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

By August 16, 2015January 26th, 202418 Comments

“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 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:

Note: One of the best ways to support the podcast is to support the sponsors. For a complete list of all RRP sponsors and their respective vanity url’s and discount codes, visit my Resources page and click “Sponsors”.


Connect With Ryan: Website | Facebook

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 and affiliated sites.

The Plantpower Way  is now available at these fine retailers!

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  • Mary-Ellen Landry says:

    Another great podcast. While I personally don’t mind, a few too many f-bombs from Ryan where not really necessary. I can hear his passion and excitement so maybe he gets caught up in it a little or maybe we are just a bit more conservative here on the east coast of Canada eh? 🙂

  • Lara Latimer says:

    This conversation was great, as always, and reinforced things I have already lived and believe. Feeling un-smugly validated and appreciate your candor.

  • Andrea Smith says:

    Loved the beginning….Rich, you mean we aren’t best friends?! haha!

  • Pouts13 says:

    Rich, just wanted to say thank you for another amazing podcast. This one is one of my favourites. Really resonated with me as I am going through my own transformation ( that will go on for as long as I live ) and dealing with ego is a really big part of it. Your content has really helped me again. Can not thank you enough. Keep up the amazing work.

  • Faye says:

    I found Ryan’s style a bit cocky and provocative on first listen. There was probably no need to publicly demean that kid who travelled all the way from Australia to try get the apprenticeship with him. However… I worked on getting past some of the bravado and to root out what was useful. Ryan’s information about stoic thought is top class. I’m working through his book which feels like a secular take on Zen Buddhism. It’s easy to read and insightful.

  • Adam Bragg says:

    Geez! Definitely one of the best episodes. Great reminder to go back to the stoics and to just plain read more! I’m in the middle of “The Obstacle is the Way” and thoroughly enjoying it. Specifically the Part II Action. Thanks guys, you gave me plenty of ways and places to take action…much better than an inspirational quote! After this, I’m going back to The Meditations, Hay’s translation of course.

  • Adam Bragg says:

    I take it you haven’t checked out the John Joseph podcast?

  • Patty says:

    I love the podcasts, Rich, and I think you’re awesome. I have one request….more Julie, more Julie, more Julie….please!!!! I LOOOOOOVE the episodes that you two do together and it’s agony waiting to every other Wednesday to hear a new one. More Julie episodes!! I really need to hear the things she talks about and that you talk about together.

  • Maureen Burke says:

    I very much enjoyed this podcast – thank you! One line was very offensive when he said if someone is a “nobody” – what a horrible way to describe a human being…his ego was massive there.

  • Michele Boyer says:

    Hi Rich ~ I loved this episode. I actually have listened to it twice, while out on the trail and then again, while driving, because there is a lot of good stuff here! I bought Ryan’s book several months ago and I keep going back to it, especially when I feel overwhelmed in my current life transition. This convo has a lot of great take-aways and tips. #fightclub #blowingitup

    this is my second favorite episode after Josh LaJauine. Whoa. Best EVER. If the people commenting here have not listened to the Josh episode…make a point. Amazing.
    Cheers and thanks!

  • Mike says:

    This was my least favorite of all the podcast. When you both started discussing peoples use of inspirational sayings, the tone of the discussion turned very “elitist” and had a “look at you dumb people” air to it. Yet, is not the study of the Stoics exactly the same? Using their words as inspiration? You then took it further with your comments on people announcing goals in their social media and again, it came across as “I never have to do that, whats wrong with you?” The one angle you failed to mention was some people announce their big plans for accountability. I love the show and what you do, but listening to you both today reminded me frankly of two people from privilege complaining about their inferiors.

  • Mitchell Katz says:

    I really enjoyed this discussion. While Ryan does have a bit of an ego, he had extraordinary insights and you were well prepared to carry on a very heady discussion. I noted that you once again expressed doubt about your ability to continue to be relevant because you are not achieving success as an athlete. I would say that you have most definitely found your path. Your message, carried forth through your writing and your podcast, is extraordinarily important and relevant. It would not matter to me if you never ran another race.

  • Sarah says:

    I’m not sure how I feel about this one. First off, the idea that professors hate Stoics is reductive and ridiculous (I’m not a prof, btw). The truth is, they recognize the limits of Stoicism, which, let’s face it, isn’t really the deepest or even most practical approach to life (See: Seneca’s mantra of assuming you will only encounter awful people all day long, which science now proves will have a negative affect on your own outlook). Also, Seneca preached a philosophy all about contemplating your own death, yet when his turn came he completely blew it (google for details).
    Ryan sounds to me like someone who read a few good books and tried to put a popular spin on them — much like his former mentor Robert Greene. But I’m not sure this kind of shallow approach is really all that helpful.
    If it motivates people, great. But his book and his persona aren’t all that convincing to me.

  • Michael Astorino says:

    Loved the podcast as I follow both Rich and Ryan. I loved the Obstacle is the Way and have handed it out to friends and family. I loved the way Ryan relates stoicism with more modern day people and how we can all be better by adopting some of it’s practices. This guy is young and brilliant and a great guest as he compliments Rich’s view on life, mindfulness, health, etc.

  • Will Kriski says:

    Amazing podcast! I admire you guys but I also worry about you a little as you are driven to produce so much, running around travelling like crazy which probably brings about a certain pressure of expectation. This is usually admired by most people but as you guys said it’s driven by things that are not necessarily healthy or possibly dysfunctional. As Ryan said you can’t sit in a pool or just veg so I feel sad about that. I guess that drive does produce amazing results though. I’m pretty happy at my smaller scale spreading the plant-based message, doing youtube vids, interacting with people on social media and being home almost the entire time with my wife and cat 🙂 Looking forward to checking out the books you guys talked about as I don’t read those books as much as I use to, now I’m really into vegetable gardening (veganic/permaculture).

  • I listened to this podcast twice in two days. Having gone through it, processed it and thought about it, I got afraid I had missed something. Incredibly eye opening and I’d recommend to all high school students as Ryan’s message holds great value to all ‘young adults’. I’ve never really been that interested in the Romans, the ancient Greeks and the history that follows these subjects. However, after the podcast I went straight through to Amazon and ordered Marcus Aurelius’ Meditations – looking so much forward to reading it!

  • JB says:

    Ryan is one cool motherf*cker. Can’t wait to get a hold of his books.

  • Tommy F says:

    Ryan strikes me as the kind of guy, that doesn’t have the whole puzzle figured out just yet.. but has quickly identified the corner pieces. It is refreshing, to see a young man with so much talent, commit to patiently cultivating the authentic truth in himself.. while co-existing in a tangled-up, impatient world looking to pre-maturely uproot such a talent for a quick cash-grab.


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