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Cover of The Obstacle Is the Way by Ryan Holiday

The Obstacle Is the Way

Ryan Holiday · 2013
Mentioned 57 times across 9 podcasts · 2018–2026
Mention timeline57 mentions
20182026
Where it's mentioned
2026
This Is How You Should Think About It | 3 Stoic Exercises to Stop Taking Life for Granted
The Daily Stoic · Nov 2026 · 10:52
“that's what this idea of the obstacle is the way means ”
It’s Not How You See It. It’s What You Make It | 18 Stoic Lessons You’ll Wish You Learned Sooner
The Daily Stoic · Oct 2026 · 3:06
“that's what he's saying when he says the obstacle is the way ”
How Much Have You Changed? | Proof That Stoicism Can Change Your Life
The Daily Stoic · Oct 2026 · 13:45
“i read the obstacle is the way ”
BONUS | Ezra Frech Before Dancing with the Stars
The Daily Stoic · Oct 2026 · 35:15
“i just did the obstacles away just had its tenth anniversary ”
10 Stoic Lessons It Took Ryan 10 Years to Understand
The Daily Stoic · Oct 2026 · 0:08
“i'd already written the obstacles the way ”
BONUS: Toxic Masculinity, Cancel Culture & Politics
The Daily Stoic · Oct 2026 · 0:16
“your book obstacles the way helped me finish my master's thesis ”
50 Stoic Rules to Live By
The Daily Stoic · Sep 2026 · 23:33
“the obstacle is the way ”
You Should Be In The Thick of It | How Oprah Discovered Stoicism
The Daily Stoic · Sep 2026 · 10:23
“i remember my book the obstacles away it made its way through professional sports ”
Annie Duke on Why We Judge Decisions by Results, Not Logic [From the Archive]
The James Altucher Show · Sep 2026 · 97:42
“i'm sure you're familiar with obstacle is the way and ego is the enemy ”
You Fought The Wall and the Wall Won | When Self-Discipline Becomes a Vice
The Daily Stoic · Sep 2026 · 15:54
“sometimes people will you know they'll order a copy of the obstacles away and say you know my my my friend just got this you know very serious cancer diagnosis ”
Stoic Lessons From 3 Cities in 3 Days
The Daily Stoic · Aug 2026 · 19:50
“the thing i write about in the obstacles away like one of the first stories that i feel like as a writer i just absolutely nailed ” ▶ tap to hear this moment · 6s
11 Final Takeaways From The Odyssey
The Daily Stoic · Aug 2026 · 30:55
“i tell the story in the obstacles the way ”
Q&A: Becoming A Dad, Health Update & Favourite Peptides - #1134
Modern Wisdom · Aug 2026 · 10:14
“i read the obstacle is the way by ryan holiday ”
Pause and Reflect…Before You Regret | When Someone Is Rude, Respond Like This
The Daily Stoic · Jul 2026 · 2:36
“obviously i wrote the obstacles away about this idea of how do we turn difficulties to our advantage ”
BONUS | Made For Working Together
The Daily Stoic · Jul 2026 · 3:53
“the famous obstacle is the way passage is about that ”
Chase Koch on Principles, Music, and Overcoming Entropy
Conversations with Tyler · Jul 2026 · 11:04
“one of the books that had a huge in influence on me was the obstacle is the way ”
12 Stoic Lessons from The Odyssey
The Daily Stoic · Jul 2026 · 20:52
“i tell the story in the obstacles of the way ”
A Stoic's Guide To Looksmaxxing
The Daily Stoic · Jun 2026 · 3:57
“in discipline is destiny and also in the obstacles of the way i talk a lot about theodore roosevelt ”
This Is How It's Meant To Be Done | It Is Well to Be Flexible
The Daily Stoic · Jun 2026 · 6:16
“when i obviously when i talk about this idea of the obstacle is the way ”
You’re Never Going to Be Perfect | Ask Daily Stoic
The Daily Stoic · May 2026 · 6:24
“to me that's kind of what the idea of the obstacle is the way is that these unpleasant unchosen undesirable situations are practice for harder things down the road ”
