In this episode, Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal missteps to famous entrepreneurial gambles, this episode is a deep dive into the art of learning from experience, knowing when to listen, and the cost of stubbornness. Plus, Holiday revisits his roots to discuss how Stoic principles can guide you in navigating feedback, balancing ambition with self-awareness, and understanding the fine line between determination and delusion.
Available now: YouTube | Apple Podcasts | Spotify | Transcript
Holiday is a New York Times bestselling author. He has written over 10 books, covering both the fundamentals of Stoicism as well as key elements of modern-day marketing and media. His most recent release is Right Thing, Right Now. Holiday has been a guest on the podcast twice before.
Timestamps:
00:00 Introduction
01:54 Elon Musk: A Case Study in Listening and Ignoring Advice
04:49 The Importance of Reflection and Journaling
07:26 Balancing Emotions and Stoic Practices
24:34 Misconceptions and Historical Context of Stoicism
29:53 The Pursuit of Excellence and Its Trade-offs
40:58 The Power of Saying No and Opportunity Costs
49:09 The Role of Anger and Emotional Control
52:58 Defining Self-Discipline
53:43 The Essence of Self-Discipline
54:29 Balancing Discipline and Life
55:09 Consistency and Overcoming Setbacks
56:09 The Struggle with Compulsive Tendencies
58:33 Navigating Competition and Personal Goals
01:01:22 Cultivating Discipline Through Physical Practice
01:02:15 Instilling Discipline in Children
01:04:22 Understanding Character and Virtue
01:23:32 The Impact of Modern Technology on Writing
01:35:04 Defining Success and Managing Expectations
