Quotes from the Obstacle is the Way by Ryan Holiday

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.

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.

Discipline in perception lets you clearly see the advantage and the proper course of action in every situation–without the pestilence of panic or fear.

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.

This is how you see the opportunity within the obstacle. It does not happen on its own. It is a process–one that results from self-discipline and logic.

Choose not to be harmed–and you won’t feel harmed. Don’t feel harmed–and you haven’t been. – Marcus Aurelius

Don’t think for a second that grace and poise and serenity are the soft attribute of some aristocrat. 

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity. Fortunately, unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty. 

Perspective is everything.

That is, when you can break apart something, or look at it from some new angle, it loses its power over you.

What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand. Think of it as selective editing–not to deceive others, but to properly orient ourselves.

And it works. Small tweaks can change what once felt like impossible tasks. Suddenly, where we felt weak, we realize we are strong. With perspective, we discover leverage we didn’t know we had. 

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

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

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. – 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.

This is how they focus their efforts. It’s a lot easier to fight addiction when you aren’t also fighting the fact that you were born, that your parents were monsters, or that you lost everything.

Focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can’t actually influence is wasted–self-indulgent and self-destructive. So much power–ours, and other people’s–is frittered away in this manner.

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.

Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliche 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.

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.

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.

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) great 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

For some reason, these days we tend to downplay the importance of aggression, of taking risks, of barreling forward. It’s probably because it’s been negatively associated with certain notions of violence or masculinity.

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.

Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with persistence and time can we cut away debris and remove impediments. Only in struggling with the impediments that made others quit can we find ourselves on untrodden territory–only by persisting and resisting can we learn what others were too impatient to be taught.

…can we acknowledge that anticipated, temporary failure certainly hurts less than catastrophic, permanent failure? Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over.

Be glad to pay the cost. 

The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the ageold 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.

Think progress, not perfection.

You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen. Or you create an alternative with so much support from other people that the opposition voluntarily abandons its views and joins your camp.

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

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.

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?

It’s an infinitely elastic formula: In every situation, that which blocks our path actually presents a new path with a new part of us. If someone you love hurts you, there is a chance to practice forgiveness. If your business fails, now you can practice acceptance. If there is nothing else you can do for yourself, at least you can try to help others.

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.

As such, the 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, and ready to work regardless of the conditions. Willing and able to continue, even during the unthinkable, even when our worst nightmares have come true.

Always prepare ourselves for more difficult times.

Always accept what we’re unable to change.

Always manage our expectations.

Always persevere.

Always learn to love our fate and what happens to us.

Always protect our inner self, retreat into ourselves.

Always submit to a greater, larger cause.

Always remind ourselves of our own mortality.

And, of course, prepare to start the cycle once more.

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).

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.

A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued.

The way life is gives you plenty to work with, plenty 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?

To do great things, we need to be able to endure tragedy and setbacks. We’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens.

“A man’s job is to make the world a better place to live in, so far as he is able–always remembering the results will be infinitesimal–and to attend to his own soul” – Leory Percy

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?

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