Book review: The Obstacle is the Way — Ryan Holiday

A book about the power of the journey — not the destination

Tramayne Monaghan
3 min readSep 21, 2020
Photo by JOHN TOWNER on Unsplash

A book that is based on the teaching of ancient Romans and used in large scale organisations and high performing athletes. This book will teach you how to use perception to create opportunity out of obstacles.

“The obstacle in the path becomes the path.”

Reframing Ideology
The book reframes reality and teaches the knowledge of understanding what you can and cannot control. This mental framework will allow you to focus on the actions needed to overcome the problems in front of you.

The Stoics teach that you need to master the art of managing your own perceptions, act wisely, and stay strong even in the most demanding circumstances. It takes skill and discipline to alter perceptions, to separate reliable signals from deceptive ones and to filter out fear. This book will teach you how to develop that discipline.

An obstacle is merely an opportunity to train yourself.

Principle One: Reality is merely a perception
As humans, we tend to overlay our own frameworks and history in every scenario. Most of our problems are just amplified by this. This makes reality subjective. Attempt to remove “you” from the situation. If you remove that filter, the solution becomes clearer. I like to pretend I am giving a piece of third party advice. The best advice I can. This truly clears my thought process into a more realistic space.

Principle Two: Theory + Action = Reality
In these teachings the only thing that matters is action. What you have learnt is a practice and it requires discipline. The hardest part of this is not avoiding problems. Reality will be crafted based on what you have learnt and the correct action is taken based on objective thoughts.

Principle Three: Memento Mori
This Latin adage is one I have thought about putting on my own body in tattooed ink. It simply means, “remember you must die”. Death is not pointless. This section teachings that the finite amount of time we have needs to be wielded carefully. Use the fleeting nature of time as a value to spur the understanding that there is nothing else nearly as hard left. Live and act as you know you must die.

Should you read this?
I must convince, I am a massive fan of Stoicism and its teachings. It has allowed me to remain conscious of emotional situations as I have grown in the leadership ranks. It has benefitted me in maintaining a clear mind so that focus and discipline are not far from my grasp. I would suggest that it has been the single largest influence on my leadership style.

This snapshot is a cheat sheet, a fast summary, but I do think it requires a read. The audiobook is great for car rides.

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Tramayne Monaghan

A love for words is driven by my desire to grow as a leader and use my lessons to grow others. Book hacks, summaries and reviews. tramayne.co.za