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.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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103 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.