The Obstacle Is The Way – by Ryan Holiday (Book review)

The timeless art of turning trials into triumph – a book that contains stoicism, strategies and a lot of historical events that will change the way you think about life!

When I first heard about this book, I was amazed about the whole concept. Intrigued, to say the least.

This was the first book that I ever bought that was written by Ryan Holiday and it threw me into the world of the stoics and how they handled their trials and tribulations.

It is a short, but powerful read. It’s definitely one of my favorite books and I hope that this article will inspire you to make it one of yours too.

This book has some main themes that are evident throughout the story and is starts with the idea of the ancient Roman emperor Marcus Aurelius.

The basic idea

According to the author himself, the book is based on a single exercise from Marcus Aurelius.

Aurelius would sit down and write down notes and life discoveries for himself as a way to better understand life and create a better version of himself in the process.

The idea of the book, and also Aurelius writings that you can find in the book Meditations, is that everything that happens to you can either be seen as an obstacle or an opportunity.

This has to do with our perception of the world and how we choose to view things that happen in our lives. We are not in control of what may happen to us, but we are always in control of ourselves and how we respond to these things and to life itself. Does this sound complicated? Read on.

Quick review of the stoics

What is particularly interesting about this book, is that it re-introduces stoicism and the stoic philosophers into modern society. It becomes this hybrid mix of ancient philosophy and modern lifestyle. Or does it?

A lot of people misinterpret philosophy for the practice of simply sitting down and think about issues or problems that might have occurred in this day and age.

This interpretation is somewhat true, but it leaves out a large chunk of information. Especially when it comes to stoicism.

The special thing about stoicism was that is was meant to be a reactive practice, where you would go out in the world and actually live out the philosophy. It was never meant to end in a simple conversation or in the mind of the philosophers. Action – is the keyword of stoicism. You would go out and practice in in the real world and not spend too much time thinking about doing so.

“Waste no more time arguing about what a good man should be. Be one.” – Marcus Aurelius

Meet the stoics

In The Obstacle Is The Way, you are going to become friends with a handful of stoic philosophers. You already know Marcus Aurelius, who, again, was the Roman emperor and became a political figure at the age of 16.

You will also meet Epictetus, who was born into slavery and then taught philosophy and lessons about life in Nicopolis. His work was never written down by Epictetus himself, but his lessons were captured in writing by Arrian, who was a student of Epictetus.

Seneca the Younger is also one of the great stoic philosophers that you will get to know in this book. He suffered a tragic death ordered by the Roman emperor Nero, where Seneca would commit suicide by cutting up his veins causing death by exsanguination.

This book is divided into three main parts – The Discipline of Perception, The Discipline of Action and The Discipline of Will.

The first part of the book

In The Discipline of Perception, you will learn that you are always in control of how you choose to perceive the world.

This has to do with how you choose to view things. If you keep telling yourself how you are being screwed over, how life is treating you poorly and all odds are against you, they begin to adapt to your words and to your way of thinking.

What you could choose to do instead is to see it as an opportunity to learn, to better yourself, to practice patience or to learn how to look at things with an objective point of view.

This has to do with you dividing any given situation up in two parts. The things you can control and those that you cannot control.

How you view the situation

An example of this is when your bus, flight or ride is running late. This is outside of your control. What you can control is your reaction to this very situation.

You could get angry, pissed off or even scream. This will not change the fact that your transportation is running late. This will only waste your energy reserves.

What you could do instead is to realize that this is the reality of the situation and then do something proactive with the time that was given to you.

You could catch up on e-mails, read a few pages in a good book or call that friend that tried to reach you last weekend. This is within your circle of control and it has to do with your perception of things.

The stoic perception

The stoics often said that no external event could make you feel something. You assign certain emotions and reactions to these events. Like in the previous example. If your transportation is running late and you get angry, you chose to become angry.

Then if you learn to control this and accept that this is one hundred percent within your control, you become more aware of your emotions and your actions within your circle of influence.

The external stimuli and your reaction to this external event are two completely different beasts. You are in total control of your internal reaction to the external event that just occurred. Regardless of what that event might be.

The stoics would go to such extremes as to say, that you choose how you respond to a family member’s death.

The death of a dear friend

Not necessarily your reaction at the very moment where you receive the news, but more about how you handle the aftermath and how your grieving process is going to be.

