I recently sat down with Ryan Holiday—one of today’s most influential thinkers on Stoicism and modern life—for a wide-ranging conversation about how to stay grounded in a moment that feels uniquely exhausting. Ryan first came to prominence as a media strategist before becoming a bestselling author, introducing millions of readers to ancient philosophy through books like The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key. His work has focused on timeless ideas about discipline, humility, and meaning—and why they matter even more in a noisy, distracted age.
In our conversation, we dig into how people should be thinking about this moment: the constant churn of outrage, anxiety, and stimulation, and how easily it traps us on the “hedonic treadmill,” endlessly chasing the next hit of validation without ever feeling satisfied. We also talk about his newest book, Wisdom Takes Work, which argues that insight and peace aren’t passive discoveries—they’re practices that require effort, patience, and intention. It’s a timely reminder that in an age designed to wear us down, real wisdom is something we have to actively build.
I really enjoyed this one, and I know you will too.
Chapters
00:00 Introduction to Stoicism and Personal Journeys
04:11 The Importance of Virtue in Modern Society
08:55 Developing Courage and Wisdom in Daily Life
12:52 The Role of Myths in Shaping Values
18:27 Navigating Political Discourse and Historical Context
20:10 Finding Personal Agency in a Complex World
26:57 Reflections on Leadership and Virtue
30:52 Conclusion and Call to Action
