On Obstacles Being The Way


Yesterday I finished reading The Obstacle Is the Way by Ryan Holiday and I couldn't be happier with having picked up this book. The entire book is excellent, and I highly recommend you read it, but I can sum it up in a few words: success is about reality distortion. Perhaps you've heard about Steve Jobs' famed reality distortion field that seemed to defy all odds and push projects to completion through sheer willpower and audacious imagination. That's not entirely accurate: that sort of willpower isn't some hocus-pocus magic, it's deliberate, and it's sort of important if you want to live happily and achieve your goals.

The basic premise of the entire book is this: There have been, are, and will be obstacles on the journey to your destination, and your success relies on your ability to turn obstacles from negative into positive things. How do you do that?

Of course, the events of the past can never change. There is no time machine, and we cannot drastically alter circumstances that we are born into or find ourselves in currently. We are left only with our own minds and our abilities to control our impulses that try to convince us of our impending doom and downfall.


In the process of turning those things around, we could stop at the point in which the problems don't seem like problems anymore. Null and void. However, that's not where The Obstacle Is The Way calls us to stop. It's not about removing the obstacle, but turning it into an advantage. How could this horrible occurrence actually be used as a unique opportunity to grow and even launch past where we would have been without it?

That's an amazing thing to think about: not only is the bad thing that happened to you not so bad after all, but it's actually something that you should be pretty happy about. It's actually a blessing that you, of all people, were able to experience. What others call a hardship or a setback, you are able to turn into a catalyst for success.

At one point or another, I heard a podcast with Jocko Willink where he described interactions from his time in the military with a subordinate of his. This subordinate would consistently come to him with some sort of bad news, some obstacle that they were encountering. Every time, Jocko didn't respond with panic, didn't respond with anger, didn't respond with frustration—he simply said "good," and would proceed to find the positive in the situation.

That's exactly what turning around obstacles is all about. There's no secret formula other than calling it good and figuring out how you're going to make it a good thing rather than a bad thing. It's deliberate, it's reality distortion, and it works in your favor to achieve amazing feats and triumphs. Or simply save you from doom and gloom.

Sometimes I try to hedge on my belief that your ability to reason is the only thing in between you and happiness, mostly because it seems like a hard thing to swallow for most people. All of the sudden, with books like The Obstacle Is The Way and videos like the one mentioned above by Jocko Willink, there's no longer an excuse to be miserable in a given situation. This isn't to say that you rid yourself of emotion, but you change perspective and move swiftly to return to your reason, and thus find ways to overcome the insurmountable.

Most of the time, it's as simple as saying:


All you have to do after you label something as good is figure out why. I guarantee you that you will find a reason. There's always a positive outcome. There's always a way to make the obstacle the way.

Diego Segura