Simplify Personal Philosophy: Media Strategist Ryan Holiday On Putting Theory Into Action
Are you iOS, Android, or Stoic? In this episode of Simplify, hear author and master of controversy, Ryan Holiday, talk about the importance of finding your personal operating system and using it to focus and fuel the work you love to do. He also has great advice on finding your fans, applying abstract theory to real life, and becoming OK with saying “I don’t know.”
“The idea that you can control other people’s opinions or that
it’s even admirable to get everyone to like you, whether that’s
a worthwhile pursuit, is not the best use of anyone’s time.”
— Ryan Holiday
You could spend hours studying philosophical theory without ever learning how to apply it in practice. In this episode of Simplify, Ryan Holiday shares his techniques for getting the most out of philosophical and ancient history books — with a little provocative marketing advice thrown in, to boot.

By the end of this episode, you’ll learn some key principles of marketing, how to find the right audience for your product, and how a little practical stoicism can make a difference to your day-to-day.
Who’s Ryan Holiday?
Ryan Holiday, bestselling author of Trust Me I’m Lying and The Obstacle Is The Way, is a media strategist, marketer, and entrepreneur. His media strategies have been used as case studies by Google, YouTube and Twitter. Holiday has written 6 books on topics from media manipulation to ancient philosophy and The New York Times credits him with bringing Stoicism—an ancient Greek school of philosophy—back to modern popularity. He currently lives in Austin, Texas.
Trust Me, I’m Lying
- 13 min reading time
- audio version available
The Obstacle is the Way
- 16 min reading time
- audio version available
Ego is the Enemy
- 12 min reading time
- audio version available
Growth Hacker Marketing
- 12 min reading time
- audio version available
What’s Simplify?
Simplify is a podcast for anybody who’s taken a close look at their habits, their happiness, their relationships, or their health and thought “There’s got to be a better way to do this.” We talk to bestselling writers, productivity wizards, sex geniuses, and happiness experts to find it for you. Life is complicated, but living it better doesn’t have to be. Simplify.
Simplify is made with love by Blinkist. Click here to try Blinkist free for 14 days with the voucher code: vanitas
Talk to us!
This season, we are collecting your voices, dear listeners (not as creepy as it sounds)!
Specifically, we’d love to hear how you would answer one of the questions we always ask our guests: “What have you discovered was much easier than you initially thought it was?”
You can just record your answer with a voice memo app of your choice and then email it to us at [email protected]. We are looking forward to listening to your responses, and stay tuned—you just might hear yourself on a future episode of Simplify!
If you want to say hi to Ben and Caitlin in the meantime, you can find them on Twitter: @bsto and @CaitlinSchiller.
Who made this?
Your hosts are Caitlin Schiller and Ben Schuman-Stoler.
Stellar research and production assistance by the outstanding Natallia Darozhkina.
Thanks to Nico Guiang for our awesome intro and outro music. Listen more on Soundcloud or check him out on Facebook.
Sound and editing by Ody Constantinou, who doesn’t carry a wallet.
Got links?
Ryan Holiday’s list of books to base your life on.
One of Holiday’s favorite books:
Philosophy as a Way of Life: Spiritual Exercises from Socrates to Foucault by Pierre Hadot
Extra credit reading
If you enjoyed this episode and would like to delve deeper into the topics we mentioned, check out this book list created to help you be more productive, strategic, and successful.