The Obstacle Is The Way — The Tim Ferriss Book Club, Book #4



This post is about the fourth book in the Tim Ferriss Book Club, which is limited to books that have dramatically impacted my life. All previous selections can be found here. Enjoy!

“Would you have a great empire? Rule over yourself.” — PUBLILIUS SYRUS

The last two weeks have been disaster after disaster for me:

  • A dear friend died unexpectedly, only miles from my home. (RIP, Seth Roberts)
  • A seven-figure business deal fell apart at the last minute.
  • Only days ago, Turner Broadcasting let me know that the May 27th digital launch of The Tim Ferriss Experiment has been canceled. Some (not all) of the higher-ups want to try selling it to traditional outlets. (Sidenote: If you bought an iTunes season pass, definitely request a refund)

Over the last 14 days, I have carried one book in my backpack to cope, all day and every day: The Obstacle Is The Way.

It has helped me to turn problems upside-down, become the calm within the storm, and even uncover unique opportunities.

“Philosophy” gets a bad rap.

Most of us know a turtleneck-wearing pseudo-intellectual who’s spent countless hours studying obscure details of Freud or post-structural lesbian feminism.  These same people sometimes purport to be “philosophical.” And for what? More often than not, to posture as a holier-than-thou jerk off. To argue over semantics that don’t matter.

Fortunately, there are a few philosophical systems that produce dramatic real-world results…without the nonsense. In other words, all substance instead of smoke.

The Obstacle Is The Way, penned by Ryan Holiday, is a collection of stories and principles about Stoicism, which I consider to be the ultimate personal “operating system” for entrepreneurs…or anyone who wants high performance under high stress.

Ryan became Director of Marketing at American Apparel at age 21 (!). He gets more heat, makes more high-stakes decisions, and take more risks in a given week than most people experience in any given quarter. He also happens to be a die-hard Stoic and incredible at putting the principles into practice.

If you want to be “anti-fragile” like Thomas Jefferson, Marcus Aurelius, and many of most dominant soldiers and investors in history, Stoicism offers the playbook.  If you want to make better decisions, if you want to smile when other people cower, it offers real tools.

To quote Andy Grove, former CEO of Intel, “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

What if you could be a person who is improved by crisis? That would give you opportunities no one else can see, let alone grasp.

It will also make you a happier human being.

Check out The Obstacle Is The Way today:

I’m not the only one who loves it. Here are just a few of many:

“Follow these precepts and you will revolutionize your life. Read this book!”
—Steven Pressfield, author of The War of Art and Gates of Fire

“A book for the bedside of every future–and current–leader in the world.”
—Robert Greene, author of The 48 Laws of Power and Mastery

“Ryan Holiday has written a brilliant and engaging book, well beyond his years…It is invaluable.”
—Honorable Frederic Block, Judge, U.S. District Court

Seriously, check out the book.

If you’d like to hear more of Ryan’s ideas, you might enjoy the podcast interview I recorded with him recently, which has gone nuts on social media:

Question of the day: What philosophies, guiding tenets, or quotes have you found most helpful in your own life? Please share in the comments!

Posted on: May 8, 2014.

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96 comments on “The Obstacle Is The Way — The Tim Ferriss Book Club, Book #4

  1. Tim take a look at, if interested about human operating systems, even though this ain’t the one I was involved with, an dis not 5based on stoicism, it is the most simple and probably mainstream way of understanding our world, development and being. Hope everything gets better! Thanks for everything


  2. It’s been my experience that if a “bad” event cannot benefit you, then it simply will not happen (even against all odds). This is a law of nature; there is no pain without purpose. I never realized how beautifully Stoicism aligned with this notion, and I am thrilled that people like you and Ryan are popularizing it.


  3. Yup! Great book! Ryan has really delivered big time!

    It’s literally a gate way drug to the school of Stoicism and general emotional intelligence understanding and application.

    Also very thorough interview on your podcast, listen to it peeps to get some Tim goodness more often!

