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

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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!

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