The Daily Stoic (November 2026); “What It Means to Be on That Hill | Seth Wickersham” on The Daily Stoic (September 2026); “The NFL Idols America Obsesses Over | Seth Wickersham (PT. 2)” on The Daily Stoic (September 2025); “The Heaviest Crown in America: The Quarterback’s Throne | Seth Wickersham (PT. 1)” on The Daily Stoic (September 2025).

What They Said

“To be a good head coach, you need a completely different skill set, a completely different ego and gall and fragile self-belief to stand in front of people and get them to follow you, not get them to run a certain play that you're calling.” — Seth Wickersham, The Daily Stoic

Talking about how success at one skill misleads people about another, the sportswriter explains why great assistant coaches often fail when promoted to head coach.

The Daily Stoic · 2026-11-07 Permalink → Listen →
The Daily Stoic Around 10:47 into the episode
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 you, not get them to run a certain play that you're calling. Like I think that it's so interesting. You look at the Bulls in the 90s and you had Phil Jackson and Tex Winner and those two were the perfect mix of that where you had one person who knew his expertise and that was designing offenses and communicating how to make this offense that ends up revolutionizing basketball and the career of Michael Jordan work. And then you have Phil Jackson who, I mean, man, if you had been writing your books in the 90s, I mean, you would have been with the Bulls every week. He would have had you in there all the time because all he was trying to do was find wisdom and find ways to get people into a common sensory experience that was separate…

Speaker 4

Look, it's been a while since I've had to fill out an expense report. That's one of the perks of not having a job, but I don't remember enjoying the experience. And certainly, I don't want my employees to waste a bunch of their time doing it. You know, you got to find the receipt. You got to guess…

Ryan Holiday

hours a week,

Speaker 4

50 weeks a year for 40 years. That's a lot of time. Your career is the biggest opportunity you have to make if you want to make a positive impact on the world. Because look, if you're a talented person, if you have talents, how you direct those talents and what you direct those talents at, it…

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

Collections They Appear In