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The Obstacle Is The Way

by Ryan Holiday

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Rating: 9 / 10

Thoughts

This is one of the first books I read on Stoicism (and philosophy in general). It has massively influenced me throughout the years. Highly recommended.


💡 Top 3-5 Ideas, Concepts, or Quotes

"The impediment to action advances action. What stands in the way becomes the way."

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).

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.

✍️ Summary

  • We try to blame others for our stance in life. There is only one thing at fault: our attitude and approach.
  • Perception
    • What matters is not the obstacles we face, but how we perceive them. How we react to them. Whether we keep our composure.
    • "We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll assent or reject. No one can force us to give up or to believe something that is untrue (such as, that a situation is absolutely hopeless or impossible to improve). Our perceptions are the thing that we’re in complete control of."
    • Do you think getting upset helps a situation? Sometimes it does. But in this situation?
    • "If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one."
    • It's not that you have to pretend your emotions do not exist. But it's important to remain in control of them.
    • Take what you fear and break it apart. The dark is just a lack of photons.
    • Learn to distinguish between what you can control and what you cannot control.
    • Look for opportunity in every obstacle.
    • "Problems are rarely as bad as we think—or rather, they are precisely as bad as we think."
  • Action
    • Meet obstacles with the right action.
    • "So 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."
    • "Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s done."
    • You're in for the long haul.
    • "Failure can be an asset if what you're trying to do is improve, learn, or do something new. It's the preceding feature of near successes."
    • Try and fail. Then try again, until you get it. Learn from your failures. Iterate.
    • Do your job and do it well.
    • Break down the process. Do each step as well as you can. It's about finishing. "Finishing the smallest task you have right in front of you and finishing it well."
    • "Think progress, not perfection."
      • "Don't think small, but make the distinction between the critical and the extra."
      • Rome was not built in a day. It's not all or nothing.
    • "Remember, sometimes the longest way around is the shortest way home."
      • "Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open."
  • Will
    • "This too shall pass"
    • "The will is the one thing we control completely, always. Whereas I can try to mitigate harmful perceptions and give 100 percent of my energy to actions, those attempts can be thwarted or inhibited. My will is different, because it is within me."
    • We have to forge our own steel backbone. This is done through physical exercise and mental practice.
      • "Mens sana in corpore sano — sound mind in a strong body"
    • "The path of least resistance is a terrible teacher."
    • Premortem: figuring out what went wrong before it happens.
    • Amor fati. Love everything that happens.
    • Perseverance.
      • "The barriers are not erected which can say to aspiring talents and industry, Thus far and no farther" — Beethoven
    • "Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger."
    • Memento Mori. Remember your mortality.
      • Reminding ourselves each day that we will die helps us treat our time as a gift
    • Navigate one obstacle and another emerges. This is what keeps life interesting. This is also what creates opportunities.

🔦📒 Highlights & Notes

Preface

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.

And then he concluded with powerful words destined for maxim.
The impediment to action advances action.
What stands in the way becomes the way.

— Marcus Aurelius

We might not be emperors, but the world is still constantly testing us. It asks: Are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?

Introduction

We’re dissatisfied with our jobs, our relationships, our place in the world. We’re trying to get somewhere, but something stands in the way.
So we do nothing.
We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.

Overcoming obstacles is a discipline of three critical steps.
It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.
It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

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 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
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

You will come across obstacles in life—fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure. You will learn that this reaction determines how successful we will be in overcoming—or possibly thriving because of—them.

You must realize: Nothing makes us feel this way; we choose to give in to such feelings. Or, like Rockefeller, choose not to.

RECOGNIZE YOUR POWER

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

We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll assent or reject. No one can force us to give up or to believe something that is untrue (such as, that a situation is absolutely hopeless or impossible to improve). Our perceptions are the thing that we’re in complete control of.

They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions.

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.

CONTROL YOUR EMOTIONS

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

When America raced to send the first men into space, they trained the astronauts in one skill more than in any other: the art of not panicking.
When people panic, they make mistakes. They override systems. They disregard procedures, ignore rules. They deviate from the plan. They become unresponsive and stop thinking clearly. They just react—not to what they need to react to, but to the survival hormones that are coursing through their veins.

As Gavin de Becker writes in The Gift of Fear, “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?”
Another way of putting it: Does getting upset provide you with more options? Sometimes it does. But in this instance?
No, I suppose not.
Well, then.

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.
But it’s what I feel.
Right, no one said anything about not feeling it. No one said you can’t ever cry.
Forget “manliness.” If you need to take a moment, by all means, go ahead. 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.

Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check—if we can keep steady no matter what happens, no matter how much external events may fluctuate.

PRACTICE OBJECTIVITY

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

The phrase “This happened and it is bad” is actually two impressions. The first—“This happened”—is objective. The second—“it is bad”—is subjective.

ALTER YOUR PERSPECTIVE

Perspective has two definitions.
Context: a sense of the larger picture of the world, not just what is immediately in front of us
Framing: an individual’s unique way of looking at the world, a way that interprets its events
Both matter, both can be effectively injected to change a situation that previously seemed intimidating or impossible.

Perspective is everything.

The task, as Pericles showed, is not to ignore fear but to explain it away. Take what you’re afraid of—when fear strikes you—and break it apart.

Remember: We choose how we’ll look at things. We retain the ability to inject perspective into a situation. We can’t change the obstacles themselves—that part of the equation is set—but the power of perspective can change how the obstacles appear. How we approach, view, and contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.

Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.

IS IT UP TO YOU?

In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices.
—EPICTETUS

To harness the same power, recovering addicts learn the Serenity Prayer.
God, grant 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.

And what is up to us?
Our emotions
Our judgments
Our creativity
Our attitude
Our perspective
Our desires
Our decisions
Our determination

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.

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.

LIVE IN THE PRESENT MOMENT

Focus on the moment, not the monsters that may or may not be up ahead.

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.

THINK DIFFERENTLY

When given an unfair task, some rightly see it as a chance to test what they’re made of—to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative.

FINDING THE OPPORTUNITY

A good person dyes events with his own color . . . and turns whatever happens to his own benefit.
—SENECA

It’s one thing to not be overwhelmed by obstacles, or discouraged or upset by them. This is something that few are able to do. But after you have controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it.

As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”

“That which doesn’t kill me makes me stronger” is not a cliché but fact.

The 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. The enemy is any perception that prevents us from seeing this.

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 DISCIPLINE OF ACTION

But you, when you’re dealt a bad hand. What’s your response? Do you fold? Or do you play it for all you’ve got? There’s an explosion, metaphoric or otherwise. Are you the guy running toward it? Or running away from it? Or worse, are you paralyzed and do nothing?
This little test of character says everything about us.

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. Or sleep in. Or wait.

No one is saying you can’t take a minute to think, Dammit, this sucks. By all means, vent. Exhale. Take stock. Just don’t take too long. Because you have to get back to work. Because each obstacle we overcome makes us stronger for the next one.
But . . .
No. No excuses. No exceptions. No way around it: It’s on you.
We don’t have the luxury of running away. Of hiding. Because we have something very specific we’re trying to do. We have an obstacle we have to lean into and transform.

No one is coming to save you. And if we’d like to go where we claim we want to go—to accomplish what we claim are our goals—there is only one way. And that’s to meet our problems with the right action.

Therefore, we can always (and only) greet our obstacles
with energy
with persistence
with a coherent and deliberate process
with iteration and resilience
with pragmatism
with strategic vision
with craftiness and savvy
and an eye for opportunity and pivotal moments

But in our lives, when our worst instincts are in control, we dally. We don’t act like Demosthenes, we act frail and are powerless to make ourselves better. We may be able to articulate a problem, even potential solutions, but then weeks, months, or sometimes years later, the problem is still there. Or it’s gotten worse. As though we expect someone else to handle it, as though we honestly believe that there is a chance of obstacles unobstacle-ing themselves.

GET MOVING

Now let’s say you’ve already done that. Fantastic. You’re already ahead of most people. But let’s ask an honest question: Could you be doing more? You probably could—there’s always more. At minimum, you could be trying harder. You might have gotten started, but your full effort isn’t in it—and that shows. Is that going to affect your results? No question.

So the first step is: Take the bat off your shoulder and give it a swing. You’ve got to start, to go anywhere.

So 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.

We talk a lot about courage as a society, but we forget that at its most basic level it’s really just taking action—whether that’s approaching someone you’re intimidated by or deciding to finally crack a book on a subject you need to learn. Just as Earhart did, all the greats you admire started by saying, Yes, let’s go. And they usually did it in less desirable circumstances than we’ll ever suffer.

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.

PRACTICE PERSISTENCE

He says the best way out is always through
And I agree to that, or in so far
As I can see no way out but through.
—ROBERT FROST

If we’re to overcome our obstacles, this is the message to broadcast—internally and externally. We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.

Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s done.

