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#111 How To Build Self-Discipline (5 Step Routine) | Ryan Holiday

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Dec 31, 2025

Guest

Ryan Holiday

Ryan Holiday, a bestselling author and media strategist known for his insights on Stoicism, dives deep into the art of self-discipline. He shares the surprising truth that discipline is not about willpower but about forming solid habits. Ryan discusses frameworks from Stoic philosophers, explaining the importance of negative visualization and building routines that foster creativity. He emphasizes the value of self-knowledge and recognizing the destructive nature of ego. With practical tips, he offers a fresh perspective on how to embrace discipline for long-term freedom.

01:24:51

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ANECDOTE

Panic Rules From Coaching The Rams

Ryan developed "panic rules" teaching the LA Rams how to respond when coverage breaks down.
He uses simple repeatable practices so hot moments don’t collapse under pressure.

insights

INSIGHT

Labor Now, Freedom Later

Hard, unpleasant labor passes quickly while its benefits endure far longer than instant pleasures.
Discipline is constraint that creates future freedom and durable rewards.

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ADVICE

Make Discipline Black And White

Pick clear, black-and-white rules (e.g., bedtime by 10 p.m.) to make discipline binary and easy to follow.
Narrow specific habits beat vague aspirations like “be more disciplined.”

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Panic Rules for Crisis Response

00:40 • 1min

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Discipline Now, Freedom Later

01:40 • 3min

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Why Rules Create Freedom

05:03 • 3min

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Small Daily Habits to Build Discipline

07:51 • 4min

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Large Uninterrupted Focus Blocks

12:15 • 4min

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Procrastination as Entitlement

Enjoying Work Rather Than Reward Chasing

19:26 • 6min

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Negative Visualization and Preparedness

25:35 • 6min

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Analog Note-Card Research System

31:36 • 2min

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Love Learning: Read Deeply and Repeatedly

33:31 • 6min

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Books That Shaped Ryan

39:37 • 3min

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Raising Kids with Timeless Stories

42:18 • 3min

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Know Thyself: Self-Knowledge Matters Most

44:54 • 3min

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How Ego Destroys Success

47:33 • 5min

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Detecting Ego in Yourself

52:44 • 2min

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The Power to Have No Opinion

54:38 • 3min

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Handling Haters and Criticism

57:40 • 8min

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Expect People to Be Difficult

01:06:05 • 2min

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Donkeys, Ranch Life, and Practical Lessons

01:08:15 • 2min

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Marketing Past: Publicity Stunts and Lessons Learned

01:10:37 • 3min

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Choosing a Different Path from Industry Culture

01:13:59 • 3min

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The Corner Office Phenomenon

01:16:50 • 3min

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Audience Capture and Creative Integrity

01:19:41 • 4min

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Closing Reflections and Recommended Reading

• Mentioned in 49 episodes

The Daily Stoic

366 Meditations on Wisdom, Perseverance, and the Art of Living

Ryan Holiday

Stephen Hanselman

'The Daily Stoic' offers daily insights and exercises drawn from Stoic philosophy, designed to cultivate wisdom, resilience, and mindfulness. Each entry provides a quote from a Stoic philosopher, followed by Ryan Holiday's reflections and actionable advice. It encourages readers to embrace challenges, practice self-control, and find meaning in everyday life. The book is structured as a year-long guide, with each day offering a new opportunity for reflection and growth. Its practical approach makes Stoicism accessible and relevant for modern readers seeking to improve their mental and emotional well-being.

#66

• Mentioned in 204 episodes

The Odyssey

Homer

The Odyssey, attributed to Homer, is an ancient Greek epic poem that tells the story of Odysseus, king of Ithaca, and his ten-year journey home after the Trojan War. The poem explores Odysseus's encounters with various mythical creatures, divine interventions, and natural challenges. Upon his return to Ithaca, he must confront the suitors who have been vying for his wife Penelope's hand in marriage. With the help of his son Telemachus and the goddess Athena, Odysseus devises a plan to defeat the suitors and reclaim his throne. The poem is a reflection on human nature, loyalty, and the consequences of one's actions, and it remains a crucial component of ancient Greek literature and Western cultural heritage.

