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🪨#34: The Obstacle Is The Way by Ryan Holiday - Book Summary & Key Takeaways

🪨#34: The Obstacle Is The Way by Ryan Holiday - Book Summary & Key Takeaways

How do we turn our Obstacles into Advantages? What are the 3 different stages we must be aware of? What are the key lessons we can take into our own lives?

September 21, 2022

Hello courageous people! 👋 Welcome to Edition 34.

This week, we are reading 📚 The Obstacle Is The Way 🖋 by Ryan Holiday.

This has been on my to-read list ever since 2019, so it feels amazing to finally have read it—and it didn’t disappoint!

With wisdom distilled from both ancient and modern philosophers, The Obstacle Is The Way does the hard lift for us on how we can work to overcome the adversities we have faced and move forward.

So let’s jump in! All text in italics are quotes taken directly from the book.

🧐 What is The Obstacle Is The Way all about?

The Obstacle Is The Way takes the wisdom of philosophers like Marcus Aurelius, Seneca and Cato (the Stoics) and translates it into a digestible form for our modern minds.

In essence, the take home message is:

“This thing in front of you. This issue. This obstacle—this frustrating, unfortunate, problematic, unexpected problem preventing you from doing what you want to do. That thing you dread or secretly hope will never happen.

What if embedded inside it or inherent in it were certain benefits—benefits only for you? What would you do?” - page 1

Where some people are taken down by their obstacles, other people are transformed:

“Good companies survive them. Great companies are improved by them.

Great individuals, like great companies, find a way to transform weakness into strength.” - page 3

So how do we become “great”? How do we transform?

“Something stands in someone’s way. They stare it down, they aren’t intimidated. Leaning into their problem or weakness or issue, they give everything they have, mentally and physically. Even though they did not always overcome it in the way they intended or expected, each individual emerged better, stronger.” - page 177

Soon we will get to 11 lessons that can help us do exactly that.

👑 The Zen Story of The King

There is an old Zen story about a king. His people had grown soft and entitled, so he went about teaching them a lesson.

He placed a giant boulder in the centre of the main road in and out of the city, blocking people from being able to get in or out.

The king hid and watches people’s reactions, looking for people to band together and do something about it.

Days passed, and no one had even tried to tackle the boulder, until

“ … a lone peasant came along on his way into town. He did not turn away. Instead he strained and strained, trying to push it out of the way. Then an idea came to him: he scrambled into the nearby woods to find something he could use for leverage.

Finally, he returned with a large branch he had crafted into a lever and deployed it to dislodge the massive rock from the road. Beneath the rock were a purse of gold coins and a note from the king, which said:

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” - page 6

Is the story a little … on the nose? Sure.

But it does demonstrate the attitude to obstacles that this book presents and advocates for us all to adopt.

✅ What are the 3 different stages we must be aware of in order to turn our obstacles into advantages?

The book is split into three distinct parts.

👀 Phase 1: Perception

👟 Phase 2: Action

💪 Phase 3: Will

Put another way,

“First, see clearly.

Next, act correctly.

Finally, endure and accept the world as it is.” - page 178

There are tools and strategies we can use to influence the way we perceive our situation, the way we take action and the will to continue.

👀 Phase 1: Perception

Perception is all about looking at the events that happen to us, and then deciding what they mean. That’s right - we get to decide.

👓 Lesson #1 - The Discipline of Perception

“Discipline in perception lets you clearly see the advantage and the proper course of action in every situation—without the pestilence of panic or fear.” - page 18

The same way that we must go to the gym if we want to train our muscles to be stronger, we must train ourselves to control our perceptions in times of stress. Here’s an example of how we can do that:

Rubin Carter was at the height of his boxing career in the 1960s when he was wrongly accused of a triple homicide. The case went to trial and he was sentenced to life in prison.

You might think that this would be the perfect situation to lose the plot completely and go to pieces, but Carter didn’t.

“Was he angry about what happened?

Of course. He was furious. But understanding that anger was not constructive, he refused to rage.

[…] Every second of his energy was to be spent on his legal case. Every waking minute was spent reading—law books, philosophy, history.” - page 20

Even if we are thrown in jail and we are deprived of our possessions, they cannot control our thoughts.

💥 Lesson #2 - Steady Your Nerves

Ulysses S. Grant was a commanding general in the US Civil War, and all reports state that he was unshakeable.

“During the Overland Campaign, Grant was surveying the scene through field glasses when an enemy shell exploded, killing the horse immediately next to him. Grant’s eyes stayed fixed on the front, never leaving the glasses. There’s another story about Grant at City Point, Union headquarters, near Richmond. Troops were unloading a steamboat and it suddenly exploded. Everyone hit the dirt except Grant, who was seen running toward the scene of the explosion as debris and shells and even bodies rained down.

That’s a man who has steadied himself properly.” - page 24-25

When steady our nerves, we can remain present and bring our best selves to tackling the problem at hand. You see,

“If our nerve holds, then nothing really did “happen”—our perception made sure it was nothing of consequence.” - page 26

🧘‍♂️ Lesson #3 - Practice Objectivity

“The phrase “This happened and it is bad” is actually two impressions.

The first—“This happened”—is objective.

The second—“it is bad”—is subjective.” - page 32

When we can steady ourselves and control our emotions, we can make a better decision about the things at hand.

🌈 Lesson #4 - Finding The Opportunity

As we have already seen in Lessons 1-3, our perception has the ability to make or break us.

