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

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The_Obstacle_Is_the_Way__The_Timeless_Art_of_Turning_Trials_into_Triumph__Ryan_Holiday__9781591846352__Amazon_com__Books

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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The Tim Ferriss Podcast, Episode 4: Ryan Holiday

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“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

This post includes:
- Sponsor intro (please visit them)
- Episode description
- Quick favor
- Show notes and tons of useful links, including mentioned books and documentaries

This episode of The Tim Ferriss Show is sponsored by HipDial, which I’ve been a fan of for ages.

I use HipDial for conference calls: no stupid PIN numbers, no hitting #, and you get a text when people join, so you don’t have to wait. It’s rocks–try it for a free month, and you’ll never go back.

Now, on to the main event…

My guest is Ryan Holiday, who became Director of Marketing at American Apparel at age 21 (!). He’s a beast.

Since dropping out of college at 19 to apprentice under strategist Robert Greene (author of The 48 Laws of Power), Ryan has advised many New York Times bestselling authors and mega-multi-platinum musicians. He is a master of the media, and he knows how to build massive buzz while responding to unexpected crises. He can compete or counterpunch with the best.

I hired Ryan to help with the launches of The 4-Hour Body and The 4-Hour Chef. His unorthodox approaches always impress me.

I loved his new book (The Obstacle Is The Way) so much that I bought the audiobook format and produced it with him. It is the newest addition to The Tim Ferriss Book Club.

In this episode, we discuss dozens of topics, including the real-world strategies he uses to thrive (not just survive) when the world is exploding around him.

And…want to win some cool stuff today? Tweet out your favorite quote or line from this episode, using the following format, and I’ll pick a few of my favorites for prizes:

“[Insert quote]” More: https://itunes.apple.com/us/podcast/the-tim-ferriss-show/id863897795?mt=2 #TFS”

To encourage other people to retweet, try and keep your entire tweet to 125 characters or fewer. The iTunes link above will be automatically shortened.

Deadline is 8:30pm PST.

QUICK FAVOR – If you haven’t already, can you pretty please:

1) Leave a review of the podcast on iTunes here?
2) Vote as “helpful” the reviews you most agree with? Here’s the link. The vast majority are 5 stars (290 out of 333), but there’s some wild Haterade, too, if that’s your thing.

Show Notes for Episodes 4 (Thanks, Ian!)

  • The surprising story of how Ryan was introduced to stoicism by Dr. Drew
  • What makes a “quake book”?
  • How Marcus Aurelius helped Ryan survive a tough breakup
  • About esoteric philosophical ideas that are excellent tools in the modern world
  • Deconstructing the “Big 3″ stoics – Seneca | Epictetus | Aurelius
  • Is stoicism compatible with material or financial success, or are they completely at odds with one another?
  • Tim’s strategy for developing connections in Silicon Valley
  • Cultivating advantageous mentorships with peak performers
  • The story of Benjamin Franklin’s lending library…

Read More

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How to Use Philosophy as a Personal Operating System: From Seneca to Musashi

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(Photo credit: Graphistolage)

The following interview is a slightly modified version of an interview that just appeared on BoingBoing.

It explores philosophical systems as personal operating systems (for better decision-making), the value of college and MBAs, and the bridge between business and military strategy, among other things.

Avi first reached out to discuss my practical obsession with the philosopher Lucius Seneca, so that’s where we start… Read More

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On The Shortness of Life: An Introduction to Seneca

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Samurai and Seneca agreed: comfort with death brings better living. (Photo: Kalandrakas)

“We don’t beat the Reaper by living longer. We beat the Reaper by living well.”
-Randy Pausch (1960-2008), The Last Lecture at Carnegie Mellon

This week, one of my friends died after a long battle with pancreatic cancer. He was in his early 30′s.

Several hours after I learned of his passing, I received an e-mail from my parents: the 10-year old daughter of a dear high school coach had been diagnosed with liver cancer. The Reaper does not discriminate. Too often, we spend time focusing on the trivial with people who contribute nothing but their own self-interest.

How do we balance protecting time with protecting relationships? How do we conquer guilt and do what is truly most important?

I often read “On The Shortness of Life,” one of Lucius Seneca‘s most famous letters, whenever I succumb to social pressure to treat time as less valuable than income, or whenever I find myself agreeing to help those who make unreasonable requests and get upset otherwise.

Seneca’s masterful diatribe hit me like a much-needed sledgehammer, and I’ve included it below. He soon became my favorite Stoic philosopher, and this will help you understand why… Read More

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Stoicism 101: A Practical Guide for Entrepreneurs

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Stoicism was born on the porch of Zeno, but it can be used in the concrete jungle.
(Photo: Blue Cinderella)

“There is nothing the busy man is less busied with than living; there is nothing harder to learn.”
-Seneca

Few of us would consider ourselves philosophers.

Most of us can recall at least one turtleneck-wearing intellectual in college who dedicated countless hours of study to the most obscure philosophical points of Marx or post-structural lesbian feminism. For what? Too often, to posture as a superior intellect at meal time or over drinks.

Fortunately, there are a few philosophical systems designed to produce dramatic real-world effects without the nonsense. Unfortunately, they get punished because they lack the ambiguity required for weeks of lectures and expensive textbooks.

In the last three years, I’ve begun to explore one philosophical system in particular: Stoicism. Though my preferred Stoic writer, Lucius Seneca, I’ve found it to be a simple and immensely practical set of rules for better results with less effort.

Ryan Holiday is 21 years old and works directly with Dov Charney as his online strategist for American Apparel. 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… Read More

338 Comments / Leave a comment or question