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How to Write a Book Like Ryan Holiday

How I Write

Wed Jun 26 2024



Marcus Aurelius' Observations and Writing Style:

  • Marcus Aurelius, a Roman emperor, exhibits exceptional writing prowess in his private diary written in Greek, which was his second language.
  • He eloquently captures the beauty found in nature's unintentional details such as loaves of bread splitting open or ripe figs bursting, showcasing an appreciation for life's simple yet captivating aspects.
  • His keen ability to notice and value these small nuances suggests a connection between the eyes of a poet and a philosopher, highlighting the significance of finding beauty in everyday moments.

Ryan Holiday on Writing Process and Momentum:

  • Ryan Holiday underscores the importance of maintaining creative momentum by emphasizing the need to immediately start the next project after completing one to prevent setbacks from affecting productivity.

Balancing Quantity and Quality in Writing:

  • Ryan Holiday discusses how consistent output can lead to improved quality over time, contrasting authors like Robert Caro who spend years on single books with his approach of producing shorter books at a faster pace.

Crafting Engaging Introductions:

  • The conversation delves into crafting impactful introductions where Ryan Holiday explains that an introduction should establish the shape and structure of a piece early on.
  • Examples are provided from various works like Kanye West's Yeezus album opening sound, Nabokov's Lolita beginning, and Michael Lewis' book "The Big Short" aligning perfectly with economic events.

Storytelling Techniques and Pacing in Writing:

  • Raymond Chandler's writing approach involved ensuring significant events occurred on every page, emphasizing the importance of maintaining a compelling pace throughout a story to keep readers engaged.
  • Stories should contain surprises or focus on well-known individuals to effectively captivate readers.
  • Layering similar stories can help demonstrate overarching themes or trends within storytelling, enhancing the impact of the narrative.

Writing Process and Self-Contained Story Units:

  • The speaker writes individual drafts for each chapter as self-contained pieces before merging them into a complete manuscript, allowing for better control over pacing and narrative flow.
  • Each section is treated as a standalone story with its own pacing and narrative arc, ensuring that it contributes meaningfully to the larger structure of the book.

Importance of Research in Storytelling Development:

  • About 80% of the speaker's improvement in storytelling comes from honing research skills over time.
  • Enhanced research abilities enable more captivating storytelling by providing deeper insights, unique angles, and engaging narratives based on thorough investigation.

Balancing Fear and Creativity in Writing:

  • Fear often hinders creative endeavors due to concerns about judgment or failure, impacting productivity within creative circles.
  • Acknowledging and addressing fear can help writers overcome mental barriers that impede progress, enabling them to start projects despite uncertainties.

Understanding Editor-Author Dynamics for Effective Collaboration:

  • Establishing clear communication with editors regarding the vision for a project ensures constructive feedback aligns with the author's goals.
  • Editors who grasp an author's intentions can offer valuable guidance that enhances rather than alters the core essence of the work being produced.

Writing Process and Research for Books:

  • The speaker highlighted the importance of creating engaging self-contained pieces in writing a book, adjusting the pacing later to ensure coherence.
  • Various materials like obituaries, articles, and ESPN pieces were utilized for research purposes during the book-writing process.
  • Improving character portrayal by showcasing both greatness and weaknesses was discussed as a key aspect of crafting well-rounded individuals within the narrative.
  • Connecting different personalities for contrast and explanation purposes was emphasized, such as understanding Lou Gehrig through Babe Ruth's perspective.

Lessons from Ryan Holiday on Writing:

  • Maintaining momentum in writing was stressed as crucial, with many individuals stopping their writing journey after completing their first book.
  • Trusting the writing process and gaining confidence through experience were noted as essential elements for successful writing endeavors.
  • Accumulating enough practice or "reps" in writing was underscored as significant. Repetition plays a vital role in enhancing skills but can be challenging due to the time-intensive nature of book writing compared to other art forms like stand-up comedy or music performances.
  • Finding alternative methods to gain storytelling practice was discussed, such as developing structured formats like daily emails containing stories to consistently engage an audience.

Volume and Consistency in Writing Career:

  • Starting a career with volume by consistently producing content was highlighted as fundamental in honing one's writing skills over time.
  • Getting accustomed to feedback from readers and actively participating in the entire content creation process regularly were mentioned as beneficial practices for personal growth and skill enhancement.