Ryan Holiday On Writing Secrets, Appreciating Books & More!


Ryan Holiday is a deep and profound modern day philosopher, a friend of mine, and one of my favorite authors.

He is the bestselling author of the new book Courage Is Calling, along with Trust Me, I’m Lying; The Obstacle Is the Way; Ego Is the Enemy; Conspiracy, and other books about marketing, culture, and the human condition, including my one of my personal favorite books of all time: Stillness Is The Key. His work has been translated into over 30 languages and has appeared everywhere from the The New York Times to Fast Company.

Ryan owns and operates the independent bookstore Painted Porch Bookshop in Bastrop, Texas. He is married and has two sons, and his family lives on a 40-acre ranch in Bastrop County, Texas.

During our discussion, you’ll discover:

-Ben reading Ryan’s article, 33 Ways to be Insanely Productive, Happy Balanced Person…03:38

-How an in-person bookstore has helped Ryan reconnect with family, health, and more…12:30

  • Started The Painted Porch bookstore in December 2020, right in the middle of the pandemic
  • The store contains Ryan’s favorite and most recommended books; not trying to compete with the big box stores
  • Great way for his two boys to interact and bond with their father on a deep level
  • Ben will have his boys “shadow” him at work, only to realize they’re not all that interested in emails, writing novels, etc.
  • Article: 33 Ways To Be An Insanely Productive, Happy Balanced Person
  • Difficulty establishing boundaries when one works from home
  • The bookstore is a dedicated work space for writing, podcasts, a place for employees to go to work, etc.
  • You watch the ecosystem grow before you, vs. selling to strangers on a Kindle or audiobook

-Virtue found in a non-urban lifestyle…26:05

  • Ryan Holiday owns a 40-acre property with small herd of cattle, garden, fruit trees, etc.
  • Purpose was to establish a more rural lifestyle
  • Nigerian dwarf goats produce milk, cheese, make fun pets
  • Introduces their children to the concept of death in very real way
  • Hygiene hypothesis
  • Having animals arounds teaches children about fundamentals of life such as child-rearing
  • Teaches a healthy fear and respect of nature (animals aren’t your friend)
  • Ben and Ryan’s children are perfectly happy in a patch of grass or pile of rocks
  • The rural environment mitigated some of the effects of the pandemic
  • Ben’s kids do wilderness school – Kamana Wilderness Awareness School
  • Tom Brown’s Tracker School 

-Some of Ryan Holiday and Ben’s daily rituals and routines…46:03

-Ryan’s writing process..51:15

  • Article on writing process by Ryan Holiday
  • Ensure all essential tasks are finished before writing
  • Think of writing as a job
  • Early thinking on note cards
  • Do actual writing on Google docs
  • Ben uses a “dream catcher” document and relies heavily on Google docs for the writing process
  • Keep “commonplace” books nearby
  • Ben uses one Evernote doc to keep track of writings, to-do’s, book ideas, etc.
  • Having to work a little bit to make a note causes one to remember it more handily

-How Ryan’s appreciation of history has grown by writing his books…1:02:55

  • People are more open to your message if it’s tied in with a story from the past
  • Personal anecdotes are also effective

-Ryan’s reading habits…1:06:27

  • Physical copies only, no Kindle or audiobooks
  • No “speed reading” secret; the more you read, the faster it goes

-Why Ryan Holiday isn’t a fan of checking out books at a library…1:10:45

  • “Disposable fiction”
  • Build your own personal library of books you want to keep forever
  • Ben has a shelf of books he wants to re-read every year
  • Like cashing a check you wrote to yourself years earlier

-How Ryan got the idea to write a book about courage…1:17:24

  • Article about the book on courage:
  • When you try to do something, it can prevent you from actually doing it

-About Ryan’s upcoming series of virtue-themed books…1:21:30

  • Courage is Calling is the first part of a series, to be followed by:
    1. Self-discipline (temperance/moderation)
    2. Justice
    3. Wisdom
  • Ben has a book soon to be released titled Endure

-And much more…

Upcoming Events:

Resources from this episode:

Ryan Holiday:

– Books:

– Other Resources:

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Do you have questions, thoughts, or feedback for Ryan or me? Leave your comments below and one of us will reply!

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