Review of “The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph‎” by Ryan Holiday

april 2019 book review

If there’s no better way to teach other than giving relevant examples, then there can’t be a more efficient way to learn how to thrive in the face of difficulties than to read about those who have done that before. For this, Ryan Holiday did a good job in distilling stories of great folks into this book. Salient lessons, whether previously learnt or not, come alive as the reader rides through.

Ryan does not lay claim to a grand idea or panacea. His ideas are neither new nor without precedents: they are Stoics’ philosophy. The organization of the material is also based on the three doctrines of Stoicism: perception, industry and perseverance. What distinguishes Ryan’s work, however, is the marriage of philosophical themes with stories set in both contemporary and ancient times. We can conveniently tag the book, a basic introduction to Stoicism.

Through storytelling, Ryan shows how altering our perception of events can be important for a less-perturbed life. Perception is key and we must learn to be objective about situations as every obstacle is an opportunity to practice a virtue: patience, humility, creativity, empathy, fortitude, courage and resourcefulness. There’s always a way around every situation and a better way to think and act on any issue. Therefore, we have to deliberately and constantly train our minds to have the right perceptive. For instance, we can demystify difficult bosses by imagining them taking out garbage. That should put a more human and vulnerable feel to how we view them.

People who will ever get anything done cannot afford to avoid the challenges they will be confronted with. Rather, they should expect “the obstacles”, and will have to walk and work through them, counting them as “fuel”. The reader is persuaded to understand that, whatever the challenges might be, other people have gone through worse and yet survived. Well, you can say “of course, I know these.” Hold on! The call is not to know, but to ingrain. And explaining these principles with narratives makes them easier to inculcate.

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Unlike many self-help books that instruct to think positively, this book not just charges to recognize advantages in disadvantages, but to stir ourselves to action, to believe there are opportunities laden in seemingly adverse situations, and persevere in making the best of them. Ryan is not suggesting we suffer unwisely, but asking us to always remember we are limited in our ability to control external causes, rightly echoing that the greatest control we have is over ourselves. We must differentiate between what is up to us and what isn’t – we take the reins when we are able to do this. The Serenity Prayer best reflect this idea: “God, grant us the serenity to accept the things we cannot change. The courage to change the things we can. And the wisdom to know the difference.”

Our attitude is absolutely under our control. Using apt examples, Ryan presents several strategies to do this. We are encouraged to accept every burden we have to bear with dignity, because out of them comes strength for future travails. There is such a thing as post-traumatic growth, meaning, what does not kill makes us stronger. A well-managed adversity can make us stronger as it forges in us, life skills that no one can take away.

It’s okay to be discouraged, but not okay to quit. Persistence means even though you are discouraged and want to quit, you put plant your feet and keep pressing on. The will to persist is fortitude and wisdom, not just about specific obstacles, but life itself. It gives us the strength to endure, contextualize and derive meaning from obstacles we cannot simply overcome. We must know that nobody is born with a “steel backbone”, individuals develop it themselves. Neither is anyone born a gladiator nor with an inner citadel. The reality is, if we’ll succeed in achieving our life goals, our will must be built. Anticipating challenging situations won’t magically make things easier, but it makes us mentally prepared and helps to fortify our will. An example was given of the baseball player, Tommy John, who repeatedly asked himself and others what his odds of success were, whenever confronted with an obstacle. He made every effort he could in attaining his objectives at the slightest indication of success.


A reader might conclude the examples were cherry picked – that contradictions were neglected. Though that may be right, we must reckon that an exception is also instructive, and they might not truly be exceptional. Even if it’s borne out of sheer luck, who says other folks can’t be that “fortunate” too? Nonetheless, whether we win or lose, the point is that we must always endeavor to conduct ourselves in the most dignified manner. That implies striving to live for a higher purpose, putting group interests before personal interests, as we never can tell who is waiting to get inspired by our stories. The truth is that Stoicism helps in this regard, and readers expecting more will have to consult the works of philosophers like Marcus Aurelius and Seneca, which the book also heavily draws upon.

One can conveniently summarize the message in “The Obstacle is the Way” thus: Do all you can, ensure you’ve done your part, and never complain about the negative outcome(s). Always tune your perspective towards every situation to be able to take right actions. Throughout history, people defy odds with this mindset. From Thomas Jefferson, an introvert who trained to express himself in writing, and ended up writing the US Declaration of Independence; to young Demosthenes, who because of his speech impediment, shaved half his head to prevent him from going out, locked himself up so he could train his voice, and turned out to be one of the greatest orators of all times. Anyone can do this because an obstacle is not a barrier!

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Here is the lyrics of “You got it in you” by Banners:
When the lights go out and leave you standing in the dark,
No one ever told you this would be so hard,
I know you think your fire is burning out,
But I still see you shining through.

You got it in you.
Not everything you hear should sound like the truth,
‘Cause nobody else’s words can define you.
Maybe you don’t see it but you’re quicker than the world can spin.
You should know what you got, ’cause you got it at your fingertips.


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