The Obstacle is the Way — Summary and Application

Originally published on October 2, 2019 on Medium.


Here are my key takeaways from the book The Obstacle is the Way by Ryan Holiday. The book is essentially an instruction guide on how to change your attitude and self-talk towards challenges. In doing so, we can take action towards progress and endure towards completion.



Here’s a poetic summary of the book from the author:

See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.

In this post, I answer four questions. Here is a clickable table of contents:


Q1: Why did the author write this book?


Q2: What are the main ideas?

  1. Perception

  2. Action

  3. Will

Q3: How have I applied this book in my life?

  1. Take your problem and pretend it’s happening to someone else.

  2. Use contrarian self-talk against panic or fear.

  3. Do a pre-mortem for important decisions.

  4. Change from “I must do this” to “I get to do this.”

  5. Focus on the process

Q4: What is my opinion on the book?


Q1: Why did the author write this book?

The author sees most people getting stuck in the face of obstacles, but some people thriving at every challenge. He wants everyone to thrive in the face of obstacles, so he studied those rare people.


He discovered that the difference between the successful and the unsuccessful is not skill but rather the method for dealing with obstacles. Since method is something anyone can learn, he wrote this book to share the method for turning obstacles into advantages.


From this book, he hopes his readers will be able to change their thinking towards obstacles from “I don’t like this” or even “This is not so bad” to “I can make this good.”


Q2: What are the main ideas from the book?

The book is organized into three parts:

  1. Perception: Your attitude towards the problem

  2. Action: Breaking problems down and turning them into opportunities

  3. Will: Cultivating perseverance that can overcome difficulty

Part 1: Perception

Our perception is how we interpret the objective events of life. It can be a source of strength or a source of weakness.


Due to evolution, our brains are wired to focus on dangers and threats. While that may have been useful back in the cavemen days, it isn’t as helpful now. Most of our obstacles aren’t life threatening anymore; instead, they are mental. Therefore, we need to upgrade our brains with new programming to perceive modern obstacles effectively. To do that, we need to learn and practice new self-talk.


“You will come across obstacles in life — fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure.”

–Ryan Holiday


When facing obstacles, we need to

  1. Be objective

  2. Control emotions

  3. Have perspective

  4. Focus on what can be controlled

1: Be objective

Being objective means removing “you” from the picture. Just think about what happens when we give advice to others. Their problems are crystal clear to us. But when we think about our own problems, we carry so much baggage. To be objective, take your situation and pretend it’s not happening to you but rather to someone else. Quickly and dispassionately size up the situation. The more you practice this, better you’ll get.


2: Control emotions

Controlling your emotions means not panicking. Panic is the worst enemy because it muddles thinking. To overcome panic, we need to imagine a second self using contrarian questions and statements against the panicking self. Here’s an example given in the book:

When you have this kind of conversion with your panicking self, those extreme emotions won’t last long.


Another option is to ask a question that Marcus Aurelius asks himself: “Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straight-forwardness?” If not, then get back to work!


3: Have Perspective

Having perspective is about reframing the situation and finding the opportunities in your obstacle. If we can do that, obstacles become something we embrace rather than avoid.


“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 an advantage, not adversity. The enemy is any perception that prevents us from seeing this.”

–Ryan Holiday


Let’s look at a common example: A bad boss. The common self-talk is, “This is hell. I’m so unlucky. I’m screwed.”


A more effective self-talk would be, “My boss is so bad that I’m willing to quit. If I’m willing to quit, then I have a good reason to reach out to contacts elsewhere and find potentially better opportunities. While I’m looking for a new opportunity, I can experiment with different tactics of trying to get along with this current boss. If things get better, great. If not, I’ll be prepared to move on.”


Let’s quickly look at some other examples from the book:

  • You have rival? Great! They keep you alert, motivate you, toughen you, help you appreciate friends, and give you an antilog (a model of whom you don’t want to become).

  • That computer glitch erased your work? Good. Now you’ll be twice as good by doing it again.

  • That business decision turned out to be a mistake? A scientist wouldn’t be upset. He’d be happy that he made progress. You should too.

  • Someone is critical towards you? Good. Lower expectations are easier to exceed.

  • Someone on your team is lazy? Good. That makes our accomplishments seem greater.

These re-framings aren’t about begrudgingly accepting a situation to be okay. It’s a complete flip from “I don’t like this” to “I can make this great.


4: Focus on what can be controlled

The most harmful addiction is believing that we can change things outside our control.

We should remember and follow the Serenity Prayer:

“God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.”

What are the things we can control?

  • Our emotions

  • Our judgments

  • Our creativity

  • Our attitude

  • Our perspective

  • Our desires

  • Our determination

What is out of our control? Pretty much everything else. The big ones are other people’s emotions and judgments, as well as disastrous events.


Once you can effectively perceive obstacles, your hands will be steadier. The next step is to act with those steady hands.


Part 2: Action

It’s worth noting again, correct perception is a prerequisite to effective action.


Sure, you can complain about your situation and feel bad for yourself. You are human after all. Just don’t take too long. You have to get back to work. No one will save you. Only you can tackle your problems.


Even if you’ve started taking action, is your full effort in it? If not, that will show in the results.

Putting in your full effort means you:

  1. Practice persistence

  2. Iterate

  3. Follow the process

  4. Don’t worry about how you look; Focus on getting the results

1: Practice persistence

Being persistent means trying new methods and approaches. For example, Thomas Edison experimented with 6000 filaments before finally finding one that worked.


“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.”

–Ryan Holiday


If you are committed to seeing it through, then temporary setbacks aren’t discouraging. They are just bumps along a long road that you intend to travel all the way down.


2: Iterate

Often, when people want to try a new solution, they invest heavily in getting everything set up perfectly before testing it. This approach is risky because if it doesn’t work, you’ve wasted a lot of time and resources.


In Silicon Valley, people don’t launch a finished product. They iterate fast by launching the Minimum Viable Product (MVP), which is the most basic version of a core idea with one or two essential features. When it fails, they should ask themselves, “What went wrong? What can be improved? What am I missing?”