    PS: Every time I cheat on slowcarb I say “Sorry Saint Ferriss” to the chuckle of my friends :p


  4. two quotes that always seem to get me through the tough times:
    1) Whether you think you can or you can’t, you’re right
    2) You can’t change yesterday, only today and tomorrow


      • No particular obstacle, just life. I don’t think it’s ever ONE thing, life is a constant series of opportunities and difficulties.

        Actually Dr. Drew Pinsky introduced me to stoicism when I was a teenager. Huffp has an article about it.


    • The book is awesome. I thought it was interesting that you bring in Nietzsche’s amor fati towards the end to wrap things up. I’m curious to know what other philosophies you’ve dug into and what drove you away from them?


  5. Fantastic and appreciated advice!

    Marcus Aurelius is an incredible example of what true wisdom looks like.

    A similarly-powerful book about the power we have to determine how events affect us is “Hannibal and Me”. I highly recommend you check it out, and expect it will similarly become a favorite.

    Thank you for the wonderful recommendation!


  6. The quote I live by is my own – which I invented at the age of 14 watching in horror as my mother turned down a 6M piece of property my grandfather offered to give her nearly 40 years ago. – “Pride doesn’t pay the rent” – I have reminded myself this quote quite often when having to “suck it up” in order to meet a bigger objective. It has helped me avoid making stupid decisions based on unnecessary emotions and perceptions that could derail me from reaching a sought after goal.


  7. ‘I believe the world is plotting to do me good today. I can’t wait to see what it is.’ – W. Clement Stone. This helps me to take actions way out of my comfort zone.


  8. Thanks for the recommendation Tim.

    I am happy to share with you a religious quote that have helped me a lot, and it is:
    Allah will provide.
    meaning that no matter how far or difficult a thing may be thought, Allah, the Creature of the Universe, the One that has the Power to do all the things can provide and will provide and will not put down any of your efforts.

    It can be seen as a religious preach, but sincerely, it has helped me a lot.


  9. This quote by Ralph Waldo Emerson had a big impact on me: “Don’t be too timid and squeamish about your actions. All life is an experiment. The more experiments you make the better.”


  10. Tim – I don’t normally comment here, but today is different.

    I’m certain you already know this, but I’ll say it for the benefit of others — When disasters happen they feel like ‘now’. But the simple truth is that they have already happened. They are already gone in the moment of becoming.

    And until Elon Musk invents time travel, that’s the way things will stay.

    We *can’t* change what has happened. We *can* change how we live in the present.

    Life is a series of moments that can be managed.

    Manage your moments.


  11. Hey guys,

    Just finished 8 hours of driving, in which I listened to the book almost twice. Dunno if you care, but I thought I’d let others know what someone else thought of the book.

    I’ve glazed over a bit of Seneca, and a bit more of Aurelius, but it was long ago. I also picked up these writers (and listened to ‘The Obstacle’), long after falling in love with Bill Glasser’s Choice Theory, and Stations of The Mind – ; which is very much akin to at least somewhat a similar message – but in a psychological counselling method. Talks a lot about having a choice, regardless of the situation, and ‘Controlling for’ certain perceptions; then acting accordingly.

    Something I’m always appreciative of is real life examples historically. Especially ones regarding success. The book is overflowing with them. To be honest, at times I felt a little bit “Meh…” about the direction; but then a real life historical example really drew me back in.

    In my sad grey lifetime, the best experience to demonstrate a stoic disposition was mastering day trading futures, when I was in a financially strained position.

    My emotions were running high. I was winning money, and losing money. It’s such an emotional roller coaster in that kind of situation; and it was recommended that I not take part in futures trading given my financial situation which I mistakenly (perhaps?) ignored.

    It wasn’t until I was able to trade without elation, or depression or anger that the practice became profitable. Much like the reference to Rockerfeller. It was a truly educational experience that I wouldn’t trade for anything. But if you really want to test your practical application of stoicism; I’d give it a shot.

