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4.0

Taking the reader through a practical and extremely balanced approach for handling failure, The Obstacle is the Way is a must-read for anyone who has struggled with crippling self-doubt, self-pity, and ennui. Through the wisdom of the Stoics and the example of history, Ryan Holiday reminds us that even great setbacks and obstacles are not the end of the world. Rather, they can become the fuel for a life well-lived. If we so choose.

As someone who feels deeply and places great value on emotions as a creative and relational force, I confess I held a bit of a grudge against Stoicism before reading this book. Not anymore though. In MBTI terms, a Stoic is a person whose Fe is controlled, and therefore channeled into healthy and constructive paths, by his Ti. A Stoic does not lose his head over the challenges, pains, and sometimes utter brokenness that life throws at him. Rather, because he takes a moment to assess the situation, he keeps a cool head and overcomes the obstacles that stand in his way. This cannot be done without feeling. Passion is necessary to fire any vision. But passion alone kills. When thwarted, unbridled passion can lead to depression, self-obsession, and pettiness. There must be something greater encompassing that passion to make the vision come to life no matter what obstacles are thrown in its way. This something is the cool-headed logic and determination of the Stoics.

I just lost a bet by admitting how good this book is, but so be it. Reading this was a humbling experience. It forced me to re-examine myself and my choices with honest eyes. I'm grateful to have read it and would recommend it to anyone seeking to discipline their mind. It's not a book of specific steps to take, and if you're looking for a self-help book you might feel like Holiday does no more than throw around trite platitudes. The aim of the book is not to give specific instructions, though. It's just a broad reminder that if we really want to live well, we better get to it. It resets the button on self-pity, and that alone makes it worth reading.