BOOK REVIEW: The Obstacle is The Way by Ryan Holiday

Updated: Jun 20


Background: The following is a book review written by a good friend of ALIVE, Harrison Welsh. Harrison is deeply passionate about the learning process, critical thinking, and the tools and practices most useful to living a happily productive life. He is a Sydney Film School graduate and is currently studying primary education at the University of Newcastle. Naturally, a keen interest for Harrison is the way we create and consume media; the different ways we engage with stories and the impact they can have on our lives. He writes incredible book and film reviews you can find here: Another Movie Boy on Instagram and Letterboxd + To.B.Read on Instagram and Goodreads.


Here is his latest review.


The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage written by Ryan Holiday highlights for readers the skills and attributes necessary to overcome impossible situations. The lessons in the book are taught through the stories of some of the most iconic and successful figures throughout history. Including, Abraham Lincoln, Amelia Earhart, Margaret Thatcher and Steve Jobs. All these icons either knowingly or not shared a similar philosophy, the philosophy of stoicism which has its roots some two thousand years ago in ancient Greece. Holiday brings the teachings of stoicism to his readers breaking it down into three parts: Perception, Action, and Will. Showing us that we thrive not in spite of adversity but because of it.


PART ONE: Perception

“Choose not to be harmed and you won’t be harmed. Don’t feel harmed and you haven’t been” - Marcus Aurelius. Perception is all about having the discipline to be objective and recognising your power to control the way you view any situation. If you are able to keep your cool and accept the challenges in your way, then you will be able to find the opportunity in the obstacle. There is much in life that is out of our control but the way we perceive things is a skill that can be practiced and cultivated. Through this practice we learn to focus on the present task, not despair about the past or feel anxious about our future but focus our attention on what we can do in this present moment. Finding the opportunity in every obstacle will take some creativity but it is that ability to think differently which allows you to challenge the status quo and prepares you with the right attitude to take the right action.


PART TWO: Action

Starting is not always easy but you cannot achieve anything without doing anything. You must create your own momentum by leaning into your obstacles with energy. This momentum will drive your persistence, once you start attacking an obstacle, quitting is no longer an option, changing paths or tactics absolutely, but never giving up. This persistence is a key to your success, as even your failures become opportunities to improve, remember, “failure shows us the way by showing us what isn’t”. Through these failures we refine our process and learn to trust in it. Our goals give us direction and it is the process, doing the right thing right now that will actually get us there. In getting the job done we focus on what works, not searching for perfectionism or acknowledgements that stroke our ego but putting our energy into achieving results. To channel this energy, return to the reason you stated the journey. What is your purpose that made you want to achieve the goal in the first place? Ultimately stoicism as interpreted by Holiday reminds us, that we must be prepared for none of it to work. You can control your perception and direct your action but there is still much that is out of your control. Be humble and accepting, ready to move on to another path if things do not work as planned.


PART 3: Will

This Is our internal power we rely on when our agency is lost, it allows us to be humble and learn from unchangeable situations. In cultivating will we prepare ourselves for the acquiescence of dark times. We prepare for the hard road and hope we don’t have to walk it. Negative anticipation can be a useful tool, this is distinct from pessimism, in that we are not falling to despair or assuming things will go wrong but rather taking a very measured and calculated assessment of how things may go and planning how you will respond. The only truly insurmountable obstacle is death, but in meditating on your own mortality your priorities and values become clearer. This clarity often pushes us to contribute to something bigger than ourselves, filling us with a sense of responsibility to improve the world and altering your perspective to see yourself as a small part of a greater whole. When your only certainty is in the present moment you learn to love everything that happens. A favourite story of mine from the book is that of Thomas Edison who when he saw his research and production facility being destroyed in a massive chemical fire told his son, “go get your mother and all her friends”, excitedly Edison said “they’ll never see a fire like this again”. Green and Yellow flames rose seven stories destroying the empire he had spent a lifetime building. Edison understood there was nothing to be gained by complaining, instead he found the joy in what most would have thought an utterly devastating situation.


“prepare to start again” once you overcome one obstacle life will inevitably throw another in your way. Because of the obstacles you have faced you have mastered your perception, honed your action and strengthened your will. Now you take on this new challenge without fear and instead with eager anticipation. The main philosophy at the heart of stoicism may seem simple or repetitive, but Holiday’s framing through the many inspiring short stories shows in practice just how powerful a philosophy it can be.

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