The Obstacle Is The Way Summary

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:

The Obstacle Is The Way Summary

Video Summary

YouTube video

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 to overcome even the biggest challenge.
  3. Use your will to accept what you cannot change and change the things you can.

Ready for some resilience? Let’s go!

The Obstacle Is The Way Summary

If you want to save this summary for later, download the free PDF and read it whenever you want.

Download PDF

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.

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. Some other good introductory reads on the topic are Lives of the Stoics (also by Ryan Holiday), and How to Be a Stoic.

Audio Summary

Listen to the audio of this summary with a free account:

Who would I recommend our 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

Last Updated on December 14, 2022

Rate this book!
This book has an average rating of 4.4 based on 10 votes.

Niklas Göke

Niklas Göke is an author and writer whose work has attracted tens of millions of readers to date. He is also the founder and CEO of Four Minute Books, a collection of over 1,000 free book summaries teaching readers 3 valuable lessons in just 4 minutes each. Born and raised in Germany, Nik also holds a Bachelor’s Degree in Business Administration & Engineering from KIT Karlsruhe and a Master’s Degree in Management & Technology from the Technical University of Munich. He lives in Munich and enjoys a great slice of salami pizza almost as much as reading — or writing — the next book — or book summary, of course!