28 Exceptional Quotes From The Obstacle Is The Way By Ryan Holiday
Originally published at ridgepoint.co on September 1, 2019.
“You’ll have far better luck toughening yourself up, than you ever will trying to take the teeth out of a world that is, at best, indifferent to your existence”
Ryan Holiday, The obstacle Is The Way
I recently flipped past the last page in Ryan Holiday’s The Obstacle Is The Way. Unlike many books I’ve read, the end result was a copy thoroughly marked up, dog eared, and with numerous sticky notes protruding from various pages. In short, the book is a classic.
Whether you’re looking to take over the world, start an electric car company, or simply to view everyday inconveniences through a more effective lens, The Obstacle Is The Way is a great place to start. It is a seminal work on the attitudes and mindset of the millennia-old philosophy of stoicism.
It is a a playbook tackling life with an open and effective mind. If you haven’t read it yet, I highly reading it and embracing the principles. If you have read it, I highly recommend reading it again.
Without further ado, here are 28 of the most remarkable quotes from Holiday’s The Obstacle Is The Way.
Attitude Is Everything
“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.”
The Obstacle Is The Way, Ryan Holiday, Pg. 2
Use It As Fuel
“This is one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for a blaze that was their ambition. Nothing could stop them, they were (and continue to be) impossible to discourage or contain. Every impediment only served to make the inferno within them burn with greater ferocity.”
The Obstacle Is The Way, Ryan Holiday, Pg. 4
Look Within The Obstacle
“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”
The Obstacle Is The Way, Ryan Holiday, Pg. 7
All You Need
“Objective judgement, now at this very moment.
Unselfish action, now at this very moment.
Willing acceptance — now at this very moment — of all external events.
That’s all you need.”
– Marcus Aurelius
The Obstacle Is The Way, Ryan Holiday, Pg. 9
Embrace Obstacles
“Obstacles are not only to be expected but embraced. Embraced? Yes, because these obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph. The obstacle is the way.
The Obstacle Is The Way, Ryan Holiday, Pg. 10
Remove Yourself From The Situation
“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.”
The Obstacle Is The Way, Ryan Holiday, Pg. 35
Explain It Away
“The Greeks understood that we often choose the ominous explanation over the simple one, to our detriment. That we are scared of obstacles because our perspective is wrong- that a simple shift in perspective can change our reaction entirely. 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.
The Obstacle Is The Way, Ryan Holiday, Pg. 37
Make The Distinction
“The most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.”
The Obstacle Is The Way, Ryan Holiday, Pg. 44
Don’t Live In Hypotheticals
“For all species other than us humans, things just are what they are. Our problem is that we’re always trying to figure out what things mean- Why things are the way they are. As though the why matters. Emerson put it best: “We cannot spend the day in explanation.” Don’t waste time on false constructs.
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.”
The Obstacle Is The Way, Ryan Holiday, Pg. 47
Problems
“Problems are rarely as bad as we think- or rather, they are precisely as bad as we think.”
The Obstacle Is The Way, Ryan Holiday, Pg. 60
Consider This
“Consider this mindset:
Never in a hurry
Never worried
Never desperate
Never stopping short.”
The Obstacle Is The Way, Ryan Holiday, Pg. 79
Quitting
“It’s okay to be discouraged. It’s not okay to quit. … It’s supposed to be hard. Your first attempts aren’t going to work. It’s going 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 angels. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.”
The Obstacle Is The Way, Ryan Holiday, Pg. 80
Fail Well
“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.Thickheaded and resistant to change, these are the types who are too self-absorbed to realize that the world doesn’t have time to plead, argue, and convince them of their errors. Soft bodied and hardheaded, they have too much armour and ego to fail well.”
The Obstacle Is The Way, Ryan Holiday, Pg. 85
Fight Entropy — Trust The Process
“When it comes to our actions, disorder and distraction are death. The unordered mind loses track of what’s in front of it- what matters- and gets distracted by thoughts of the future. The process is order, it keeps our perceptions in check and our actions in sync.”
