Most people think discipline is about willpower. Ryan Holiday knows better — it's about habit. After writing multiple bestselling books on Stoicism and spending decades studying history's highest performers, the author of The Obstacle Is The Way and Ego Is The Enemy has cracked the code on why the world's hardest workers aren't just talented or lucky. They've built systems that make discipline inevitable.

In this raw conversation, Ryan breaks down the exact frameworks used by Marcus Aurelius, Seneca, and Epictetus to stay calm under fire, make sharper decisions under pressure, and most importantly — get things done. We dive into why discipline isn't something you are but something you do, how the Stoics battled procrastination (Seneca said all fools are always getting ready to start), and why negative visualization beats positive manifestation every time. Ryan reveals his actual research process (analog note cards, not AI shortcuts), why he reads the same books over and over, and how to inoculate yourself against audience capture when everyone's telling you what to create.

But this isn't theory — it's applied philosophy. We get into why waking up early is useless if you stay up till 2 AM, how to make hard things black and white so you can't rationalize exceptions, and why your calendar should have large blocks of white space, not meetings. Ryan walks through his panic rules from coaching the LA Rams, why ego destroys more empires than external obstacles, and how he went from running publicity stunts and media manipulation campaigns to building one of the most disciplined creative practices in the world. If you've ever felt like discipline is this vague thing you either have or don't, or if you're tired of procrastinating on the life you know you should be building, this episode will change how you think about work, focus, and what it actually takes to win.

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00:00:00 Introduction

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