Ryan Holiday

Holiday credits the success of his books mostly to Stoic philosophy rather than himself.

“the reason the books work is 90% the philosophy and 10% me”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:51:12

Holiday urges people to read more history and consume less real-time news to understand events in context.

“People watch too much news and don't read enough history”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 22:19

Holiday argues Stoicism means processing emotions and asking whether they are productive, not suppressing them.

“To me, it's about processing that emotion asking yourself, hey, is this productive or not productive?”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 17:58

Holiday says his youngest son attended an outdoor nature school for pre-K and kindergarten.

“he did kindergarten and pre-K for several years at an outdoor school”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 2:35:31

Holiday says he evaluates commitments by how many of his children's bedtimes they would cost him.

“I try to measure like the stuff that I do or I say yes to, I measure it in bedtimes”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 2:32:31

Holiday says his publisher doubted a Stoicism book, paying him less than half his previous advance for The Obstacle Is the Way.

“For the book that became The Obstacles Away, I took less than half what I got for Trust Me, I'm Lying”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:42:14

Holiday argues ego undermines rather than fuels ambition.

“I actually think ego is the enemy of the ambition that you have”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:37:58

Holiday cites Aristotle to argue virtue is a practiced habit rather than a fixed trait.

“It's a verb, not a noun. It's a thing you are doing or not doing”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:32:39

Holiday argues that both cowardice and courage spread through example.

“like acts of courage, like cowardice is contagious and so is courage”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:31:17

Holiday argues independent creators are more directly exposed to audience capture because fewer intermediaries sit between them and payment.

“So like audience capture, there's fewer intermediaries between the creator and the sort of payment structure”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 57:51

Holiday says research found emotional extremity is the top predictor of content going viral, incentivizing exaggeration.

“they found that like the valence of the extremeness of the emotion is, like, the number one predictor of virality”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 50:58

Holiday condemns 'alpha male' Stoicism influencers, arguing the philosophy is centered on virtue and justice.

“stoicism is not a recipe for making you a better sociopath”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 3:07:32

Holiday praises Audie Murphy for declining cigarette and alcohol endorsements to avoid modeling them for children.

“he turns down all drug sorry all cigarette and alcohol endorsements because he doesn't want to model that for kids”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 3:05:07

Holiday rejects speed reading, saying he reads at a medium pace but devotes a lot of time to reading.

“I would say I read at a medium speed. I just spend a lot of time reading”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 2:59:10

Holiday highlights Seneca's idea that death lies in the time already lived rather than in the future.

“he says it's wrong to think of death as something that happens in the future”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:56:36

Holiday argues the founders designed ambition to check ambition and that eroded governmental and cultural checks are alarming.

“the founders set up a system where ambition was supposed to be a check against ambition, right?”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:21:34

Holiday says the Jade Helm conspiracy was later found to have been largely amplified by foreign actors.

“it came out in the years after that this was mostly like a foreign sort of... propagated theory”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 1:07:14

Holiday says Trust Me, I'm Lying was essentially an early book about fake news.

“I mean, I basically wrote a book on fake news in 2011”

The Shawn Ryan Show: #321 Ryan Holiday - The Stoic Survival Guide (Jul 13, 2026) · Listen from 48:28