The Obstacle is the Way is a fantastic and instructive read all about how to overcome any obstacle or challenge and turn it into an advantage. From author Ryan Holiday, The Obstacle is the Way draws on key historical figures and stoic philosophy to communicate its message. No matter what background you come from, your area of expertise or goals for the future, everyone can learn a valuable lesson from this book.
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- PART 1: PERCEPTION
- PART 2: ACTION
- PART 3: WILL
- FINAL THOUGHTS
PART 1: PERCEPTION
Perception is 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.
The Discipline of Perception
There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try to:
- be objective
- control emotions and keep an even keel
- choose to see the good in a situation
- steady our nerves
- ignore what disturbs or limits others
- place things in perspective
- revert to the present moment
- 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.
Recognise Your Power
Through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles.
There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means. That’s a thought that changes everything, doesn’t it?
Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves. Or whether we will tell one at all. Welcome to the power of perception. Applicable in each and every situation, impossible to obstruct. It can only be relinquished. And that is your decision.Through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstaclesClick To Tweet
Steady Your Nerves
Regardless of how much actual danger we’re in, stress puts us at the potential whim of our baser—fearful—instinctual reactions.
But we’re ready for that. We’re collected and serious and aren’t going to be frightened off. This means preparing for the realities of our situation, steadying our nerves so we can throw our best at it. Steeling ourselves. Shaking off the bad stuff as it happens and soldiering on—staring straight ahead as though nothing has happened. Because, as you now realize, it’s true. If your nerve holds, then nothing really did “happen”—our perception made sure it was nothing of consequence.
Control Your Emotion
When faced with a stressful situation or obstacle, try having this conversation (below) with yourself and see how those extreme emotions hold up. They won’t last long, trust that:
Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?
Nope – Then get back to work!
Subconsciously, we should be constantly asking ourselves this question: Do I need to freak out about this?
The phrase “This happened and it is bad” is actually two impressions. Firstly—“This happened”—is objective. Secondly—“it is bad”—is subjective.
Objectivity means removing “you” – the subjective part – from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious. Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.
Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do? How much more quickly and dispassionately could you size up the scenario and its options? You could write it off, greet it calmly.
Alter Your Perspective
Perspective has two definitions:
1) Context: a sense of the larger picture of the world, not just what is immediately in front of us.
2) Framing: an individual’s unique way of looking at the world, a way that interprets its events.
The difference between the right and the wrong perspective is everything.
How we interpret the events in our lives, our perspective, is the framework for our forthcoming response—whether there will even be one or whether we’ll just lie there and take it.
Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.Where the head goes, the body follows. Perception precedes action. Click To Tweet
Is It Up to You?
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
- and our determination
This is our playing field, so to speak. Everything there is fair game.
What is not up to us? Well, you know, everything else. The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.
If what’s up to us is the playing field, then what is not up to us are the rules and conditions of the game. Factors that winning athletes make the best of and don’t spend time arguing against (because there is no point).
When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t. That’s the difference between the people who can accomplish great things, and the people who find it impossible to stay sober—to avoid not just drugs or alcohol but all addictions.
Live In the Present Moment
It doesn’t matter whether this is the worst time to be alive or the best, whether you’re in a good job market or a bad one, or that the obstacle you face is intimidating or burdensome. What matters is that right now is right now.
The implications of our obstacle are theoretical—they exist in the past and the future. We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.
You can take the trouble you’re dealing with and use it as an opportunity to focus on the present moment. To ignore the totality of your situation and learn to be content with what happens, as it happens. Try to have no “way” that the future needs to be to confirm your predictions, because you didn’t make any. To let each new moment be a refresh wiping clear what came before and what others were hoping would come next.
Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph?
This is why we shouldn’t listen too closely to what other people say (or to what the voice in our head says, either). We’ll find ourselves erring on the side of accomplishing nothing.
Be open. Question. Though of course we don’t control reality, our perceptions do influence it.
Finding the Opportunity
Sports psychologists recently did a study of elite athletes who were struck with some adversity or serious injury. Initially, each reported feeling isolation, emotional disruption, and doubts about their athletic ability. Yet afterward, each reported gaining a desire to help others, additional perspective, and realization of their own strengths. In other words, every fear and doubt they felt during the injury turned into greater abilities in those exact areas.
It’s a beautiful idea. Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliché but fact.
A struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. Any perception that prevents us from seeing this is the enemy.
Of all the strategies we’ve talked about, this is the one you can always use. Everything can be flipped, seen with this kind of gaze: a piercing look that ignores the package and sees only the gift.
Prepare to Act
Problems are rarely as bad as we think—or rather, they are precisely as bad as we think.
It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary and post hoc).
