The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

"The Obstacle is the Way" is Ryan Holiday’s case for ancient Stoicism as a practical philosophical choice for modern entrepreneurs and do-ers. And I must admit, I’m sold. But I’m conflicted about how to rate this book. On one hand, the message is compelling and the presentation is clear. But on the other... the book is just a compilation of quotes and stories of wise old Stoic dudes and practitioners. Ryan does a fantastic job of selecting examples - both ancient and modern - and arranging them in a coherent narrative, but the book feels like a grab-bag of Stoicism. Still... it's not a bad intro to the topic and Ryan includes a nice Stoic Reading List at the end that points the reader towards other sources of Stoic inspiration.

This book makes for a great companion to Manson's less intellectually pretentious and significantly more profane "The Subtle Art of Not Giving a F*ck".

My highlights below.


But in a scant eighty-five words Marcus Aurelius so clearly defined and articulated a timeless idea that he eclipses the great names of those who came before him: Chrysippus, Zeno, Cleanthes, Ariston, Apollonius, Junius Rusticus, Epictetus, Seneca, Musonius Rufus. It is more than enough for us. "Our actions may be impeded... but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting... The impediment to action advances action. What stands in the way becomes the way."

And from what we know, he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity. The power he held never seemed to go to his head—neither did the stress or burden. He rarely rose to excess or anger, and never to hatred or bitterness.

As Matthew Arnold, the essayist, remarked in 1863, in Marcus we find a man who held the highest and most powerful station in the world — and the universal verdict of the people around him was that he proved himself worthy of it.

John D. Rockefeller had it — for him it was cool headedness and self-discipline. Demosthenes, the great Athenian orator, had it — for him it was a relentless drive to improve himself through action and practice. Abraham Lincoln had it — for him it was humility, endurance, and compassionate will. There are other names you’ll see again and again in this book: Ulysses S. Grant. Thomas Edison. Margaret Thatcher. Samuel Zemurray. Amelia Earhart. Erwin Rommel. Dwight D. Eisenhower. Richard Wright. Jack Johnson. Theodore Roosevelt. Steve Jobs. James Stockdale. Laura Ingalls Wilder. Barack Obama.

Subjected to those pressures, these individuals were transformed. They were transformed along the lines that Andy Grove, former CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

“The Things which hurt,” Benjamin Franklin wrote, “instruct.”

PART I - Perception

To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives. It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear. But it’s worth it, for what’s left is truth.

We must try:

  • To be objective
  • To control emotions and keep an even keel
  • To choose to see the good in a situation
  • To steady our nerves
  • To ignore what disturbs or limits others
  • To place things in perspective
  • To revert to the present moment
  • To focus on what can be controlled
    This is how you see the opportunity within the obstacle. It does not happen on its own. It is a process — one that results from self-discipline and logic.

Choose not to be harmed — and you won’t feel harmed. Don’t feel harmed — and you haven’t been. —MARCUS AURELIUS

“Nothing either good or bad, but thinking makes it so,” as Shakespeare put it.

When we aim high, pressure and stress obligingly come along for the ride. Stuff is going to happen that catches us off guard, threatens or scares us. Surprises (unpleasant ones, mostly) are almost guaranteed. The risk of being overwhelmed is always there. In these situations, talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill. We must possess, as Voltaire once explained about the secret to the great military success of the first Duke of Marlborough, that “tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head.”

Would you have a great empire? Rule over yourself. —PUBLIUS SYRUS

In space, the difference between life and death lies in emotional regulation.

Real strength lies in the control or, as Nassim Taleb put it, the domestication of one’s emotions, not in pretending they don’t exist.

Or try Marcus’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?

Don’t let the force of an impression when it first hit you knock you off your feet; just say to it: Hold on a moment; let me see who you are and what you represent. Let me put you to the test. —EPICTETUS

To paraphrase Nietzsche, sometimes being superficial — taking things only at first glance — is the most profound approach.

The Stoics use contempt as an agent to lay things bare and “to strip away the legend that encrusts them.” Epictetus told his students, when they’d quote some great thinker, to picture themselves observing the person having sex. It’s funny, you should try it the next time someone intimidates you or makes you feel insecure. See them in your mind, grunting, groaning, and awkward in their private life — just like the rest of us. Marcus Aurelius had a version of this exercise where he’d describe glamorous or expensive things without their euphemisms — roasted meat is a dead animal and vintage wine is old, fermented grapes. The aim was to see these things as they really are, without any of the ornamentation.

So what does it matter, Pericles replied, when the cause of the darkness differs? The Greeks were clever. But beneath this particular quip is the fundamental notion that girds not just Stoic philosophy but cognitive psychology: Perspective is everything. That is, when you can break apart something, or look at it from some new angle, it loses its power over you. Fear is debilitating, distracting, tiring, and often irrational. Pericles understood this completely, and he was able to use the power of perspective to defeat it.

He understood that as a professional athlete his job was to parse the difference between the unlikely and the impossible. Seeing that minuscule distinction was what made him who he was.

Behind the Serenity Prayer is a two-thousand-year-old Stoic phrase: “ta eph’hemin, ta ouk eph’hemin.” What is up to us, what is not up to us. And what is up to us? Our emotions. Our judgments. Our creativity. Our attitude. Our perspective. Our desires. Our decisions. Our determination.

