One of my favorite questions to ask my teachers and mentors is “Who are your teachers and mentors?”

Today I wanted to introduce you to one of my teachers and mentors. His name is Ryan Holiday. Ryan’s very unusual. He’s one of the most well read people I know. He has a voracious appetite for reading and has had an exceptional career in industry as a marketer.

He’s recently completed a massive research project on how to overcome extreme adversity, and has approached this topic historically, philosophically, practically, and biographically.

Ryan shares his research in his new book, titled The Obstacle is The Way.  I strongly recommend this book — it has profoundly impacted my life and helped me overcome adversities in my personal life these past few months.

I’ve asked him to share some of the insights from his latest research. Here’s Ryan:


When I first met Victor three years ago, he was probably the quietest, most unassuming guy at Tim Ferriss’ Opening the Kimono conference. What I quickly realized was that despite this demeanor, he would become the one attendee who made all the powerful friends at the conference and one of the most generous connectors — and in a strange way, an inspiration to me.

How? See, in addition to this site, Victor is the author of a great but underrated book, The Recession-Proof Business. Even though I knew Victor and had talked with him extensively, he never mentioned it.

I discovered this completely independently of our friendship, in fact, while researching for my book on the Roman philosophy known as Stoicism, which I have since titled The Obstacle Is The Way.

What I wanted to know was this: What are the case studies of people who have thrived during economic calamities? I wanted examples of brave individuals who had refused to allow macro-economic events to prevent them from creating businesses and finding success. People who had actually thrived in negative conditions.

Victor gave me a great start. The list of recession-proof businesses that were founded during a depression or economic crisis is shocking. It includes companies like Fedex, Walt Disney Company, Hewlett Packard, and Standard Oil.

So how did the obstacle become the way for these folks?

Well for starters, they didn’t throw themselves some pity party. They didn’t care — or even stop to think — that they were in a depression. They didn’t know whether it would get better or worse, they just knew what was.

The fact is half the companies in the Fortune 500 were started during a bear market or recession. Half. The point is that most people start from a less than ideal position and do just fine. It’s not unfair, it’s universal.

When subjected to adverse circumstances, these great companies were transformed along the lines that Andy Grove, former CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

These great companies were able to practice what ancient Stoics like Marcus Aurelius and Epictetus practiced every day: seeing things as they truly, actually are, not as we’ve made them in our minds.

Real examples from greats that graduated from what John D. Rockefeller coined, “the school of adversity and stress” provide us with a framework for stripping away our harmful perceptions to allow us to do what we’ve always been capable of: Acting boldly.

The entrepreneurial greats of our era like Steve Jobs and Elon Musk seem like animals, blessed to have no time and no ability to think about the way things should be, or how they’d prefer them to be.

But that spirit is not a birthright. No, they trained themselves to see the opportunity inside the obstacles they faced. They discovered that what matters most is not what the crisis is but how we see it, how we react to it, and whether we keep our composure.

Consider the brilliant strategic advice of Rahm Emanuel: “You never want an opportunity to go to waste…[A] crisis provides the opportunity for us to do things that you could not do before.” Because it is when people least expect it we can achieve our biggest victories.

Great leaders like Abraham Lincoln and Dwight D. Eisenhower turned times of crisis into opportunities, accomplishing things they never would have been able to otherwise.

Great individuals, like great companies, find a way to transform weakness into strength. They took what should have held them back — what in fact might be holding you back right this very second — and used it to move forward.

As it turns out, this is one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition.

My book The Obstacle Is The Way shares the collective wisdom of icons like John D. Rockefeller, Amelia Earhart, and Steve Jobs to help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles.

Using timeless philosophical principles laid down by the ancient Stoics, it reveals a formula for turning adversity into an advantage. It is a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity, and will teach you how to get unstuck and unleashed.

It shows you how the obstacle is actually an opportunity.


I’ve found Ryan’s book profoundly insightful — and I rarely say that about anything.

It has prompted a complete paradigm shift in how I think about adversity. Using the approach Ryan has identified has brought me a surprising amount of peace — probably the most peace I’ve ever felt in my life.

I consider The Obstacle is the Way to be mandatory reading for anyone determined to be a super achiever, who’d also like to be one with peace of mind and without stress.

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