#321 Ryan Holiday - The Stoic Survival Guide
Episode of The Shawn Ryan Show · July 13, 2026 · 3 h 13 min
Shawn Ryan and author Ryan Holiday discuss Stoicism, emotions and revenge, media incentives, political courage, ego, mortality, fatherhood, wealth, and reading.
Summary
Author Ryan Holiday joined host Shawn Ryan for a wide-ranging conversation on applying Stoic philosophy to modern life. Holiday opened by gifting books, including Marcus Aurelius's Meditations and James Stockdale's writings, then argued that Stoicism is not about suppressing emotion but about processing feelings and returning to center, citing accounts of Marcus Aurelius weeping. Ryan described his own struggles with anger, revenge fantasies, and political frustration, and his experience with psychedelic treatment.
Holiday recounted discovering Stoicism in college, working as marketing director at American Apparel, and writing Trust Me, I'm Lying, which he described as an early book on fake news. He argued that attention-driven incentives, the clip economy, and audience capture distort information, and that foreign actors exploit these weaknesses, citing the Jade Helm conspiracy. The two discussed why politicians fail to act on conscience; Ryan said he no longer hosts politicians and believes public conversation matters more than lobbying decision makers, while Holiday stressed checks and balances, the dangers of leaders surrounded by yes-men, and courage as a habit.
Later segments covered ego and humility, memento mori and Seneca's idea that death lies behind us, and extended discussion of fatherhood: picking battles, sharing parenting labor, measuring commitments in missed bedtimes, following children's curiosity, raising non-entitled kids amid wealth, and apologizing to children. Holiday called speed reading a scam and made a case for reading. In closing, responding to a question about Audie Murphy, he praised Murphy's moral courage and condemned Andrew Tate and 'alpha male' Stoicism, emphasizing justice as the fourth Stoic virtue.
Chapters
- 0:05
Book gifts
Holiday presents books including Meditations, Stockdale's writings, a Churchill parenting book, and Freak Kingdom.
- 10:21
Introduction and Stoicism for anxiety
Ryan introduces Holiday and relays a Patreon question about applying Stoicism to anxiety and depression.
- 16:13
Emotions and the release valve
Holiday explains Stoicism's origins and argues it means processing rather than bottling up emotion.
- 21:12
Politics, history, and revenge
The pair discuss political frustration, historical perspective, revenge fantasies, and protecting one's mind.
- 42:47
Origins, American Apparel, and media
Holiday recounts discovering Stoicism, his American Apparel years, and the media incentives described in Trust Me, I'm Lying.
- 1:10:37
Power, courage, and politicians
They discuss culture versus decision makers, why politicians avoid conscience votes, and courage as a habit.
- 1:20:16
Hypocrisy and checks and balances
Holiday argues leaders need honest feedback, citing Hadrian, Marcus Aurelius, Putin, and Lincoln.
- 1:37:22
Ego and humility
Holiday discusses ego as the enemy of ambition, trusting one's gut, and staying humble amid success.
- 1:54:52
Mortality and memento mori
The conversation turns to how brushes with death fade and Seneca's view that time passed belongs to death.
- 2:05:04
Fatherhood
Holiday shares parenting lessons on picking battles, shared labor, bedtimes, and nurturing curiosity.
- 2:39:35
Raising kids amid wealth
They discuss preventing entitlement, leading by example, and apologizing to children.
- 2:58:32
Reading
Holiday calls speed reading a scam and argues for making time to read.
- 3:03:16
Audie Murphy and alpha male Stoicism
Holiday praises Audie Murphy's moral courage and criticizes Andrew Tate and virtue-free Stoicism.
Key points
What was said, by whom, with the exact words. Timestamps jump to the moment.
- Ryan Holiday
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?”
- Ryan Holiday
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”
- Shawn Ryan
Ryan says psychedelic treatment in Mexico four years ago led him to stop drinking entirely.
“I began treatment in Mexico four years ago. I haven't had a drop of booze since”
- Ryan Holiday
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”
- Ryan Holiday
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”
Listen from 50:58 · Media credibility and independent journalism
- Ryan Holiday
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”
Listen from 57:51 · Media credibility and independent journalism
- Shawn Ryan
Ryan says he no longer hosts politicians, even friends running for office, because they tell audiences what they want to hear.
