Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More (#169)


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.



#169: Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More

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:

Twitter | Website

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

Posted on: June 25, 2016.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here's a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.

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37 comments on “Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More (#169)

  1. Love your work mate, been following you for a long time Tim! I’ve used a lot of your lessons from your book and now I find myself travelling the world as a keynote speaker. Craziest thing is that I use magic tricks as my metaphor and I am now speaking to US business all over and I am an Australian!

    You’ve been an amazing influence mate, just wanted to let you know. Appreciate you very much mate.


  2. Hi and thank you both for sharing such a stimulating conversation. Started listening in bed at 2am and managed an hour before falling asleep; woke up, rewound but gave up till morning! I especially loved the references to the ancient philosophers.

    You’re the consummate marketer, Ryan. I say this in awe, not criticism, even if I don’t always condone the tactics you use. I wonder how much of what you say, do and write publicly is about self-promotion. I sometimes get a sense you’re putting on a show, and your true self and ego come through when you’re provoked. Please excuse me if I’m wrong but there seem to be some trigger issues for you – example, media, Gawker. What do you do to temper your responses?

    You mentioned journaling and being public about what you care about as ways to improve yourself where ego is concerned. This I guess you would refer to as working towards a paradigm shift. On provocations, Epitectus goes on to basically say, take a deep breath first. I’m curious about what you do to control any impulses you may have to react instinctively or egotistically to external stimuli like online comments.

    When you do respond to someone calling you out online – how much of it is ego at work? What if what we do is perceived as egotistical even if we are (we think) simply defending our work and views? Sure, we should be able to express our thoughts freely, and self-censorship and political correctness can sometimes be more harmful than good. But while we shouldn’t have to worry about what others think of us, aren’t we lacking self-awareness and empathy – and letting ego rule – if we ignore the fact that our words can come across as (be?) dismissive or arrogant, that our actions can impact others negatively, however unintended.

    Really enjoyed this one, Tim. Thanks again.

    Liked by 1 person

  3. QUESTION OF THE DAY: What was your favorite quote or lesson from this episode?

    Definitely this question:
    How does knowledge become experience?

    I believe it’s one of those questions – you answer it and the quality of your life improves dramatically in almost all areas.
    Because we all know, in most cases, what it is we got to do to change the situation we are not satisfied with, but we do not always apply that knowledge.
    Why and how we change it?
    For each of us the answer is different. How-tos, methods, techniques – something different will work perfectly for every person. Discovering those how-tos is one task everyone should be concerned with, if one wants to change anything in life, achieve anything.

    I used to be a person who needed to know as much as possible – I didn’t achieve much being that.
    Only when I started being less concerned with knowledge and more concerned with practice/experience things started to shift the way I wanted.

    Instead of simply stating what I didn’t like about the situation I started asking: “How can I change it? What are the actions/practices required?”

    Sometimes i wake up having lots of doubts and negative self-talk. I catch it. And ask myself:
    “Why is that I’m feeling this way? What do I need to do to change it?”

    Now rarely an undesirable situation sticks for long.

    Thank you Tim and Ryan! Great talk! Lots of takeaways!


    • Awesome to read your changes! I think Tim has made a huge impact on the world with this journey he’s on! He’s got so many followers and I know that each person who listens to his podcasts or reads his book is getting a gem out of each one – I sure am! Keep being true to yourself! 🙂

      Liked by 1 person

      • Hi Michael, thanks for saying this! 🙂 Tim’s work definitely changed my life in a lot of ways and keeps changing me 🙂 – it’s not only his own journey and things I learn from his work directly but also the world his work introduced me to! All the amazing people, things, thoughts… I can’t even measure how much I’ve changed because of his work and all the ripples it produced directly and indirectly. It’s mind blowing and I’m infinitely grateful! 🙂


  4. Tim! This episode was awesome. I hope you will also check out Eric Volz’s story – he manages a different kind of crisis for a living: institutionalized kidnapping. He worked on the Amanda Knox case, as well as the Three Hikers Iran case. He works at the David House Agency ( helping families out of international crisis.


  5. Hello Tim, I only discovered you this year, but you inspired me to start some side work that I have always been passionate about doing. I have not yet traveled, it is on my “to-do” list, as I have only started these ventures over the past month. I’ve been networking and attempting to find people interested, but I feel I am missing something.

