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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?

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?”

“Failure shows us the way — by showing us what isn’t the way.”

–Ryan Holiday

That’s why stories of great successes are often preceded by epic failures. Iterating fast helps you feedback faster, and it makes you stronger from failure.

3: Follow the process

“The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.”

–Ryan Holiday

Following the process means focusing on doing the next step rather than thinking about how daunting and long the path is. Doing this keeps our perceptions and actions in sync, and it prevents us from getting distracted or unfocused.

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

We often have an ideal image of how we’ll overcome an obstacle. But life rarely works out like that. And when that happens, we become attached to our imagined method. Don’t worry about the method. Focus on getting the results.

“We wrongly assume that moving forward is the only way to progress, the only way we can win. Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path.”

–Ryan Holiday

For example, Martin Luther Kind told his followers to meet physical force with peace. In doing so, they made the enemy seem evil and indefensible.

Another example: I heard a story (not from the book) about a woman trying to get her husband to go vegetarian after hearing a talk about how healthy it is. She came home that day and declared she’s going to stop cooking meat for the family. She wanted her family to be healthier, and she was trying to push the solution with brute force. That didn’t work. Her husband just went out more to eat meat.

When she talked to her teacher, the teacher told her, “You can’t be so abrasive. You need to help him change slowly. This week, cook 3 types of meat dishes. Next week, 2 types. 1 month later, 1 type. Meanwhile, learn how to cook delicious vegetarian dishes so that he’ll complement your cooking and want more of those dishes. Bring him to dinners with other vegetarians from our class. They’ll inevitably talk about how good the food is. Tell him how important his health is to you, and how these recent studies and book explains why vegetarianism is healthier. Slowly, he’ll voluntarily eat vegetarian without any pushing from you.” She followed his advice and sure enough, the husband naturally ate vegetarian after a couple months. The method wasn’t what she initially envisioned, but she got the results.

Part 3: Will

Perception is the discipline for the mind. Action is the discipline for the body. Will is the discipline for the heart. Having strong will allows you to endure hardship along your journey.

To cultivate will, we need to

  1. Anticipate failure

  2. Accept what’s outside your control

  3. Love everything that happens

  4. Persevere

  5. Prepare to start again

1: Anticipate failure

Things rarely go according to plan, and we rarely get what we think we deserve. Yet people constantly deny these two facts and are shocked by what happens.

To not fall into that trap, the Stoics had an exercise called premeditatio malorum. It means premeditation of evils. They meditate on what might go wrong so that they’re not surprised if it happens.

In more recent times, psychologist Gary Klein developed a mental exercise called the pre-mortem. In this exercise, you declare that the project failed spectacularly even though the project hasn’t even launched yet. Then you ask your future self, “What went wrong?”

The pre-mortem conversation with ourselves may sound something like this:

  • What if…? Then I will…

  • What if…? Instead I’ll just…

  • What if…? No problem, I can always…

  • What if…? It will suck, but I’ll be okay.

The worst thing that can happen is not something going wrong. Let’s be honest, that’s inevitable. The worst thing that can happen is something going wrong AND catching you by surprise. That’s because unexpected failure is discouraging and hurts. But doing a pre-mortem makes it less likely that you’ll be surprised, and it’ll give you strength to move on and make use of failure.

“The world might call you a pessimist. Who cares? It’s far better to seem like a downer than to be blindsided or caught off guard.”

–Ryan Holiday

2: Accept what’s outside your control

Life is like driving. There are many things outside our control, like traffic rules.

“If someone we know took traffic signals personally, we would judge them insane. Yet this is exactly what life is doing to us. It tells us to come to a stop here. Or that some intersection is blocked or that a particular road has been rerouted through an inconvenient detour. We can’t argue or yell this problem away. We simply accept it. That is not to say we allow it to prevent us from reaching our ultimate destination. But it does change the way we travel to get there and the duration of the trip.”

–Ryan Holiday

In life, we also have weaknesses. Some people use those weaknesses as an excuse for why they can’t achieve their goal. Others accept their unchangeable weaknesses so that they can fully advance their strengths.

For example, Thomas Edison was almost deaf. Helen Keller was deaf and blind. But they accepted their unchangeable weaknesses rather than resenting them, and that allowed them to develop different but powerful senses to adjust to their reality.

