Choosing Inside or Outside: Seneca’s Dilemma

They debate Seneca’s decision to serve Nero, moral compromises, and whether to influence power from within.

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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

We also put together a free companion guide for this episode with all the takeaways, references, and tools to help you get your sh*t together once and for all. Download it here: https://solvedpodcast.com/stoicism

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Produced by Drew Birnie Research by Zenya Giatzoglou, Katherine Wei, & Gage Greer Edited by SJ van Breda Director of Photography Jess Choi Thumbnail by Jonathan Sippel

Chapters:

00:00 Introduction

02:49 Setting the Scene: Ancient Greece After Alexander

06:44 The Story of Zeno: Founder of Stoicism

13:58 The Four Stoic Virtues

44:20 Virtue 1: Courage

53:17 Virtue 2: Temperance (Discipline)

1:05:01 Virtue 3: Justice

1:08:51 Virtue 4: Wisdom

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

1:33:10 Cato the Younger: The Stoic Martyr

1:39:06 Seneca: The Conflicted Philosopher