    I wanted to ask if you ever had to look for investors and if so, how did you find them?

    PS-Thanks for the motivation and keep up the good work!


  6. Tim – I find your “deconstructing world class performers” to be very helpful in maneuvering through life’s choices.
    Ever think about “deconstructing” an ordinary but extremely effective Mom & Wife? A different twist with potential appeal and impact to a much broader audience – parents / families / young adults.
    In a few words, I know no one with more common sense and ability to raise a healthy & effective family (son – USNA grad & Marine Officer; daughter UofM Nurse & Nurse Pract Grad Pgm) than my wife Louise ( & strong personality to boot!). From her communicative – focused upbringing to behavior reinforced parenting.
    May be outside your comfort zone, but worth the challenge.
    Thanks for all your work.


  7. Tim, love your podcasts, but would love more to be able to read transcripts! Takes much less time to read than to listen. Some I want to listen to, but with others, I just want the information in the quickest way possible. Please consider! Others make transcripts available. Thanks for all you’re doing.


  8. Thanks for the clean show notes, I just realized that the ones I was trying to take were a mess and they were just trying to say the same things! Related to the content of this episode, I’d actually been reading about and books by a few of the people mentioned and this just felt full circle for me. Like reading Wait But Why’s blog about Elon, Paul Graham’s high school essays, etc. I’m going to go check out some of the books and make sure I actually have an actionable item by the end of them since I’m guilty of not doing that.. I’m currently interested in Deep Work and Ego is the Enemy. I can relate really deeply with both as of right now.

    I’ve currently been facing the beloved societal high school graduation question, “So what are your plans for the fall?”. So in honor of you and the “What do you do for a living” question you love, I’m tempted to say, “Why do you care? Do you need any ideas?”. 🙂

    Thanks for these podcasts though, it makes me feel like I’m apart of the conversation and feeling included around intelligent people doing awesome things.


  9. Thanks for the clean show notes, I just realized that the ones I was trying to take were a mess and they were just trying to say the same things! Related to the content of this episode, I’d actually been reading about and books by a few of the people mentioned and this just felt full circle for me. Like reading Wait But Why’s blog dissecting Elon (which I guess Elon called him up and wanted to be interviewed which lead to a 4 part series but I recommend the last one if you only choose one), Paul Graham’s high school essays, etc. I’m going to go check out some of the books and make sure I actually have an actionable item by the end of them since I’m guilty of not doing that.. I’m currently interested in Deep Work and Ego is the Enemy. I can relate really deeply with both as of right now.

    I’ve currently been facing the beloved societal high school graduation question, “So what are your plans for the fall?”. So in honor of you and the “What do you do for a living” question you love, I’m tempted to say, “Why do you care? Do you need any ideas?”. 🙂

    Thanks for these podcasts though, it makes me feel like I’m apart of the conversation and feeling included around intelligent people doing awesome things.

    This is the super long detailed blog post I mentioned above which definitely “deconstructs the world-class performer” Elon Musk. It’s about Elon and an in-depth analysis of how he thinks and first principles and yeah A+. I printed it out!


  10. Hey,
    Heaps of gems, but especially I loved this quote

    “My biggest concern for the U.S specifically is the existential death of free speech driven by (among other people) the college students who are going on witch hunts. With this very Fahrenheit 451 mentality – anyone who causes discomfort, anyone who offends, anyone who ,god forbid, questions the accusations of racist, sexist, (…) , or asks at least how are we defining these terms should be lynched (from a career stand point) at the very least.”

    So thanks for highlighting the issue, I believe this over inclanation to be offended causes a lot of social and especially political misunderstanding in the UK. It also slowly creeps into the Russian society where college-aged demographic starts to believe that this is how democracy actually works,causing further social division without adressing the real issues, imo.


    Can’t believe you still didn’t get Kelly Slater (the surfer) on the podcast: an 11 times World Champ, a ground breaking enterpreneur – he’s right up your alley mate


  11. Tim,

    Been following what you do since 4HWW – ourstanding stuff that has been very helpful to me.

    During this podcast, there were a number of spots where Bryan was responding to a question that was never asked – were these edits?