“I even have friends that are running for Senate, for Congress, for whatever places in the administration doesn't matter, you know, and, um, I won't have them on”
Listen from 1:01:25 · Media credibility and independent journalism
- Ryan Holiday
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”
- Shawn Ryan
Ryan argues that starting public conversations has more impact than lobbying decision makers directly.
“It's the conversation that happens that engages the population has a much, much bigger impact than going directly to the decision maker”
- Ryan Holiday
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?”
Listen from 1:21:34 · Separation of powers in the United States
- Shawn Ryan
Ryan recounts hitting back at a congressman who attacked him earlier in the year, saying the congressman is no longer in office.
“I went right back at him and now he's no longer in fucking Congress”
- Ryan Holiday
Holiday argues that both cowardice and courage spread through example.
“like acts of courage, like cowardice is contagious and so is courage”
- Ryan Holiday
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”
- Ryan Holiday
Holiday argues ego undermines rather than fuels ambition.
“I actually think ego is the enemy of the ambition that you have”
- Ryan Holiday
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”
- 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”
- Ryan Holiday
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”
- Ryan Holiday
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”
- Ryan Holiday
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”
- Ryan Holiday
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”
- Ryan Holiday
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”
- Ryan Holiday
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”
People
In the conversation
- Shawn RyanFormer U.S. Navy SEAL and CIA contractor, host of the Shawn Ryan Show
- Ryan HolidayAmerican author on Stoicism and founder of Daily Stoic
Discussed
- Marcus AureliusRoman emperor and Stoic philosopher whose Meditations Fullmer studied
- EpictetusGreek Stoic philosopher and former slave
- SenecaRoman Stoic philosopher and adviser to Nero
- James StockdaleU.S. Navy vice admiral and Vietnam POW who applied Stoicism in captivity
- Steve RinellaAmerican outdoorsman and author, host of MeatEater
- Hunter S. ThompsonAmerican journalist and founder of gonzo journalism
- Winston ChurchillBritish prime minister during the Second World War
- Elon MuskEntrepreneur behind X, xAI and SpaceX, discussed in AI competition
- Adam KinzingerFormer U.S. congressman quoted on congressional passivity
- Bob CorkerFormer U.S. senator cited as having lost prospects after criticizing the White House
- Thomas MassieKentucky congressman facing a Trump-backed primary challenge
- HadrianRoman emperor who selected Marcus Aurelius's line of succession
- Zeno of CitiumFounder of Stoicism
- Audie MurphyMost decorated American soldier of World War II and actor
- Andrew TateOnline influencer cited as an example of the manosphere
- Robert GreeneElizabethan writer credited with the 'upstart crow' pamphlet
- Matthew McConaugheyAmerican actor quoted on parenting with money
- Vladimir PutinPresident of Russia
Topics
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From the publisher
Ryan Holiday is a bestselling author and one of the most influential modern voices on Stoicism. His 12 books, including The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key, have sold more than 10 million copies worldwide. He's also the founder of Daily Stoic, a media company that reaches millions through books, podcasts, newsletters, and YouTube. In 2025, Ryan completed his four-book Stoic Virtues series and followed it with a sold-out international speaking tour. Shawn Ryan Show Sponsors: Sheath. The underwear of legends. Go to https://www.sheath.com/SRS and use code SRS for 20% off. Visit https://drinkag1.com/SRS to get a free AG1 Travel Case with 7 free AG1 Travel Packs in your Welcome Kit with your first AG1 subscription order while supplies last. Control Body Odor ANYWHERE with @shop.mando and get 20% off with promo code SRS at https://shopmando.com! #mandopod For problems worth solving — get started with Claude at — https://Claude.ai/srs Ready to upgrade your eyewear? Check them out at https://roka.com and use code SRS for 20% off sitewide. Ryan Holiday Links: Website - https://ryanholiday.net Daily Stoic - https://dailystoic.com Ryan Holiday IG - https://www.instagram.com/ryanholiday Daily Stoic IG - https://www.instagram.com/dailystoic Painted Porch Bookshop IG - https://www.instagram.com/paintedporchbookshop X - https://x.com/dailystoic Learn more about your ad choices. Visit podcastchoices.com/adchoices
Summary, chapters and key points were generated from the episode transcript on September 30, 2026. Quotes are checked word for word against the transcript.