Remember and remind yourself of a phrase favored by Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

There’s no need to sweat this or feel rushed. No need to get upset or despair. You’re not going anywhere—you’re not going to be counted out. You’re in this for the long haul.

In other words: It’s supposed to be hard. Your first attempts aren’t going to work. It’s goings to take a lot out of you—but energy is an asset we can always find more of. It’s a renewable resource. Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.

When people ask where we are, what we’re doing, how that “situation” is coming along, the answer should be clear: We’re working on it. We’re getting closer. When setbacks come, we respond by working twice as hard.

ITERATE

What is defeat? Nothing but education; nothing but the first steps to something better.
—WENDELL PHILLIPS

As engineers now like to quip: Failure is a Feature.
But it’s no joke. Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes. There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.

In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up—a start-up of one. And that means changing the relationship with failure. It means iterating, failing, and improving. Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.

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.

On the path to successful action, we will fail—possibly many times. And that’s okay. It can be a good thing, even. Action and failure are two sides of the same coin. One doesn’t come without the other. What breaks this critical connection down is when people stop acting—because they’ve taken failure the wrong way.

When failure does come, ask: What went wrong here? What can be improved? What am I missing? This helps birth alternative ways of doing what needs to be done, ways that are often much better than what we started with. Failure puts you in corners you have to think your way out of. It is a source of breakthroughs.

The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not learn from it. To continue to try the same thing over and over (which is the definition of insanity for a reason). People fail in small ways all the time. But they don’t learn. They don’t listen. They don’t see the problems that failure exposes. It doesn’t make them better.

FOLLOW THE PROCESS

In the chaos of sport, as in life, process provides us a way.
It says: 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.

The road to back-to-back championships is just that, a road. And you travel along a road in steps. 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. Not the other team, not the scoreboard or the crowd.

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.

Whether it’s pursuing the pinnacle of success in your field or simply surviving some awful or trying ordeal, the same approach works. Don’t think about the end—think about surviving. Making it from meal to meal, break to break, checkpoint to checkpoint, paycheck to paycheck, one day at a time.

Like a relentless machine, subjugating resistance each and every way it exists, little by little. Moving forward, one step at a time. Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it.

DO YOUR JOB, DO IT RIGHT

The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is someone else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions.
In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.

How you do anything is how you can do everything.
We can always act right.

WHAT’S RIGHT IS WHAT WORKS

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.

IN PRAISE OF THE FLANK ATTACK

What’s your first instinct when faced with a challenge? Is it to outspend the competition? Argue with people in an attempt to change long-held opinions? Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open.

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.

Remember, sometimes the longest way around is the shortest way home.

USE OBSTACLES AGAINST THEMSELVES

Opposites work. Nonaction can be action. It uses the power of others and allows us to absorb their power as our own. Letting them—or the obstacle—do the work for us.
Just ask the Russians, who defeated Napoléon and the Nazis not by rigidly protecting their borders but by retreating into the interior and leaving the winter to do their work on the enemy, bogged down in battles far from home. Is this an action? You bet it is.

Yes, sometimes we need to learn from Amelia Earhart and just take action. But we also have to be ready to see that restraint might be the best action for us to take. Sometimes in your life you need to have patience—wait for temporary obstacles to fizzle out. Let two jousting egos sort themselves out instead of jumping immediately into the fray. Sometimes a problem needs less of you—fewer people period—and not more.

CHANNEL YOUR ENERGY

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.
It’s a power that drives our opponents and competitors nuts. They think we’re toying with them. It’s maddening—like we aren’t even trying, like we’ve tuned out the world. Like we’re immune to external stressors and limitations on the march toward our goals.
Because we are.

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?
If you don’t take that, it’s on you.

Ordinary people shy away from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They are their best in these situations. They turn personal tragedy or misfortune—really anything, everything—to their advantage.

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.

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.

Anyone in pursuit of a goal comes face-to-face with this time and time again. Sometimes, no amount of planning, no amount of thinking—no matter how hard we try or patiently we persist—will change the fact that some things just aren’t going to work.

THE DISCIPLINE OF THE WILL

“This too shall pass” was Lincoln’s favorite saying, one he once said was applicable in any and every situation one could encounter.

This is the avenue for the final discipline: the Will. If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always. Whereas I can try to mitigate harmful perceptions and give 100 percent of my energy to actions, those attempts can be thwarted or inhibited. My will is different, because it is within me.

Will is fortitude and wisdom—not just about specific obstacles but about life itself and where the obstacles we are facing fit within it. It gives us ultimate strength. As in: the strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome (which, as it happens, is the way of flipping the unflippable).

Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?

