RYAN HOLIDAY: Why wisdom takes work (and smart people still do stupid things)

Mar 17, 2026

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Why do genius-level intellects fall for conspiracy theories? How does someone who taught himself rocket science from Soviet manuals end up believing nonsense on social media?

Ryan Holiday – bestselling author of The Daily Stoic, Ego is the Enemy, and The Obstacle is the Way – joins me on Crisis What Crisis to explore why intelligence doesn't protect you from stupidity, why modern life's frictionlessness is making us weaker, and what ancient Stoic philosophy can teach us about navigating today's world.

In this conversation, we discuss Elon Musk's descent into conspiracy theories, why judging young men from reading philosophy is dangerous, what Marcus Aurelius would make of AI, and why Victor Frankl warned in 1979 that our "too soft" world would lead to emptiness.

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WHAT YOU'LL HEAR:

Why "making a massive contrarian bet that works" can be brain-destroying
The Stoic POW who tapped Epictetus through prison walls in Vietnam
Why young men desperately need philosophy (not less of it)
How to guard against your own stupidity while pursuing wisdom
What Marcus Aurelius would say about your Instagram habits

LESSONS YOU'LL LEARN:

Intelligence DOES NOT EQUAL wisdom – being brilliant at one thing doesn't protect you from being an idiot about others
Stay a student forever – Marcus Aurelius, the philosopher-king, made a point of always staying a student
Friction builds resilience – a frictionless life leaves you vulnerable when reality intervenes
You don't control what happens, only how you respond
Wisdom takes work – it's not something you're born with; it's the result of hard work, experience, and time

CHAPTERS:

00:00 – Introduction: The Modern Day Philosopher King

02:37 – What is Stoicism? (Explained for people in crisis)

07:58 – Why Ryan turned to ancient philosophy at 19

10:11 – The marketing career he walked away from

13:25 – What if Ryan never discovered Stoicism?

15:02 – Does Stoicism have a "toxic masculinity" problem?

19:16 – Why choose Stoicism over Instagram wealth?

22:07 – What is wisdom and how do you get it?

24:53 – Elon Musk: A cautionary tale of genius + stupidity

27:42 – Will we ever have philosophical leaders again?

30:11 – Victor Frankl's 1979 warning: Life is too soft