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The Obstacle is the Way

by Ryan Holiday
clock16-minute read
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The Obstacle is the Way
How to turn your biggest failure into your biggest success. We’ve all heard the old saying is that life is 10% what happens to you and 90% what you make of it. That should be an empowering life philosophy, but we don’t always live into it. Ryan Holiday wants to change that and that’s why The Obstacle is the Way examines the strength and resilience of Stoic historical figures in order to chart a path to success through adversity. By demonstrating how some of the early stoics learned to triumph because of their tribulations, Holiday demonstrates a tried and true path to success that anyone can follow.
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The Obstacle is the Way
"The Obstacle is the Way" Summary
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Summary by Alyssa Burnette. Audiobook narrated by Alex Smith
What do you do when you encounter failure? Let’s say you’ve been nervous about tossing your hat into the ring for that promotion or launching your new startup, and after all that stress and time and effort, you go for it… only to fail. So, how do you handle that? It’s tempting to internalize that failure, to assume that it means something about us and that we are doomed to never succeed. As a result, you might think the best course of action is to curl up in a ball and never leave your bed. Why bother when you’re only going to fail, anyway? But sadly, this is precisely the mentality that keeps so many of us from achieving success.
The author wisely recognizes that this mentality is toxic and that’s why he wants to present us with some examples of success stories throughout the ages — people who have recognized that the presence of an obstacle isn’t a signal to give up. Instead, it’s a sign to keep fighting, because — as we’ll see through the course of this summary — the obstacle is the way to success.
Chapter 1: Turn Your Obstacles Into Your Strengths
That might sound odd, but I promise that statement isn’t a mistake. Because even though we often perceive obstacles as being counterproductive to our success, the truth is that they can actually be used to our advantage! If you find yourself asking how, you’re not alone; our natural instinct is to never to see an obstacle as a positive. After all, if they were positive, they wouldn’t get in the way of our big promotion, us passing the test, or any of the other things that we want. But obstacles can reveal other hidden positives: ones that help us develop our moral character and the strengths that will enable us to succeed in life. But, as is the case with most good things, it doesn’t come easily; we have to work for it. So, if we want to turn an obstacle into a strength, here are three things we need to work on.
For starters, we have to work on our attitude or the way we see the problem. You remember how, earlier in the introduction, we discussed the old cliche that life is 10% what happens to you and 90% what you make of it? Well, as corny as it might sound, most cliches become well-worn platitudes for a reason. And in this case, that’s because it really is true. So, if you really want to use your obstacle to your advantage, you need to change the way you think about it. Okay, so maybe it’s the opposite of the outcome you wanted. But what else can we take away from this moment? What positive lessons can it teach us? To put this into context, the author provides an example of one notable success story.
Today, we know John Rockefeller as one of the wealthiest self-made men in America; he stands as an icon of power and success. But how did he get there?Rockefeller himself cited the life lessons he learned while observing others as one reason for his success. For example, when he was just 18 years old, he witnessed the big financial crisis of 1857. The city was, understandably, awash with panic and this panic caused people to make unwise decisions. Rockefeller was attentive enough to notice this and he realized at a young age that making snap decisions based on panic almost guaranteed failure. This prompted additional introspection as he began to watch closely and parse out the specifics of those wrong decisions. He wanted to know what specific actions amounted to failure and how he could avoid making the same mistakes. And after carefully observing the lives and failures of others, he made deliberate choices about what to avoid in his own future.
This perspective enabled him to alter his view of the crisis and focus instead on the advantages available to him, like his opportunity to learn new things and better himself. And as he learned how to stay calm under pressure and resist the temptation to panic, he was honing the very qualities that would make him a successful businessman. So, as you can see, Rockefeller’s story sets a positive example by demonstrating how we can use obstacles to our advantage if we simply alter our perception. But it’s not enough to stop there. Because if you want to truly conquer your obstacle, you also have to take action. But how do you know what the right action is? How do you tell the difference between getting ahead of your problem and reacting out of panic?
A key difference can be found through the example of Amelia Earhart. As in the case of Rockefeller, we know Earhart today for her success as a pilot. But she also had an obstacle to overcome. In her case, however, that obstacle was represented by sexism rather than a financial crisis. Because in the misogynistic culture of the early twentieth century, there was no place for female pilots. But that wasn’t about to stop Amelia Earhart! Instead of giving up on her dream, she decided to wait and work toward the right opportunity.
To survive, she took a job that she didn’t really like and that wasn’t her dream, believing that she could keep working at this to make money until she could pursue her real dream. And as she funded her day-to-day existence through her boring job, she used her time on the side to look for creative ways to break into the aviation industry. Her opportunity knocked one random day when she got a call saying that there was funding available for the first-ever female transatlantic flight. Misogyny persisted, however, by dictating that she could be on the plane… but not as a pilot. Instead, she would be flying as an unpaid passenger. Of course, this wasn’t her dream at all, but it was a step in the right direction. So she took the opportunity, knowing that she could use it as a stepping stone — and indeed it was! Her unpaid trip on the first femaletransatlantic flight served as a launching pad for her illustrious career and she never regretted it.
So, from each of these examples, we can see that your attitude and the action you take to overcome your obstacle are two of the three key things that will help you turn your obstacle into an advantage.
Chapter 2: How to Handle Big Obstacles
So, now that we’ve looked at two great examples of success stories, it’s time to take a closer look at our own strategies and how we can apply these principles in our lives. For starters, we can see that we need to begin by asking how we can turn each obstacle into an advantage. But we often forget that this can also be applied to even the biggest obstacles we encounter — even the ones that seem too horrifying to hold the promise of any silver lining. For example, what would you do if you were accused of a crime you didn’t commit? What if you were wrongfully convicted of that crime and sentenced to life in prison? I think we can all agree that would feel like the biggest of big obstacles. So big, in fact, that it might feel it’s impossible to turn it to your advantage.
But believe it or not, even with an obstacle exactly like that, it’s possible to use that struggle as a strength — just ask boxer Rubin Carter! In the 1960s, Rubin “Hurricane” Carter had his successful boxing career cut short by a wrongful conviction for a triple homicide. He was subsequently sentenced to life in prison. At that point — imprisoned, cut off from his life, his career, and everyone he loved — no one would have blamed Rubin for giving up. But Rubin skilfully employed the strategies we discussed in the previous chapter. Of course he knew that he hadn’t killed three people and he wasn’t going to give up on fighting for his rights. But he also knew that he couldn’t afford to let his anger at this injustice consume him. So, he decided to change his attitude about the situation and see how he could find the positives.
And as a result — even though nobody wants to go to prison — his time in prison was one that cultivated growth. While he continued to pursue his case through the appropriate legal channels, Rubin used his time to educate himself. Because he had always preferred movement and exercise to sitting quietly with a book, he recognized that there was a gap in his life and that he could use this time to fill it. Even though it took 19 long years for him to be released, Rubin later wrote that he felt he was still free in his mind; when his sentence was overturned, he was simply free in body as well. What did he mean by that? By being free in his mind, he meant that he hadn’t allowed himself to be shackled with the chains of anger, worry, and fear. He was still free because he maintained an attitude that allowed him the freedom to learn, grow, and make the best of his situation.
Now, the way Rubin handled this situation might sound impossible, but really, anybody can do it! So, how can you achieve his free perspective? The author advises that the first step is emotionally distancing yourself from your personal circumstances. Of course, that’s hard to do because it’s happening to you, but don’t let the necessity of hard work scare you. Because if you can put in the work and cultivate this perspective, you’ll find that it will quite literally change your outlook on life. You might find a few strategies helpful for getting into the objective zone. For starters, you could imagine that you’re giving advice to a friend who’s in this situation.
No matter how much we love our friends, we’re always more objective when we give them advice because it’s not happening to us personally. So, start by imagining you’re advising a friend and think about what you would say. As a general rule, no matter what the problem is, we always try to help our friends look on the bright side. “Sure,” we might say, “what happened is really bad, but don’t give up! You can’t lose hope! Let’s try these solutions to make the best of it and you’ll be back on your feet in no time!” That’s what we would usually say to a friend, so that’s how we should advise ourselves. And we can apply that logic to any setback we face, whether it’s losing a job, getting rejected, or even being wrongfully convicted of a crime.
The author suggests that you can also try another option, which is to follow the logic of the Stoics. Stoicism is a school of Hellenistic philosophy that was heavily practiced in ancient Greece; those who practiced it were, obviously, referred to as “the Stoics.” Stoicism holds that self-control and emotional fortitude are the pillars for achieving success in the face of adversity. (So, pretty much exactly what we’ve been saying about turning your obstacles to your advantage!) They also believed that becoming an unbiased and objective thinker (exactly like Rubin Carter’s example) was the key to reaching emotional enlightenment. If you can do this, they believed, then you can avoid being ruled by destructive emotions. Mastering your emotions will then bring you closer to discovering the universal truth (which they believe is logic) and letting this truth guide your life. Oh, and their core guiding philosophy? It just so happened to be called “the obstacle is the way!”
Chapter 3: Overcoming Destructive Emotions
So, now that we’ve taken a look at the Stoics’ philosophy on overcoming destructive emotions and seen how that plays into Ryan Holiday’s ideology, let’s take a look at those destructive emotions and the steps we can take to overcome them. For starters, we can contextualize these emotions by thinking about them in the context where we usually experience them: obstacles. Because, let’s be honest, no one has ever reacted to the loss of their job or the death of a loved one by saying, “Woo-hoo! I’m soglad that happened!” Instead, we tend to feel anger, frustration, fear, or rage. We might be overwhelmed by worry or depression. We might find ourselves crippled by anxiety. All of these emotions are normal responses to upsetting events, but they’re also destructive. That’s because each of these emotions are so powerful that they can distort our perception and prevent us from viewing anything rationally. And that’s exactly why we have to overcome them.
So, how do we do that? Well, according to the Stoics, the key is to steel your nerves. It’s quite a vivid image, isn’t it — the mental picture of your emotions coated with steel armor? How would we feel if that were really the case? Would we feel protected and less likely to be overcome by negative feelings? We probably would! So here’s what we can do to (metaphorically) make that happen. The author recommends that you start by preparing yourself for every eventuality. However, that doesn’t mean to panic, worry, and wrack our brains as we imagine the worst possible outcomes for every event. (And if you’re like me, that might be your idea of “preparing!”) Instead, this means that we need to brace ourselves on a foundation of calm by recognizing that no matter what happens, we will be okay.
You can build this foundation by asking yourself “If this, then what?” questions. This type of question asks you to evaluate the possible outcome of your worst nightmare by considering what would happen and how you would (realistically) respond. For example, you could hypothesize, “If my husband left me… then what?” Most likely, you would be devastated, heartbroken. You might cry for days or even weeks. You might feel as though your world has fallen apart. But realistically, you would not cease to exist and your life would not be over. After a period of grieving and possibly with the help of a therapist, you would move on and find that life has meaning and you can still find joy even after your worst fear has come true. And truth be told, this is the same for every situation we will encounter. Because if we can prepare ourselves with the knowledge that, no matter what, we will be okay, then we can stay calm in the face of any trial.
Chapter 4: Final Summary
It’s easy to get overwhelmed by our emotions or to feel as though the obstacles we encounter are immovable. But Ryan Holiday wants you to know that it doesn’t have to be that way. If you instead embrace the knowledge that the obstacle can be the way forward to success, you can begin to feel empowered instead of overwhelmed. You can use that obstacle as a learning opportunity and ask yourself what it can teach you instead of seeing how it can defeat you.
And by practicing the teachings of the Stoics, you can learn to overcome destructive emotions. The Stoics believed that powering through the obstacle is the keyto success and that mastering your emotions will help you achieve that goal. So, if you keep that goal as your guiding principle, you can learn to alter your perspective, take the right action, remain calm no matter what, and make the most out of every obstacle you encounter. And if you put these strategies into practice, you will find that no matter what obstacle gets in your way, your heart and mind will remain free from the negative emotions that disempower you.

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