Ryan Holiday — Turning the Tables (#410)

Welcome to The Tim Ferriss Show! It is — usually — my job to sit down with world-class performers of all different types to tease out the habits, routines, favorite books, and so on that you can apply and test in your own life. This time we have a “turning the tables” episode. What does that mean? Well, I will not be the one doing the interviewing. Instead, I will be the one being interviewed by my friend, Ryan Holiday.

So who is this Ryan fella?

Ryan Holiday (TW/IG: @RyanHoliday) is one of the world’s foremost thinkers and writers on ancient philosophy and its place in modern life. He is a sought-after speaker and strategist and the author of many bestselling books, including The Obstacle Is the Way, Ego Is the Enemy, and The Daily Stoic. His books have been translated into more than 30 languages and have sold more than two million copies worldwide. He lives with his family outside of Austin, Texas. You can subscribe to receive his writing at RyanHoliday.net and DailyStoic.com. Ryan was also the fourth-ever guest on the podcast in the very beginning, and he has written multiple popular guest posts for my blog, which you can find at tim.blog.

His latest book is Stillness Is the Key, which was an instant #1 New York Times bestseller and Wall Street Journal bestseller.

I also recommend checking out the interview on YouTube, if you like, as I made sure to have video from multiple angles for this episode. Just go to youtube.com/timferriss.

Please enjoy! 

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. You can also watch the conversation on YouTube

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode with Ryan Holiday? — In this conversation, we discuss the “big three” Stoics, how Stoicism applies to the modern world, and how to improve your decision-making when stakes are high (stream below or right-click here to download):


  • Connect with Ryan Holiday:

RyanHoliday.net | Daily Stoic | Twitter | Facebook | Instagram


  • How adopting and taking care of a dog has taught me to be better to myself and others (and why this isn’t necessarily the right approach to personal improvement for everyone). [05:50]
  • Putting us at odds with our evolutionary programming, is the nature of modern life conducive to fostering neuroses and self-absorption to the point where we have to consciously cultivate empathy? [16:48]
  • Why did I decide to move to Austin, and how do I feel about the decision a few years into it? How does it compare to — and contrast with — other cities where I’ve lived and spent time? [20:02]
  • Competition is for losers. [29:49]
  • We’ve covered why I decided to come to Austin, but what really motivated my decision to leave the Bay Area? What historically drives my need to, as Ryan says, “walk away at the top” whether it’s from investing or the fulfillment of a seemingly impossible book deadline? [31:03]
  • Journaling as a way to think up new ideas rather than merely capturing them (Thanks, Kevin Kelly!), and the perks of remembering that big life choices — like moving to another city or dropping out of college — don’t have to be treated as irrevocable if we want to expand our palette of life experiences and become contenders in our craft(s) of choice. [38:21]
  • Contrary to popular belief, I’m very risk-averse. So when I weigh good risk vs. bad risk, here’s how I consider what there is to be gained even in the case of “failure.” [45:43]
  • Fear-setting, premeditatio malorum, and how I cultivate walkaway power with my own projects. [52:10]
  • Energy management, the value of simplicity, and the question I ask myself now when weighing my potential involvement in any project. [56:54]
  • Why I prefer conducting experiments that promote deliberate lifestyle design and quality of life improvements now to the typical “slave, save, retire” formula so ingrained in the American work ethic. [1:01:12]
  • Even though it can be challenging to shift gears mid-career, just remember: no one can condemn you to do anything for life just because you’re good at it — except for yourself. [1:07:29]
  • Costs of inaction, non-morbid ruminations on mortality, and the Stoic reminder of Memento Mori (“Remember you must die”) — that life is not on an indefinite lease. [1:09:05]
  • Why, even if you keep all your money in a mattress, studying good investors is worth a lot — especially if you’ve ever had a bad math teacher. Remember: anyone who’s alive invests to some capacity, whether it’s capital, time, or energy. Here are some books I recommend that should get you started. [1:15:32]
  • What are you going to care about if you’re lucky enough to get older than you are right now? [1:21:19]
  • How exploring the distinction between correlation and causation becomes even more absurd when contributing factors get downplayed or overlooked entirely and lazy media outlets report on extrapolations made from poorly understood abstracts — and the opportunity this spells for those willing to pay attention (whether they’re investors, inventors, designers, or athletes). [1:24:23]
  • The history of Uber — from a misunderstood concept that was universally mocked by investors to a multi-billion dollar valuation — illustrates this phenomenon and drives home the usefulness of the one percent as a demographic of price-insensitive guinea pigs for prototype testing. [1:30:35]
  • At any given point, we’re all getting it wrong. So how have I honed the ability to get it right at least some of the time when opportunities hiding in plain sight are ripe for the spotting? [1:33:44]
  • On learning from the experiences of others, sharing our experiences so others might learn from us, and trying to make sense of those who — for whatever reason — choose not to. [1:35:10]
  • When life’s so short, how do I decide what gets added to my reading list? What’s my methodology for breaking down books, and where do I get the knowledge that saves me painful (and time-expensive) trial and error? [1:41:46]
  • Why keeping on top of things is a losing game when you’re more accurately striving to get to the bottom of things. [1:52:47]
  • Parting thoughts and Stoic farewells. [1:55:31]