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

The Obstacle Is the Way - The Timeless Art of Turning Trials into Triumph by Ryan Holiday

Our Wise Guide: “The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

We are stuck, stymied, frustrated. But it needn’t be this way. There is a formula for success that’s been followed by the icons of history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—a formula that let them turn obstacles into opportunities. Faced with impossible situations, they found the astounding triumphs we all seek.

These men and women were not exceptionally brilliant, lucky, or gifted. Their success came from timeless philosophical principles laid down by a Roman emperor who struggled to articulate a method for excellence in any and all situations.

This book reveals that formula for the first time—and shows us how we can turn our own adversity into advantage.


each obstacle, each impediment, each thing that seems to be blocking the path to success is itself the path to success. In other words, every obstacle, everything that seems to be standing in your way, is itself the way. Hence the title.

Marcus Aurelius, the Roman emperor and Stoic philosopher, put it thus: “The impediment to action advances action. What stands in the way becomes the way.”

This isn’t about seeing the silver lining in every situation. It’s not about being a cup-half-full kind of person. You don’t have to throw on a pair of rose-colored glasses. Seeing the opportunities hidden in every obstacle is not about being relentlessly optimistic.

Rather, it’s about being clear-eyed, logical, reasonable, prepared and pragmatic – prepared for whatever life might throw at you and pragmatic both in how you perceive your circumstances and in how you respond to them. It’s not about ignoring obstacles; it’s about approaching them in the most effective way.

This shortform summary has three sections, just like the book: Perception, Action, and Will. These are the three ingredients to flipping any situation, to taking a negative and turning it into a positive.

Perception is the starting point: learning to regard what most people would call an obstacle – an economic downturn, a traffic jam, a personal disability, anything – as a path to success.

Action is next: perceiving the path is the beginning, but it won’t bring you much unless you act, unless you take that path.

And then there’s Will: the energy, the determination, the will to stay on the path, to keep walking even when the going gets tough.

All of this is simple enough. But that doesn’t mean it’s easy to put into practice. So let’s look at some examples of people who’ve done it – people who’ve taken disadvantages, setbacks, hardships, inauspicious circumstances and flipped them over, revealing what they truly were: hidden pathways to success.

Key idea 1
Perception: the opportunity in adversity.
John D. Rockefeller, the famous oil baron, learned the art of perception in the crucible of crisis.

In 1855, Rockefeller was sixteen years old. He was just starting out as a bookkeeper, with aspirations to become an investor. Two years later, the Panic of 1857 struck, sending America spiraling into a crippling financial crisis – the greatest market depression in history. All around Rockefeller, people began abandoning careers in finance. They were afraid, panicked, perceiving what was happening as a horrible disaster.

Rockefeller could have done the same. He could have panicked, scrambled to switch careers. But he didn’t. Rather than losing his nerve, he decided to treat this economic cataclysm as an opportunity to learn, to observe, to figure out what he might do right in the future by watching what people were doing wrong in the present.

In other words, he leveraged the power of perception. Perception is all about the meaning you impose on events. Is a financial crisis a terrifying disaster, something to run from? Or is it a learning opportunity, something to observe? It’s up to you. One way of perceiving it deprives you of power. The other way gives you power.

And we all know what kind of power Rockefeller accrued. By the time he was 40, Rockefeller alone controlled 90 percent of oil refineries in the United States. The secret to his success was an investment strategy driven by level-headed logic – not reactive emotions. He didn’t invest because the market told him to, or because everyone else was doing it. And when he did make investments, he was able to remain confident and see things through, even as others sold their shares out of fear. Rockefeller was wise, resilient, adaptable, and completely calm amid the chaos. These characteristics constituted the foundation on which he built his empire.

So how can we be a bit more like Rockefeller? Well, here are three tips. If you’re faced with a major obstacle, something that’s truly daunting or intimidating or frightening, try to:

  • Focus on what you can control; ignore what you can’t
  • Remain objective; don’t get caught up in subjective emotions or projections
  • Stay in the present moment; don’t spiral into regrets about the past or worries about the future

You already possess the qualities necessary to perceive the opportunity in any obstacle: logic, objectivity, reason, cool-headedness. Deploying them is just a matter of discipline, practice, and habit.

