The Obstacle Is The Way Summary

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1-Sentence-Summary: 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.

Read in: 4 minutes

Favorite quote from the author:

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:

1. Imagine you’re advising yourself as a friend to keep an objective perspective.

2. Large obstacles have large weaknesses – identify them and use them against them.
3. Use your will to accept what you cannot change and change the things you can.

Ready for some resilience? Let’s go!

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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.

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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.

The Obstacle Is The Way Review

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.

Read full summary on Blinkist

Get the book on Amazon

Learn more about the author

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What else can you learn from the blinks?
Why Amelia Earhart had to remain very flexible with her actions before becoming
the first female pilot
How to turn a prison sentence into an advantage
When reacting to your emotions isn’t the best idea, and how it saved Ulysses S.
Grant’s life
How George Clooney made the context of his roles into what got him hired
Which ancient Greek proved that discipline always wins, and why he did it with
pebbles in his mouth
Why Walt Disney and HP would never have been successful if they hadn’t focused
on their day-to-day activities instead of the bigger picture
The most important thing that helped Odysseus find his way home

Who would I recommend The Obstacle Is The Way summary

to?
The 25 year old, who grabs more than he can handle (aka me) and could use some
patience, the 49 year old, self-employed creative, who spends a lot of time worrying
about how her next project will be received, and anyone who’s never heard of Seneca

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