What does it actually mean to live like a Stoic? In this wide-ranging conversation with bestselling author and modern Stoicism evangelist Ryan Holiday, we unpack the origins of Stoic philosophy, why it exploded during turbulent times in ancient Greece and Rome, and how its principles—like courage, temperance, justice, and wisdom—still apply in a world filled with chaos, anxiety, and uncertainty. From shipwrecked merchants to emperors journaling their fears, this episode explores why some of the most powerful figures in history turned to Stoicism not just for answers—but for survival.

We also dig into how Stoicism overlaps with modern psychology, why it’s gaining traction among young men, and whether its rising popularity is being misunderstood or misused. If you’ve ever wondered whether Stoicism means being emotionless, if it’s compatible with ambition, or if it actually makes you a better person, this episode is your one-stop masterclass.

Order Ryan Holiday’s new book, Wisdom Takes Work: https://www.amazon.com/Wisdom-Takes-Work-Repeat-Virtues/dp/0593191730

Chapters:

02:49 CHAPTER 1: Setting the Scene: Ancient Greece After Alexander

13:58 CHAPTER 2: The Four Stoic Virtues

1:25:51 CHAPTER 3: Roman Conquest and the Spread of Stoicism

1:39:06 CHAPTER 4: Seneca: The Conflicted Philosopher

1:55:50 CHAPTER 5: Epictetus: The Slave Philosopher

2:07:28 CHAPTER 6: Marcus Aurelius: The Philosopher Emperor

2:20:18 CHAPTER 7: Stoicism Through History

2:32:45 CHAPTER 8: Stoicism and Modern Psychology

2:41:09 CHAPTER 9: The Modern Stoicism Revival

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