Key idea 2
Perception: recognizing your power.
In the 1960s the then celebrated boxer Rubin “Hurricane” Carter was accused of a triple homicide. He was innocent. He’d done nothing wrong, let alone murder three people. Still, he was given three life sentences – and sent to prison.

At this point, he faced a choice. He could relinquish his power and submit to the situation, accepting the system’s perception of him as a criminal. Or he could hold onto his power despite the situation, and act, despite his imprisonment, like the innocent man he was.

He chose the path of power.

As he entered prison, he announced to the warden that he refused to be “treated like a prisoner” – that, though he didn’t wield the power to walk free, he would never be powerless.

He still had power over his perception. He still had power over his choices. He refused to perceive himself as a prisoner, and he chose to act accordingly, refusing everything that had anything to do with the prison. Uniforms, prison food, visitors, parole hearings – he refused them all.

And he used his time to study history, philosophy, the law – anything that would help him overturn his case. Carter entered prison when he was 29; he left when he was 49, his case having finally been overturned. He spent 19 years in prison – but Carter wouldn’t have said those years were stolen, just as he refused to say he was powerless.

He may have been in a horrible place. But he was always in control – in control of his choices, his thoughts, his reactions, his perception. That’s a kind of control, a kind of power, that no one could deprive him of.

We all possess this power. People may betray you. Fate may deal you a crummy hand. You may face setback after setback. But in almost every situation, you still have the power of your perception: How will you choose to see the situation? How will you choose to react?

Remember that “good” and “bad” are concepts that we impose. In reality, there’s a situation, an event. The story we tell ourselves about this event – that’s what makes it good or bad or anything in between.

The story you tell – or don’t tell – is entirely up to you. That’s the power of perception. That’s what Rubin Carter knew. So what will you choose? How will you perceive the obstacles before you? The power is yours. It always has been and it always will be.

Key idea 3
Perception: altering your perspective.
During the Peloponnesian War, the general Pericles and his men were at sea when, suddenly, darkness fell like a curtain. A solar eclipse had caused day to turn to night. Pericles’s soldiers, confused, surprised, began to panic. But their leader, Pericles, remained calm.

He removed his cloak and approached the man in charge of steering the ship. Holding the cloak in front of the man’s face, he asked whether the darkness frightened him.

The man: Of course not.

A rough paraphrase of Pericles’s response: Then what the heck are you afraid of? Why fear one form of darkness but not the other?

It’s an entertaining anecdote – but it has a profound point. Perspective is everything.

The men on board had attributed meaning to the solar eclipse, perceiving it as ominous, a portent of ills to come. In other words, they’d chosen a disempowering perception: darkness caused by the overlap of celestial bodies is ominous. Pericles, on the other hand, chose an empowering perception: one kind of darkness is the same as any other. So unless you’re irrationally afraid of the dark, there’s nothing to fear.

The way you look at something, the way you perceive it, is what determines whether it’s frightening or exciting, fun or miserable, good or bad. And the perception you choose is always up to you.

Another example:

When George Clooney first came to Hollywood, he was like any other actor: he struggled. For years, each audition ended in a rejection. This hurt. He was talented; he knew that. But no one seemed to see it – so he became dejected, blaming the system for overlooking his obvious talent.

We do this all the time. We blame companies for not hiring us. We blame attractive strangers for not flirting with us. We want to be seen; we want to be chosen. And we get hurt when we’re not.

But this is only one way of perceiving the situation. There is a way to flip it.

Clooney realized that landing a role was not his obstacle; it was the film producers’. They were the ones who desperately needed to find the right actor. They needed him, not the other way around. He wasn’t a humble nobody hoping for his big break – he was the dream actor they’d been waiting for.

This simple perspective shift changed everything.

In subsequent auditions, he projected competence and confidence, not only as an actor but as someone who’d do what needed to be done – someone who, on camera and off, would make the producers’ lives easy.

