The Obstacle Is the Way – Ryan Holiday

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph – by Ryan Holiday
Date read: 1/30/17. Recommendation: 9/10.

One of the most accessible modern introductions to Stoic philosophy. Holiday examines the inevitable obstacles we all face in life, how to better frame them as opportunities to practice virtue, and how to harness them to create momentum of our own. He structures the book around the three interconnected disciplines required to overcome any obstacle: perception, action, and will. There's an incredible amount of knowledge packed into these 200 pages. No matter what challenges you face or where you're trying to go, it's a great resource for fine tuning your attitude, strategy, and mental toughness. Inspired by Marcus Aurelius, "The impediment to action advances action. What stands in the way becomes the way."

See my notes below or Amazon for details and reviews.


My notes:

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

Obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.

As it turns out, this is the one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition.

Not "be positive" but learn to be ceaselessly creative and opportunistic. Not: This is not so bad. But: I can make this good.

Sangfroid: unflappable coolness under pressure.

Most people can't access this part of themselves, they are slaves to impulses and instincts they have never questioned.

Talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill.

"Would you have a great empire? Rule over yourself." -Publius Syrus

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.

This is the skill that must be cultivated - freedom from disturbance and perturbation - so you can focus your energy exclusively on solving problems, rather than reacting to them.

"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

In the writings of the Stoics, we see an exercise that might well be described as Contemptuous Expressions. The Stoics use contempt as an agent to lay things bare and to "strip away the legend that encrusts them."
     -Strip things of their glamour, meat is a dead animal, wine is old grapes -- Marcus Aurelius
     -Allows us to see things as they really are.

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.

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

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.

Remember that this moment is not your life, it's just a moment in your life. Focus on what is in front of you, right now. Ignore what it "represents" or it "means" or "why it happened to you."

"Genius is the ability to put into effect what is in your mind. There's no other definition of it." -F. Scott Fitzgerald

Psychologists call it adversarial growth or 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.

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.

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...

It's okay to be discouraged. It's not okay to quit. To know you want to quit but to plant your feet and keep inching forward – that's persistence.

Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.

The one way to guarantee we don't benefit from failure - to ensure it is a bad thing - is to not learn from it.

Everything we do matters...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.

Think progress, not perfection.

"The Great Captain will take even the most hazardous indirect approach - if necessary over mountains, deserts or swamps with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach." -B.H. Liddell Hart

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.

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.

It means that very few obstacles are ever too big for us...Remember, a castle can be an intimidating, impenetrable fortress, or it can be turned into a prison when surrounded.

Adversity can harden you. Or it can loosen you up and make you better - if you let it.

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.

"Nothing happens to the wise man against his expectations." -Seneca

When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence.

The hubris at the core of this notion that we can change everything is somewhat new.

Amor fati: a love of fate
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.

"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." -Leroy Percy

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.

Death doesn't make life pointless, but rather purposeful.

Embracing the precariousness of our own existence can be exhilarating and empowering.

The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who "transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking."