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What We Learned From Ryan Holiday's 'The Obstacle Is The Way'

Lessons from Obstacle is the Way

‘Perception is reality’, ‘The impossible journey is the one you never begin’ and ‘Good is the enemy of great’ . Have you heard any of these before?

Well, I actually think these can all be fundamentals of success and happiness if applied correctly and I will be using our book of the month The Obstacle is The Way by Ryan Holiday to do this.

In the book, Ryan Holiday brings ancient wisdom and Stoic philosophy to life by applying Stoic principles to figures in history and their own attitudes and actions at the time. He shows obstacles didn’t deter these people, how instead they made them stronger and allowed them to thrive. What stands in the way becomes the way.

It’s astounding how relevant the stoic teachings still are today and when I read the book I certainly felt connected to those that lived in ancient times.

In the book, we are shown how we can transform roadblocks into success and shift our perspective.

I have personally recommended the book to many friends and colleagues and integrated its principles into my sales training to great effect. A recent employee of mine reported that it had quite literally changed her life.

I’ll stop kissing Holiday’s ass and carry on with the blog…


Perception is reality. Your perception is your reality, everyone views the world through their own lens, whether you are a glass half full or half empty kind of person or if you saw a black and blue or white and gold in the dress everyone went nuts about.

‘For there is nothing either good or bad, but thinking makes it so.’ – Shakespeare

Human beings have the fantastic ability to choose their perception of anything. When Thomas Edison’s research facility was burning down and he watched his life’s work literally disappear before his eyes he was famously quoted saying to his shell shocked son ‘“Go get your mother and all her friends. They'll never see a fire like this again.”

When you encounter an obstacle what is your perception of it? Do you start catastrophising or do you see it as an opportunity to learn and grow or increase your gains going where most are too afraid to venture?

We must first take a step back from our obstacle and view it objectively. Usually, our first reactions to adversity, in general, are not the best. Anger, despair, tears and some broken inanimate objects. While these are perfectly natural reactions kicked up from our monkey brains, they aren’t particularly helpful for us or our loved ones. 

These reactions also don’t typically help solve our problems.

If we are self-aware, we can plan for obstacles, keeping the stoic teachings front of mind we can use a malleable perspective to see an obstacle’s hidden advantages.

Ask yourself ‘What can I do to turn this obstacle into an advantage?’, ‘What will I learn from this?’ For example, that customer complaint could, instead of a course of anxiety, be an opportunity to show your integrity and excellent service to your client.


The impossible journey is the one you never begin.

Once you have the correct perspective you must take action to overcome your obstacle and this action must be persistent.

We must be disciplined in our actions to derive the change we desire. Take Edison for example, he went through 6,000 different types of material before he discovered the correct filament for the incandescent lightbulb.

He had to fail 5,999 times, learn from it, pick himself up and go again before he finally realised great success.

If you focus on each moment and in doing the best job you can in the moment that will feed into the overall process and eventually your goals. A mountain may seem insurmountable if considered as one giant obstacle but if broken down into smaller more focused steps it becomes much more achievable.


So, good is the enemy of great. 

This is a phrase that resonates with me a lot working in teams and leading people.

You often need to set the standard for what great is and just like how water will take the path of least resistance, generally people will toe the line and produce ‘good’.

When you start listening to that voice within that’s telling you you’ve probably done enough for the day, that you have worked really hard (when you know you haven’t really), that your ankle all of a sudden now hurts so it’s probably time to give it a rest you may just be letting your inner bitch win while you settle for good.

We must have will, this is what channels our perception and action allowing us to focus on what is in our control, not worrying about what’s out of our control.

By keeping your vision and your personal mission front of mind you can steamroller through the obstacles in your way, safe in the knowledge that each one brings you one step closer to your vision. 

If you strive for greatness in the moment the process will take care of the rest.

The obstacle is the way. 

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