Next up, we’ll be looking at Action. But remember: the action you take depends on the perspective you take. If you perceive something in the right way, you’ll act in the right way – that is, in the way most likely to bring success. So, whatever situation you find yourself in, ask yourself: Does my perspective benefit me? Or am I afraid, daunted, insecure because I’m looking at this the wrong way? Am I mistaking an eclipse for an evil portent? Am I regarding myself as a problem when I’m actually the solution? You control your perception – and perception is everything.

Key idea 4
Action: the power of discipline.
Recognizing the power you have in every situation, defanging daunting situations by shifting your perspective, realizing that a problem is only a problem if you perceive it that way: this is the beginning. Next comes action.

You don’t need to be naively optimistic to act. Remember: perception doesn’t mean seeing everything through rose-tinted glasses. Seeing things clearly, reasonably, logically, coolly – that’s what perception is about. It’s not about ignoring or diminishing problems. It’s about stripping away emotion, subtracting meaning rather than imposing it. A task may truly be difficult. But you don’t need to make it more difficult by losing your head. Same goes for action. It’s not about ignoring potential difficulties. It’s not about being brash. It’s about being bold.

Look at the situation. Look at it rationally and logically. And then, knowing exactly what you’re up against, act. If you can be flexible, persistent, disciplined, tackling each task one at a time, you can achieve whatever you set out to do. Take aim at your target, and keep that target in mind, but then focus all your energy on the steps necessary to get there. That is the key to effective action.

Let’s take an example:

Demosthenes was the greatest orator of ancient Athens. But, if you’d met him in his early years, you’d never have predicted his future success.

As a boy, he was small, weak, effeminate, sickly. His father died when he was seven, leaving him a handsome inheritance – which his guardians stole. With no money to pay tutors, Demosthenes got no education. Oh, and he had a speech impediment. Abandoned, betrayed, awkward, downtrodden: there was hardly an obstacle Demosthenes didn’t face.

But instead of being utterly crushed by his circumstances – as, let’s face it, most of us would be – he came up with a plan. And he had the steel-hard discipline, forged in the fire of hardship, to follow through.

To conquer his speech impediment, he recited speeches. He did this while running. While yelling into the wind. While his mouth was full of pebbles. He taught himself to recite entire speeches after taking only one breath.

And then he studied. In a room he’d built for himself underground, he studied the law, he practiced speeches, he refined arguments. He knew that studying so much would be hard, so he shaved half his head, so that he’d be too ashamed to appear in public. Discipline, discipline, discipline: each action a step toward his goal.

What was that goal? Taking his guardians to court and reclaiming his inheritance.

Long story short: he got what remained of his inheritance, single-handedly out-arguing every lawyer that was thrown at him. By then, though, the money was beside the point. He’d established himself as a dazzling orator and a shrewd student of the law – gifts worth more than any inheritance.

So what’s your goal? Whatever it is, you can learn from Demosthenes. Develop a strategic vision. And then persist. Getting to where you want to be is only a matter of discipline.

Key idea 5
Action: trust the process.
Let’s take a moment and dissect Demosthenes’s process. He had a big goal: reclaim his stolen inheritance. But he didn’t immediately try to accomplish that goal. He didn’t take them to court as soon as he could. He followed a process: focusing all his energies on the small steps that would get him from point A to point Z. It seems obvious enough – but it’s all too common for people, when pursuing some huge goal, to try to skip the small steps, to jump from A to Z without taking care of B, C, D, and all the rest.

Demosthenes was disciplined. He was persistent. He was determined. But he also had a process.

Or, in the words of Nick Saban, head coach of one of the best college football teams in the United States, the University of Alabama’s Crimson Tide, he had the process. The process says: You’re facing a big, daunting task? Forget about the big picture. Don’t worry about winning the national championships. Don’t worry about winning a legal case even though you have a speech impediment. Ignore that. Focus on what needs to happen right now. Focus on this task. This drill. This speech exercise. This single, small step.

The path to success is precisely that: a path. All paths must be walked one step at a time. So focus on this step. Execute it well. And then focus on the next step.