    One thing I think the book skipped over in the practical application of success was the application of integrity. I suppose that is a given; and one might envision that a person turning obstacles without integrity into integrous ones would do just that. But if a plan of action to turn an obstacle into an opportunity or ‘way’; and the individual making the plan comes from a person who doesn’t have the practice of following their own word; the plan is faulty from the start.

    Integrity might be a given; I’m sure Aurelius pitched it pretty hard. Long term success is impossible without vigilant and disciplined integrity.

    The book prompted me to turn what I think is a potential billion dollar project I’m working on; into an ‘at least a million’ dollar project and provided a more concrete attitude – should the worst happen. A mindset I’m very thankful for, and haven’t really read since :-

    ‘…someone would probably spit on my head from a highrise balcony while I’m feeding food scraps to a stray dog, which would then spook and bite me squarely on the face’.

    Despite the odd ‘meh’ moment; it’s a great audio book. I don’t listen to too many books more than once; but because of the yielded result of plans and actions from reading it; I will continue to program myself with it. I think I personally found The Art of Learning more entertaining – probably because it was more personal – but much less practical; and I haven’t listened to it again.

    I especially enjoyed the interview at the end. The second time I listened was directly after I finished the interview part between Tim and Ryan. I don’t know if it was because it was the second time or because of the interview; but I felt like I jived with Ryan a lot more after getting to know him in the interview. It also solidified my assertion that Tim is a dork…which I find very encouraging :)

    I know it isn’t common practice; but it might be interesting to measure the retention or usefulness to a cohort that had the interview first vs interview last.

    Question for Ryan: In your lifetime; did you ‘come in’ at a level of integrity where what you say and what you do are the same? Is this something you had to work on or demand of yourself consciously? Do you think this definition of integrity is required for success?

    I’d really like to read a collaborative study on success between yourself and an Australian guy named ‘Peter Burow’, who calls the process of ‘The Obstacle’; ‘conversion’ . That is; turning limbic tension into neocortex nobility.
    The same message delivered neurobiologically.

    thanks for the great read.


    • Hey Man, thanks for putting the time to writing this. You said you traded Future, you should look for “Anti-Fragile” from Nassim Nicholas Taleb.
      Keep going, and let’s make this billion dollar business



  12. Will def buy this book!

    Some of The Quotes in my daily reminder:

    Morrie (From The book Tuesdays With Morrie)
    1. “Remember what I said about detachment? Let it go. Tell yourself, ‘That’s the feeling, I’m going to separate from it now.’ And walk away.”
    2. “Do what the Buddhists do. Every day, have a little bird on your shoulder that asks, ‘Is today the day? Am I ready? Am I doing all I need to do? Am I being the person I want to be?”

    The Plant’s blown up. A variety of things don’t work. Keep goin! – Jack Welch

    REREAD These articles by Tim Ferriss ( WORKS LIKE MAGIC!
    1. The Prescription for Self-Doubt: Watch This Video
    2. “Productivity” Tricks for the Neurotic, Manic-Depressive, and Crazy (Like Me)


  13. I absolutely LOVE this book so far. Currently mid-way through and it’s already one of my favorite books. Can’t wait to finish it and then go back and apply the teachings to my life!


  14. Something I never understood about the TV show thing…why do you need them? You’re supplying the majority of the viewers, why not keep 100% of the revenue, 100% of the control, and sell your own show right here?


  15. Great Tim, will definately buy this book!

    Love the podcast as well. Really like that you dig DEEP into the subject(s) which both you and the guest have a lot of knowledge and opinions.

    4 Questions for Ryan about The Obstacle is The Way and books in general. Would really help me and hopefully other readers to get some pro reading advice :) :

    1. How quickly do you get a book “into your system” and really benefit and improve your life through the wisdom you gain?

    2. What is your way to really “get” a book? (Re-reads, notes etc)

    3. Do you use the same approach to every book, or is there different ways to get the best out of different books?

    4. How should I approach/read/study this book?



    • I know Tim doesn’t like links here so I won’t put them but I have a few posts about this on my site and on Thought Catalog. Look for “How To Read A Lot” “The Note Card System” and “Read To Lead”


  16. My personal favorite is – What other people think of you is none of your business. I also like – You may think adventure is dangerous, try routine-it’s lethal.


  17. Tim,

    I truly appreciate your work but how do you like DRM?

    See more at link under my name which is a link to my comment #136 under your post “Book Club #3: The Art of Learning”.

    Steve Jobs (who also hates DRM)


  18. From Bill Cosby, “In order to succeed, your desire for success should be greater than your fear of failure.” Very good quote


  19. Dear Tim,
    As a person who works in the entertainment/education industry in silicon valley, I can deeply relate how soul crushing these decisions can feel. We fight hard for things we are passionate about and go 20 rounds with suits that translate our passion and our art into facts, figures and my personal favorite the demographic reach. You just wish they would have said no in the first place so you would not have spent all that time and energy banging on doors and rallying the troops to support you.

    In times likes these I have held on to the 12 principles that Colin Powell has laid out. In this case these 2 seem to fit.

    #3. “Don’t be buffaloed by experts and elites. Experts often possess more data than judgement”.
    - Always question what the experts say if you don’t understand. Don’t assume that they know more than you, and certainly don’t be cowed into accepting something that you don’t fully understand.
    - Anytime I’ve been in a pitch meeting I’ve been bombarded with marketing data that in my heart never truly gave an accurate account of what the target audience really felt. Thus I accepted decisions that should have never been made and the result was things I cared a great deal about died on the floor before they ever got out the door.

    Thus I learned to accept #9

    #9. “Never let your ego get so close to your project that when your project goes, your ego goes with it”.
    - Change is stifled by leaders that “cling to their turf”. Effective leaders create a climate where people’s worth is determined by their willingness to learn new skills and take on new responsibilities.
    -I could talk for hours about this but take comfort in this. You have done right by your fans, changed many lives and have built an army of fans that trust you and really want to see what you will do next. I am one of them. Please keep up the great work.

    If you ever want coffee and a guitar lessons or a drum lesson. hit me up. I’ve studied with many of the worlds finest
    P.S sorry for the long post. I never comment but felt compelled .
    P.P.S Dear grammar Nazi’s please be kind, writing was never my strong suit


  20. Great thoughts I’ve heard include “Those that say it can’t be done will not be allowed to talk to those doing it.”


  21. Hey Ryan, phenomenal book you’ve created. It’s like you’ve taken the greatest material the world has made and translated, condensed, and simplified it into powerful thoughts. It’s already saved my ass in a crisis, the value exceed the cost of the book by far. It’s the OS for any human.

    As far as the questions go, here’s a few (pick and choose):
    1) How do you advise entrepreneurs to find time to read? (Many times while reading, the mind wonders and thinks to a billon other things to take care of at that moment, how can one make reading a priority?)

    2) Approx. how many books do you consume a week? How can people read faster without losing comprehension?

    3) What’s your favorite chapter (The Obstacle Is The Way) that didn’t make it in the book (If any)? And, can I get my hands on that?

    4) If physical books are you thing, why did you make Growth Hacker an ebook at the beginning? Do you recommend first-time writers to do the same?

    5) What’s your sleeping pattern like normally, and what’s you sleeping pattern like when it’s crunch time? (8hrs of sleep vs 5hrs of sleep with power naps?)

    6) American Apparel: What’s your favorite ad you created?

    7) What’s a book, song, quote you love?

    I apologize for the dump of questions, these were my top that I wanted to ask you. I’ll have you on the podcast (The DOcast) one day, maybe next book.



    • Unfortunately there is no magical way to make reading a priority other than making it a priority. Nobody asks me how I make time to eat or sleep, right? I tend to be a binge reader. So at least one a week but sometimes 5. In terms of Growth Hacker Marketing–it was a test of the market. Why make a physical book if I wasn’t sure how it would do? In this case, the paperback comes out in Sept so it worked out well.