The Obstacle Is The Way, Ryan Holiday, Pg. 85
On The Meaning of Life
“The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” A 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.
Right action- unselfish, dedicated, masterful, creative- that is the answer to that question. That’s one way to find the meaning of life. And how to turn every obstacle into an opportunity.
If you see any of this as a burden, you’re looking at it the wrong way.
Because all we need to do is those three little duties- to try hard, to be honest, and to help others and ourselves.
That’s all that’s been asked of us. No more and no less.
Sure, the goal is important. But never forget that each individual instance matters, too- each is a snapshot of the whole. The whole isn’t certain, only the instances are.
How you do anything is how you can do everything.
We can always act right.”
The Obstacle Is The Way, Ryan Holiday, Pg. 96
Obstacle to Opportunity
“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.”
The Obstacle Is The Way, Ryan Holiday, Pg. 123
The Power of Surrender
“We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times. Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength.”
The Obstacle Is The Way, Ryan Holiday, Pg. 125
Suffering as Preparation
“Lincoln’s personal challenges had been so intense that he came to believe they were destined for him in some way, and that the depression, especially, was a unique experience that prepared him for greater things. He learned to endure all this, articulate it, and find benefit and meaning from it. Understanding this is key to understand the man’s greatness.
The Obstacle Is The Way, Ryan Holiday, Pg. 128
The World Doesn’t Care
“You’ll have far better luck toughening yourself up, than you ever will trying to take the teeth out of a world that is, at best, indifferent to your existence”
The Obstacle Is The Way, Ryan Holiday, Pg. 137
Stop Setting Yourself Up To Fail
“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.”
The Obstacle Is The Way, Ryan Holiday, Pg. 140
It’s Complicated
“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 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.
The Obstacle Is The Way, Ryan Holiday, Pg. 141
On Constraints
“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. Would we rather have everything? Sure, but that isn’t up to us.”
The Obstacle Is The Way, Ryan Holiday, Pg. 145
On Genius
“True genius, is a mind of large general powers accidentally determined in some particular direction. -Dr. Samuel Johnson.”
The Obstacle Is The Way, Ryan Holiday, Pg. 145
On Perseverance
“The good thing about true perseverance is that it can’t be stopped by anything besides death.”
The Obstacle Is The Way, Ryan Holiday, Pg. 159
Know Your Role
“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.”
“Stop pretending that what you’re going through is somehow special or unfair. 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.
This kind of myopia is what convinces us, to our own detriment, that we’re the centre of the universe. When really, there is a world beyond our own personal experience filled with people who have dealt with worse. We’re not special or unique simply by virtue of being. We’re all, at varying points in our lives, the subject of random and often incomprehensible events.”
The Obstacle Is The Way, Ryan Holiday, Pg. 165
Remember This: Memento Mori
“Every culture has its own way of teaching the same lesson: Memento mori, the Romans would remind themselves. Remember you are mortal.
It seems weird to think that we’d forget this or need to be reminded of it, but clearly, we do.
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.
Otherwise, we wouldn’t spend so much time obsessing over trivialities, or trying to become famous, make more money than we could ever spend in our lifetime, or make plans far off in the future. All of these are negated by death. All these assumptions presume that death won’t affect us, or at least, not when we don’t want it to. The paths of glory, Thomas Gray wrote, lead but to the grave.
The Obstacle Is The Way, Ryan Holiday, Pg. 168
Fate and Freedom
“We can see the “bad” things that happen in our lives with gratitude and not with regret because we turn them from disaster to real benefit- from defeat to victory.
Fate Doesn’t have to be fatalistic. It can be destiny and freedom just as easily.”
The Obstacle Is The Way, Ryan Holiday, Pg. 178
Above All
“See things for what they are.
Do what we can.
Endure and bear what we must.”
The Obstacle Is The Way, Ryan Holiday, Pg. 180
If any of these struck your fancy, I highly recommend picking up the book on Amazon.
If you want more nuggets on how to tackle life, stoicism, and other general musings, see our other articles.
Originally published at ridgepoint.co on September 1, 2019.
