• Jason Griffing

In Praise of the Flank Attack

This Impactful Idea comes from Ryan Holiday's excellent book, "The Obstacle is the Way".


“Whoever cannot seek The unforeseen sees nothing, For the known way Is an impasse

— Heraclitus


As Holiday describes, American history paints a triumphant picture of General George Washington during the Revolutionary War. Sitting tall atop his horse, chest out, sword pointed ahead, he leads his men into a pitched battle. In actuality, Washington exhibited very little lust for battle. Instead, he relied on a wily, cautious, and evasive strategy to grind the British down.

“His most glorious ‘victory’ [Trenton] wasn’t even a direct battle with the British. Instead, Washington, nearly at the end of his rope, crossed the Delaware at dawn on Christmas Day to attack a group of sleeping German mercenaries [Hessians] who may or may not have been drunk.”

It’s no surprise, then, that Washington’s legacy has been inflated. Movies and stories teach us that wars are won and lost in giant, head-to-clashes between great armies. There’s just one problem—it’s not true. In reality, only a statistically tiny portion of the decisive victories in military history are the result of a direct attack on the enemy’s main army. Like Washington’s army, ultimate victory usually belongs to those who apply just the right amount of force, in just the right place, at just the right time.


The Impact:

What do you do when you’re facing a problem? Do you grit your teeth and attack it head on? Instead, take a step back. Be strategic. There might be an easier way.

“Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open.”

Let’s say you have a philosophical disagreement with a business partner that threatens the very core of your working relationship. Do you exert full force, attempting to bend their long-held opinions and beliefs to your view of the world? Good luck with that.


Instead, look for ways to apply “calculated force”. Ask questions. Lots of them. Look for openings. Seek common ground. Identify weaknesses in their logic. And when you find them, even then resist the urge to attack head-on. Use them to get a foothold. Probe some more. Practice the art of letting them get your way.

“You’re acting like a real strategist. You aren’t just throwing your weight around and hoping it works. You’re not wasting your energy in battles driven by ego and pride rather than tactical advantage. Believe it or not, THIS is the hard way. That’s why it works.”

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