Interview With Ryan Holiday, Author Of, The Obstacle Is The Way

Ryan Holiday's newest book is, The Obstacle is the Way: The Timeless Art of Turning Adversity to Advantage.

Deeply influenced by the Roman emperor, Marcus Aurelius, and ancient Stoic principles, Holiday shows leaders how to turn setbacks or problems into a platform for achieving goals by controlling perceptions through swift and energetic action and true force of will.

  • "Great individuals, like great companies, find a way to transform weakness into strength," explains Holiday.

Recently, Holiday shared insights into his book with me.  But first some background. Holiday is a prominent writer on strategy and business, and author of, Trust Me, I'm Lying.

After dropping out of college at 19, he apprenticed under Robert Greene, author of, The 48 Laws of Power.

In The Obstacle is the Way, Holiday pulls from stories throughout history, illustrating how icons such as John D. Rockefeller, Amelia Earhart, Abraham Lincoln and Steve Jobs took what appeared to be nearly impossible situations and made some truly astounding lemonade.

1.  Why this book now?

Holiday:  I believe that you write the book that you have to write. And this is a book I’ve really wanted to write for a while. I first discovered this Stoic exercise, of turning obstacles upside down, when I was 20 years old. Since then it’s been seared into my brain regardless of what I’ve done and I’ve always tried to think about my problems and opportunities in life through that frame.

I left college right as the financial crisis hit, which was scary. And as I worked through the dip I saw how unprepared everyone was because we all operated on assumptions or promises that didn’t exist anymore. I wanted to go back in history and ancient philosophy, to find people who overcame difficult situations. Everyone faces difficult and sometimes terrible circumstances, but clearly there’s been much worse things in history that people have overcome and I used ancient philosophy to find the strategies that those people used to come to terms with adversity and thrive despite it.

So it’s also directed toward to my peers who I saw struggling to adjust to the hand we’ve been dealt with the financial crisis and unemployment. I saw a lot of people acting entitled or defeated regarding their prospects and I wanted to give them the approach I learned to get through it.

2.  What is the single most important concept you want readers to take away from the book?

Holiday:  I think the most important idea of the book is the Stoic maxim that the book is based on:

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

The first section of the book is about the discipline of perception, which is essential to overcoming adversity. Instead of giving into panic, fear, and anxiety when we are faced with an obstacle, we can flip it on its head and instead look for an advantage or positive to pull from it.

Marcus Aurelius has another great quote about this, “Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.” It’s so important not to given into our basest emotions and instincts when we are hit in the mouth in life. Because there is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.

The people I write about in the book, like John D. Rockefeller, Thomas Edison and Amelia Earhart, were all able to adjust their perceptions and separate themselves from the events in their lives. But it wasn’t natural for them, it was learned behavior. They learned to not give in to their immediate, emotional reactions to the obstacles that inevitably came their way. This is what allowed them to act boldly and succeed in the face of tremendous adversity.

3.  How do you think your career would be different had you finished college?

Holiday:  I was actually thinking about this recently for a column I wrote. I think I probably would have ended up more or less in the same place, but would have taken a much different path to get there.

Ambitious people who want to do great things aren't held back by the decision to finish school or not. They don’t see these types of obstacles as road blocks, but as opportunities to prove themselves. So I think it’s important to bet on yourself when it comes to the “big” decisions in your life, because then you’re able to develop a self-confidence and self-sufficiency that can be very valuable down the road.

4.  Do you expect this book to be as controversial as Greene's The 48 Laws of Power and Mastery?

Holiday:  I didn't necessarily set out to write a controversial book like I did with Trust Me, I'm Lying, so I don't think so. But unlike other books, The Obstacle Way isn’t written to puff you up or fill your head with meaningless platitudes. It was written for people who want to accomplish things in the real world, not just put the book back on the shelf and forget about it when you’re done with it. So its been interesting so far to see the reactions from readers so far.

Robert's books are controversial because he brought to light a lot of the darker behaviors and motivations that he saw other people exhibit in his life. But if The Obstacle Is The Way could have half the success that The 48 Laws of Power has had I'd be thrilled.

5.  If you could have been an apprentice to someone featured in the book (The Obstacle is the Way)  in a prior life, who would that person have been?

Holiday:  I’ve been lucky enough to have apprenticed under two great people already in my short career. Robert Greene, who taught me how to be a great researcher and write well. Then Dov Charney at American Apparel, who taught me everything I know about business today. If I had to choose someone else, I might pick a great philosopher like Marcus Aurelius or Epictetus. Or perhaps a great general like William T. Sherman.

 Learn more about the books Holiday recommends.


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