#271

• Mentioned in 82 episodes

Trust Me, I'm Lying

Confessions of a Media Manipulator

Ryan Holiday

In 'Trust Me, I'm Lying,' Ryan Holiday exposes the inner workings of the online media system, detailing how rumors and false information can quickly spread from low-level blogs to major news outlets. The book highlights the role of marketers and media manipulators in this process, driven by the toxic economics of the news business. Holiday shares his own experiences as a media manipulator and provides insights into the social science behind why this system is so vulnerable to manipulation. He also offers advice on how to spot and combat these manipulative tactics.

#52

• Mentioned in 224 episodes

Ego is the Enemy

Ryan Holiday

In *Ego Is the Enemy*, Ryan Holiday delves into the concept of ego and its detrimental effects on personal and professional success. The book is divided into three sections: Aspiration, Success, and Failure, each offering valuable lessons and perspectives. Holiday draws on a vast array of stories and examples from literature, philosophy, and history, featuring figures such as George Marshall, Jackie Robinson, Katharine Graham, Bill Belichick, and Eleanor Roosevelt. These individuals achieved great success by conquering their own egos, and their strategies and tactics are presented as models for readers. The book emphasizes the importance of staying grounded, continually learning, and embracing a mindset of growth rather than letting ego hinder development.

#111

• Mentioned in 145 episodes

Mastery

Robert Greene

In 'Mastery', Robert Greene argues that mastery is not an innate talent but a skill that can be developed through a rigorous process. The book outlines several key stages: finding your life's task, undergoing an ideal apprenticeship, finding the right mentor, acquiring social intelligence, and fusing intuitive with rational thinking. Greene draws on the lives of historical and contemporary masters such as Mozart, Einstein, and Temple Grandin to illustrate his points. He emphasizes the importance of deep practice, self-directed learning, and the ability to read and navigate social dynamics. The book challenges the conventional notion of genius as a genetic gift and offers practical steps for anyone to achieve mastery in their chosen field.

#8719

• Mentioned in 5 episodes

Letters to a young contrarian

Christopher Hitchens

In this book, Christopher Hitchens addresses a hypothetical young reader, offering advice on how to cultivate a contrarian mindset. He draws on historical examples of dissenters like Émile Zola, Rosa Parks, and George Orwell to illustrate the importance of questioning authority and challenging consensus. The book covers a range of topics including politics, economics, and religion, and encourages readers to seek out argument and disputation as a means of intellectual growth. Hitchens also critiques various forms of dogma and advocates for a life of critical thinking and moral courage.

#7887

• Mentioned in 6 episodes

Wisdom at Work

Chip Conley

Chip Conley's "Wisdom at Work" explores the concept of the modern elder, emphasizing the value of experience and wisdom in today's rapidly changing world. The book challenges traditional notions of aging and retirement, suggesting that older individuals can maintain relevance and contribute significantly to society. Conley shares his personal journey, including near-death experiences and career transitions, to illustrate his points. He offers practical advice and strategies for navigating midlife transitions, fostering creativity, and cultivating wisdom. The book encourages readers to embrace lifelong learning and find purpose in their second half of life.

#10

• Mentioned in 418 episodes

The obstacle is the way

Ryan Holiday

In 'The Obstacle Is the Way', Ryan Holiday presents a framework for turning obstacles into successes. Drawing from the philosophy of Stoicism and the writings of Marcus Aurelius, Holiday outlines three disciplines: perception, action, and will. He illustrates these principles with historical anecdotes from figures such as John D. Rockefeller, Amelia Earhart, Ulysses S. Grant, and Steve Jobs. The book emphasizes the importance of perception in shaping one's response to obstacles, the need for intentional and creative action, and the cultivation of will to persist through challenges. Holiday argues that by adopting these Stoic principles, individuals can transform their obstacles into opportunities for growth and success.

