Episode 51: Ryan Holiday

An interview with Ryan Holiday about his life philosophies, how to disconnect from technology to be more present, achieving stillness, stoicism’s affect on his parenting and his best career advice.

Welcome to the 51st episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

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This episodes guest:

My guest today is bestselling author, marketer and entrepreneur, Ryan Holiday. Born in Sacramento, California, Ryan dropped out of college at age 19 to apprentice under notable authors including Tucker Max, Tim Ferriss and Robert Greene, supporting their book marketing campaigns. After helping launch The 50^th Law, Robert connected Ryan to American Apparel founder Dov Charney. Ryan served as the Director of Marketing for the company from 2009 until 2014, where he was responsible for many notable media stunts, which became the inspiration for his first book Trust Me, I’m Lying. Since then, he’s written several other books, including The Obstacle Is The Way, Ego Is the Enemy and his latest, Stillness Is the Key. I’ve known Ryan for many years and have always been impressed by his dedication to writing a book each year, how he supports the author community and his unique lifestyle, living on a farm outside of Austin, Texas. I was especially excited to have a discussion with Ryan about his new book because it’s relevant to my book, further emphasizing the importance of taking time away from technology to be present.

Video interview from New York City:

The 5 questions questions I ask in this episode:

It’s been seven years of knowing you and this is our fourth interview. So after all of this time, what’s most changed for you and what’s remained the same in terms of your philosophy and how you live your life?
People feel like they need to constantly be connected. How can people start to disconnect so they can be more present?
How do you define stillness, what’s the feeling like when you’re achieved stillness and why should people try to do that?
How will raise your kid differently after studying stoicism and other ancient philosophies?
What’s your best piece of career advice?

Follow Ryan’s journey: