1: The year was 1915. Deep in the jungles of Central America, two rival American fruit companies urgently wanted to acquire the same five thousand acres of land.

The challenge? Two different people claimed to own the deed to the plantation. “In the no-man’s-land between Honduras and Guatemala, neither company was able to tell who was the rightful owner so they could buy it from them,” writes Ryan Holiday in The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

One of the two competing companies was big and indomitable. It was one of the most powerful corporations in the United States: United Fruit. The second company was “crafty and cunning,” Ryan writes. It was a small, wannabe, owned by Samuel Zemurray.

United Fruit “lawyered-up,” sending down a team of high-powered attorneys. “They set out in search of every file and scrap of paper in the country, ready to pay whatever it cost to win. Money, time, and resources were no object,” Ryan writes.

Samuel knew he wouldn’t be able to “out-lawyer” United Fruit. “So he didn’t,” writes Ryan. “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? Yes, he did. And it was over: “The land was his. Forget the rule book, settle the issue,” Ryan observes.

2: What a great example of pragmatism in action. This is how we get things done!

“Sometimes we do it this way. Sometimes that way. Not deploying the tactics we learned in school but adapting them to fit each and every situation,” he writes. “Any way that works—that’s the motto.”

There are many ways to get from point A to point B. “Pragmatism is not so much realism as flexibility,” Ryan tells us. “But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.”

3: Ryan suggests we think: progress. Not perfection. “The first iPhone was revolutionary, but it still shipped without a copy-and-paste feature or a handful of other features Apple would have liked to have included,” Ryan writes. “Steve Jobs, the supposed perfectionist, knew that at some point, you have to compromise. What mattered was that you got it done and it worked.”

Our goal? To think like a “radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible,” Ryan suggests. “Under this kind of force, obstacles break apart.”

More tomorrow!


Reflection: Consider a current challenge. Ask: What am I missing? What are all my options? How might I focus on progress, not perfection?

Action: Journal about it.

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