Ryan Holiday’s The Obstacle Is The Way Will Change Your Life With These Three ‘Simple’ Principles

Early this year I became a full time member of Medium, and one of the first writers that caught my attention after I joined was Ryan Holiday. He it was who introduced me to Stoicism for the first time. His articles are also some of what helped me to get back on track with reading and writing.

So when a friend mentioned that he wanted to begin reading The Obstacle Is The Way, I decided to ‘read along’. This decision is one I am very glad I took because reading the book with others helped me to be accountable, and the discussions helped to understand better how to apply lessons learnt from the book to everyday life.

On the book itself, Holiday as expected delivered a humdinger. The obstacle is the way employs principles from the stoic masters and philosophers of old, as well as many historical figures who were confronted with obstacles and turned them into stepping stones to greatness.

A friend in my discussion group succinctly described the book as follows:

a call to reflect on how we view life and it challenges; a call to simplify and clarify our reactions to issues, pay attention to what is working and be at peace with what is outside your control. It opens us up to how much power we posses in taking charge of our mind and thought process.

Holiday in the book discusses how we can surmount challenges and obstacles using three main principles:

Perception, Action, and Will.

Using these three ideas,  he discusses how dealing with obstacles and handling them through their application can change our general  outlook to problems and life as a whole. Holiday surmises that the

‘the obstacle in the path becomes the path. and that within every obstacle is an opportunity to improve our condition.’

To do this however, we must first decide how we see and perceive things. He explains  that we can learn to alter our perspective by learning to control our emotions, analysing situations objectively,  living in the moment, and understanding that somethings are just beyond our control. The only thing we can control is us, our reactions and whats on the inside. He suggests that our perceptions determine to a large degree what we are capable of and sometimes even reality itself. To many in-fact,  their perception is their reality so the importance of perception shaping how we deal with obstacles and ultimately life cannot be overemphasised.

The second way Holiday proposes that we deal with obstacles which are inevitable in life is through action. In the book, he explains that success in life will depend largely on what we go through and how you react to it. 

 It doesn’t matter what happens to you or where you come from. It matters what you do with what happens and what you’ve been given.

He goes on to say that the way to deal with the remora life throws our way after carefully analysing and perceiving objectively is to do something about the situation by taking action because ‘obstacles don’t unobstacle themselves’. We must be ready to exert energy, iterate, persist, be deliberate, strategic, have an eye for opportunity and pivotal moments, refuse to accept defeat, get moving and quit procrastinating.

Holiday agrees that sometimes in taking action, we fail. But even in failure there is a lesson, because failure shows us the way by showing us what isn’t the way. And when this happens we can take action again and move on to what is next, applying this principles and lessons learnt from past experiences.

The third principle that Holiday discusses is Will. Will is the internal power we possess that cannot be affected by the outside world. It is the final and perhaps most important quality we must possess especially when we have tried everything (action) to change and make a situation better. It is what we need to turn a situation that is undeniably negative and unchangeable into a humble experience. Holiday  distinguishes  ‘true will’ as quiet humility, resilience, and flexibility, against the other type of will which is l…weakness disguised by bluster and ambition that never stands the test of time, or lasts when we are tested by real obstacles.

“Nobody is born with a steel backbone, we have to forge that ourselves”, Holiday says about the power of will and building of the inner citadel. Our inner citadel is the force inside of us that no external adversity can ever break down. It is what fortifies us and helps to build the power of will, which is what gets us through the toughest obstacles and helps us to accept them, learn from them and grow through them. The inner citadel is however not something we are born with but a structure we develop over time through our experiences.

Still on will, he discusses  how anticipating the worst, acquiescing when situations are unchangeable, accepting and loving everything that happens as part of the journey, meditating on life’s biggest and surest obstacle death can help us to turn obstacles around and deal with them. And after all is said and done, after analysing, perceiving properly, taking the best action and accepting what we can not change, we must be ready to try, and try and again, because life is a ‘Marathon’. We must learn to conserve our energy and accept that every challenge is just one of many to come.

What makes this book very interesting is that Holiday doesn’t just postulate, he uses the experiences and true life stories of some of the greatest leaders in history, and shows how they used these principles to turn situations an average person would regard as insurmountable to their advantage.

We are encouraged to use the principles discussed in the book to

See clearly; act correctly; and then finally endure and accept the world as it is.

He ends by reminding us that each experience perceived correctly makes us stronger and helps us to gather strength as we go.

While some of the principles Holiday discussed in this book are not novel, seeing how people like Marcus Aurelius, George Washington, Thomas Edison applied them helps give a clearer perspective, as well as see that just like us, they were ordinary people who refused to remain average or be stopped by the obstacles of life. They chose to

See things for what they were, did what they could, and endured what they had to.

But most importantly they understood that the blocked path is now the path, what once impeded action now advances it, and that the Obstacle really is the way.

Holiday delivered a life changing lulu of a book on this, one that I recommend should be read more than once to help fully grasp the principles and consciously apply them.