Ryan Holiday

The Timeless Art of Turning Trials into Triumph - Ryan Holiday

by Dona Winger from nourishmewellness.com


“Our actions may be impeded…but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.” -Marcus Aurelius

The idea that an obstacle can become an opportunity with a bit of a reframe or shift of mindset is attractive to say the least. If we can turn hardship into advantage, we can succeed where others fail, grow during crisis, advance in spite of what holds us back. In this way, our enemies become our best teachers, what doesn’t kill us makes us stronger, and what will be will be.

These are Stoic principles. Within The Obstacle is the Way, Ryan Holiday does not explain Stoicism in depth or give a history lesson, he provides examples of prominent figures, both ancient and modern, who have used Stoic principles to overcome failure or succeed despite obstacles.

How can we possibly be expected to thrive when the economy is bad, we’re too old, we haven’t had the opportunities, we don’t have the education, we don’t have support, we’re the wrong race or gender, time is short, the rules changed, or our competition is too big?

Ryan Holiday provides three steps to overcoming any obstacle. Perception, Action, and Will.



“Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been. -Marcus Aurelius

It isn’t the event that determines our fate, but rather our judgment about the event. The actual thing that happened is neutral. It just happened. The fact that it happened to you is, while unfortunate, irrelevant.

Along the same lines, what is possible is simply a matter of perspective. If your colleagues believe an idea is impossible, it is to your advantage to find a way to make it happen. Pushing forward and believing in your ability to succeed, you will turn this obstacle into leverage.

In short, it can be a good day or a bad day. The choice is up to us and our perception.



“Action is commonplace. Right action is not.”

Taking small steps, one at a time, but always in the right direction, is the key to chipping away at any obstacle. Talking about what is possible is all well and good, but lots of people talk. Taking focused action is what sets us apart from others.

Action does not mean that we go at everything with a take-no-prisoners approach. Rather, approaching the situation with creative boldness is the key. Be courageous and patient with your eye ever on the prize. Continue to move ever forward.



“If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.”

What happens when we have done everything we can think of, but the obstacle still looms large and there seems to be no way in sight? This is when most give up, throwing in the towel, giving it up as a bad job. This is also what separates the average from the great. Here, perseverance is key.

In this section, Ryan Holiday differentiates between the art of acquiescence and brute strength. The former suggests working with the situation and using flexibility to encourage a solution. Rolling with the punches, so to speak. Finding a way when there doesn’t seem to be a way. The later includes rigid iron will. While tenacity is a good thing, it becomes a liability when one becomes so rigidly attached to the process that alternative solutions are not considered.

Will means finding a way when every way seems to have been closed off.


Amor Fati

This is my favorite part. Amor Fatitranslates to “a love of fate”. It implies a love of everything.

“To do great things, we need to be able to endure tragedy and setbacks.”

When terrible tragedy, or simply inconvenience, graces your life, find something good about it. Smile despite enduring hardship. Because, what is the alternative? Enduring hardship while acting bitter about it? Which do you think is a better use of your energy and has a better chance of ensuring you not only survive, but thrive during hard times?

Happiness, and therefore success, is something we decide to have.


Memento Mori

“Our fear of death is a looming obstacle in our lives. It shapes our decisions, our outlook, an our actions”

We end with the principle of Momento morior remembering that you are mortal and your life could end at anytime. Rather than this being a depressing topic, it ought to be inspiring.

If we knew we were to die tomorrow, how would we live today? Considering our impending demise, we offer forgiveness, take focused action, love more deeply, take advantage of every opportunity, and generally live life to the fullest. If we do this everyday, how much more wonderful would life become?


What separates those who persevere and those who don’t? Are the historical figures who succeeded despite enduring impossible situations simply more gifted than the ones who didn’t? Did they have better opportunities? Not necessarily. This book will highlight what actually set them apart and how you can use these principles, too.


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Published June 19th, 2018