Ryan Holiday — How to Use Stoicism to Choose Alive Time Over Dead Time (#419)

“Anger is often what pain looks like when it shows itself in public.”

Krista Tippett

Ryan Holiday (@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 WayEgo 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.

This episode focuses on Stoic philosophy and how to apply it in our current uncertain times.

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 interview on YouTube.

This podcast is brought to you by LegalZoom and Trello. More on both below. 

#419: Ryan Holiday — How to Use Stoicism to Choose Alive Time Over Dead Time


This episode is brought to you by LegalZoom. I’ve used this service for many of my businesses, as have quite a few of the icons on this podcast, including Automattic CEO Matt Mullenweg of WordPress fame.

LegalZoom is a reliable resource that more than a million people have already trusted for everything from setting up wills, proper trademark searches, forming LLCs, setting up non-profits, or finding simple cease-and-desist letter templates.

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This episode is also brought to you by Trello. Now, more than ever, teams must come together and work together virtually to handle challenges, opportunities, and everything in between. Trello, part of Atlassian’s collaborative suite, is an app with an easy-to-understand visual format and tons of features that make working with your team more functional and more fun. Teams of all shapes and sizes—and companies like Google, Fender, and even Costco—all use Trello to collaborate and get work done.

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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 empathy cultivation, why competition is for losers, lifestyle design, reading list methodology, and much more. (Stream below or right-click here to download):


  • Connect with Ryan Holiday:

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


  • How do the ideas of the ancient Stoics help me face the trials and tribulations tracked in by our apparent apocalyptic horseman du jour during the age of COVID-19 — for example, the roller coaster ride that my stock portfolio’s value has become? [05:12]
  • Contemplating the amount of war, pestilence, and famine the world’s gone through since the Marcus Aurelius statue that sits on Ryan’s desk was carved in 1840 — and reminding ourselves that as bad as things get, history marches on (with or without us). [11:27]
  • How Ryan prepared in anticipation of the pandemic, what he’s been struggling with most since then, and what I’ve been doing to cope with the same struggle. [12:48]
  • It doesn’t matter how many opportunities you miss; it matters how many opportunities you take advantage of. [16:06]
  • There are times when I may make very fast good decisions, but I almost never make good rushed decisions. [21:08]
  • How would the Stoics suggest processing the anger we might be feeling over our government’s delayed response toward the pandemic — especially if we were already advocating precaution in the weeks before and being denounced as Chicken Littles for our trouble? [00:00]
  • How am I thinking about fear, and what would I say to someone who’s feeling overwhelmed by fear right now — for themselves and loved ones — under circumstances that are “unfair” and beyond anyone’s control? [31:48]
  • How can you make the next three to six months something you look back upon as a sacred time that you really treasure, not just survive? Is it going to be “alive time or dead time,” as Robert Greene would say? [40:17]
  • A few more thoughts on fear. [45:05]
  • Why I’m confident (and optimistic) that crisis will overcome incompetence in how the United States comes out of this ordeal. [48:08]
  • When stuff breaks down, real leaders stand up — like Emperor Marcus Aurelius working to keep Rome’s economy going during 15 years of a pandemic instead of fleeing to the countryside for safety. With different levels of skills and resources, how might we each channel our inner Stoic to be of service to the world during this crisis — and see it as an opportunity rather than something to simply be survived? And can you simultaneously be a pleasure-loving Epicurean and duty-bound Stoic? [51:08]
  • Since anger and complaining accomplish about the same amount of nothing, quarantine might be an excellent time to revisit Will Bowen’s 21-day no-complaint experiment. [1:02:20]
  • And if you want to further your contribution to ensuring the world doesn’t grind to a total standstill, maybe try the Daily Stoic’s Alive Time, Dead Time Challenge! [1:04:18]
  • Using this rare window of time to foster a sense of community where it has largely broken down. [1:05:15]
  • The origin story of the expression “alive time or dead time,” how some of the most brilliant minds have expressed their greatest work during times of quarantine, and parting thoughts. [1:06:16]