Turn The Tables | Billy Oppenheimer Asks Ryan Holiday About His Writing Evolution and Creative Fulfillment

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Sep 7, 2024

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.

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ANECDOTE

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.

INSIGHT

Mentorship Dynamics

Effective mentors establish clear boundaries and avoid excessive familiarity early on.
They observe and assess mentees' development before significant investment.

ADVICE

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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