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.

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.

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(00:00) Intro

(02:20) When to Ignore 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