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. Such good stuff. I’ve been a proponent of stoicism for years, and I’ve seen it have some great impact on some of my friends. It’s empowering, realizing that you may not always have control over your surroundings or your circumstances, but you can always control yourself and how you act. I’ll definitely check this book out.


  2. “As A Man Thinketh” by James Allen has always been a favorite of mine.

    “A man only begins to be a man when he ceases to whine and revile, and commences to search for the hidden justice which regulates his life. And he adapts his mind to that regulating factor, he ceases to accuse others as the cause of his condition, and builds himself up in strong and noble thoughts; ceases to kick against circumstances, but begins to use them as aids to his more rapid progress, and as a means of the hidden powers and possibilities within himself.”


  3. Tim, sorry to hear about the loss of your friend. Less important, bad sad nonetheless is the cancellation of TTFE, I hope it can be resurrected.
    If anyone has the tools to cope with setbacks like these it is you Sir, thank you for always sharing with us. Love your podcasts too.


  4. Hi Tim. Sorry that you had a couple of terrible weeks. Please remember that your work has transformed many, many lives, and you can be very proud of that.


  5. “Nothing in the world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan Press On! has solved and always will solve the problems of the human race.” ~Calvin Coolidge


  6. I loved the title alone and bought the book – but the audiobook is incredibly boring to me. If you’re considering buying the audiobook listen to the preview first because I want to cut my ears off. I suggest the print version or 3–4 Adderall.


      • Just two additional pieces of feedback Ryan:

        1). I mean absolutely no disrespect, I thought the book was wonderful as a whole, but I do not think your narration does the book justice. I can understand the appeal of narrating your own book, but your voice does not suit book narration.

        2). Correct me if i’m wrong, but the last hour+ was Tim’s 1st (or 2nd) podcast. I thought it was slightly misleading to advertise the book at one length without including the fact that 15-20% was material freely available online.



      • Ryan AMAZING book! It’s one of those books that comes at the right time in your life and truly changes everything, thank you. I also listened to the audio tape. I thought it was just as powerful as the book, if not more.


  7. I think when you get the crazy feeling that a book found you and came into your life for a reason is a reflection of how well an author portrays astounding material.

    I have had this feeling with two books in particular, The Four Hour Body and The Obstacle Is The Way. Thank you guys.

    Has anybody else ever felt this way before?


  8. Hi Tim,

    thanks for having Ryan. This episode somehow had the biggest impact of all your episodes i listened to until now. Especially the thing with “friends are people you can have a nice long dinner with”. Makes perfect sense.

    Ryan is a really impressive person in that he´s incredibly productive and focused at such a young age. I feel like focus is really a key point here. Looking forward to listening to the 5th episode! Definitely gonna have to do that soon!

    Keep kicking, tim!


  9. Sounds interesting. I think i’ll check it out as part of my research for a book I’m writing. Thanks Tim, loving this book club idea and the books you’re suggesting so far!


  10. “…It has helped me to turn problems upside-down, become the calm within the storm, and even uncover unique opportunities.” I think if you have an inner confidence that is what allows you to be calm. Getting external reassurance that you are on the right path (in this case from the book) can help deliver that calm. Thanks for sharing.


  11. Thank you Tim for sharing this book with us! I just started listening and I’m already blown away. All entrepreneurs experience tough times and it’s just like you said, these tough times make the difference between success and failure.

    Hope everything’s going better for you in the future!



  12. Every Book Club pick is a must-read. Loving the Obstacle Is The Way and can’t wait for the next selection. Ryan Holiday is a rockstar. For any that missed it, Tim’s podcast with him is killer.


  13. I’m halfway through the book, and while it’s interesting, I feel it really lacks practical advices, exercises that would make it immediately useful. Maybe I’m spoiled by Tim’s books, but I can’t help feeling TOITW too general.


  14. Personally, this concept has proven true over and over. One of the greatest tenants that I live by is the understanding that there is a gap between stimulus (cause) and response (effect). I am not ruled by causes but, instead, have the freedom to choose a response in every circumstance. Victor Frankl and other existential thinkers such as Kierkegard have had a substantial impact on my thinking as well.


  15. Pure gold! Right book right time for me too. “What matters most is not what our obstacles are but how we see them, how we react to them and whether we keep our composure.”
    FYI- I am an audiobook fiend and this 1 was as good as any mate. Cheers RH and TF


  16. Hello there! I know this is somewhat off topic but I was wondering if you knew where I could locate a captcha plugin for my comment form?

    I’m using the same blog platform as yours and I’m having trouble finding one?
    Thanks a lot!


  17. Great to reconnect with you via the book club, Tim. So sorry about the tragic trio of the past couple of weeks.

    Question of the Day: The quote I live by most: “People are always blaming their circumstances for what they are. I don’t believe in circumstances. The people who get on in this world are the people who get up and look for the circumstances they want, and if they can’t find them, make them.” -George Bernard Shaw


  18. Here’s mine I use on my kids all the time… and my high school students too:

    My job is to give you opportunities to be awesome! Your job is to take that opportunity!


    Life sucks if you suck – so don’t suck! (My high school students love this one – they tried to get it trending on twitter)


  19. Tim,

    I’m sorry for your loss. Please note that the average time to grieve a loved one is 5 years, and cannot ever be rushed. I’ve found the best way to deal with adversity, setbacks and the like is to completely acknowledge that this is happening, meaning that anything that resembles avoiding, ignoring, or attempting to escape only serves to further increase the power it has. Often it helps to verbalize what you’re feeling, even if you are just saying it to yourself. Audibly saying, “let go” is also quite powerful. Intellectualizing isn’t enough, feelings seek to be felt.

    Japanese Zen monks reference the concept of “nen,” which translates into thought impulse. Each nen represent a minor disturbance and can pass easily if you acknowledge them. Once acknowledged you to can re-enter the present as your full self. When left unattended, they accumulate, and can lead to a variety of psychosis. As you’ve mentioned elsewhere, it pays to travel light.

    Some suggestions for your journey:

    Zen Training by Katsuki Sekida
    This is the definitive book on meditation, which contains detailed commentary on the physiology of meditation both moving and traditional.

    Six Thinking Hats by Edward de Bono
    Describes building parallel thinking models, and one of the most effective ways to get a team pulling in the same direction at the same time. The decision making process can be dramatically reduced using this model.

    Thank you for taking the time to write 4HB, my wife and I have lost over 13 pounds each on the slow-carb diet, and can’t ever envision eating any other way. Switching to Paleo two years ago brought results, but nothing compared to what your program delivered. I’m never counting calories again, and I really don’t want to know how many are in the half dozen donuts I consume as a mid-morning snack each Saturday!