Book Review: “The Obstacle Is the Way”

Book: The Obstacle Is the Way by Ryan Holiday
Reviewer: Bobby Powers

My Thoughts: 10 of 10
This book was my gateway drug to Stoic philosophy—as it is for many people. Holiday introduces modern readers to the ancient, enduring wisdom of philosophers Marcus Aurelius, Seneca, and Epictetus while weaving in stories from business, athletics, and art. If you're trying to develop more grit and a positive perspective on challenges, buy this book.

What I Learned from the Book

One of the most important life lessons anyone can learn is to focus on what you can control and not worry about what you can't. That concept lives at the core of Stoicism, and it's a useful mindset for approaching any challenge. As a few examples of what we can and can't control:

  • Controllable: Your work ethic, your preparation, your perspective, the way you rebound after failure
  • Uncontrollable: The weather, others' emotions, others' opinions of you and your work

All of us will face challenges in life. And when we face challenges, we can view them as devastating roadblocks or we can view them as fuel. Which perspective do you think leads to more success and happiness?

"It's not just: How can I think this is not so bad? No, it is how to will yourself to see that this must be good—an opportunity to gain a new foothold, move forward, or go in a better direction. Not 'be positive' but learn to be ceaselessly creative and opportunistic.

Not: This is not so bad.
But: I can make this good."

Selected Quotes & Ideas from the Book

Inspiration from Marcus Aurelius

  • "In the year 170, at night in his tent on the front lines of the war in Germania, Marcus Aurelius, the emperor of the Roman Empire, sat down to write...Not to an audience or for publication but to himself, for himself. And what he wrote is undoubtedly one of history's most effective formulas for overcoming every negative situation we may encounter in life. A formula for thriving not just in spite of whatever happens but because of it."
  • "The impediment to action advances action. What stands in the way becomes the way." -Marcus Aurelius, writing in his journal
  • "And from what we know, he truly saw each and every one of these obstacles (plague, infidelity, betrayal, war, etc.) as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity."
  • "Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?"

Using Difficulty to Thrive

  • "Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them." -Andy Grove, former CEO of Intel
  • "Great individuals, like great companies, find a way to transform weakness into strength...Like oxygen to a fire, obstacles become fuel for the blaze that was their ambition."
  • "If all this book does is make facing and dismantling such stumbling blocks a little easier, it will be enough. But my aim is higher. I want to show you the way to turn every obstacle into an advantage."

Control What You Can Control, Forget About Everything Else

  • "Choose not to be harmed—and you won't feel harmed. Don't feel harmed—and you haven't been." -Marcus Aurelius
  • "We decide what we will make of each and every situation. We decide whether we'll break or whether we'll resist...Our perceptions are the thing that we're in complete control of."
  • "In other words, through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles. There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means."
  • "Would you have a great empire? Rule over yourself." -Publius Syrus
  • "Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective."
  • "Problems are rarely as bad as we think—or rather, they are precisely as bad we think. It's a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head."
  • "If someone we knew 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."

Take Immediate Action

  • "The thing standing in your way isn't going anywhere." You need to act.
  • "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."
  • "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."
  • "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. There is a certain humility required in the approach...But so what? What matters is whether a certain approach gets you to where you want to go."

You Will Fail—and That's Okay

  • "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."
  • "Like any good school, learning from failure isn't free. The tuition is paid in discomfort and having to start over. Be glad to pay the cost. There will be no better teacher for your career, for your book, for your new venture."
  • "It's time you understand that the world is telling you something with each and every failure and action. It's feedback—giving you precise instructions on how to improve, it's trying to wake you up from your cluelessness. It's trying to teach you something. Listen."
  • "Ordinary people shy away from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They are their best in these situations. They turn personal tragedy or misfortune—really anything, everything—to their advantage."

Prepare for the Worst

  • "The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves."
  • "It's better to meditate on what could happen, to probe for weaknesses in our plans, so those inevitable failures can be correctly perceived, appropriately addressed, or simply endured."
  • "We're prepared in advance for adversity—it's other people who are not. In other words, this bad luck is actually a chance for us to make up some time. We're like runners who train on hills or at altitude so they can beat the runners who expected the course would be flat."

Assorted Wisdom

  • "Be fearful when others are greedy and greedy when others are fearful." -Warren Buffett
  • "If you're not humble, life will visit humbleness upon you." -Mike Tyson
  • "The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who 'transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.' It's a loop that becomes easier over time."

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