Empathy Is Not Weakness | Will Guidara
The Daily Stoic · May 2026 · 28:42
“there's actually a story i added to the 10year anniversary edition of the ops goes away ”
Gavin Newsom on Ego, Power, and Stoicism
The Daily Stoic · May 2026 · 1:14
“it turned out that the gavin newsome had read uh the obstacles the way and was reading meditations ”
No, This Is The Mission | Kindness Is Always The Right Response
The Daily Stoic · May 2026 · 1:49
“last year was the 10year anniversary of the obstacle is away and now it's the 11th year anniversary of it i just it's uh not anything i could have imagined without that book ”
BONUS | 6 Stoic Rules of Arete (Excellence)
The Daily Stoic · May 2026 · 2:33
“and that leads us to the sixth and final one the obstacle is the way ”
How to Build an Online Affiliate Marketing Empire with Minimal Employees and Maximum Profits with Spencer Mecham
Entrepreneurs on Fire · May 2026 · 12:08
“the obstacle is the way by ryan holiday ”
This is the Part To Love | How a Stoic Deals with Obnoxious People
The Daily Stoic · May 2026 · 8:36
“marx realis's passage about the obstacle is the way you know what he's talking about when he says the obstacle is the way ”
Uncovering Your Superpower to Become a Successful Entrepreneur with Joshua Centers: An EOFire Classic from 2022
Entrepreneurs on Fire · May 2026 · 7:58
“the obstacle is the way by ryan holiday ”
How to Create a Time and Financial Freedom Creating Business NOW with Clay Clark: An EOFire Classic from 2022
Entrepreneurs on Fire · May 2026 · 17:15
“the obstacle is the way by ryan holliday ”
Anti-Time Management: The Power of Time Tipping with Richie Norton: An EOFire Classic from 2022
Entrepreneurs on Fire · May 2026 · 15:47
“the obstacle is the way by ryan holliday ”
What You Need is a Small Crisis | Show, Not Tell, What You Know
The Daily Stoic · May 2026 · 2:29
“and obviously that's the idea behind the obstacle is the way which i wrote about over 10 years ago now ”
Marcus Aurelius's Rules for Living a Better Life
The Daily Stoic · Apr 2026 · 4:11
“that's what the obstacle is the way is ”
Kyle Carpenter on Courage, Survival, and What Comes After
The Daily Stoic · Apr 2026 · 29:53
“i wrote this book the obstacle is a way ”
Autism Services That Change Lives with Cristina Busu
Entrepreneurs on Fire · Apr 2026 · 10:58
“the obstacle is the way by ryan holiday and so many more ”
Happy Days with Gabby Bernstein: An EOFire Classic from 2022
Entrepreneurs on Fire · Apr 2026 · 9:25
“the obstacle is the way by ryan holiday ”
Privacy is a Prerequisite for Democracy. How and Why to Use Signal with Guy Kawasaki
Entrepreneurs on Fire · Apr 2026 · 8:40
“the obstacle is the way by ryan holliday ”
Empower Yourself with This | Why You Need to Get In the Arena
The Daily Stoic · Apr 2026 · 10:20
“i wrote about him obstacles away and then i wrote about him in discipline is destiny ”
Simplifying Payroll for Small Business Owners with Roberto Masiero: An EOFire Classic from 2022
Entrepreneurs on Fire · Apr 2026 · 10:33
“the obstacle is the way by ryan holiday ”
The 5-Step Stoic Routine for Clear Thinking | Maria Semple
The Daily Stoic · Apr 2026 · 2:09
“oprah had read the obstacle as the way ”
From Bedroom Startup to Global Brand: How I Built Foundr & Sold an Ecomm Business with Nathan Chan
Entrepreneurs on Fire · Apr 2026 · 10:22
“the obstacle is the way by ryan holiday ”
LinkedIn Secrets for Busy Entrepreneurs: Grow your Sales, Authority, and Impact with Only 2 Hours a Week with Yesim Saydan: An EOFire Classic from 2022