  22. Advaita-Vedanta. Everything is one. When you get it – there really is no problems left. Though, it can be difficult to get over the usual momentum of thinking. But honestly, most people who talk about it – misunderstand it, in my opinion.


  23. Dear Tim,

    I’m so sorry you lost your friend so suddenly. He sounds like he was a wonderful inspiration and gift to know. Take care,



  24. This Latin phrase was posted on my cubicle wall (before I finally quit a 14 year stint in government to strike it out on my own) which kept my final goal in mind, that of leaving the safe place for the unknown:

    ” Aut Viam Inveniam Aut Faciam”….attributed saying by the Carthginian general Hannibal before he crossed the Alps: “I will find a way or make one”.

    The other phrase I kept written in private because it’s quasi-religious and was prohibited at my former position. It’s attributed to the Pope John XXIII who was recent canonized a saint in my faith. He once stated: “Consult not your fears, but your hopes a dreams. Think not about your frustrations, but about your unfulfilled potential. Concern yourself not with what you tried and failed in, but with what still is possible for your to do.”

    I’m sorry about your recent challenges, but I’m sure you will find the strength to overcome and make peace with them.


  25. Ryan Holiday tells his readers to do the job in front of them, but he did not do the job of publishing his book when it was in front of him. He or his agent could have insisted that Penguin hire copy editors. No book by a man of his competence and resources should go out into the world full of grammatical errors and misused words. It is an insult.


    • Welcome to publishing Mary, things go wrong. Someone in production messed up the subtitle. Proceeding despite imperfections is part of life. Taking errors as an insult, on the other hand, is a recipe for rage and anger.


  26. Nietzsche and Taleb are the biggest perspective-shifters for me. Seneca is the biggest keeper of sanity. Krishnamurti is the best at shocking me into the present moment. And Emerson is the…. SELF-RELIANCE!

    “There is a time in every man’s education when he arrives at the conviction that ENVY IS IGNORANCE; THAT IMITATION IS SUICIDE; that he must take himself for better, for worse, as his portion; that though the wide universe is full of good, no kernel of nourishing corn can come to him but through his toil bestowed on that plot of ground which is given to him to till. The power which resides in him is new in nature, and none but he knows what that is which he can do, nor does he know until he has tried.”


  27. The four books in your book club are not the same as those mentioned in “The Four Hour Workweek” . I only have an audio version of the book, so please respond with those four book names. Great book by the way. Enjoyed every minute of eight and a half hours!


  28. > studying obscure details of Wittgenstein or post-structural lesbian feminism. And for what? More often than not, to posture as a holier-than-thou jerk off. To argue over semantics that don’t matter.

    Woah, woah, woah! Let’s give Wittgenstein a chance here! He’s the exact opposite of postmodernist mental masturbation.

    Wittgenstein’s philosophy is designed to be “therapeutic”. He saw philosophy as “a battle against the bewitchment of our intelligence by language”.

    By practicing Wittgenstein’s philosophy, you get clear on what is and what isn’t “semantics that don’t matter”, or what he called sense and nonsense. His own summary of his philosophy: ” What can be said at all can be said clearly; and whereof one cannot speak thereof one must be silent.”

    It’s hard to find a more practical philosophy than that.


  29. Ironically, to answer your question of the day honestly: post-structuralism has been the biggest influence on how I live my life. I think most people misunderstand what it’s about, including the turtle-neck wearing pseudo-intellectuals that you’re talking about. Post-structuralism is much more about critically assessing the conceptual tools that we use everyday so that we can improve our lives (and our society).

    But a guiding tenet I always try to remember is a quote from Nietzsche: “I want to learn more and more to see as beautiful what is necessary in things; then I shall be one of those who make things beautiful…I do not want to wage war against what is ugly. I do not want to accuse; I do not even want to accuse those who accuse. Looking away shall be my only negation. And all in all and on the whole: some day I wish to be only a Yes-sayer.”