Practical Philosophy, Career Advice, and Tools For Better Learning -- With Ryan Holiday

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Today, I speak with a writer and thinker whose work I’ve admired for years -- Ryan Holiday. As many of you know, I've shared his insights on my Instagram page from time to time over the years.

If you're not familiar with Ryan, here's a little background:

He’s a writer and media strategist. He dropped out of college when he was 19 to apprentice under best-selling author Robert Greene, author of The 48 Laws of Power (another one of my favorite writers and books).

From there he went on to become the director of marketing for American Apparel -- at 19 years old! 

Today, he has a creative agency called Brass Check, and advises massive companies such as Google and Complex, as well as many prominent best-selling authors (including more of my favorites) like Neil Strauss, Tony Robbins and Tim Ferriss, to name a few.

Philosophy is the ultimate self-help. It’s the important work we should be doing. Because if you’re not going to do it, then who is? And if you’re not going to do it NOW, then when are you going to do it?
— Ryan Holiday

Ryan is the author of seven books, including The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, and Perennial Seller. He also has a new book out now called Conspiracy.

The Obstacle Is the Way is probably my personal favorite. It addresses the subject of perspective exceptionally well and has tons of practical insights and strategies for turning trials into triumph.

In our conversation, I ask Ryan about his mindset and attitude toward philosophy, reading, his early success and much more. One of my favorite parts is when Ryan talks about how he writes about the things he struggles with and the things he works on every day. I really related to him about that.

You can connect with Ryan on Twitter, Facebook, and Instagram @RyanHoliday or through his website ryanholiday.net.

I’d love to hear your biggest takeaway from the episode. Let me know by leaving a review on iTunes with something that resonated with you in this episode. (I read every single review).

Show Notes and Time Stamps

  • The mindset and career strategy that contributed to much of Ryan’s early success (6:00)
  • How Ryan became an apprentice/mentee to author Robert Greene (8:00)
  • The importance of a network (11:25)
  • One of Ryan’s biggest takeaways from his relationship with Robert Greene (14:15)
  • Why Ryan gravitates toward Stoicism as a guiding philosophy for his life (21:00)
  • Why ancient philosophy often bears out modern day truths (25:15)
  • The ultimate purpose of philosophy and the benefits of Stoicism (27:00)
  • How Ryan cultivates the ability to think clearly and rationally (32:00)
  • Ryan’s philosophy for dealing with criticism (35:30)
  • Why it’s important to have a predetermined philosophy for your life (38:30)
  • Ryan’s note taking process for remembering what he reads (42:15)
  • How Ryan deals with overthinking (47:25)
  • Some of the books and movies that have influenced Ryan (50:00)


Books & Other Resources Mentioned In This Episode

Check out Ryan’s latest book: Conspiracy.


If you enjoy this episode and find value in this podcast, I humbly ask you to please subscribe and/or leave me a review on iTunes. Or you can just share this podcast with a friend who you think might find value in it. If you’ve already done any of these, I want to take a moment to sincerely thank you. I truly appreciate your support.

If you have any suggestions for future guests or topics you’d like to hear covered, you can email podcast@thinkgrowprosper.org.

What did you think about this episode? Leave me a comment below!


Ruben Chavez is a writer, personal development educator, and host of The Think Grow Podcast. His Instagram account, ThinkGrowProsper, has amassed over 3 million followers. Along with his blog, these platforms are his way of inspiring and connecting with thoughtful, creative, and ambitious people just like you.