The Obstacle Is the Way by Ryan Holiday [Actionable Summary]

This is a comprehensive summary of the book The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday. Covering the key ideas and proposing practical ways for achieving what’s mentioned in the text. Written by book fanatic and online librarian Ivaylo Durmonski.

Printable: Download this summary to read offline.

The Book In Three Or More Sentences:

“Let’s talk about failure and how to deal with obstacles,” is kind of what Ryan Holiday said when starting to write this book. While tiny, The Obstacle Is the Way covers a lot of ground. By sharing various stories of history’s most famous names, Ryan Holiday wants to inspire us. To give us the mental tools we need to deal with hardship and spot opportunities in even the cruelest situations life throws at us.

The Core Idea:

Mr. Holiday argues that to get better at overcoming obstacles you need to be skilled at three disciplines: perception, action, and the will. This trio of steps, and the accompanying substeps, are going to ease your way uphill. Yes, it’s always uphill. There are always more obstacles to come. The more you accomplish, the more things will stand in your way.


  • The better version of yourself is waiting on the other side of the hurdle.
  • Don’t believe the person saying you can’t do it. Use his negativity for inspiration.
  • It’s not going to be easy. Actually, it’s supposed to be hard.

The 5 Key Lessons From The Obstacle Is the Way:

Lesson #1: The Obstacle Becomes The Way

There’s a big rock standing in your way? You should definitely move it. That’s now your main task in life.

That’s pretty much the main topic of the book. Whatever stands in your way, becomes the way.

And these are not my words, neither the words of Ryan Holiday. In fact, a very powerful man said it first: Marcus Aurelius. Here’s what he stated:

The impediment to action advances action. What stands in the way becomes the way.” Marcus Aurelius

Regardless of your financial situation, your background, and your rank in the company you work for, there are always obstacles. Always difficulties trying to sabotage your existence: workers protesting against you, rising unemployment, network failure crashing your whole system, a nasty disease that strikes your siblings, a high school bully who’s making your life difficult, etc.

Identify the obstacle that is blocking your path and don’t turn away. Analyze the situation. Look for opportunities. Search for solutions. Then, act. Push till you’re over the hurdle. On the other side, a new person is going to greet you. Your new improved self.

The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” Zen Proverb

Lesson #2: Spot The Opportunity in Every Disaster

Obstacles feel paralyzing. That’s normal. Even common these days. After all, in the cozy 21 century with fresh water, electricity, the holy internet, we expect everything to be effortless, easy, pain-free. But it’s not. And when it’s not, when things are not working out the way we want them to, we start to panic.

When we’re facing a difficult situation, we feel distressed and we call our parents for help. Or worse, hide behind our desk, in the basement, or eat the whole jar of chocolate.

It’s of major importance to understand that our lives are not, and never will be, hurdle-free.

On a daily basis, we’re facing difficulties that either help us improve or make our lives miserable.

Regardless of what stands in your way, the way you see the problem is what matters. If you consider a task impossible, this will mean that it’s impossible.

Or in other words, we have the choice to decide whether something can be done or cannot be done. Our perception plays a major role in our problem-solving rodeo.

If you’re accused, thrown out of your comfort zone, facing seemingly impossible to handle challenges, don’t let your emotions control you. Steady your nerves. Ignore the one who says that what you’re trying to do is impossible. Place things in perspective and find the best course of action to move forward.

Lesson #3: Act In The Best Interest of Your Goals

If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.” Ryan Holiday

The second major theme in the book is taking action – the first being putting things in perspective.

A lot of folks criticize the book by saying that it lacks advice for overcoming the obstacles we face. “There is no real advice, only anecdotes,” they say. Well, yes. What do you expect? Someone doing the work for you?

These folks are just too lazy to take full ownership of their problems.

There’s no way to do something about a problem other than taking some sort of action. Or as the author writes, “It’s supposed to be hard. Your first attempts aren’t going to work. It’s goings to take a lot out of you.”

And action, of course, is not simply doing random things. Massaging your feet while you’re not getting any new orders won’t help you move forward in your business. You need a plan. You need to iterate. You need to prepare for failure. You need to get ready for years of hard work. You need to be mentally set that handling this hardship, bump on the road, whatever, is going to take you time, and be ok with it.

It’s not going to be easy. What you’re doing won’t be achieved in a month, nor in a year. But it can be done. With the right strategy and the correct mentality, the difficulty that is causing a disruption in your life can surely be conquered.

Oh, and yes, don’t aim for perfect. Aim for making progress.

Lesson #4: Will Is The Only Thing We Have Full Control Over

Yes, will. But not Will Smith. Your willingness to push yourself despite the difficulties is the final component of the obstacle-tackling cocktail that will aid you in your quest for greatness.

Will, is something you have full control over. It’s your internal power. Your inner ability to keep going. To keep pushing. To keep fighting.

