Raising Kids with Timeless Stories

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 00:01:06 Panic Rules: What To Do When Everything Falls Apart 00:03:05 Discipline Now, Freedom Later: The Labor Will Pass 00:07:37 The Simplest Daily Habit to Build Discipline 00:11:59 Large Uninterrupted Blocks of Time: The Secret to Success 00:16:09 Procrastination is Arrogant: It Assumes You Have Forever 00:22:39 Enjoying the Journey: Why the Work Matters More Than the Reward 00:28:22 Negative Visualization: Why the Stoics Planned for the Worst 00:33:10 The Note Card System: How Ryan Remembers Everything 00:34:52 You Must Love Learning If You Would Possess It 00:43:14 Know Thyself: The Oracle of Delphi's Most Important Command 00:46:05 Ego is the Enemy: How It Destroys Success 00:53:16 The Power to Have No Opinion 01:00:06 Haters, Criticism, and the Statistical Certainty of Dislike 01:18:04 Audience Capture: When Your Audience Has You 01:09:04 From Marketing Manipulator to Stoic Philosopher 01:15:17 The Corner Office Phenomenon: Looking Down the Hall 01:17:01 Are Humans Contagious? Culture, Values, and Becoming Who You Spend Time With 01:06:44 Should We All Get a Donkey? Life Lessons from the Ranch 01:21:15 Final Reflections: The Path That's Yours Alone

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