Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More
“If ego has told you that you know everything, all of a sudden it’s impossible for you to learn.” – Ryan Holiday
Ryan Holiday (@RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy.
Ryan and I cover a lot in this conversation, including:
Meltdowns and how Ryan handles them
Workaholics Anonymous — How it works, what worked for him, what didn’t
The tipping points for his last book, The Obstacle Is the Way
External versus internal obstacles
Sherman versus Grant leadership and “success”
Howard Hughes versus Elon Musk
Thinking of “first principles”
If you only have 5 minutes, listen to what Ryan believes is one of the biggest threats to your creativity.
Enjoy!
Listen to it on iTunes.
Stream by clicking here.
Download as an MP3 by right-clicking here and choosing “save as.”
Want to hear another podcast with Ryan Holiday? — In this episode, 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):
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QUESTION OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.
Scroll below for links and show notes…
Selected Links from the Episode
Connect with Ryan Holiday:
Ego Is the Enemy by Ryan Holiday
The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday
The Tim Ferriss Podcast, Episode 4: Ryan Holiday
The Canvas Strategy — What Ben Franklin and Bill Belichick Have in Common
Our Brand is Crisis
American Apparel
Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising by Ryan Holiday
Workaholics Anonymous
How a book on Stoicism became wildly popular at every level of the NFL by Greg Bishop, Sports Illustrated
Pioneering coach George Raveling’s surprising connection to MLK by Seth Davis, Sports Illustrated
1,000 True Fans by Kevin Kelly
Small Giants: Companies That Choose to Be Great Instead of Big by Bo Burlingham
Sherman: Soldier, Realist, American by B. H. Liddell Hart
Billions
The 4-Hour Workweek by Timothy Ferriss
Isocrates, Volume I: To Demonicus. To Nicocles. Nicocles or the Cyprians. Panegyricus. To Philip. Archidamus.
Kanye West’s $53 Million Debt, Explained by Emily Jane Fox, Vanity Fair
The Spruce Goose
The Aviator
Howard Hughes: His Life and Madness by Donald L. Barlett and James B. Steele
TWA
Elon Musk Uses This Ancient Critical-thinking Strategy to Outsmart Everybody Else by Drake Baer, Business Insider
SpaceX
Knowledge of [Aristotle’s] First Principles
Tesla Motors
Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance
Fahrenheit 451: A Novel by Ray Bradbury
The Real Reason We Need to Stop Trying to Protect Everyone’s Feelings
Dilbert by Ryan Holiday, The Observer
Timeline of Breitbart’s [Shirley] Sherrod Smear by Media Matters
Gay pastor admits he faked homophobic slur on Whole Foods cake
Single Dose of Hallucinogen May Create Lasting Personality Change from John’s Hopkins Medicine
Deep Work: Rules for Focused Success in a Distracted World by Cal Newport
Dexa Scans
Coach.me
Stickk.com
DietBet
Real Mind Control: The 21-Day No-Complaint Experiment
The Five-Minute Journal
Show Notes
Why I think about Ryan Holiday every morning. [07:30]
Ryan talks about his tattoos. [08:10]
Ryan tells us about the hostile takeover of American Apparel and how it forced him to face some hard truths. [10:27]
The importance of having a ripcord in a contract. [17:32]
You wouldn’t like Ryan when he’s stressed and chaotic. [19:01]
At Workaholics Anonymous meetings, they say: “It’s human being, not human doing.” [23:16]
Ryan talks about how The Obstacle Is the Way was quickly picked up in the world of professional sports. [30:01]
For Ryan, the selective fame associated with writing for people he respects is preferable to the generalized fame of a household name. [36:50]
Why does Ryan focus on ego in his latest book? [39:18]
Ryan explains the way an unchecked ego can distort reality and stunt our ability to learn and improve. [42:57]
Sherman vs. Grant [45:23]
“If you start believing in your greatness, it is the death of your creativity.” -Marina Abramović [52:12]
Just because someone seems successful to you doesn’t mean they’ve accomplished what’s important to them. [56:02]
The life of Howard Hughes is a cautionary tale. [57:44]
Just because a megalomaniac asks for your advice doesn’t mean they’re going to process it rationally. [1:01:05]
Hughes vs. Musk [1:06:48]
How Elon Musk went to Aristotle’s First Principles at the formation of SpaceX. [1:06:59]
Why worrying about offending — or being offended easily — stifles creativity. [1:18:07]
Save the ammo for the right targets. [1:20:39]
Ryan’s practices and routines for reducing ego. [1:21:45]
On the importance of social accountability for self-improvement. [1:23:48]
The no-complaint experiment. [1:26:24]
Advice Ryan would give to people who want to use the principles from his book in real life. [1:27:50]
“Keep your identity small.” -Paul Graham [1:32:26]
People Mentioned
Elon Musk
Sandra Bullock
Robert Greene
Marcus Aurelius
Dov Charney
Shane Parrish
Michael Lombardi
John Schneider
Garrett Gilkey
Shaka Smart
George Raveling
Dr. Martin Luther King, Jr.
Arnold Schwarzenegger
Chris Sommer
Eric Weinstein
Peter Thiel
Kevin Kelly
Sigmund Freud
Bill Walsh
Cyril Connolly
Epictetus
William Tecumseh Sherman
Ulysses S. Grant
Napoleon Bonaparte
B. H. Liddell Hart
Bernie Madoff
Marina Abramović
Brian Koppelman
Isocrates
Steve Jobs
Kanye West
Howard Hughes
Richard Nixon
John DeLorean
Ferdinand Lewis Alcindor, Jr.
Aristotle
Curt Schilling
Donald Trump
Ray Bradbury
Scott Adams
Shirley Sherrod
Cal Newport
Will Bowen
Plutarch
Archilochus
Tony Robbins
Paul Graham