#32

• Mentioned in 276 episodes

The 48 laws of power

Robert Greene

In 'The 48 Laws of Power', Robert Greene and Joost Elffers synthesize three thousand years of the history of power into 48 laws. These laws are derived from the philosophies of Machiavelli, Sun Tzu, and Carl Von Clausewitz, as well as the lives of influential figures such as Henry Kissinger and P.T. Barnum. The book provides tactics, concepts, and lessons on how to achieve and maintain power, emphasizing prudence, confidence, and self-preservation. Each law is illustrated with historical examples and is designed to help readers understand and navigate the dynamics of power in various aspects of life, including work, social hierarchies, and politics.

#1404

• Mentioned in 26 episodes

A Calendar of Wisdom

Daily Thoughts to Nourish the Soul, Written and Selected from the World's Sacred Texts

Leo Tolstoy

This collection is a day-by-day guide that illuminates the path of a life worth living. It features gems of inspiration and wisdom from various historical figures including Epictetus, Marcus Aurelius, Lao-Tzu, Buddha, Pascal, Jesus, Muhammad, Confucius, Emerson, Kant, Ruskin, Seneca, Socrates, and Thoreau. Tolstoy considered this work his most important contribution to humanity, and it was widely read in pre-revolutionary Russia before being banned and forgotten under Communism. Recently rediscovered, it has been praised for its timeless wisdom and inspiration.

#287

• Mentioned in 80 episodes

The Laws of Human Nature

Robert Greene

In 'The Laws of Human Nature,' Robert Greene delves into the complexities of human behavior, identifying 18 laws that govern our actions and motivations. Drawing from historical figures such as Pericles, Queen Elizabeth I, and Martin Luther King Jr., Greene provides insights into how to detach from emotions, master self-control, develop empathy, and see beyond people's masks. The book is designed to help readers become better judges of character, manage their thought patterns, and influence others more effectively. It emphasizes the importance of self-awareness and understanding one's own flaws to make better decisions in personal and professional life.

• Mentioned in 952 episodes

Meditations

Marcus Aurelius

Meditations is a series of private writings composed by Marcus Aurelius, one of Rome's greatest emperors, as he struggled to understand himself and make sense of the universe. Written between 170 and 180 CE while on military campaigns, this work combines Stoic philosophy with personal observations on leadership, duty, mortality, and human nature. Through twelve books of intimate thoughts never intended for publication, Marcus Aurelius explores themes of self-improvement, resilience in the face of adversity, and living virtuously while accepting what cannot be changed.

#1516

• Mentioned in 24 episodes

Self-Reliance

Ralph Waldo Emerson

Published in 1841, 'Self-Reliance' is one of Ralph Waldo Emerson's most famous essays. It advocates for individualism, urging readers to trust their own unique powers and intuition rather than conforming to societal norms. Emerson argues that true happiness and fulfillment come from living an authentic, self-reliant life, free from the pressures of conformity and institutionalized religion. The essay is a cornerstone of Transcendentalist philosophy, emphasizing themes such as nonconformity, the authority of the individual, and the importance of personal growth and self-trust.

#3151

• Mentioned in 13 episodes

Civil Disobedience

Henry David Thoreau

In 'Civil Disobedience', Thoreau argues that individuals should prioritize their conscience over the dictates of laws. He criticizes American social institutions and policies, particularly slavery and the Mexican-American War. Thoreau contends that government derives its power from the majority rather than from legitimate viewpoints and that people should refuse to follow unjust laws. He recounts his own acts of civil disobedience, including refusing to pay taxes and spending a night in jail, as a model for moral resistance against oppressive laws. Thoreau emphasizes the importance of accepting the consequences of such actions and argues that true reform cannot come from within the government but through individual acts of defiance.

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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