The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage Paperback – 2001

The Obstacle is the Way digs into how knowledge and reason are in fact the highest good, as well as how to stay indifferent to pleasure and pain and how to respond to the vicissitudes of fortune objectively. The key is to not let your emotions color your perception of the world.

Ryan not only provides a great review of stoicism, he does an excellent job at articulating exactly how this school of thought can be applied to any problems that you might be facing now as you try to advance your career or transition from academia into a new career. He also provides an ample number of takeaways in the book. The Obstacle is the Way goes beyond the philosophy of stoicism simply by making the philosophy actionable. Reading this book will make you take action. Rational action.

If you're looking to:

-Take your career to the next level by getting a promotion (even though someone else is standing in your way)
-Transition out of academia and into a new career to finally get paid what you're worth (even though you don't have any business connections)
-Quit your job and start your own business so you never have to work for anyone again (even though you don't know how to run a business)

...then this book is for you. The Obstacle is the Way is rooted in concrete, everlasting principles, not processes or fads that come and go with the wind. By reading this book, you will understand these principles and you will be able to make use of them to get what you want.

If you want to get ahead, the Obstacle is the Way is highly recommended.

No doubt, you are trying to get ahead in whatever ‘getting ahead’ means to you. But so often an obstacle seems to stand in your way. Yes, there are a few people who report having planned their charmed life or their business success and had it unfold almost exactly as planned, and with style and elegance. Amazing, but never true. Most people blocked by the obstacles of time, money, connections, opportunity and more, do nothing.
This book has a fascinating take on ‘being stuck’ – it is a primer on how to turn adversity to advantage, as the subtitle explains.
Let me state upfront – I am bored by motivational talks and books. I find very little about them interesting or useful twelve hours later. This book is not a motivational text, though it is motivating as many good books are.
The “Ancient Art” of the subtitle is referring to the wisdom and insight of the Stoic philosophers. These writings or thoughts influenced all the people Holiday uses as examples of this approach to obstacles of life. The circumstances of these people would leave most disoriented, reactive, torn and even paralyzed. As Holiday shows “some seem to turn those very obstacles, which stymie us, into launching pads for themselves.”
Knowing that there are heroes doesn’t help us to become heroes, but knowing how they became heroes, does. The value of this book is that it offers an ancient and profound method and framework for understanding, appreciating, and acting in the face of the obstacles life throws at us.
Turning obstacles into the way forward takes many forms. For the great Athenian orator, Demosthenes, it was a relentless drive to improve himself through action and practice. For Abraham Lincoln it was humility, endurance, and compassionate will. In each case, all the people cited in this book were not born with the attributes it took to succeed, and many faced unimaginable horrors, from imprisonment to debilitating illnesses, and of course the day-to-day frustrations we all endure.
So, what did they do? “They had the ability to see obstacles for what they were, the ingenuity to tackle them, and the will to endure a world mostly beyond their comprehension and control,” Holiday explains.
The perspective is not a self-delusional, positive and happy one, ‘this is not so bad’, but rather, ‘I can make this good’.
The starting point is maintaining a state of mind that one of Holiday’s examples, the extraordinary businessman, John D. Rockefeller, had perfected: cool headedness and self-discipline.
When America send the first astronauts into space, they trained them in one skill more than in any other: the art of not panicking. When people panic, they make mistakes. They just react, but not to what they need to react to, but to their survival hormones. At 150 miles above Earth, panic is suicide. Panic had to be trained out of the astronauts and it does not go easily. It must be trained away, through persistent, repeated attempts at not panicking, until you don’t.
Talent isn’t the most important characteristic for success, grace and poise are, because these precede the opportunity to deploy your talent.
The action after the panic allows for a change of perception that is a prerequisite for right action. George Clooney spent his first years in Hollywood getting rejected at every audition. He desperately wanted the producers and directors to like him, and they didn’t. He blamed them for not seeing how good he was. His life changed when he changed perspective, from self-centredness to that of other-centeredness, not possible in panic mode.
Producers need to find the right actor to cast in their film, and they all hope that the next person to walk into the room is the right actor. When Clooney realized that he was the answer to their prayers, not the other way around, his performance improved and so did his career.
Consider the refusal to fund your company. I could be an obstacle, or a call for a change of action. Getting the person to fund you this isn’t up to you, but the decision to refine and improve your presentation is.
Consider the number of exceptional businesses started during depressions or economic crises.
Fortune magazine was founded soon after the crash of 1929. Hewlett-Packard, and Revlon in the Great Depression. General Motors in the panic of 1907. Microsoft in the recession in 1973-75. LinkedIn during the burst of the dot-com bubble. Half the companies in the Fortune 500 were started under adverse conditions.
Rather than focus on the difficulties of an economy in free-fall, they focused on what they needed to do to succeed, and that produced the difference. This difference requires presence of mind.
Andy Grove, former CEO of Intel, said “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” In like fashion, great individuals find a way to transform weakness into strength.
This is essentially a very practical book which will introduce you to a wealth of important ideas beyond what I have introduced in this column. They will be of extraordinary value as you try to facedown business crises.

Readability Light --+- Serious
Insights High +---- Low
Practical High -+--- Low

*Ian Mann of Gateways consults internationally on leadership and strategy and is the author of the soon to be released ‘Executive Update’.

I'm into self-improvement and optimization, and many of the podcasts I listened to have mentioned Ryan Holiday and his books, primarily this one and Ego is the Enemy. I have a lot of books on my shelf, but Ryan's writing truly stands out. The chapters are short, effective, and extremely well-written. It's actually entertaining to read this book, which consists of short stories that will genuinely change your mindset.

Most chapters are only 4-8 pages long, but they pack a punch. They are easy to read, but so thoughtful and packed with content that you can spend days just going over and absorbing the lessons from a single chapter. On the other hand, you can also read 100+ pages in one sitting, because it's truly hard to put down the book.

Usually books like this will feel boring - like you've already heard the subject hundreds of times and can anticipate what's coming next, leaving your mind to wander. Ryan's books are rare, instead they read like a hidden treasure, as the knowledge in the books is powerful, but easily read and applied. I've since ordered and read all of Ryan's books, and they are gold. Anytime I feel stuck in life, I know I can pick up this book and receive motivation and insight to keep conquering seemingly insurmountable challenges. Timeless and can be read again and again.

A must read if you are serious about changing your life for the better. My greatest take away amongst many? Philosophy is about actions.

"The Obstacle is the Way" is one of those rare self-help / personal development books that actually can make a difference in your life. Unlike all those "you only have to believe hard enough / wish for something hard enough, and it will appear" books, this book shows you how to really get closer to your goals. And the author is also honest about one important fact: miracles don't just happen on their own, dreams don't just come true without any input from yourself. Ryan Holiday shows you what hinders you, and how you can use these obstacles to your advantage. I found this book to be well written and also quite useful. It was fantastic and refreshing to read a book that is written by an author who doesn't follow the mainstream "Secret". It also became quite clear that Mr Holiday has read quite a few good personal development books himself, and you might find yourself inspired to follow his example.