The Obstacle Is the Way - By Ryan Holiday

Date read: 
February 1, 2018
See My Collection of 50+ Book Notes

My Thoughts

Good introduction to bringing stoic philosophy into your daily life and the 21st century. Filled with lots of thought-inspiring maxims and quotes. Lacking in depth on some aspects, but offers a lot of actionable advice.

Summary Notes

Most of us are paralyzed. Whatever our individual goals, most of us sit frozen before the many obstacles that lie ahead of us.

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

"Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them."
Great individuals like great companies find a way to transform weakness into strength.
(This is what Nassim Taleb calls 'Anti-Fragility'; the ability to use stressors and crises to grow and improve)

A better way to deal with obstacles: is not "This is not so bad," but "I can make this good."

People who had it a lot worse than you succeeded.
Athletes who were too small. Pilots whose eyesight wasn't good enough. Dreamers ahead of their time. Members of this race and that. Dropouts and dyslexics. Bastards, immigrants, nouveaux rihes, sticklers, believers, and dreamers.
They practiced harder. Looked for shortcuts and weakspots. Discerned allies among strange faces. Everything was an obstacle they had to flip.

Great times are great softeners.


During an economic crisis, Rockefeller quietly saved his money and watched what others did wrong. The greater the chaos, the calmer Rockefeller would become. As Warren Buffet put it: "Be fearful when others are greedy and greedy when others are fearful."

When you see crisis, try to see opportunity. Seen properly, everything is a chance to move forward.

"Choose not to be harmed - and you won't feel harmed. Don't feel harmed - and you haven't been"
- Marcus Aurelius

He had made his choice. This can't harm me - I might not have wanted it to happen, but I decide how it will affect me. No one else has the right.

There is the event itself and the story we tell ourselves about what it means.

Fear & getting upset

Regardless of how much actual danger we're in, stress puts us at the whim of our fearful instinctual reaction.

In training astronauts:
Panic is suicide. So panic has to be trained out.

With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity.

Apatheia: Old Greek term for keeping steady no matter what happens.

Does getting upset provide you with more options?
Probably not.

Real strength lies in the control of one's emotions, not in pretending they don't exist.

The simplest mantra:
"I am not going to die from this. I am not going to die from this. I am not going to die from this."

Use contempt to lay things bare.
Roasted meat is a dead animal and vintage wine is old fermented grapes.
Picture great and intimidating people having sex, grunting and groaning.


Objectivity means removing 'you' from the equation. Take your situation and pretend it is not happening to you.
(As Jordan Peterson puts it; 'What would you do if you had to solve this problem for a friend? ')

We often choose the ominous explanation over the simple one.

It's your choice to put 'I' in front of something. These add an extra element: you in relation to the obstacle, rather than just the obstacle itself.

One terrible meeting is nothing in a lifetime of meetings. One missed deal is just one deal.

What can you control?

If there was even a 1% chance, he was ready to take it and make good use of it - ready to give every ounce of effort and energy he had to make it happen. If effort would affect the outcome, he would die on the field before he let that chance go to waste.

Whether it took one year or ten years, he wouldn't give up until there was absolutely nothing left that they could do. He would die on the field before he quit.

What's up to us?

  • Our emotions
  • Our judgements
  • Our creativity
  • Our attitude
  • Our perspective
  • Our desires
  • Our decisions
  • Our determination

To argue, to complain, or worse, to just give up. These are choices.

That someone decided not to fund your company isn't up to you. But the decision to refine and improve your pitch? That is.
(This also goes for not getting a job, getting rejected by a girl, etc.)

Half the companies on the Fortune 500 were started during a bear market or recession. Half.

Those who survive it, survive because they took things day by day. Focus on the moment, not the monsters that may or may not be up ahead.

Focus on what is in front of you right now. Ignore what it 'represents' or it 'means' or 'why it happened to you'.

Jobs had a much more aggressive idea of what was and wasn't possible. To him, when you factored in vision and work ethic, much of life was malleable.

The idea that no one has ever done this or that is a good thing.

Adversarial growth or post-traumatic growth: "That which doesn't kill me makes me stronger"

The worst thing to happen is never the event, but the event and losing your head. Because then you'll have two problems.


Action is the solution and the cure to our predicaments.

Nearly every wrong that can be inflicted on a child befell Demosthenes. None of it was fair, none of it was right. Most of us would have given up right there and then. But Demosthenes did not. Every moment, every conversation, every transaction was an opportunity for him to improve his art. In the process of dealing with his reality, he created a far better one.

If there's a big explosion, metaphoric or otherwise. Are you the one running towards it? Or running away from it? Or worse, are you paralyzed and do nothing

People turn shit into sugar all the time - shit that's a lot worse than whatever we're dealing with.
We don't have the luxury of running away.