Entrepreneurs on Fire · Apr 2026 · 11:32
“the obstacle is the way by ryan holliday ”
One Crucial Action To Transform Your Business with Kendra Prospero
Entrepreneurs on Fire · Apr 2026 · 10:04
“the obstacle is the way by ryan holiday ”
Make the Most of Your Life | Jim Collins
The Daily Stoic · Apr 2026 · 0:39
“she had just read my book the obstacles away ”
Upgrade Your Life with Rob Luna: An EOFire Classic from 2022
Entrepreneurs on Fire · Apr 2026 · 12:25
“the obstacle is the way by ryan holiday ”
How to Scale Your Business to 7-8+ Figures with Laser-Targeted 3D YouTube Ads with Aleric Heck: An EOFire Classic from 2022
Entrepreneurs on Fire · Apr 2026 · 10:44
“the obstacle is the way by ryan holliday ”
2025
When ‘genius’ becomes a trap, with author Ryan Holiday
Masters of Scale · Oct 2025 · 4:24
“who turned me on to the obstacles the way ” ▶ tap to hear this moment · 3s
2024
#762: Coach George Raveling and Claire Hughes Johnson
The Tim Ferriss Show · Aug 2024 · 29:38
“the books that i've given away the most lately are ryan's two books obstacles and ego is the enemy ” ▶ tap to hear this moment · 7s
2022
Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More
My First Million · Oct 2022 · 11:40
“my advance on the obstacles away was seventy five thousand dollars ” ▶ tap to hear this moment · 3s
Les Snead: Building a Super Bowl Champion
The Knowledge Project · Aug 2022 · 74:44
“i've talked with ron holiday about this he wrote the book you know the obstacle is away okay there's an obstacle there ” ▶ tap to hear this moment · 6s
Ryan Holiday on The Economics of Book Writing, Why You’re Monetizing Your Media Business All Wrong, His Split with Tucker Max, and More
My First Million · Feb 2022 · 25:24
“the daily stoic and the obstacle is the way ” ▶ tap to hear this moment · 2s
#564: Performance Psychologist Michael Gervais — Fear{less} with Tim Ferriss
The Tim Ferriss Show · Jan 2022 · 37:05
“about a book on stoicism the obstacle is the way that it sort of m w somehow found its way into the ranks of the nfl including the seahawks ” ▶ tap to hear this moment · 9s
#128 Ryan Holiday: A Stoic Life
The Knowledge Project · Jan 2022 · 1:28
“his books include the obstacle is the way the daily stoic and most recently courage is calling ” ▶ tap to hear this moment · 5s
2021
#207 - How to Make Millions by Unbundling Etsy
My First Million · Aug 2021 · 34:07
“he's got a bunch of yeah so he's got obstacles way ego and this whole idea is ” ▶ tap to hear this moment · 4s
2020
#474: Matthew McConaughey — The Power of “No, Thank You,” Key Life Lessons, 30+ Years of Diary Notes, and The Art of Catching Greenlights
The Tim Ferriss Show · Oct 2020 · 55:16
“i will say this you know his other book obstacles the is is the way ” ▶ tap to hear this moment · 4s
#419: Ryan Holiday — How to Use Stoicism to Choose Alive Time Over Dead Time
The Tim Ferriss Show · Apr 2020 · 5:04
“the author of many best selling books including the obstacle is the way ” ▶ tap to hear this moment · 4s
#410: Ryan Holiday — Turning the Tables
The Tim Ferriss Show · Feb 2020 · 5:53
“including the blockbuster the obstacle is the way which has been used by many of the top coaches and competitors in the nfl ” ▶ tap to hear this moment · 7s
2018
#332: Coach George Raveling — A Legend on Sports, Business, and The Great Game of Life
The Tim Ferriss Show · Aug 2018 · 65:56
“ryan's two books obstacles and and ego is the enemy ” ▶ tap to hear this moment · 4s
#319: How to Succeed in High-Stress Situations
The Tim Ferriss Show · Jun 2018 · 2:31
“one of them is the obstacle is the way by ryan holiday ” ▶ tap to hear this moment · 4s