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Ryan Holiday

I bring on the fascinating Ryan Holiday, the entrepreneur and everyman philosopher, and the two of us discuss a sequence of Stillness is the Key, Ryan's latest book, which left me near tears when I finished it. Stillness debuted last month at No. 1 on the New York Times bestseller list and is the last in a trilogy of books which uses ancient philosophy, modern politics, sports and the acquired wisdom of the world leaders to instruct us all on How to Live. I told Ryan that Stillness might be the best book in the series, and the chapter we discuss today is my favorite. 


Ryan writes a lot on Stoicism, an ancient philosophy that, unlike others, never lost its bearings in the thin-air abstractions of metaphysics  and instead dwelt on the practical applications of leading a satisfying life. (Readers of this and the Friday email might remember how one of my favorite books is Marcus Aurelius' Meditations. Aurelius, a Stoic, wrote the book while he ruled Rome as its emperor.) Ryan's first book in his trilogy, The Obstacle is the Way, did a lot of work to bring Stoicism to a modern audience. It was translated into 30 languages. Bill Belichick and the New England Patriots became fans. Stillness is the Key distills not only what Ryan thinks about Stoicism but what he has read outside it. And yet my conversation with Ryan is never stuffy. If anything it's profane, and also funny, vulnerable and warm-hearted. 


About those books we discuss: Let's start with the Stoic writers. 


This is a good entrée for Epictetus, who is not quite as accessible a writer as Seneca. Seneca was a senator in Rome and the Tao of Seneca is a book of his letters that offers great advice on life. I have a Google Doc that's just passage after passage of the Tao. 


We already talked Aurelius. Start with Ryan's The Obstacle is the Way or Meditations itself. William Irvine's A Guide to the Good Life: The Ancient Art of Stoic Joy is also a wonderful primer on Aurelius and Stoicism. 


Some Kind of Monster really is as good a music documentary as Ryan says. 


The Subtle Art of Not Giving a F*ck is where you can read so much more than the story of Dave Mustaine and Metallica. I liked it a lot. 


Robert Greene's The 48 Laws of Power  is a merciless, unethical and invigorating examination of when to grab power for yourself, and why, based on history's most powerful figures. I haven't read another book like it, not even The Prince


Ryan and I discuss at length the Kurt Vonnegut poem that's the basis for the story of "Enough." Of course, Maria Popova has already written at length about Vonnegut's poem and the story behind Vonnegut's life lesson, which he learned from fellow author Joseph Heller. 


"Comparison is the thief of joy:" Theodore Roosevelt said it, and Ryan put it to good use in our conversation.

I think you'll get as much out of the episode as I did. Once you do, please rate and review the pod.

Stillness is the Key
The Obstacle is the Way
Guide to the Good Life
The Subtle Art...
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