BUILD YOUR INNER CITADEL

Nobody is born with a steel backbone. We have to forge that ourselves.
We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice (mens sana in corpore sano—sound mind in a strong body).

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.
Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel?
Because these things will happen to you. No one knows when or how, but their appearance is certain. And life will demand an answer. You chose this for yourself, a life of doing things. Now you better be prepared for what it entails. It’s your armor plating. It doesn’t make you invincible, but it helps prepare you for when fortune shifts . . . and it always does.

This is strikingly similar to what the Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down. An important caveat is that we are not born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us.

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.

ANTICIPATION (THINKING NEGATIVELY)

A CEO calls her staff into the conference room on the eve of the launch of a major new initiative. They file in and take their seats around the table. She calls the meeting to attention and begins: “I have bad news. The project has failed spectacularly. Tell me what went wrong?”
What?! But we haven’t even launched yet . . .
That’s the point. The CEO is forcing an exercise in hindsight—in advance. She is using a technique designed by psychologist Gary Klein known as a premortem.

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.”

Always prepared for disruption, always working that disruption into our plans. Fitted, as they say, for defeat or victory. And let’s be honest, a pleasant surprise is a lot better than an unpleasant one.
What if . . .
Then I will . . .
What if . . .
Instead I’ll just . . .
What if . . .
No problem, we can always . . .
And in the case where nothing could be done, the Stoics would use it as an important practice to do something the rest of us too often fail to do: manage expectations. Because sometimes the only answer to “What if . . .” is, It will suck but we’ll be okay.

THE ART OF ACQUIESCENCE

After you’ve distinguished between the things that are up to you and the things that aren’t (ta eph’hemin, ta ouk eph’hemin), and the break comes down to something you don’t control . . . you’ve got only one option: acceptance.
The shot didn’t go in.
The stock went to zero.
The weather disrupted the shipment.
Say it with me: C’est la vie. It’s all fine.

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.
We’re indifferent and that’s not a weakness

As Francis Bacon once said, nature, in order to be commanded, must be obeyed

LOVE EVERYTHING THAT HAPPENS: AMOR FATI

Your obstacle may not be so serious or violent. But they are nevertheless significant and outside your control. They warrant only one response: a smile. As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones.

The goal is:
Not: I’m okay with this.
Not: I think I feel good about this.
But: I feel great about it.
Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it.

It’s a little unnatural, I know, to feel gratitude for things we never wanted to happen in the first place. But we know, at this point, the opportunities and benefits that lie within adversities. We know that in overcoming them, we emerge stronger, sharper, empowered. There is little reason to delay these feelings. To begrudgingly acknowledge later that it was for the best, when we could have felt that in advance because it was inevitable.
You love it because it’s all fuel. And you don’t just want fuel. You need it. You can’t go anywhere without it. No one or no thing can. So you’re grateful for it. That is not to say that the good will always outweigh the bad. Or that it comes free and without cost. But there is always some good—even if only barely perceptible at first—contained within the bad.
And we can find it and be cheerful because of it.

The next step 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.

PERSEVERANCE

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.

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.

This is perseverance. And with it, Emerson said, “with the exercise of self-trust, new powers shall appear.” The good thing about true perseverance is that it can’t be stopped by anything besides death. To quote Beethoven: “The barriers are not erected which can say to aspiring talents and industry, Thus far and no farther.”

SOMETHING BIGGER THAN YOURSELF

Stop making it harder on yourself by thinking about I, I, I. Stop putting that dangerous “I” in front of events. I did this. I was so smart. I had that. I deserve better than this. No wonder you take losses personally, no wonder you feel so alone. You’ve inflated your own role and importance.
Start thinking: Unity over Self. We’re in this together.

Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.

MEDITATE ON YOUR MORTALITY

Part of the reason we have so much trouble with acceptance is because our relationship with our own existence is totally messed up. We may not say it, but deep down we act and behave like we’re invincible. Like we’re impervious to the trials and tribulations of morality. That stuff happens to other people, not to ME. I have plenty of time left.
We forget how light our grip on life really is.

Remember the serenity prayer: If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things—it is not in our control how long we will live or what will come and take us from life. 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.

Every culture has its own way of teaching the same lesson: Memento mori, the Romans would remind themselves. Remember you are mortal.

Reminding ourselves each day that we will die helps us treat our time as a gift

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. Each time, 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.

Final Thoughts: The Obstacle Becomes the Way

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.

There’s a saying in Latin: Vires acquirit eundo (We gather strength as we go). That’s how it works. That’s our motto.

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