Do you mourn their death or will you celebrate their lives and choose to associate it with a happy feeling or will it only cause you pain? This has to do with your perception.

This has to do with you acknowledging these emotions and then making a rational decision on whether you should act on them or if they will create negative results by doing so. You hear the thought, but you choose if that very thought is helpful or if it is distracting you and turning your head away from your target. Always forward!

You always have the option of choosing not to act on a given emotion. This is what separates us from the animals. We have our triggers and our reactions, but what makes us different is that we always have a choice. That is what the second section is about – The Discipline of Action!

Section number two

This is how perception and action are linked together. Often times, people are afraid of failure. This will cause them to avoid doing things or taking risks that could possibly end up becoming what is known as a failure. Here is how you avoid making the mistake of avoiding mistakes.

If you would stop avoiding failure and manage your perception, you could begin to view failure as a chance to learn, see it as feedback and see that failure is the way to perfection, since failure is the only path to success.

This section has to do with your ability for resilience and how quickly you can adapt to a situation where a plan backfires. How fast can you get back on track? Or better still. Never derail and lose your internal compass?

You wanna change your perspective, how you view things and manage your perception and just take action. You need to work on your flexibility and stop caring about how it will look in the making. The end results are what matters. Regardless how you get there and when it will work because it eventually will since you are in control of your perceptions and actions.

“Plans are nothing; planning is everything.” – Dwight D. Eisenhower

Action with direction

This should not, however, be mistaken for any kind of action. We are talking about directed action. Action with a purpose.

Your actions must be based upon your perceptions and lead you towards your goal. Your actions should be your stepping stones towards you end goal and they should, therefore, be treated as such.

You need to be creative about your actions, but also apply a lot of courage. This has nothing to do with pure strength and just running amok like a wild animal.

It is persistent and directional actions over time that follow the compass that will lead you to whatever you set out to achieve in life or in business.

The Discipline of Will

The third section of the book is the one about will. This is not mean to be confused with willpower, as it has a far greater impact and importance than sheer willpower, according to the author.

This section has to do with perseverance and being persistent in life. This is both when you decide to keep grinding on your project, even though it might feel impossible or you are experiencing turmoil.

This also has to do with life in general and how you keep at it. Even when things get hard. How you overcome obstacles while keeping your head straight and above water.

This is your internal power that cannot be shut down or in any way affected by the outside world. This is you keeping it together and when you soldier on, even though the world is on fire and everything around you comes crashing down. You keep at it, no matter what. That is will.

The world is testing you

You need to be prepared because the world will never cease to throw curve balls in your direction and the higher up you climb, the more negative and unchangeable situations will come your way.

That is just the laws of nature and the will is what keeps your eyes on the target and what makes you keep pressing on. Even when it feels impossible to do so or that it is no use to continue down the path.

You need to embrace everything that is happening to you. Amor Fati. You got to have a love of fate. The obstacle becomes the way and whatever stands in your way, you can flip upside down and turn it into an advantage or a learning experience.

If a building is burning, whatever is standing in the way of the fire fuels the fire. If a wall and a door are in the way, it will most certainly catch fire. That is how you wanna view your struggles and obstacles. You are the fire and whatever “stands in the way, becomes the way“. That is the conclusion of the Three Disciplines of The Obstacle Is The Way.

This is fuel!

Whatever may happen to you in the future will become the fuel that ignites the fire that will keep you on your path to mastery!

This is what happens when you are in control of what you can change and you take advantage of the things you cannot change and you learn from them.

A lot of successful people have used these stoic methods to overcome obstacles. People like Steve Jobs, John D. Rockefeller, Amelia Earhart and Ulysses S, just to name a few.

This is an awesome read for any aspiring musician, artist, manager or anyone who is looking for solutions to overcome obstacles and win the game of life and business.


This book has helped me become a more active thinker and it has taught me how to overcome daily obstacles, but also more excruciating ones that are blocking the way.

The Obstacle Is The Way has helped me with problem-solving and it has brought to my attention, that you are in control of your reactions to external events and that you no longer have to suffer the consequences of your irresponsible reactions to external situations that are beyond your control.

This is without a doubt a book worth checking out. It’s a short read and the only problem that I have with this book is that it ends. I would like to read more, but Ryan Holiday has written several books that are all worth checking out.

Make sure you check this book out and don’t forget to express your thoughts in the comment section since you know how to combine words into sentences.


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