The thing about the process is that it’s soothing. The path ahead is long, filled with twists and turns and unknown dangers. No matter. That does not concern us. All that concerns us is this step. Then this one. Steps executed perfectly, with total focus.

It sounds obvious, but think about it: How many times have you not pursued a goal because it seems too big? I can’t write a book! That’s way too much work; where would I even start? That’s where the process comes in. Don’t focus on the end goal. Focus on what’s right in front of you, what you can do now, no matter how small. Can you write a sentence? The process can take care of the rest.

Accomplishing major goals is not about brilliance or superhuman strength. It’s not about natural endowments or lucky breaks. It’s about taking one step after the other, completing one small task, and then the next, and the next. Trust the process. Relax into it. That’s the only way to walk the path to success, whether you’re a linebacker, an aspiring orator, or someone with humble dreams of someday writing a book.

Key idea 6
Action: it might not work.
We’re about to move to the next section: Will. Before we do, though, a quick reminder: it’s not always going to work. You may flip an obstacle with ease, shifting your perspective, perceiving it in the most advantageous way possible, seizing your power. You may then take correct action: setting a goal, breaking it down into individual steps, executing each step with excellence and total focus. Still: it might not work.

Some obstacles are insurmountable. Some paths, through no fault of our own, are not passable.

If you run up against an obstacle that simply cannot be overcome, keep in mind: You have tried. Nothing can – nothing ever should – prevent you from trying. If you’ve tried, and persisted in trying, and realized that no amount of trying will flip this obstacle, this boulder in your path, then you can deploy again the skills that you’ve already learned. Use this as an opportunity to reinforce other skills or qualities in yourself. That’s the beauty of the formula.

You’ve worked and worked on your relationship but your partner leaves you anyway? Buried in the sadness and anger is an opportunity – an opportunity to foster the qualities of forgiveness and selfless love. The company you’ve founded ends up floundering? Practice accepting that some things are out of your hands.

If you’ve done your best – your true best – there’s nothing else you can do. And there’s nothing else you’re required to do.

Action implies risk. The risk that things won’t go your way. The risk that you’ll be thwarted by external events. That’s fine. Sometimes, there’s nothing you can do: things won’t work out the way you want. What you can do is be prepared. Not afraid. Not daunted. Prepared – willing to accept whatever happens and ready to move on, boldly, with acceptance, and eager to see what might happen next.

That way, there are no failures. Only lessons. With that in mind, let’s move to the final section.

Key idea 7
Will: accept what you can’t change, and change what you can.
Will is often confused with really, really wanting something. People think: If I want this thing really badly, then I’ve got it: will. But true will has more to do with acceptance than with force. It is our final refuge in the face of trying circumstances. It’s an internal power – the thing that enables us to do what we discussed in the last chapter: accept, with grace and humility, what we can’t change; be resilient enough, and flexible enough, to move on when we don’t get our way.

The great Stoic thinkers – Marcus Aurelius, Epictetus, Seneca – were masters of will. They focused their will by keeping a single question front and center: What can I control, and what can I not control? They knew that we truly only control one thing: our mind. Everything external to the mind – other people’s actions, natural events, the inevitability of death – is outside our control. All that the mind contains, though? Our emotions, judgments, attitudes, responses, decisions – these are within our control.

What can you do with this information? Well, you can build what the Stoics called an Inner Citadel – a metaphorical internal structure that is impervious to the vagaries of the external world. The Stoics stress that no one is born with an Inner Citadel. This is important. You have to build your Citadel. You have to work at it.

It’s often assumed that abilities are inborn. Most people assume that, if they were born with a disadvantage, they’re stuck with it for life. This is simply not true.

Take the example of Theodore Roosevelt. He was born with terrible asthma. He was born privileged, with an able mind, but even slight exercise would result in an attack, and he’d have to stay in bed for weeks. Most people would have resigned themselves to their fate. Not Roosevelt.