When it comes to overcoming obstacles, it isn’t just the ability to avoid a negative spiral, or decide that a situation is a neutral one—we can actually decide that a situation could be good for us:

“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.” - page 57

We can train our minds to see obstacles as training mechanisms and a fast track to propelling us to the next level we are trying to reach.

👟 Phase 2: Action

When we say action, we aren’t just talking about any action. It is the action that is in service of the greater mission, of the whole. Only through action can we take down the obstacles before us.

🏃‍♂️ Lesson #5 - Start Moving

“Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.” - page 75

We have to start exactly as we are, where we are, with the resources we have.

🏋️‍♀️ Lesson #6 - Practice Persistence

Too often, especially in the media these days we see things presented as an overnight success. But barely anything is actually an overnight success.

Take Thomas Edison for example.

In 1878, he wasn’t the only person trying to invent the lightbulb.

“But he was the only man willing to test six thousand different filaments—including one made from the beard hair of one of his men—inching closer each time to the one that would finally work. And, of course, he eventually found it—proving that genius often really is just persistence in disguise.” - page 78

He had outlasted his competitors, his investors and even the press. Many would believe that he cracked it through some stroke of genius, when in reality,

“ … it was the slow pressure, repeated from many different angles, the elimination of so many other more promising options, that slowly and surely churned the solution to the top of the pile.” - page 79

Simply not giving up is a significant portion of the fight.

😥 Lesson #7 - Change Your Relationship With Failure

When we try, try and try again (just like Edison did) it forces us to adjust our relationship with failure.

“Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail. On the path to successful action, we will fail—possibly many times. And that’s okay. It can be a good thing, even. Action and failure are two sides of the same coin. One doesn’t come without the other.” - page 83

In fact,

“Failure shows us the way—by showing us what isn’t the way.” - page 86

🗂 Lesson #8 - Follow The Process

“Process provides us a way. It says: Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize.” - page 87

If the thing we are having to tackle, we just have to do one thing: break it down. And if it’s still too big? Break it down again.

Eventually,

“ … when you really get it right, even the hardest things become manageable. Because the process is relaxing. Under its influence, we needn’t panic.” - page 88

When we follow the process, all we have to do is take a deep breath and do the very next part of it that is in front of us. That action will lead us right into the next action and the next action.

“Everything in order, everything connected.” - page 89

We just need to trust the process.

💪 Phase 3: Will

What is Will?

It is our internal power. It is what we can hold onto when our agency is all but gone, because unfortunately there will be times where there may not be a lot of actions that we can take in order to change a situation. This is when we need to use our Will to endure.

🧠 Lesson #9 - The Discipline of Will

No matter what situation we find ourselves in, we can always do these things:

🙂 Lesson #10 - The Art of Acquiescence

“After you’ve distinguished between the things that are up to you and the things that aren’t, and the break comes down to something you don’t control… you’ve got only one option: acceptance.

When the problem lies outside of us, we are better for accepting it and moving on.” - page 146

As the Stoics would say, there are certain things which are left up to the “will of the Gods”.

🥰 Lesson #11 - Love Everything That Happens

When Thomas Edison was 67 years old, he returned home a little earlier than usual one evening from work. After dinner, a man ran in off the street saying that a large fire had broken out at his laboratory a few miles away.

Fire engines came from nearby towns and they did everything they could, but the blaze was not to be contained. It was fuelled by different chemicals, sending green and yellow flames seven stories into the air. His life’s work was gone.

Edison made his way to the fire and looked for his son. When he found him, Edison said to him,

“Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.”

“What?!”

“Don’t worry,” Edison calmed him. “It’s all right. We’ve just got rid of a lot of rubbish.” - page 150

In a way that is an incredible reaction. But was there really another appropriate response?

“What should Edison have done? Wept? Gotten angry? Quit and gone home? What, exactly, would that have accomplished?

You know the answer now: nothing. So he didn’t waste time indulging himself.” - page 151

🤯 🤯 🤯

Again (I sit here reminding myself 🤪) all of these strategies take practice.

😌 Summing Up

If we can learn to master these tools and strategies, an exciting world awaits us.

“Simply flipping the obstacles that life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round.” - page 174

If we take one quote with us from this book into our daily lives, this is the one I’d recommend:

“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.” - page 180

I don’t know about you, but I suuuuuuure have a lot of practicing to do to reach Stoic level. Time to get started.

Until next week my friends,Eleanor ❤️🙏

🧠 Resources & Links

🤝 Human Rights list of Mental Health Support Services

🖥 Ryan Holiday’s Website with resources

📸 Follow Ryan Holiday on Instagram - 451k followers

🐥 Follow Ryan Holiday on Twitter - 515k followers

📕 Next week’s book

Coming out next Wednesday 28th September 2022 is edition #35:📚 Unbound: My Story of Liberation and the Birth of the Me Too Movement🖋 by Tarana Burke

“From the founder and activist behind one of the largest movements of the twenty-first century, the me too movement, Tarana Burke debuts a powerful memoir about her own journey to saying those two simple yet infinitely powerful words and how she brought empathy back to an entire generation.Unbound is the story of an inimitable woman's inner strength and perseverance, all in pursuit of bringing healing to her community and the world around her, but it is also a story of possibility, of empathy, of power, and of the leader we all have inside ourselves. In sharing her path toward healing and saying me too, Tarana reaches out a hand to help us all on our own journeys.”