The Obstacle is the Way


Who is Ryan Holiday?

Ryan Holiday is an interesting man. He is a media strategist and a prominent writer about business and strategy. Yet his words are so full of philosophical wisdom that he imparts so convincingly and well. Ryan dropped out of college at the age of nineteen to apprentice with Robert Green (author of The 48 Laws of Power). One thing leads to another as he further climbs the ladder of success and today he is the best selling author of several books. The Obstacle is the Way is the first of three books.

I just happened to see this cute little book at the bookstore, and just picked it up on a whim, with no background idea of who the author is or what the book is about. Guess what? I am a convert. I loved this book so much, so much so, I went ahead and bought his other books too (Ego is the Enemy and Stillness is the Key). I found so much practical wisdom, and his stories of real-life people, past and present, make for such an illuminating read.

The Book

The book is split into three parts: 1. Perception; 2. Action; and 3. Will. I won’t get into the details and the chapter headings are pretty much self-explanatory.

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“Overcoming obstacles is a discipline of three critical steps.

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.” (page 9)


The dictionary defines Stocisim as “the endurance of pain or hardship without the display of feelings and without complaint.” The other definition it gives is “an ancient Greek school of philosophy founded at Athens by Zeno of Citium. The school taught that virtue, the highest good, is based on knowledge; the wise live in harmony with the divine Reason (also identified with Fate and Providence) that governs nature, and are indifferent to the vicissitudes of fortune and to pleasure and pain.”

Stoicism is what drives the book. The author is a huge believer in this particular school of thought, and a lot of his practical advice makes sense.


I could fill this post up with lots and lots of his words here. I could literally share one important take away from each of his chapters. That’s how much I picked up from his book. A lot of it has to do with realigning our perspectives towards the problems, then merely tackling them in new ways and ultimately developing that will to tackle upcoming issues.

If you can look past the Stoicism school of belief, I feel there is a lot we can learn from.

“Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive, and in the process, inch the world forward a little bit.

Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. be strong for them, and it will make you stronger.” (page 166).

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