The demand on you is this: Once you see the world as it is, for what it is, you must act. The proper perception—objective, rational, ambitious, clean—isolates the obstacle and exposes it for what it is.
A clearer head makes for steadier hands. And then those hands must be put to work. Good use.
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PART 2: ACTION
What is action? Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action. Everything must be done in the service of the whole. Step by step, action by action, we’ll dismantle the obstacles in front of us. With persistence and flexibility, we’ll act in the best interest of our goals.
The Discipline of Action
We’ve all done it. Said: “I am so [overwhelmed, tired, stressed, busy, blocked, outmatched].” And then what do we do about it? Go out and party. Or treat ourselves. Sleep in. Or wait.
It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.
We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage.
Therefore we can always greet our obstacles with:
- a coherent and deliberate process
- iteration and resilience
- strategic vision
- craftiness and savvy
- and an eye for opportunity and pivotal moments
Are you ready to get to work?
“We must all either wear out or rust out, every one of us. My choice is to wear out.”
When you’re frustrated in pursuit of your own goals, don’t sit there and complain that you don’t have what you want or that this obstacle won’t budge. If you haven’t even tried yet, then of course you will still be in the exact same place. You haven’t actually pursued anything.
Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass.If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.Click To Tweet
The thing standing in your way isn’t going anywhere. You’re not going to outthink it or outcreate it with some world-changing epiphany. You’ve got to look at it and the people around you, who have begun their inevitable chorus of doubts and excuses, and say, as Margaret Thatcher famously did: “You turn if you want to. The lady’s not for turning.”
Too many people think that great victories like Thomas Edison’s (inventor of the light bulb) came from a flash of insight. That they cracked the problem with pure genius. In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other more 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.
It’s okay to be discouraged. But it’s not okay to quit. To know you want to quit but to plant your feet and keep inching closer until you take the impenetrable fortress you’ve decided to lay siege to in your own life—that’s persistence.
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In Silicon Valley, start-ups don’t launch with polished, finished businesses. Instead, they release their “Minimum Viable Product” (MVP)—the most basic version of their core idea with only one or two essential features.
The point is to immediately see how customers respond. And, if that response is poor, to be able to fail cheaply and quickly. To avoid making or investing in a product customers do not want.
Now it's time you understand that the world is telling you something with each and every failure and action. It’s feedback—giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something. Listen. Lessons come hard only if you’re deaf to them. Don’t be.
Being able to see and understand the world this way is part and parcel of overturning obstacles. Here, a negative becomes a positive. We turn what would otherwise be disappointment into opportunity. Failure shows us the way—by showing us what isn’t the way.
Follow the Process
Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize.
Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that. Saban’s process is exclusively this—existing in the present, taking it one step at a time, not getting distracted by anything else.
We want to have goals, yes, so everything we do can be in the service of something purposeful. When we know what we’re really setting out to do, the obstacles that arise tend to seem smaller, more manageable. When we don’t, each one looms larger and seems impossible. Goals help put the blips and bumps in proper proportion.
The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.
Do Your Job, Do it Right
Everything we do matters—whether it’s making smoothies while you save up money or studying for the bar—even after you already achieved the success you sought. Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires.
Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is our priority, vanity falls away.
We will be and do many things in our lives. Some are prestigious, some are onerous, none are beneath us. 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.
What’s Right is What Works
The Stoics had a saying: “Don’t go expecting Plato’s Republic.”
Because you’re never going to find that kind of perfection. Instead, do the best with what you’ve got. Not that pragmatism is inherently at odds with idealism or pushing the ball forward. The first iPhone was revolutionary, but it still shipped without a copy-and-paste feature or a handful of other features Apple would have liked to have included. Steve Jobs, the supposed perfectionist, knew that at some point, you have to compromise. What mattered was that you got it done and it worked.
Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection.
Under this kind of force, obstacles break apart. They have no choice. Since you’re going around them or making them irrelevant, there is nothing for them to resist.
In Praise of the Flank Attack
Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-to-head attack. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle.
In fact, having the advantage of size or strength or power is often the birthing ground for true and fatal weakness. The inertia of success makes it much harder to truly develop good technique. People or companies who have that size advantage never really have to learn the process when they’ve been able to coast on brute force. And that works for them . . . until it doesn’t. Until they meet you and you make quick work of them with deft and oblique maneuvers, when you refuse to face them in the one setting they know: head-to-head.
You’re acting like a real strategist. Not just throwing your weight around and hoping it works. You’re not wasting your energy in battles driven by ego and pride rather than tactical advantage.
Use Obstacles Against Themselves
Gandhi didn’t fight for independence for India. The British Empire did all of the fighting—and, as it happens, all of the losing.
Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you. You can use the actions of others against themselves instead of acting yourself.
Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive.
This should be great solace. It means that very few obstacles are ever too big for us. Because that bigness might in fact be an advantage. Because we can use that bigness against the obstacle itself. Remember, a castle can be an intimidating, impenetrable fortress, or it can be turned into a prison when surrounded. The difference is simply a shift in action and approach.
Channel Your Energy
Instead of giving in to frustration, we can put it to good use. It can power our actions, which, unlike our disposition, become stronger and better when loose and bold. While others obsess with observing the rules, we’re subtly undermining them and subverting them to our advantage.
Think of an athlete “in the pocket,” “in the zone,” “on a streak,” and the seemingly insurmountable obstacles that fall in the face of that effortless state. Enormous deficits collapse, every pass or shot hits its intended target, fatigue melts away. Those athletes might be stopped from carrying out this or that action, but not from their goal. External factors influence the path, but not the direction: forward.
What setbacks in our lives could resist that elegant, fluid, and powerful mastery?
To be physically and mentally loose takes no talent. That’s just recklessness. (We want right action, not action period.) To be physically and mentally tight? That’s called anxiety. It doesn’t work, either. Eventually we snap. But physical looseness combined with mental restraint? That is powerful.
Seize The Offensive
At certain moments in our brief existences we are faced with great trials. Often those trials are frustrating, unfortunate, or unfair. They seem to come exactly when we think we need them the least. The question is: Do we accept this as an exclusively negative event, or can we get past whatever negativity or adversity it represents and mount an offensive? Or more precisely, can we see that this “problem” presents an opportunity for a solution that we have long been waiting for?
In many battles, as in life, the two opposing forces will often reach a point of mutual exhaustion. It’s the one who rises the next morning after a long day of fighting and rallies, instead of retreating—the one who says, I intend to attack and whip them right here and now—who will carry victory home . . . intelligently.
The obstacle is not only turned upside down but used as a catapult.
Prepare for None of It to Work
Perceptions can be managed. Actions can be directed. We can always think clearly, respond creatively. Look for opportunity, seize the initiative. What we can’t do is control the world around us—not as much as we’d like to, anyway. We might perceive things well, then act rightly, and fail anyway.
Run it through your head like this: Nothing can ever prevent us from trying. Ever.
All creativity and dedication aside, after we’ve tried, some obstacles may turn out to be impossible to overcome. Some actions are rendered impossible, some paths impassable. Some things are bigger than us. This is not necessarily a bad thing. Because we can turn that obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill—even if it is just learning to accept that bad things happen, or practicing humility.
We have it within us to be the type of people who try to get things done, try with everything we’ve got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next.
Is that you? Because it can be.
PART 3: WILL
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.
The Discipline of Will
Will is the critical third discipline. We can think, act, and finally adjust to a world that is inherently unpredictable. The will is what prepares us for this, protects us against it, and allows us to thrive and be happy in spite of it. It is also the most difficult of all the disciplines. It’s what allows us to stand undisturbed while others wilt and give in to disorder. Confident, calm, ready to work regardless of the conditions. Willing and able to continue, even during the unthinkable, even when our worst nightmares have come true.
It’s much easier to control our perceptions and emotions than it is to give up our desire to control other people and events. Often, it’s easier to persist in our efforts and actions than to endure the uncomfortable or the painful. It’s easier to think and act than it is to practice wisdom.
Build Your Inner Citadel
No one is born a gladiator. No one is born with an Inner Citadel. If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built.
To be great at something takes practice. Obstacles and adversity are no different. Though it would be easier to sit back and enjoy a cushy modern life, the upside of preparation is that we’re not disposed to lose all of it—least of all our heads—when someone or something suddenly messes with our plans.
It’s almost a cliché at this point, but the observation that the way to strengthen an arch is to put weight on it—because it binds the stones together, and only with tension does it hold weight—is a great metaphor.
“The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted.
Anticipation (Thinking Negatively)
Your world is ruled by external factors. Promises aren’t kept. You don’t always get what is rightfully yours, even if you earned it. Not everything is as clean and straightforward as the games they play in business school. Be prepared for this.
If this comes as a constant surprise each and every time it occurs, you’re not only going to be miserable, you’re going to have a much harder time accepting it and moving on to attempts number two, three, and four. The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.
As a result of our anticipation, we understand the range of potential outcomes and know that they are not all good (they rarely are). We can accommodate ourselves to any of them. We understand that it could possibly all go wrong. And now we can get back to the task at hand.
