The Daily Stoic Turn The Tables | Billy Oppenheimer Asks Ryan Holiday About His Writing Evolution and Creative Fulfillment
In this conversation, Billy Oppenheimer, Ryan Holiday's research assistant and newsletter writer, dives deep into Ryan's writing journey. They discuss Robert Greene's pivotal advice to reject an early book offer and how Stoic philosophy has shaped Ryan's evolving style. Ryan shares insights on mentorship, the balance between personal creativity and audience expectations, and his favorite aspects of the creative process. Through their dialogue, the importance of nuance and authenticity in storytelling takes center stage, inspiring listeners to explore their own writing paths.
55:58
Early Book Deal
- Ryan Holiday was offered a book deal early in his career after writing a Stoicism article.
- Robert Greene advised him to decline due to the poor terms and Ryan's young age.
Mentorship Dynamics
- Effective mentors establish clear boundaries and avoid excessive familiarity early on.
- They observe and assess mentees' development before significant investment.
Finding Your Style
- When emulating a role model, identify their unique strengths and respectfully deviate.
- Create your distinct style by adapting shared elements while avoiding direct imitation.
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Intro
00:00 • 4min
Navigating Mentorship and Stoic Influence in Writing
04:25 • 16min
The Journey of Writing and Creative Growth
20:14 • 4min
Evolving Storytelling: Lessons from Early Writings
24:13 • 11min
The Intersection of Writing and Content Creation
35:32 • 5min
Navigating Passion and Audience Engagement
40:05 • 12min
Navigating the Labyrinth of Collaboration and Research
52:34 • 8min
Upcoming Events and Podcast Engagements
01:00:31 • 2min
How They Succeeded
Orison Sweet Marden
In 'How They Succeeded', Orison Swett Marden explores the lives of successful individuals from various fields, including business, politics, and the arts.
The book emphasizes the importance of hard work, perseverance, and positive thinking in achieving success.
It profiles figures like Abraham Lincoln, Thomas Edison, and Helen Keller, highlighting their struggles and triumphs to inspire readers.
Humilitas
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John Dixon
The anxiety of influence
a theory of poetry
Harold Bloom
In 'The Anxiety of Influence', Harold Bloom presents a theory of poetry that explores how poets are influenced by their precursors and how they strive to create original work despite this influence.
Bloom argues that poets must engage in a process of 'poetic misprision', or creative misreading, to carve out their own space in the literary canon.
The book is divided into six revisionary ratios, drawing on Freudian psychoanalysis and classical rhetoric.
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 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.
Gates of fire
Steven Pressfield
Gates of Fire tells the story of the Battle of Thermopylae through the eyes of Xeones, a wounded Greek soldier who recounts his life and the events leading up to the battle.
The novel explores Spartan culture, the rigorous training regimen known as the *agoge*, and the heroic stand of the Spartans against the overwhelming forces of the Persian Empire.
The story is framed as a series of interviews between Xeones and members of the Persian court, detailing the battle and its aftermath, as well as the personal and philosophical aspects of Spartan warfare and culture.
Histories
Herodotus
The Histories by Herodotus is a foundational work in Western historical literature.
It chronicles the Greco-Persian Wars (499–479 BCE) and provides a comprehensive background on the rise and organization of the Persian Empire.
The work is divided into nine books, each named after one of the Muses.
Herodotus describes the conflicts between the Greeks and Persians, including key battles such as Marathon, Thermopylae, Salamis, Plataea, and Mycale.
He also delves into the cultural, ethnographical, geographical, and historiographical aspects of the civilizations involved, offering a rich tapestry of historical and mythological narratives.
Despite some criticisms for including legendary accounts, much of Herodotus's work has been validated by modern historians and archaeologists.
Self-help
Samuel Smiles
Published in 1859, 'Self-Help' by Samuel Smiles is a landmark in the self-help genre.
The book advocates for personal responsibility and the virtues of hard work, industry, and character.
It uses numerous biographical examples, including those of George Stephenson and Josiah Wedgwood, to illustrate how individuals can achieve success through their own efforts.
The book was highly influential in Victorian Britain and beyond, selling over a quarter of a million copies by the time of Smiles' death in 1904.
It has been translated into many languages and remains a significant text in the history of self-help literature.
The lives of the most excellent painters, sculptors, and architects
Giorgio Vasari
This book, written by Giorgio Vasari, is a series of artist biographies that chronicles the development of Italian art across three centuries.
It begins with Cimabue and Giotto, representing the infancy of art, and progresses through the youthful vigor of artists like Donatello, Brunelleschi, and Masaccio, to the mature period dominated by Leonardo, Raphael, and Michelangelo.
Vasari’s work is notable for its historical trends, character sketches, and anecdotes that bring the artists and their works vividly to life.
The book was first published in 1550 and expanded in 1568, making it a foundational text in the field of art history.
The sun also rises
Ernest Hemingway
Originally published in 1926, 'The Sun Also Rises' is Ernest Hemingway’s first novel and a classic example of his spare but powerful writing style.
The novel follows a group of young American and British expatriates as they wander through Europe in the mid-1920s, capturing the moods, feelings, and attitudes of the cynical and disillusioned Lost Generation.
The story centers around Jake Barnes, a World War I veteran and journalist, and Lady Brett Ashley, as they journey from the wild nightlife of 1920s Paris to the brutal bullfighting rings of Spain.
The novel portrays an age of moral bankruptcy, spiritual dissolution, unrealized love, and vanishing illusions, reflecting the existential disillusionment characteristic of the Lost Generation.
Letters from a Stoic
Seneca
Seneca's "Letters from a Stoic" comprises a collection of personal letters offering practical advice on living a virtuous life according to Stoic principles.
Written to Lucilius, a friend and student, the letters cover a wide range of topics, including dealing with adversity, managing emotions, and finding inner peace.
Seneca's writing style is engaging and relatable, making complex philosophical concepts accessible to a wider audience.
The letters offer timeless wisdom on self-improvement and ethical living.
They remain a valuable resource for anyone seeking guidance on navigating life's challenges.
Why did Robert Greene advise Ryan to turn down his first book offer? How does Ryan balance writing about his personal interests and what his audience is expecting? Billy Oppenheimer, Ryan's research assistant, is asking Ryan these questions and many more in today's episode.
Ryan talks about what people get wrong about mentorship, the evolution of his writing style, how the writings of the Stoics have influenced him, what his favorite part of the creative process is, and more.
Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.
🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour
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