On Purpose with Jay Shetty

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Ryan Holiday ON: Eliminating Fear From Your Life & Push Past Them This Year

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Jan 24, 2022

Guest

Ryan Holiday

Jay Shetty welcomes Ryan Holiday, bestselling author and media personality celebrated for his works on Stoicism. They discuss how comfort can hinder growth and the importance of taking risks. Ryan emphasizes that courage is essential for personal evolution and how community engagement can deepen connections, especially when facing challenges like opening a bookstore during a pandemic. The conversation explores transforming envy into growth and the power of literature in fostering resilience and understanding, promoting the idea that true liberation comes from confronting fears.

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ADVICE

Book Recommendations

Ask smart people you admire for book recommendations to accelerate learning.
Reading books they recommend gives you valuable insights and can even spark lasting connections.

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ANECDOTE

Discovering Stoicism

Ryan Holiday's life changed after reading "Meditations" by Marcus Aurelius, recommended by Dr. Drew.
He was struck by Aurelius's practicality and focus on handling everyday frustrations with reason.

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ANECDOTE

Following Through

Ryan Holiday followed up with Dr. Drew after reading his recommendation, which led to a lasting friendship.
Many people ask for recommendations, but few do the work of reading.

Get the Snipd Podcast app to discover more snips from this episode

Navigating Growth and Resilience

02:23 • 14min

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Courage, Connection, and Self-Worth

16:06 • 14min

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Embracing Indifference and Confronting Fear

30:24 • 12min

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Embracing Risk for Greater Good

42:18 • 9min

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Transforming Envy into Growth

50:55 • 18min

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Exploring Transformative Literature and Community Connections

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.

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.

Never Split the Difference

Negotiating As If Your Life Depended On It

Tahl Raz

Chris Voss

VOSS/RAZ

This book, written by former FBI hostage negotiator Chris Voss and co-author Tahl Raz, provides a masterclass in influencing others through negotiation. It distills the Voss method, revealing skills such as establishing rapport, creating trust with tactical empathy, and transforming conflict into collaboration. The book is filled with real-life examples from Voss's career, illustrating how these techniques can be applied in both professional and personal life to achieve goals and defuse potential crises.

The Daily Stoic

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

Ryan Holiday

Stephen Hanselman

This book provides 366 meditations on Stoic wisdom, featuring new translations of passages from Epictetus, Marcus Aurelius, Seneca, and other Stoic philosophers. Each day, readers are presented with a Stoic lesson explained in modern language, along with advice on how to apply these lessons in everyday life. The book is organized temporally and thematically across the twelve months of the year, making it a daily resource for practicing Stoicism.

In 'Stillness is the Key', Ryan Holiday explores the concept of inner stillness as a universal principle across different philosophical and religious traditions, including Stoicism, Buddhism, Epicureanism, and more. The book is divided into three sections: stillness of the mind, stillness of the spirit, and stillness of the body. Holiday argues that cultivating stillness allows for better decision-making, increased focus, and a more fulfilling life. He uses anecdotes from historical figures and contemporary examples to illustrate the importance of moderation, patience, and self-awareness in achieving this state of stillness.

Courage Is Calling

Ryan Holiday

In 'Courage Is Calling', Ryan Holiday explores the virtue of courage through engaging stories about historic and contemporary leaders such as Florence Nightingale, Ulysses S. Grant, Abraham Lincoln, and Dr. Martin Luther King Jr. The book breaks down the elements of fear, cowardice, bravery, and heroism, and shows how to conquer fear and practice courage in daily life. Holiday also shares personal anecdotes, including his own experiences with courage and cowardice, to emphasize the importance of choosing to act courageously despite the presence of fear.

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.

The Enchiridion

Epictetus

Tony Darnell

Thomas Wentworth Higginson

The Enchiridion is a concise summary of the basic ideas of Stoic philosophy and provides techniques for transforming these principles into a way of life. It was compiled by Arrian from the teachings of Epictetus and is notable for its practical advice on moral conduct in various life situations. Unlike the Discourses, which present Epictetus' teachings in a more dynamic and situational context, the Enchiridion is a more structured and concise guide to Stoic living.

Yes to Life in Spite of Everything

Viktor E. Frankl

This book is based on a series of public lectures Viktor E. Frankl gave in Vienna eleven months after his liberation from Nazi concentration camps. Frankl discusses his central thoughts on meaning, resilience, and the importance of embracing life even in the face of great adversity. He explores the maxim 'Live as if you were living for the second time' and argues that every crisis contains opportunity. Despite the horrors of the camps, Frankl learned from his fellow inmates that it is always possible to 'say yes to life', a profound and timeless lesson for all.

Do you want to meditate daily with me? Go to go.calm.com/onpurpose to get 40% off a Calm Premium Membership. That's only $42 for the whole year! Experience the Daily Jay. Only on Calm

Jay Shetty talks to Ryan Holiday about why being too comfortable won’t help you grow. When you take risks, you prepare yourself to be mentally and emotionally present and be ready for what may happen. Taking risks without fearing what might happen is the foundation that allows us to evolve for better even when constraints are present and some things are just out of our control.

Ryan is a Wall Street Journal bestselling author, book store owner, public-relations strategist, and host of the podcast The Daily Stoic. Some of his best selling books are The Obstacle Is The Way, Ego Is the Enemy, Stillness is the Key, and The Daily Stoic. He owns and operates Painted Porch Bookshop, an independent bookstore in Bastrop, Texas. He lives on a 40-acre ranch in Bastrop County, Texas with his wife and two sons.

What to Listen For:

00:00 Intro
04:42 It takes 10,000 hours to get to mastery
05:45 Opening a bookstore during the pandemic
10:27 How do you know which books to read?
17:36 What courage truly means
20:37 We’re all self-interested people but we value other people’s opinion
26:17 If you’re in a place where you identify with external results, you become vulnerable
30:34 Cultivating the ability to push through your fear
33:55 Being too comfortable makes you afraid to take risks
40:25 Deciding not to see the world as a zero sum place
45:00 When you make trade offs that aren’t worth it
46:07 Just how much is out of your control?
48:54 Positive changes out of situational constraints
51:17 What is heroism?
55:58 Ryan on Fast Five

Episode Resources

Ryan Holiday | Website
Ryan Holiday | Twitter
Ryan Holiday | Facebook
Ryan Holiday | Instagram
Ryan Holiday | Books

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