Simply acting won’t be enough because once something is done – say you launch a new product to make more sales – you can’t control how people will react to the new update. But you can control your willingness to keep doing things even if everything is seemingly going downhill. Even if seemingly no one is liking your new feature.

Stoics called will the Inner Citadel. Ryan Holiday refers to it as a muscle, as a “steel backbone.”

And how do you forge your own Citadel?

By strengthening your body and mind when times are good. By doing hard work even when things are thriving. When you do this, you’ll be better prepared for the difficult times that will surely come.

One strategy to forge a steel mentality is by practicing the premortem technique.

This tactic is about imagining things going completely wrong, in advance, and preparing for the worst that can happen.

When you have a plan for a nasty situation, you’ll be one step ahead when something bad actually happens. You won’t be surprised, you’ll be ready and you won’t let your emotions consume you.

We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good.” Ryan Holiday

Lesson #5: Obstacles Never Disappear

You just graduated? You beat a fierce opponent? You won a prize?

Nope. It’s not over. You don’t retire and “live happily ever after.” Real life is what happens after the final scene in the movies.

Beating one opponent. Winning one prize is just part of the process. To reserve your spot on the podium of greatness, you need to understand one important thing about obstacles: they never end.

“But my mom told me that after I graduate everything will be nice and easy!” well, sorry to say it but your mother was wrong. I know, it feels daunting. Crushing. Mentally unacceptable. But life is full of obstacles. The more you conquer, the more they appear.

Like a boxer who is trying to make a living punching dudes on a ring, you don’t schedule a match with weaker boxers. If you want to advance in your career, every next match will be with an even stronger opponent. That’s how life is for all of us – or at least the ones who want to achieve beyond average results.

The good news is that we get better. Each new obstacle offers lessons that allow us to be better prepared for the next challenges. But that doesn’t mean that we should train less. Not at all. It simply means that we’ll grow a thick skin and stop being afraid when challenges arise.

On the contrary, the more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.” Ryan Holiday

Actionable Notes:

  • The art of not panicking: What do we do when deadlines are getting closer? We panic. And what happens when we panic? We do stupid stuff. We forget the procedures and we break things. Not panicking in contrast, will allow you to see things more clearly and avoid damaging goods. How to do it? Ask yourself, “Will getting upset provide me with more options? Help me in the situation?” If it won’t, stop for a moment to calm your mind.
  • Spot opportunities in the obstacles: The main difference between ordinary people and extraordinary ones is how they view obstacles. Most folks hide behind the bushes when troubles arise on the horizon. Exactly the opposite is what successful people do – they see the “problem” as a challenge, as an opportunity to improve themselves, a way to gain even more sweet success. There’s sweetness in every bitterness. To find it, you need a taste of the battle.
  • Practice postmortem: We disappoint others and ourselves not because we’re not good, but because we’re not properly prepared. Imagine what could go wrong in advance. Consider all situations, all options, and all variances of how things might turn out. This exercise of future-looking – called postmortem – will help you improve before bad things happen. Therefore, be ready when bad things actually happen.
  • See yourself as a start-up: What start-ups are really good at? Two main things: 1) creating something out of nothing, 2) not afraid of being wrong. Point two is what makes them what they are. By constantly failing, and not giving up, they reach a point where they have something the market wants. If you change your relationship with failure, see it as simply a path towards where you want to go, you won’t feel discouraged when things don’t work out for the first time. Rather, you’ll feel motivated to get better.
  • Break it down into pieces: If your eyes see a big heavy rock in front of you, your mind should see a lot of tiny rocks glued together. Probably you can’t move one big rock alone, but you can surely move 100 small rocks out of the way. That’s how you should approach all challenges. Not by mindlessly throwing yourself at the big task, but by crafting a step-by-step process to handle the situation. Contrary to what Hollywood movies what to sell us, overcoming obstacles lies in processes, not so much in blind courage.

Commentary and My Personal Takeaway

Probably you won’t find anything new in this book in terms of handling obstacles – spot the opportunity in every tough situation, break the challenge into pieces to handle it, etc. However, you’ll get something much more valuable – motivation.

The stories shared inside The Obstacles is The Way, and how key players in our history coped with adversity, will help you find solutions in your daily life.

The way Ryan Holiday structured this book is exceptionally good. Instead of long chapters with a never-ending resolution, you get short sections each covering one story and each offering one specific lesson.

If you’re trying to run a business in tough conditions or you’re baffled every time a challenge arises, you should definitely consider this book.

Key takeaway?

Obstacles never cease to exist. Deflecting them or trying to hide from them will only cause you harm. When times are good, improve yourself. This way you’ll be better prepared when bad things actually start to take place.

Notable Quotes:

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.” Ryan Holiday

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.” Ryan Holiday

As it turns out, this is one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition. Nothing could stop them, they were (and continue to be) impossible to discourage or contain.” Ryan Holiday

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