There are 3 books in the The Way, the Enemy and the Key series. The newest book is Stillness is the Key which came out in 2019.

1
The Obstacle Is the Way

Book cover of The Obstacle Is the Way
We give up too easily. With a simple change of attitude, what seem like insurmountable obstacles become once-in-a-lifetime opportunities. Ryan Holiday, who dropped out of college at nineteen to serve as an apprentice to bestselling 'modern Machiavelli' Robert Greene and is now a media consultant for billion-dollar brands, draws on…
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2
Ego Is the Enemy

Book cover of Ego Is the Enemy
A powerful meditation on the nature and dangers of ego, from the author of the #1 New York Times bestseller Stillness is the Key, and Obstacle is the Way - over 1 million copies sold

'Re-read it each year. It's that important' Derek Sivers, author of Anything You Want

'Ryan…