Resilience — The Obstacle is the Way

New book from Ryan Clark Holiday comes at a perfect time for a military stressed by war.


We hear the word often in our Army today. After thirteen exhausting years of war, our men and women in uniform have many problems ahead of them—the stress of combat, strained family lives, and rising suicide rates. To combat them, Army leaders have emphasized resilience—the ability to overcome adversity, and be stronger for it.

Of course, the concept is hardly new. The great Stoics of the ancient world had long known, as Nietzche puts it, that which does not kill me makes me stronger.

Resilience is also a central theme in Ryan Clark Holiday’s second book, The Obstacle is the Way: The Timeless Art of Turning Trials Into Triumphs, due to be published this month.

Holiday, a protégé of author Robert Greene (The 33 Strategies of War), delves into the lives of men and women spanning nearly 3,000 years of history to discover the key to overcoming adversity in our lives.

To be fair, there is no secret to overcoming obstacles. As Holiday points out, the greats throughout history have long unlocked the secret of triumphing over adversity. Yet, Holiday is one of the first to codify their method of success into three simple concepts: perceptionaction, and will.


We all encounter obstacles, whether it be that toxic leader at work, tough financial times, or the burden of another deployment. The giants of history had their fair share of obstacles, too—often far and above what we could even comprehend. What allowed them to overcome their obstacles?
Every one of us will encounter adversity. We have no control over it. Throughout his book, Holiday often refers to the Serenity Prayer: “Give me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference”.

So how do we understand the difference? The greats did so by altering their perception. They remained calm in the face of adversity, and they regarded the obstacles in their own lives—be they wars, imprisonment, or physical hardship—as an opportunity. Indeed, through a life devoted to self-discipline, they were able see difficulties for what they really were, and began to ultimately conceive of a plan for overcoming, conquering, and eventually transcending them.


What do you do in the face of adversity?

For many, it’s resignation.

Humans have an amazing capacity for self-deception. We often tell ourselves, that goal wasn’t worth achieving anywayThat obstacle was too bigIt’s not worth the effortYou’ll only look foolish.

So we give up. We give in to life’s distractions. We never conquer our fears.

Nonsense, says Holiday. And so say the greats.

With an illuminating biographical anecdotes reminiscent of those found in Robert Greene’s PowerSeduction, and War trilogy, Holiday alludes to the persistence of one of history’s most legendary Generals, Ulysses S. Grant.

Grant spent weeks trying to crack the defenses of Vicksburg—one of the most heavily fortified positions in the Confederacy.

How did he do it? Forget tactics—he did it through ingenuity, audacity, and outright persistence. As Holiday explains:

Too many people think that great victories like Grant’s…came from a flash of insight. That [he] cracked the problem with pure genius. In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other promising options that slowly and surely churned the solution to the top of the pile. Their genius was unity of purpose, deafness to doubt, and the desire to stay at it. So what if this method isn’t as “scientific” or “proper” as others? The important part is that it works.


Of course, be prepared for your best attempts to fail. Some enemies simply won’t be vanquished with a snap of the finger or a deft maneuver. That’s where resilience comes in.

Holiday explores resilience by drawing from one of the most inspiring figures in history: Abraham Lincoln. Your struggles—as insurmountable as they might seem—pale with those of Lincoln’s. Of course, American schoolchildren are well aware of the immense task America’s sixteenth president faced in trying to preserve the Union through four years of bloody civil war. But few are aware of the deep personal struggles which plagued Lincoln throughout his life—poverty, depression, repeated failure in the political realm. Lincoln drew on those hardships during times of crisis.

Schooled in suffering…Lincoln learned to ‘comfort those who suffer too’. This, too, is part of the will—to think of others, to make the best of a terrible situation that we tried to prevent but could not, to deal with fate with cheerfulness and compassion. Lincoln’s words went to the peoples’ hearts because they came from his, because he had access to a part of the human experience that many had walled themselves off from. His personal pain was an advantage.

Indeed, read the words of the Gettysburg Address, or Lincoln’s letter to Mrs. Bixby. You’ll find this was a man defined by his hardships; Lincoln had learned to be a more effective leader for ability to weather adversity—in other words, resilience.

The Verdict

The Obstacle is the Way might be described as “applied Stoicism”. Holiday doesn’t delve too deeply into Stoic philosophy—this is a practical guide to resilience. In much the same vein as his mentor, Robert Greene, Holiday’s crisp, clear sentences have a lyrical quality about them, and you’ll find yourself at the end in no time. Also like Greene, Holiday draws extensively on biographical vignettes from rousing historical figures from all walks of life—emperors and prisoners, astronauts and slaves.

Let’s face it—most of us are exposed to resilience only through stale bullets on PowerPoint slides and soulless computer-based training. Holiday has given us a living, breathing guide to resilience. As humans, we learn best through stories, and Ryan Clark Holiday has delivered them spades.

The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph goes on sale 1 May for $24.95.

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