To prevent ourselves from feeling like the center of the universe and feeling like victims, we can use contrarian self-talk again. Here’s some examples from the book:

  • Lost money? At least you didn’t lose a friend.

  • Lost that job? At least you didn’t lose a limb.

  • Lost your house? You could have lost everything.

Once we accept what’s outside our control, we can fully advance what’s in our control.

3: Love everything that happens

The next step after acceptance is changing our view from “I must to this” to “I get to do this.

The author uses the example of Jack Johnson, the ascendant black boxing champion in a racist America. The crowd hated him, but he enjoyed each match with a smile. There’s no value in any other reaction. Should he hate the crowd for hating him? What good would that do? Bitterness was their burden and Johnson refused to pick it up.

“In your worst moments, picture Johnson: always calm, always in control, genuinely loving the opportunity to prove himself, to perform for people, whether they wanted him to succeed or not. Each remark bringing the response it deserved and no more — letting the opponent dig his own grade. Until the fight ended with Jeffries [the opponent] on the floor and every doubt about Johnson silenced.”

–Ryan Holiday

The goal is not to tell ourselves, “I’m okay with this. I think I feel good about this.” The goal is to tell ourselves, “I feel great about this. If it was meant to happen, it would’ve happened. And I’m glad that it did when it did. I’m going to make the best out of it.” Then proceed to do exactly that.

Remember: We don’t get to choose what happens to us, but we do get to choose how we feel about it. And there’s just no benefit to choosing any other feeling than good.

“It’s a little unnatural, I know, to feel gratitude for things we never wanted to happen in the first place, but we know, at this point, the opportunities and benefits that lie within adversities. We know that in overcoming them, we emerge stronger, sharper, empowered.”

–Ryan Holiday

4: Persevere

Earlier in part 2, we talked about persistence in action. Persistence is being determined to solve the problem in front of you. Perseverance is determination to overcome all obstacles on your path, until the very end. True perseverance can’t be stopped by anything except death.

In fact, one of the ways to increase your perseverance is by meditating on your mortality. By thinking about our death, we can gain clarity on our priorities and gain energy to act on them.

Another way to increase perseverance is to focus on something bigger than ourselves. When we focus on helping others, our fears and troubles diminish. If you can’t solve this problem, ask yourself, “How can I at least make this better for other people?”

Remember that what lays ahead of obstacles is more obstacles. We must always persevere.

“Life is not about one obstacle, but many. What’s required of us is not some short-sighted focus on a single facet of a problem, but simply a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.”

–Ryan Holiday

5: Prepare to Start Again

“Just when you think you’ve successfully navigated one obstacle, another emerges. But that’s what keeps life interesting. And as you’re starting to see, that ‘s what creates opportunities.”

–Ryan Holiday

When we know how to deal with obstacles, we can see the opportunities in them and improve because of them. We no longer are afraid of them, but instead we are excited and cheerfully anticipating the next round.

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

I’ve applied 5 big ideas from the book into my own 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

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

Recently, I got a new member on my team who doesn’t seem to get along with me very well. It’s not that we don’t get along, but just not as well as other people. To figure out why, I compared our values, tendency, and Myers-Brigg.

Logically, I could see why we didn’t get along as well as with others. First, we have different values about work and conscientiousness. Second, he naturally resists other people’s expectations while I expect people to quickly meet expectations so long as they’re justified. Third, I’m focusing on team harmony, which is not a natural focus for his personality. And fourth, we just have different interests. Basically, it was clear on paper that two people with our traits aren’t super compatible.

In my head, I told myself that I want to build a good team culture, where everyone gets along with each other. The fact that one person was resisting my efforts, even though I explained my intent, was frustrating.

So I went outside my head and imagined if my colleague was having my problem, what would I tell him? Well, I would say, “Don’t try to change what’s outside your control. You can’t change the way he is. If he doesn’t care about getting along with the team, then you should respect that to have harmony with him. Besides, the more you push him to do something, the more he’ll resist. That’s just his nature. Just let him be and treat him the way he wants to be treated, not the way you want to be treated.”

Then I proceeded to follow that advice. Doing this mental exercise really gave me clarity on what I should do.

2 Use contrarian self-talk against panic and fear.

Recently, one of my managers criticized me in writing, and I thought the criticism was unfair. My heart rate went up, palms got a little sweaty. I needed to calm down and control my emotions before replying. So I attempted contrarian self-talk.

