The Obstacle is the Way – The Timeless Art of Turning Trials into Triumph, by Ryan Holiday

Why this book:  Selected by my SEAL/SWCC candidates reading group to read as preparation for basic SEAL/SWCC training.  Also this is a key book in the canon of Stoic literature that has helped Ryan Holiday bring Stoic values to the attention of many Americans. 

Summary in 5 sentences: The premise of this book is that obstacles, challenges, problems should be viewed not simply as inconveniences that stand in our way,  but as MEANS to grow stronger, wiser,  more resilient, more successful.  This process begins with the right attitude and seeing the challenges clearly for what they are, which he describes in the first section of the book, entitled Perspective. Secondly we must take action appropriate to our clear vision and attitude, a process which he describes in a the second section entitled Action.  And finally we must have the wisdom to see and accept the world as it is, to persevere and endure with the course of action we have chosen, but also to know when to change course and try something new,  which he describes in a section entitled Will.  His message is that how we respond to challenges not only reveals our character but more importantly enriches, shapes and strengthens it.

My Impressions:  The message of this book is in its title – whatever may appear to be an obstacle that may stand in the way of achieving what we want, a challenge, a problem, a seemingly insurmountable barrier, beckons us to not only overcome it, but also to make us better,, challenging us to develop our creativity, resilience, insight, wisdom and strength.  It is a short book – 186 short pages – divided into three sections, each of which provides often well known, occasionally lesser known examples of people who have achieved great things BY overcoming, not in spite of overcoming obstacles in their way.

The Obstacle is the Way is divided into discussions of Perception, Action, and Will and each of those sections has chapters that address different aspects of that main idea.   Though there is a strong overlap between the sections and the chapters, the ideas reinforce each other from different perspectives and give Holiday a variety of venues to tell different stories with different nuances to support his thesis.

PERCEPTION: This section basically advises the reader to take the long view, keep the big picture in mind, and not to get too caught up in the immediate challenges and problems that may seem insurmountable.  He says that the right perspective has a strange way of cutting obstacles and adversity down to manageable size.  He advocates attempting to minimize one’s emotional and personal responses to a problem and instead,  to seek to be as objective as possible.  We can defeat emotion with logic he argues.  He suggests we place things in a broader perspective,  to focus on the present and what we can control right now, to help us steady our nerves.  He says “there is the event itself, and the story we tell ourselves about what it means… WE decide what story to tell ourselves.”

He points out that perspective has two key parts – Context – seeing and looking at the larger picture, and Framing – our own way to look at a problem and how we understand and interpret it.  Part of perception is to see that burdens and blessings are not mutually exclusive.  He then segues into the next section by noting that perception precedes “action,” and “right action” follows “right perception.” 

ACTION:  The main point of this section is that a great and positive attitude is just the beginning.  If obstacles or challenges are to make us stronger, wiser, more resilient, we have to take action, and act with deliberation, boldness, and persistence.  He often repeats the Stoic mantra of “No excuses. No exceptions.  It’s on you.” It doesn’t matter what happens to you, or even what happens.  All that truly matters is how you respond – YOUR action.   He emphasizes that we must not be afraid of failure, noting that action and failure are two sides of the same coin, and that boldness means not being afraid of failure.  When we fail, we learn – we find out what we didn’t see, what we did poorly, what doesn’t work, what isn’t the way.  It is up to us to turn disappointment into opportunity.

WILL This was my favorite section -as it emphasizes the individual’s responsibility to maintain the big picture as we implement our Stoic Perspective and Action.   He says, that “If Perception and Action were the disciplines of the mind and the body, Will is the discipline of the heart and the soul…Will is fortitude and wisdom…gives us ultimate strength…to endure, contextualize, and derive meaning from obstacles we cannot simply overcome.”  Will is more subtle- he lists a number of qualities that include managing expectations, accepting what we are unable to change (and the wisdom to know the difference.)

He has a whole chapter in this section on the wisdom of anticipating and preparing for failure or disappointment – this balances  the positive attitude and belief in oneself we read in Perception. He points to the wisdom of conducting what he calls a premortem – if our plan doesn’t work, what probably went wrong, and how do we anticipate and better prepare for these challenges (military planners do this, sometimes to excess.)  He distinguishes between acceptance, and giving up.  Not the same – the Stoic sage knows when good judgment says it’s time to move on,  or to pivot, and try something else. 

In this section he has a chapter with a title he borrowed from Nietzsche “Amor Fati” Love your fate and all that happens.  He has a chapter focussed on perseverance, which he distinguishes from persistence. “Perseverance. Force of purpose. Indomitable will… traits uniquely part of the American DNA.” And he offers us a chapter advising us of the wisdom of mediating on our own mortality.


Throughout the book Holiday provides anecdotes and stories to support his points, providing examples and inspiration from people who most Americans have revered and been inspired by.  We learn from the lives of such well known figures as Abraham Lincoln, Ulysses Grant,  James Stockdale, Thomas Edison, Erwin Rommel, Amelia Earhardt, Tommy John, George Clooney, Hurricane Carter, Teddy Roosevelt, Ralph Waldo Emerson, Marcus Aurelius, Epictetus, others.  

This book is full of wisdom and useful epigrams and aphorisms, backed up with examples.  The distinctions he makes between Perception, Action, and Will are to me somewhat artificial:  As I was reviewing this book to summarize those three parts, I found so much in each that would fit in the other two.    But that doesn’t take away from the value of reading the same point made several times, reinforced in different contexts and in different sections. 

Much of what he offers is also available in different form and tone in Michael Manson’s clever book: The Subtle Art of Not Giving a F*cK (my review here) written primarily to appeal to Gen X and Gen Y young adults.   Holiday’s The Obstacle is the Way will appeal to a more mature audience, in a more didactic style, and more easily lends itself to being picked up and opened to a random spot and extracting a bit of wisdom – which is what one would expect from the author of The Daily Stoic.  

“You will have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is  – at best – indifferent to your existence.”  p137  In this little book, he provides a prescription for how to do that – beginning with attitude, then action, then wisdom and perseverance.  

About schoultz

CEO of Fifth Factor Leadership - Speaker, consultant, coach. Formerly Director, Master of Science in Global Leadership at University of San Diego; prior to that, 30 years in the Navy as a Naval Special Warfare (SEAL) officer.
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