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The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage

von Ryan Holiday

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  • The impediment to action advances action. What stands in the way becomes the way.

  • Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?

  • What holds you back? The Physical? Size. Race. Distance. Disability. Money. The Mental? Fear. Uncertainty. Inexperience. Prejudice.

  • All great victories, be they in politics, business, art, or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus, and daring.

  • Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.

  • Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance—now at this very moment—of all external events. That’s all you need.

  • He had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.

  • We decide what we will make of each and every situation.

  • If an unjust prison sentence can be not only salvaged but transformative and beneficial, then for our purposes, nothing we’ll experience is likely without potential benefit. In fact, if we have our wits fully about us, we can step back and remember that situations, by themselves, cannot be good or bad. This is something—a judgment—that we, as human beings, bring to them with our perceptions.

  • 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.

  • What we’re forgetting in that instance, as billionaire serial entrepreneur Richard Branson likes to say, is that “business opportunities are like buses; there’s always another coming around.” One meeting is nothing in a lifetime of meetings, one deal is just one deal. In fact, we may have actually dodged a bullet. The next opportunity might be better.

  • George Clooney spent his first years in Hollywood getting rejected at auditions. He wanted the producers and directors to like him, but they didn’t and it hurt and he blamed the system for not seeing how good he was.

  • And what is up to us? Our emotions Our judgments Our creativity Our attitude Our perspective Our desires Our decisions Our determination This is our playing field, so to speak.

  • What is not up to us? Well, you know, everything else. The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.

  • The point is that most people start from disadvantage (often with no idea they are doing so) and do just fine. It’s not unfair, it’s universal. Those who survive it, survive because they took things day by day—that’s the real secret.

  • It doesn’t matter whether this is the worst time to be alive or the best, whether you’re in a good job market or a bad one, or that the obstacle you face is intimidating or burdensome. What matters is that right now is right now.

  • You know what she said to that offer? She said yes. Because that’s what people who defy the odds do. That’s how people who become great at things—whether it’s flying or blowing through gender stereotypes—do. They start. Anywhere. Anyhow. They don’t care if the conditions are perfect or if they’re being slighted. Because they know that once they get started, if they can just get some momentum, they can make it work.

  • While you’re sleeping, traveling, attending meetings, or messing around online, the same thing is happening to you. You’re going soft. You’re not aggressive enough. You’re not pressing ahead. You’ve got a million reasons why you can’t move at a faster pace. This all makes the obstacles in your life loom very large.

  • Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss 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. There’s a saying about how the Irish ship captain located all the rocks in the harbor—using the bottom of his boat. Whatever works, right?

  • “Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand.”

  • Another president, James Garfield, paid his way through college in 1851 by persuading his school, the Western Reserve Eclectic Institute, to let him be the janitor in exchange for tuition. He did the job every day smiling and without a hint of shame. Each morning, he’d ring the university’s bell tower to start the classes—his day already having long begun—and stomp to class with cheer and eagerness. Within just one year of starting at the school he was a professor—teaching a full course load in addition to his studies. By his twenty-sixth birthday he was the dean. This is what happens when you do your job—whatever it is—and do it well.

  • These men went from humble poverty to power by always doing what they were asked to do—and doing it right and with real pride. And doing it better than anyone else. In fact, doing it well because no one else wanted to do it.

  • Steve Jobs cared even about the inside of his products, making sure they were beautifully designed even though the users would never see them. Taught by his father—who finished even the back of his cabinets though they would be hidden against the wall—to think like a craftsman. In every design predicament, Jobs knew his marching orders: Respect the craft and make something beautiful.

  • Zemurray, the tiny, uneducated competitor, was outmatched, right? He couldn’t play their game. So he didn’t. Flexible, fluid, and defiant, he just met separately with both of the supposed owners and bought the land from each of them. He paid twice, sure, but it was over. The land was his. Forget the rule book, settle the issue.

  • Part of the reason why a certain skill often seems so effortless for great masters is not just because they’ve mastered the process—they really are doing less than the rest of us who don’t know any better. They choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.

  • Because (a) you’re robust and resilient enough to handle whatever occurs, (b) you can’t do anything about it anyway, and (c) you’re looking at a big-enough picture and long-enough time line that whatever you have to accept is still only a negligible blip on the way to your goal.

  • We forget how light our grip on life really is.

  • Remember the serenity prayer: If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things—it is not in our control how long we will live or what will come and take us from life. But thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.

  • To be sure, no one is saying you’ve got to do it all at once. Margaret Thatcher didn’t become known as the Iron Lady until she was sixty years old. There’s a saying in Latin: Vires acquirit eundo (We gather strength as we go). That’s how it works. That’s our motto.