This is kind of unfair.

Sure. But is it pretty common that employees get unfairly criticized by managers?


Has this person complained or exaggerated about other people?


So should you be taking this too seriously?

I guess not.

Is doing what he asks of you even a big deal? Or are you just having a big ego right now?

No it’s not a big deal. I guess trying to explain myself is just having a big ego.

Then don’t bother trying to argue or explain yourself. Just accept it and do what he asks.


Side note: Having this second-self using contrarian questions and statements against the panicking-self reminds me of Ray Dalio’s book, Principles, saying we have a primitive brain and a rational brain. The panicking self is the primitive brain, wired to see danger and threats. The second-self is the rational brain.

3: Do a pre-mortem for important decisions.

In the near future, I’ll be leaving my job and looking for a new one. So that’s a perfect reason for me to do a pre-mortem contemplation:

  • What if I don’t find a job quickly? Then I’ll be patient in making sure I find a suitable job rather than any job. Good idea.

  • What if other people judge you and worry about you for not finding a job quickly? Then I’ll practice calmness and emphasize that I’m focusing on the long-term by looking for a suitable job. Besides, letting their worry seep into me is not going to help anybody. True.

  • What if you can’t find a suitable job? Then I’ll lower my expectations. It doesn’t have to be perfect. I’ll still be okay. And I can pursue my passion projects during my spare time. Okay fair point.

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

I’m a teacher, and this semester, I’ve had to cover classes for other teachers. My initial reaction was “Ugh. I have to cover. That takes away time and energy for me to do my own job and handle my own courses. And I even have to develop lessons for a course that I’m not going to be teaching.

To change my mindset towards “I get to do this”, which is kind of hard actually, I had to use that contrarian voice again.

I don’t like covering.

Does anyone like covering?

Probably not.

Are you the only one covering?

No. Some people have even more covering than me.

Do you like the classes that you’re covering?

Yeah, the students are good.

Does everyone like the classes that they’re covering?

No some teachers have much more difficult classes.

So you’re rather lucky then.


Do you gain anything useful from covering?

Well, I met a cool teacher. And even though I’m doing extra work that someone else should be doing, at least I know it’ll be helpful to the students.

So can you bring that positive energy at attitude to this task of covering?


Like the author says, it does feel unnatural, but it’s certainly more helpful than complaining and feeling like a victim.

5: Focus on the process.

Let’s just use writing this blog post as an example. When I think about organizing and synthesizing all my notes on a book into a concise and useful blog post, it’s a big task in my head. It usually takes one to two days of focused effort.

Focusing on the process means I stop thinking about how daunting the road is and just start walking. First, open Evernote. Then, open the note with my book notes. Then, open Word. Then, put in the headings. Then start writing the introduction. Etc.

To help myself stay focused, I’ll often listen to the same song or playlist on repeat. If I my mind ever starts losing focus, it’ll usually notice the song, and the song serves as a reminder to get back to work.

Eventually, I’ll be done my first draft, and it’ll feel like time passed so quickly. That’s my experience of focusing on the process.

Side note: Focusing on the process reminds me of what David Allen calls next actions, as in, what is the very next action you need to take towards a goal? Get clear and that, and then go do it. Usually, the next action is very small, like sitting down on your chair, then opening the files, then writing the first sentence, then finishing the introduction, etc. It’s very process-focused.

Q4: What is my opinion of the book?

Would I recommend this book? Yes.

It can make you aware of your crippling self-talk and give you a new pattern of self-talk that’s empowering. I’m someone who enjoys practicality and logic, so I enjoyed this book because each chapter was short, practical, and logical.

After recently reading Principles by Ray Dalio, I’ve started to view people as machines with a computer program. Essentially, we’ve all been unconsciously given a program by our biology and our upbringing, but most of us never stop to question the effectiveness of that program.

This book gave me a new program to run when facing challenges. My inherited program was to dislike and avoid dealing with challenges. This new program says to anticipate challenges, be persistent and flexible in dealing with them, accept the things outside your control so you can focus on finding solutions, and love everything that happens to you because there’s no better reaction.

Transitioning from the old program to a new one will take effort and practice, like working out or developing any new habit, but the rewards are certainly worth it. Many thanks to Ryan Holiday for the great book!

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