The Art of Acquiescience
Thomas Jefferson: born quiet, contemplative, and reserved—purportedly with a speech impediment. Compared to the great orators of his time—Patrick Henry, John Wesley, Edmund Burke—he was a terrible public speaker. His heart set on politics, he had two options: Fight against this sentence, or accept it.
If someone we knew took traffic signals personally, we would judge them insane. Yet this is exactly what life is doing to us. It tells us to come to a stop here. Or that some intersection is blocked or that a particular road has been rerouted through an inconvenient detour. We can’t argue or yell this problem away. We simply accept it.
The way life is gives you plenty to work with, plenty to leave your imprint on. Taking people and events as they are is quite enough material already. Follow where the events take you, like water rolling down a hill—it always gets to the bottom eventually, doesn’t it?
Because (a) you’re robust and resilient enough to handle whatever occurs, (b) you can’t do anything about it anyway, and (c) you’re looking at a big-enough picture and long-enough time line that whatever you have to accept is still only a negligible blip on the way to your goal.
Love Everything That Happens: Amor Fati
After we discard our expectations and accept what happens to us, after understanding that certain things—particularly bad things—are outside our control, is this: loving whatever happens to us and facing it with unfailing cheerfulness. It is the act of turning what we must do into what we get to do.
We put our energies and emotions and exertions where they will have real impact. This is that place. We will tell ourselves: This is what I’ve got to do or put up with? Well, I might as well be happy about it.
We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good? We can choose to render a good account of ourselves. If the event must occur, Amor fati (a love of fate) is the response. Don’t waste a second looking back at your expectations. Face forward, and face it with a smug little grin.
If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after—and then the fight after that and the fight after that, until the end.
Life is not about one obstacle, but many. What’s required of us is not some shortsighted focus on a single facet of a problem, but simply a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.
We will overcome every obstacle—and there will be many in life—until we get there. Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance. And, of course, they work in conjunction with each other.We will overcome every obstacle—and there will be many in life—until we get there.Click To Tweet
Something Bigger Thank Yourself
Sometimes when we are personally stuck with some intractable or impossible problem, one of the best ways to create opportunities or new avenues for movement is to think: If I can’t solve this for myself, how can I at least make this better for other people? Take it for granted, for a second, that there is nothing else in it for us, nothing we can do for ourselves. How can we use this situation to benefit others? How can we salvage some good out of this? If not for me, then for my family or the others I’m leading or those who might later find themselves in a similar situation.
What doesn’t help anyone is making this all about you, all the time. Why did this happen to me? What am I going to do about this? You’ll be shocked by how much of the hopelessness lifts when we reach that conclusion. Because now we have something to do.
Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive, and in the process, inch the world forward a little bit. Be strong for others, and it will make you stronger.
Meditate on Your Morality
It doesn’t matter who you are or how many things you have left to be done, somewhere there is someone who would kill you for a thousand dollars or for a vile of crack or for getting in their way. A car can hit you in an intersection and drive your teeth back into your skull. That’s it. It will all be over. Today, tomorrow, someday soon.
It’s a cliché question to ask, What would I change about my life if the doctor told me I had cancer? After our answer, we inevitably comfort ourselves with the same insidious lie: Well, thank God I don’t have cancer.
But thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating. And since this is true, we ought to make use of it. Instead of denying—or worse, fearing—our mortality, we can embrace it.
Prepare to Start Again
The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges.
But that’s what keeps life interesting. And as you’re starting to see, that’s what creates opportunities. Life is a process of breaking through these impediments—a series of fortified lines that we must break through. Each time, you’ll learn something, you’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you.
Passing one obstacle simply says you’re worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt.
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You are now schooled in the art of managing your perceptions and impressions. Like Rockefeller, you’re cool under pressure, immune to insults and abuse. You see opportunity in the darkest of places. You are able to direct your actions with energy and persistence. Like Demosthenes, you assume responsibility for yourself—teaching yourself, compensating for disadvantages, and pursuing your rightful calling and place in the world.
You are iron-spined and possess a great and powerful will. Like Lincoln, you realize that life is a trial. It will not be easy, but you are prepared to give it everything you have regardless, ready to endure, persevere, and inspire others.
The names of countless other practitioners escape us, but they dealt with the same problems and obstacles. This philosophy helped them navigate those successfully. They quietly overcame what life threw at them and, in fact, thrived because of it.
They were nothing special, nothing that we are not just as capable of being. What they did was simple (simple, not easy). But let’s say it once again just to remind ourselves:
See things for what they are.
Do what we can.
Endure and bear what we must.
What blocked the path now is a path.
What once impeded action advances action.
The Obstacle is the Way.
This summary is not intended as a replacement for the original book and all quotes are credited to the above mentioned author and publisher.