"You never want a good crisis to go to waste... A crisis provides the opportunity for us to do things that you could not do before."

Say yes.
Because that's what people who defy the odds do. They start. Anywhere. Anyhow. They don't care if the conditions are perfect or if they're being slighted.
If they can just get started, if they can just get some momentum, they can make it work.

Could you be doing more? You probably could - there's always more. At minimum, you could be trying harder. When flying, you can't ever let up your flying speed - if you do, you crash.
Those who attack problems and life with the most initiative and energy usually win.

All the greats you admire started by saying, Yes, let's go. If you want momentum, you'll have to create it yourself.

Life speeds on the bold and favors the brave. It's the one who rises the morning after a long day of fighting and rallies, instead of retreating, who will carry victory home.

"You never want a good crisis to go to waste... A crisis provides the opportunity for us to do things that you could not do before.

One step at a time

Grant's victory over the South wouldn't be pretty, but it was inexorable.

Genius is often just persistence in disguise.

Seek to embrace 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.

Working at it works. It's that simple - but not easy. When setbacks come, respond by working twice as hard.

Mindset to adopt:
Never in a hurry
Never worried
Never desperate
Never stopping short

View yourself like a startup - a startup of one.
Your capacity to try, try, try is inextricably linked with your ability and tolerance to fail, fail, fail.

Break it down in little pieces.
Simply do what you need to do right now.
And do it well.
And then move on to the next.
Follow the process and not the prize.
Excellence is a matter of steps.

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.

Think about surviving. Making it from meal to meal, paycheck to paycheck, one day at a time.

We are A-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y.

Progress, not perfection.

Do your work right and do it with pride. And do it better than anyone else. Everything is a chance to do and be your best.

Don't worry about the "right" way. Any way that works - that's the motto.

As they say in Brazilian jujitsu: It doesn't matter how you get your opponents to the ground, only that you do.

Think progress, not perfection.

To be physically and mentally tight?
That's called anxiety. It doesn't work.
But physical looseness combined with mental restraint? That's powerful.


Lincoln's real strength was his will: the way he was able to resign himself to an onerous task without giving in to hopelessness, the way he could contain both humor and deathly seriousness, the way he could use his own private turmoil to teach and help others, the way he was able to rise above the din. Had the war gone on even longer, Lincoln would have led his people through it.

Be 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.

Could you actually handle yourself if things suddenly got worse?

Not everyone accepts their bad start in life.
They remake their bodies and their lives with activities and exercise.
They prepare themselves for the hard road.

Jewish saying: "In every generation a person is obligated to view himself as if he were the one who went out of Egypt."

A premortem: look to envision what could go wrong, what will go wrong, in advance, before you start.

Be ready for anything

"Nothing happens to the wise man against his expectation."

A writer like Seneca would begin by reviewing or rehearsing his plans, to take a trip. And then he would go over the things that could go wrong or prevent it from happening: a storm could arise, the captain could fall ill, the ship could be attacked by pirates.

Always be prepared for disruption, always working that disruption into our plans. (Make sure your life is anti-fragile and Black Swans will not negatively affect you)

The only guarantee is that things will go wrong. The only thing we can use to mitigate this is anticipation.

The worst thing that can happen is not something going wrong, but something going wrong and it catching you by surprise. Unexpected failure is discouraging.

The person ready to be disappointed won't be

Endure hardship

When faced with obstacles impossible to overcome, remember this: You don't have to like something to master it. Move around.

Remember: things can always be worse.

"My formula for greatness in a human being is amor fati: That one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary... but to love it."
- Nietzsche

Change the narrative: "This is what I've got to do or put up with? Well, I might as well be happy about it" Cheerfulness in all situations, especially the bad ones.

Persistence = solving some problem by hammering until the break occurs.
Perseverance = the long game. It's winning by not walking off the field until after it's over and you've won.

What's required is a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.

The secret to Magellan's success was his ability to endure hunger better than the other men

Nothing other than death can keep us from following Churchill's old acronym: KBO. Keep Buggering On.

Life is merciless

Whatever trouble you're having - no matter how difficult - is not some unique misfortune picked out especially for you. It just is what it is.

Deep down, we act and behave like we're invincible. Like we're impervious to the trials and tribulations of mortality. That stuff happens to other people, not to ME. I have plenty of time left.

"The paths of glory lead but to the grave"

The diagnosis is terminal for all of us. A death sentence has been decreed. Each second, probability is eating away at the chances that we'll be alive tomorrow; something is coming and you'l never be able to stop it. Be ready for when that day comes.

The more you accomplish, the more things will stand in your way.
Passing one obstacle simply says you're worthy of more.

Life is a marathon and not a sprint. Understand that each battle is only one of many. Most importantly, keep it all in real perspective.

See things for what they are. Do what you can. Endure and bear what you must.

Related Notes

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