    Lastly, I wanted to get the transcript but you asked for my email, again. I was already signed up with 5-bullet Friday when I gave my email for the speed reading PDF; after that I started getting two emails for everything (5 bullet, podcast, etc). I’m afraid I might get 3 if I give my email address for the transcript. Can you cull your lists for dupes?



  12. Hi Mr Ferriss.
    I’ll be brief. I’m from Perth Australia and see a natural practisioner for bursitis in both shoulders. I was wandering if you would be able to do a podcast about this guy, Rob Bondonno Natural Health at He does something called Bio Muscular stimulation (I think). I’ve had a range of ailments over the years and have experimented with all sorts of people that should be able to help but can’t for some reason or another. This guy is the exception.

    Even if you don’t do a podcast with him, (to let the world know this sort of therapy is out there), would you be able to do one about different therapies on repairing the body, without surgery, in the many ways there are grains of sand, please.

    I know he’s been looking for a long time, about ten years, for something out there that does something similar. He’s now starting to do a PHD on this method of his.

    Thank you for your work. Keep being curious.


  13. Enjoyable and instructive as always. You started it by saying you had ‘too much tea’ or something similar… your end of things did seem a little less precise than usual. Maybe there’s a useful data point there in terms of how you prep for these things?

    The excerpt Ryan read in a previous podcast on the canvas strategy was great and an important summation of some of the self-help/performance psychology classics I’ve read based on the recommendations of many of your guests since I’ve started listening to your podcast. I look forward to reading his books and hearing more from both of you.


  14. Hi Tim!

    Great podcast with Ryan. I found Ryan’s previous book a great reminder in my day to day life. I found that when the tough was going, I would lose focus and rather switch off into other activities that felt safe and comfortable.

    This podcast couldn’t have come at a better time, where I have felt that the ego within is pushing me to strive for success that doesn’t sit right with my being. So I really appreciate you and Ryan recording this podcast. Most definitely will be picking up, Ego is the enemy.


  15. I actually liked the topics Ryan discussed, but I had to stop the podcast. It was painful!! His speech is worse than nails on a chalk board. When you can’t see someone in person and all you have is their voice, their speech becomes paramount. He says “like” “” and “uh…” more often than saying true words. He rarely completed a full sentence and had trouble articulating details that led to the main point. Ryan has great points, but if this is his profession he MUST go to a speech coach. Run, do not walk. Hell, take a sonic jet if you need.


  16. Tim,

    I was unable to relate to your introduction of Ryan as one of the people who has seen the most obstacles for his age/something like that. From the backstory that followed, it sure was a challenging time for him but nothing like what you described initially.


  17. The practice of focusing on valuing things that cannot be taken away is a profound concept. Wonder what are examples of what to value? One idea is to value the experience with people but not an experience with a particular person.


  18. Thanks for the outstanding episode Ryan and Tim. This definitely one that I am going to have to review again. Tons of great advise and resources referenced!

    Although, it was just a small mention during the interview, the point that stuck in my head the strongest with Tim’s analogy of the 6 bullets per year and save the ammo for the right targets! Great leadership advise!

    Thanks again!


  19. Did anyone catch the comment about being offended? It was something to the effect that when you feel offended, look back to yourself as to why you feel that way. By Epictetus perhaps? I can’t seem to find it again.


  20. Hi Tim and Ryan,

    I’ve often heard you refer to yourself as a very ‘Type A’, competitive person and wondered if you had any thoughts or advice for people who are the opposite of this? I’m thinking specifically of my Dad who is a very go with the flow, unambitious kind of person who many people say has wasted his potential. It seems the ego is not the enemy in the case, in fact probably the opposite.


  21. Book finally came out in the UK as well, can’t wait to catch up with Ryan again when he will pop in to record his interview for London Real


  22. Loved the book – I learned a ton and it should be required reading as i saw a lot of myself in the negative examples. It’s a great reminder that we are most vulnerable to ourselves at our highest and lowest points
    i wouldn’t want to misinterpret it as a tool for compliance – maybe it could be read alongside linchpin by Seth Godin to even out the – trust me… do as i say and good things will happen… and here’s a book to prove it… – vibe


  23. The book Ego is the Enemy is a great book. Just finished it. Hard to take but I can see how my ego has affected my business over the years, the good, the bad and the ugly.


  24. Yeah, this episode for me was AMAZING! This one is added into the list that I want to listen to a few times over…