“The Obstacle is the Way” Gives Unusual Advice for Success


The Obstacle is the Way is a book to show us that the way to work through the pain isn’t it to keep pushing, it’s to perceive your situation differently.

obstacle is the way

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How many times have you said, or thought, “This is HARD!  I don’t want to!” If you’re like most entrepreneurs (and you’re honest with yourself), this conversation happens multiple times on a daily basis.  Most of the time, it’s in your head and most of the time you push through it anyway.

So what is it about obstacles that stops so many people and inspires others to achieve past the obstacle?

That is exactly the topic of The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday (@RyanHoliday).  If you remember, he’s the author of Trust Me, I’m Lying; a no-holds-barred, tell-it-like-it-is book about how we are all being manipulated by the media.  But this book is written in a much softer tone, and yet still contains much of the passion that you’ll find in his previous book.  Maybe his style has matured – like a fine wine.

It’s Not So Much About What Happens, It’s About What You Make It Mean

Holiday’s mission in this book is to show us all that the way to work through the pain isn’t it to keep pushing, it’s to perceive your situation differently.  Instead of seeing your challenges as obstacles, turn them on their head and imagine that your obstacles are really the way to an answer.

He does this in a three-fold way; perception, action and will:

“It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.”

In each chapter of the book, Holiday shares many, many examples from the great people in history and the world.  In fact, what I found most inspiring in the book is his reminder that these “great ones” or great examples of people that he stresses that it wasn’t their intelligence, luck or particular gifts that made it possible for them to succeed, but rather their focus on these principles and this process.

Ryan Holiday: Marketing Hacker, Life Hacker, All Around Interesting Guy

You know, sometimes those bio’s they write in books don’t give you the full story about a person.  In fact, I thought the bio that was written in the jacket fell a little flat.

So I went searching for the “real” Ryan Holiday (per his Trust Me, I’m Lying book, there’s no such thing and I couldn’t ask his mother).  Instead, what I found was a series of interviews which reveal a young, focused and dedicated marketer who is profoundly clear on who he is in the world and his commitment to building brands in a focused, efficient and effective way.

In one interview he was asked about his favorite marketing hacks and there was one that totally resonated with me:

“Stop thinking marketing is something that happens after the product is done. Make something you think people truly, undeniably want and like. Improve your product based on early feedback and response.”

It’s really interesting to watch his growth, evolution and wisdom increase over time and with the acquisition of more and more experience in today’s business environment.

You Need The Obstacle Is The Way

I received this book as a review copy from a publicist and it sat around for, I’m not sure how long, until I was moved to read it.  Don’t do what I did – don’t wait.

If you’re having a moment where you’re feeling a deep sense of struggle, frustration and inadequacy, you’ll want to have this book close at hand.

The great thing is that it isn’t overtly philosophical and hard to read.  In fact, after you’ve read it once all the way through, keep it at your desk or coffee table and just pick it up and turn to a random page – it will do you good.

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Ivana Taylor Ivana Taylor is the Book Editor for Small Business Trends. She is responsible for directing the site’s book review program and manages the team of professional book reviewers. She also spearheads the annual Small Business Book Awards. Ivana publishes DIYMarketers, where she shares daily do-it-yourself marketing tips, and is co-author of "Excel for Marketing Managers."

4 Reactions
  1. I really like the title of the book. That in itself is a lesson: the obstacle is the way.

    And it is true, it’s how you look at it – that’s what determines whether it’s truly an obstacle at all.

    Thanks for reviewing the book.

  2. Jessica M. / Thanks for bringing this to my attoetinn. I’ve had a regular profile on facebook for a long time for my company. But, when I hit 5000 friends, they would not let me do anything else. Your article makes sense, I need to make a page and get people to go like my facebook page instead of the regular profile. I’ll be sharing this with my friends too.~Jessica M.