The Obstacle Is The Way by Ryan Holiday – Book Review

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

Throughout our lives, we will be faced with obstacles, adversity, and hardships. This sadly is something we cannot control. What we CAN control however is our mindset and how we approach these obstacles. In The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph Ryan Holiday explains a formula for success utilized by some of the history’s most prominent figures such as John D. Rockefeller, Amelia Earhart, Steve Jobs, and more.

Combining timeless quotes and historical accounts Ryan provides a framework based in Roman Stoicism that these figures utilized to find meaning and excellence in every situation. The framework consists of three major components.


“Desperation, despair, fear, powerlessness – these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings. Or, like Rockefeller, choose not to”

What exactly is perception? It’s how we see and understand what occurs around us – and what we decide those events will mean. What WE decide those events will mean. Ryan examines John D. Rockefeller and Warren Buffet and their infamous ability to remain calm when others panicked. They made choices not through reacting to circumstances but by accepting them and seeing beyond the immediate to find a silver lining, learning, or benefit from what many would see as a misfortune.


“Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence.”

Taking action is commonplace. However taking the right action, directed action, is not. We must break down our obstacles into smaller directed actions, and step by step with persistence and flexibility, begin to break them down. Nick Saban famously tells all incoming freshman he will not tolerate anyone talking about winning a National Championship. You only focus on this catch, this block, this play, and if you keep your focus there, in the end, we will have our championship. Likewise, when you fall do not dwell. No one is saying you cannot stop and think “wow this really sucks” but take your moment, brush it off and move.


“If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.”

Many times our obstacles can be unchangeable or undeniably negative. We must turn this into a learning experience, a humbling experience, or a chance to provide some comfort to others… that is willpower. When we are faced with an obstacle or issue that is undeniably bad or that we simply cannot move our will must persevere. It is in these times that our true selves show and how we handle these trials will show the world what we are made of. By using these as a chance to do as much good as possible we truly show we are an unstoppable force.

Throughout The Obstacle is The Way Holiday uses example after example from history’s greatest achievers to demonstrate these points. His book has become a staple for many corporations, startups, and sports teams. These lessons and stories have remained true for thousands of years and will still ring true in another thousand.

The Obstacle is The Way is a fantastic resource for anyone who wants to take a fresh look at life’s trials and equip themselves to always use the experience to make themselves better.


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