Genius is the ability to put into effect what is in your mind. There’s no other definition of it. —F. SCOTT FITZGERALD

PART II - Action

Confident in his new strengths, driven on by his own toil, they were no match. Demosthenes eventually won. Only a fraction of the original inheritance remained, but the money had become secondary. Demosthenes’s reputation as an orator, ability to command a crowd and his peerless knowledge of the intricacies of the law, was worth more than whatever remained of a once-great fortune.

We must all either wear out or rust out, every one of us. My choice is to wear out. —THEODORE ROOSEVELT

German Field Marshal General Erwin Rommel, on the other hand, loved it. He saw war as a game. A dangerous, reckless, untidy, fast-paced game. And, most important, he took to this game with incredible energy and was perennially pushing his troops forward. The German troops had a saying about him: Where Rommel is, there is the front. That’s the next step: ramming your feet into the stirrups and really going for it.

At Vicksburg, Grant learned two things. First, persistence and pertinacity were incredible assets and probably his main assets as a leader. Second, as often is the result from such dedication, in exhausting all the other traditional options, he’d been forced to try something new. That option — cutting loose from his supply trains and living off the spoils of hostile territory — was a previously untested strategy that the North could now use to slowly deplete the South of its resources and will to fight.

Great entrepreneurs are: never wedded to a position never afraid to lose a little of their investment, never bitter or embarrassed, never out of the game for long.

The process is about finishing. Finishing games. Finishing workouts. Finishing film sessions. Finishing drives. Finishing reps. Finishing plays. Finishing blocks. Finishing the smallest task you have right in front of you and finishing it well.

To whatever we face, our job is to respond with: hard work, honesty. helping others as best we can. You should never have to ask yourself, But what am I supposed to do now? Because you know the answer: your job.

In a study of some 30 conflicts comprising more than 280 campaigns from ancient to modern history, the brilliant strategist and historian B. H. Liddell Hart came to a stunning conclusion: In only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main army. Only six. That’s 2 percent. If not from pitched battles, where do we find victory? From everywhere else. From the flanks. From the unexpected. From the psychological. From drawing opponents out from their defenses. From the untraditional. From anything but... As Hart writes in his masterwork Strategy: [T]he Great Captain will take even the most hazardous indirect approach — if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.

The great philosopher Søren Kierkegaard rarely sought to convince people directly from a position of authority. Instead of lecturing, he practiced a method he called “indirect communication.” Kierkegaard would write under pseudonyms, where each fake personality would embody a different platform or perspective — writing multiple times on the same subject from multiple angles to convey his point emotionally and dramatically. He would rarely tell the reader “do this” or “think that.” Instead he would show new ways of looking at or understanding the world. You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there.

When we want things too badly we can be our own worst enemy. In our eagerness, we strip the very screw we want to turn and make it impossible to ever get what we want. We spin our tires in the snow or mud and dig a deeper rut — one that we’ll never get out of.

It’s at the seemingly bad moments, when people least expect it, that we can act swiftly and unexpectedly to pull off a big victory. While others are arrested by discouragement, we are not. We see the moment differently, and act accordingly. Ignore the politics and focus on the brilliant strategic advice that Obama’s adviser Rahm Emanuel, once gave him. “You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. [A] crisis provides the opportunity for us to do things that you could not do before.

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? Will is our internal power, which can never be affected by the outside world. It is our final trump card. 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.

As crafty and ambitious and smart as he was, Lincoln’s real strength was his will: the way he was able to resign himself to an onerous task without giving in to hopelessness, the way he could contain both humor and deadly seriousness, the way he could use his own private turmoil to teach and help others, the way he was able to rise above the din and see politics philosophically. “This too shall pass” was Lincoln’s favorite saying, one he once said was applicable in any and every situation one could encounter.

A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish. Your plan and the way things turn out rarely resemble each other. What you think you deserve is also rarely what you’ll get. Yet we constantly deny this fact and are repeatedly shocked by the events of the world as they unfold. It’s ridiculous. Stop setting yourself up for a fall. No one has ever said this better than Mike Tyson, who, reflecting on the collapse of his fortune and fame, told a reporter, “If you’re not humble, life will visit humbleness upon you.”

Today, the premortem is increasingly popular in business circles, from start-ups to Fortune 500 companies and the Harvard Business Review. But like all great ideas, it is actually nothing new. The credit goes to the Stoics. They even had a better name: premeditatio malorum (premeditation of evils).

Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories, threatening to destroy the entire empire Edison had spent his life building. Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees, looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.”

As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones. Who knows where Edison and Johnson learned this epithet, but they clearly did.

The Germans have a word for it: Sitzfleisch. Staying power. Winning by sticking your ass to the seat and not leaving until after it’s over.

When Antonio Pigafetta, the assistant to Magellan on his trip around the world, reflected on his boss’s greatest and most admirable skill, what do you think he said? It had nothing to do with sailing. The secret to his success, Pigafetta said, was Magellan’s ability to endure hunger better than the other men.

For instance, Montaigne once wrote of an ancient drinking game in which participants took turns holding up a painting of a corpse inside a coffin and toasting to it: “Drink and be merry for when you’re dead you will look like this.”

Memento mori, the Romans would remind themselves. Remember you are mortal.

On the contrary, the more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.

FINAL THOUGHTS - The Obstacle Becomes the Way

The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.” It’s a loop that becomes easier over time.

POSTSCRIPT - You’re Now a Philosopher. Congratulations.

The political thinker John Stuart Mill wrote of Marcus Aurelius and Stoicism in his famous treatise On Liberty, calling it “the highest ethical product of the ancient mind.”