The Obstacle Is The Way is a modern take on the ancient philosophy of Stoicism, which helps you endure the struggles of life with grace and resilience by drawing lessons from ancient heroes, former presidents, modern actors, athletes, and how they turned adversity into success, thanks to the power of perception, action and will.
I know you can’t really call people ‘versatile,’ but if you could, I don’t think there’s a man it’d more apply to than Ryan Holiday. If I could have a person in Swiss army knife format to bring wherever I go, I’d pick him. Online marketing, press and media coverage, growth hacking, relationship building, book publishing and now Stoic philosophy, there’s no stopping this guy.
The Obstacle Is The Way takes ancient philosophy, applies it to the success stories of ancient heroes, historic figures and modern celebrities and CEOs, and derives a framework from it, which you can follow to face the struggles of your own life with the right perception, actions and the will to see them through.
Here are 3 great lessons that will help you follow in Seneca’s footsteps:
- Imagine you’re advising yourself as a friend to keep an objective perspective.
- Large obstacles have large weaknesses – identify them and use them against them.
- Use your will to accept what you cannot change and change the things you can.
Ready for some resilience? Let’s go!
Lesson 1: Imagine you’re advising yourself as a friend to keep an objective perspective.
Have you ever wondered why the solutions to our friends’ problems are sometimes so obvious to us, yet they can’t see them? “Dude, if you can’t pass that test, just take a crash course like you did with your driver’s license, remember?”
Damn. I could’ve thought of that.
But you didn’t. The reason why is perspective. Our initial reaction when we run into an obstacle is always emotional. We get frustrated, angry and think there’s no way to solve this problem.
However, when we look at other peoples’ problems, we don’t get so worked up about them and perceive them objectively. That’s what allows us to see a lot clearer, react accordingly and give much better advice on how to tackle them.
But you can be your own friend too. Imagine you are your best friend and try to tell yourself how to get past that obstacle, keeping in mind your skills and assets, but forgetting about the emotions.
Stoics did this too, they just imagined what a sage – an all-knowing, enlightened person – would do.
Lesson 2: The bigger the obstacle, the larger its weak spot – use it against the obstacle!
Alexander the Great once faced a huge obstacle. Literally. Bucephalus was one of the best horses in all of ancient Greece. A giant black stallion, with black skin, endless endurance and an indomitable will, no one could tame Bucephalus.
Whenever someone approached him, Bucephalus would fight off the rider with fury. Alexander saw his weak spot and used it against him. He made Bucephalus run in a straight line, until he could run no more. Exhausted from using all its energy in an angry sprint, Alexander mounted the horse, and from that moment on, he and Bucephalus were an inseparable unit.
Just like in this story, or in science-fiction movies, where huge monsters and gigantic creatures always have a fatal weak spot, the biggest obstacles in our lives often also have large weaknesses, which can be used against them.
For example, Jerry Weintraub had a really mean sergeant when he was in the army, who’d always treat him poorly and make fun of his name. One day, standing in line to get food, Jerry whispered into his ear: “I’m going to kill you.” Startled, his sergeant yelled at him. Jerry repeated: “One day, when you’re alone, I’m going to find you, and I’m going to kill you.” The sergeant completely lost it and hit Jerry in the face.
One complaint to the colonel later, the sergeant was gone. His anger and intolerance of cocky talk were his downfall.
All obstacles have weaknesses – you just have to look for them!
Lesson 3: Your will is best used to accept the things you cannot change and change the things you can.
Once you have the right perspective and know which actions you should take, getting past your obstacle is a matter of will. Your will enables you to stay persistent and not give up before you eventually find the solution and can move past your problem.
The stoic advice on cultivating that will suggests you accept the things you can’t change, and instead focus on changing the things you do have control over.
Natural events, other people’s choices and actions, sickness, death and economic ups and downs are all part of that first category – external factors. However, your emotions, judgements, attitudes, responses, reactions and decisions are all yours.
Take Thomas Edison, for example. When he was 67 years old, his entire laboratory burned down, including all of his experiments, prototypes, notes and research. Facing the facts he decided to start over, instead of mourning over a million dollar loss he could do nothing about. Once he’d “gotten rid of a lot of old rubbish”, as he called it, he could start fresh and ended up making $10 million in profit by the end of the next year.
Whatever you can’t change is not yours to complain about.
My personal take-aways
Maybe it’s because this sort of philosophy speaks more to introverts, like me, but I love Stoicism. It provides such a great balance to the YOLO-ish, hedonic society we live in today, which is all about clicks, bite-sized videos that barely cover our 8-second attention span, and finding the next purchase to satisfy our consumption cravings for a week at best.
Ryan’s take on this ancient philosophy is refreshing, because in The Obstacle Is The Way, he draws on a wide range of individuals, mixing the history with the present and evergreen advice with contemporary tips. Many of the examples have made it into the summary on Blinkist as well, so if you’re unfamiliar with Stoicism, I recommend you use that as a starting point and take it from there.
The Obstacle Is the Way by Ryan Holiday
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The Obstacle Is the Way Summary
The Book in Three Sentences
What stands in the way becomes the way.
Focus on the things you can control, let go of everything else and turn every new obstacle into an opportunity to get better, stronger, and tougher.
It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.
The Five Big Ideas
“The impediment to action advances action. What stands in the way becomes the way”.
“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”.
“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”.
“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”.
“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.
The Obstacle Is the Way Summary
“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.”
“The impediment to action advances action. What stands in the way becomes the way.”
“Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?”
“The world is 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?”
“Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.”
The only this at fault is our attitude and approach.
“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”—Andy Grove
“Great individuals, like great companies, find a way to transform weakness into strength. It’s a rather amazing and even touching feat. They took what should have held them back—what in fact might be holding you back right this very second—and used it to move forward.”
“We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.”
“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.”
John D. Rockerfella had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.
“Nothing makes us feel [desperate, afraid, powerless etc.]; we choose to give in to such feelings. Or, like Rockefeller, choose not to.”
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
“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.”
“Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree.”
“We decide what story to tell ourselves. Or whether we will tell one at all.”
“Defiance and acceptance come together well in the following principle: There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.”
“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?”—Gavin de Becker in The Gift of Fear
“Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?”—Marcus Aurelius
“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.”
“In The Book of Five Rings, [Musashi] notes the difference between observing and perceiving. The perceiving eye is weak, he wrote; the observing eye is strong.”
“Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there.”
“Everything about our animalistic brains tries to compress the space between impression and perception.”
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.
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.
“Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.”
“Focus on the moment, not the monsters that may or may not be up ahead.”
“Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than the goal, which will inevitably triumph?”
“There is good in everything if only we look for it.”—Laura Ingalls Wilder
“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 the advantage, not adversity. The enemy is any perception that prevents us from seeing this. ”
“Once you see the world as it is, for what it is, you must act.”
“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.”
“The only way you’ll do something spectacular is by using it all to your advantage.”
“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.”
“[Nick Saban’s] 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.”
“We don’t get to choose what happens to us, but we can always choose how we feel about it.”
“Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.”
Other Books by Ryan Holiday
Ego Is the Enemy
Recommended Reading
If you like The Obstacle Is the Way, you may also like the following books:
A Guide to the Good Life by William B. Irvine
Meditations by Marcus Aurelius
Buy The Book: The Obstacle Is the Way
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