The Obstacle Is The Way – Motivation And A Book Review

The Obstacle Is The Way – Motivation And A Book Review

The Most Inspiring Book I’ve Read All Year

Although I love fiction, and can get lost in it for hours, to start the day I prefer non-fiction, especially inspiring non-fiction, to kick-start a positive attitude that can stick with me all day.

Ryan Holiday’s The Obstacle is The Way: The Timeless Art of Turning Trials into Triumph is the most inspiring non-fiction I’ve read all year. It’s so good, I’m making it one of my stocking stuffer for friends and family.

If you’ve ever experienced set-backs (who hasn’t?). If you’re in a time of growth, transition or stagnation in your life. If you want to take on the BS life throws at you with a renewed vigor and a fresh perspective, I highly recommend this book.



One of the keys to this book’s greatness, as with most things in life, is its simplicity. Ryan managed to boil down an ancient Greek philosophy to a formula, the formula for turning obstacles into opportunities. He shows countless examples of “history’s icons” using this formula to find success in life. And he tells it all simply and succinctly.

At a little over 200 pages, The Obstacle Is The Way is an easy read, but don’t mistake it for an unsophisticated one.

The Formula

Control Your Perceptions, Take Action, Build Your Willpower, Rinse and Repeat

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What Is Perception?

It’s how we see and understand what occurs around us – and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness.

Controlling your perceptions takes discipline and self-awareness. We won’t be able to, just one day, decide that we’ll no longer be emotional, subjective and shortsighted in our thinking. It takes practice, it takes skill, it takes discipline to recognize your immediate, emotional response and separate it from the truth.

But it’s worth it, for what’s left is truth.

Ryan recently published a post expanding on the “How To Think About Obstacles” process. Here are the 7 steps he lists:

  1. Steady Your Nerves
  2. Control Your Emotions
  3. Practice Objectivity
  4. Practice Contemptuous Expressions
  5. Alter Your Perspective
  6. Live In The Present Moment
  7. Look For The Opportunity

This post is a great compendium to The Obstacle Is The Way, I highly recommend reading them together.

Why Action?

Because …

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

Too often, we know what our problems are. Most of the time we even know what the right solution is. But instead of dismantling these obstacles in front of us through action, we create new ones. We build up our fears, we exaggerate the risks, we spend more energy on choosing the right path than taking the first step.

Relevant xkcd
Relevant xkcd

Instead, we must practice Ryan’s advice (not just once, but with consistency):

Tell yourself: The time for that has passed. The wind is rising. The bell’s been rung. Get started, get moving.

But getting started’s not enough. We must also Practice Persistence.

Ryan tells two fantastic stories of action and persistence.

One of Ulysses S. Grant struggling against the defenses of Vicksburg, a city critical to the Confederacy’s stranglehold on the Mississippi. After a year of struggle, where others would have pulled back, Grant found an innovative solution that would eventually win him the war.

The second is of Nikolai Tesla spending a year in Thomas Edison’s lab during the development of his lightbulb. Tesla remarked, during this time – that if Edison needed to find a needle in a haystack, he’d simply “examine straw after straw until he found the object of his search”.

These stories teach us that genius is not a flash of inspiration.

Their genius was unity of purpose, deafness to doubt, and the desire to stay at it.

Ryan takes this storytelling approach to teach us about other aspects of the discipline of action. Here are some of my favorite quotes and concepts from the other action chapters.

  • Iterate: embrace failure and feedback.
  • Follow The Process: don’t think about the pot at the end of the rainbow; stay in the moment, get 1% better today.
  • Do Your Job, Do It Right: “Whatever is rightly done, however humble, is noble.”
  • What’s Right Is What Works: As Deng Xiaoping said “I don’t care if the cat is black or white, as long as it catches mice.”
  • In Praise Of The Flank Attack: Take a step back, find leverage and go around the problem.
  • Use Obstacles Against Themselves: “Just ask the Russians, who defeated Napoleon and the Nazis not by rigidly protecting their borders, but by retreating into the interior and leaving winter to do their work … Is this action? You bet it is.”
  • Channel Your Energy: “Physical looseness combined with mental restraint? That is powerful.”
  • Size The Offensive: to be honest, I felt this chapter was repetitive of the start.
  • Finally, Prepare For None Of It To Work: “In the meantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases.” – Seneca

What Is Will?

Ryan refers to will as “our final trump card”. It’s the one thing that can’t be influenced by the outside world. No matter what happens, you will is under your power.

Placed in some situation that seem unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power. But that needs to be cultivated. We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times.

Abraham Lincoln had will in spades. Even though he suffered with depression he strove to alley suffering in others. Even in the midst of national turmoil, he could be heard saying, “this too shall pass”.

Leadership requires determination and energy. And certain situations, at times, call on leaders to marshal that determined energy simply to endure. To provide strength in terrible times.

Theodore Roosevelt learned to build his inner will at a young age, when he trained his body to overcome asthma, sickness and frailness. He build mental strength through physical labor (sound mind in a strong body – mens sana in corpore sano).

Thomas Jefferson, on the other hand, accepted his limitations. He was quiet and reserved – a terrible public speaker. Wanting to be a politician, he accepted the lot he was dealt and channeled his energy into writing. Growing his skills as a writer gave Jefferson the opportunity to write one of the most important documents in history – The Declaration of Independence.

If perception and action were disciplines of the mind and body, then Will is the discipline of the soul.

To sum up, Ryan leans on his greatest inspiration – Marcus Aurelius, Roman Emperor, stoic author of Meditations and “that good king” in the movie Gladiator.

Late in his life, Marcus was betrayed when his good friend and most trusted general, Avidius Cassius, started a civil war in Syria. Marcus told his men, fighting their own, that “we will settle this affair well and show all mankind that there is a right way to deal even with civil wars.”

In the greatest tragedy we find purpose, happiness and opportunity.

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