Turning Adversity To Advantage: Ryan Holiday on Why The Obstacle Is The Way

“The impediment to action advances action. What stands in the way becomes the way.”

Marcus Aurelius

I love talking to smart people. Today’s guest is certainly that — and so much more.

Contravening millennial stereotypes, Ryan Holiday is a prolific, rising literary talent. A maverick media strategist. Not to mention a philosopher of sorts — a guy with big ideas often at odds with the status quo.

An autodidact, Ryan dropped out of college at nineteen to apprentice under acclaimed author Robert Greene, author of (among many other great books) The 48 Laws of Power*, later graduating to advise many New York Times bestselling authors like Tim Ferriss and RRP #154 alum Tucker Max, multiplatinum musicians like Linkin Park and startups like Casey Neistat’s ( RRP 73 & RRP 144 ) recently launched social media platform Beme.

By the time he was legally allowed to drink (21!) Ryan had already ascended to director of marketing duties at American Apparel, where his iconoclastic campaigns and tactics have been used as case studies by Twitter, YouTube, and Google and written about in places like AdAge, the New York Times, and Fast Company.

Ryan is also the bestselling author of 3 books, including Trust Me I’m Lying* – a highly entertaining and admittedly disturbing first hand look at the machinations behind digital media’s dark underbelly — and The Obstacle Is The Way* – a modern and practical reframing of stoicism, the ancient Roman philosophy originated by guys like Marcus Aurelius, Seneca and Epictetus, with a focus on functional applicability of stoic principles for turning modern day obstacles into opportunities and adversity to advantage.

If you think philosophy is purely academic — a useless waste of time reserved for the arrogant intellectual elite — Ryan has a message for you:

think again.

I really love this book. I found it to be eminently practical. An incredibly insightful and utilitarian tool box for navigating crises, strengthening character and maximizing excellence in any situation, irrespective of circumstance.

On RyanHoliday.net and places like Thought Catalog and Observer (where he is editor at large), Ryan writes frequently on a wide variety of business and marketing related subject matters. But it’s his fresh and unique take on real life stuff that keeps me coming back.

A voracious reader, I highly suggest everyone subscribe to Ryan’s monthly reading recommendation newsletter of books he’s read, reviewed and thinks you will like. It’s great.

This is a really interesting conversation about many things, not the least of which is Ryan’s perspective on stoicism as a primer for conceptualizing, confronting and ultimately overcoming whatever scenario befalls you. It’s a conversation about our collective misunderstanding when it comes to the importance of the struggle as gift — the importance of the journey beyond the success equation as formative of character and self-esteem. It’s about doable strategies for overcoming the barriers that too often hold us back. And it’s about reconciling the fundamental principles of stoicism with our misguided inclination to short cut — aka ‘hack’ — our way to a fulfilling and sustainable result.

Plus, we take an interesting dive into the machinations of modern marketing culture in our click bait obsessed, shadenfreude-infused, internet shaming world, including parameters for discerning the internet snake oil salesman from the valuable content provider.

All told, this conversation explores:

  • stoicism as practical philosophy
  • goal-setting & social networking: manipulation v. motivation
  • turning inspiration into action
  • reigning in ego and survivorship bias
  • our mistaken perception of happiness & success
  • the importance of humility and service
  • navigating obligation with joy
  • the importance of being present

I sincerely hope you enjoy our discussion.

How can stoicism help you navigate personal and professional obstacles? I’d love to hear about it in the comments section below.

Peace + Plants,


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Thanks to this week’s sponsor:

Harrys.com: Type in my coupon code “ROLL” at purchase for $5 off your starter set and get an entire month’s worth of shaving for just $10. Go to Harrys.com today!


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Background, Context & Reference:

Notable People Discussed in today’s podcast:

Related Podcasts You Might Enjoy:

Production, music & sound design by Tyler Piatt. Additional production by Chris Swan. Graphic art by Shawn Patterson.

*Disclosure:Books and products denoted with an asterisk are hyperlinked to an affiliate program. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

The Plantpower Way  is now available at these fine retailers!

Amazon*  |  Barnes & Noble  |  IndieBound  |  Penguin

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