With the encouragement and help of his father, he battled the asthma he’d been born with. At the age of twelve, in a gym constructed by his father, he began exercising, strengthening his upper body, slowly improving his lungs. Ten years later, and his asthma was all but gone. He’d worked away his weakness.

Life put many obstacles in Roosevelt’s path. His wife died, then his mother. He had to contend with fierce political opponents. Attempts were made on his life. But he was prepared. He’d built his strength – and kept building it, every day, throughout his life.

So ask yourself: Are you prepared for what life will throw at you? Because it will throw things. Loss, reversals of fate, hardship and unhappiness. There’s nothing you can do about that. What you can do is be prepared. You can, like Roosevelt, strengthen your body. What kind of structure must you create, what kind of Inner Citadel – so that, when the hardship comes, you’re strong enough to accept it and continue on the path?

Key idea 8
Will: be ready to persevere.
After fighting in Troy for ten long years, Odysseus, the protagonist of Homer’s epic poem, the Odyssey, finally sets sail for home. What happens then? Ten years of obstacles. On his ill-fated journey home, he is held prisoner, faces numerous temptations, loses all of his men, encounters dangerous whirlpools, and even fights off a cyclops and a six-headed monster. Eventually, though, after 20 years of war and hardship, he does get home, reunited at last with his wife and son.

How did he do it? What enabled him to keep going, to keep fighting, despite a world of hardship? Short answer: perseverance.

Perseverance is often confused with persistence. But the two are not the same. Persistence is throwing everything you’ve got at a single problem, a single obstacle. It’s trying to breach the gates of Troy again and again – until you find the solution, your own Trojan horse.

Perseverance is different. It’s being in it for the long haul. Being ready to face all the obstacles – the temptations, the whirlpools, the cyclops and the six-headed monster – that life will put in your path. It’s a matter of will. If persistence is like energy, then perseverance is like endurance.

Odysseus had ample opportunity to despair, to give up, to give in. But he didn’t. He persisted through it all, through everything the gods threw at him. Despair? That wouldn’t have brought him any closer to Ithaca. Complaining? Same story. He had the endurance to work through it all, one obstacle after another, until he’d achieved his aim and reached his beloved home.

Life is a series of obstacles. If you flip one, get ready to flip the next. If you can’t overcome this one, don’t quit – persevere. It’s up to you whether you keep trying. It’s up to you whether you tap out or get up.

So why stand in your own way? You’ve got it in you to get there – even if it takes 20 years.

Key idea 9
Will: meditate on death and get ready to begin again.
It may sound morbid – but we’re all going to die. Not today, you might think – and that may be true. But each day that we don’t die, death draws nearer.

Death is out of our control. It is not something that we should worry about. But it is something we should think about, because it can give our life renewed purpose, renewed urgency. You don’t know when death will come – so the time to take the reins, to focus on the things you can control, is right now.

Death is an insurmountable obstacle. There’s no way around it. But we can still use it. In the face of death, all other obstacles and irritants seem far less troublesome. Why get upset when you get cut off in traffic? Why worry too much? Why not be gracious, kind, appreciative? Death is coming. Why not live life the right way?

If you can do this, if you can turn even this most dread obstacle to your advantage, then what obstacle can’t you overcome?

One last thing before we conclude: remember that you’ll always have to begin again. One obstacle down? Get ready for the next one. Get ready for overcoming an obstacle to create a new obstacle. This might sound exhausting – but the more you do it, the better you’ll get, and the better the opportunities you’ll find will become. So keep going. Unshaken. Unhurried. Moving with creativity and determination.

Knowing that obstacles aren’t to be feared. They’re to be embraced. They don’t stand in the path. They are the path. So bring ‘em on.

Final summary

The key message in this book:

Perception, Action, Will: these are the three steps to turning obstacles into opportunities, adversity into advantage. By perceiving obstacles objectively, recognizing your power, and altering your perception; by acting with discipline and diligence, trusting the process; and by deploying your will, persevering no matter what – by leveraging these steps you’ll be able to transform life’s obstacles into the fire that fuels your success.

Back to blog
1 of 4

Get Your Own Expert Coach in Health, Wellness and Reflection