In Praise of the Flank Attack

Continuning my The Obstacle is the Way project, a chapter on the underdog.


This chapter begins talking of George Washington. It points out that he never led large armies in masterful attacks against other armies, but instead specialized in attacking the British where they were weak, and withdrawing troops who would have been lost in open conflicts.

Of course, I’m reading this after listening to the Hamilton soundtrack so often that I can’t read anything by him in another voice. Still, this paragraph is good:

Never attack where it is obvious, Washington told his men. Don’t attack as the enemy would expect, he explained, instead, “Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success.” He had a powerful sense of whic minor skirmishes would feel and look like major victories.

Ryan Holiday’s point isn’t to belittle Washington, or even to “bring him off a pedestal.” Instead, he’s saying that the genius we admire about him was his ability to do what worked for him, not what worked for his enemies.

To me, this is prescient in an era in which we say things like “we have to sacrifice some civil liberties because the terrorists don’t accept liberties.” Or, less politically, “if you want to operate an online business, you have to track your customers or you’re going to lose out against the big companies who do.”

There’s something attractive to me about abandoning the idea that, to beat the biggest player in the ring, you have to do what that player is doing.

The chapter includes a few other examples, including a basketball superstar I’ve never heard of (me and sports, I guess).

Then, there’s something valuable towards the end:

The way that works isn’t always the most impressive. Sometimes it even feels like you’re taking a shortcut or fighting unfairly. There’s a lot of pressure to try to match people move for move, as if sticking with what works for you is somehow cheating. Let me save you the guilt and self-flagellation: It’s not.

All in all, I liked this chapter. Upon reflection, I don’t know that it said anything that wasn’t in the other chapters, but it was presented well and, as I get to work on the next steps in my own idea, I needed the encouragement to do something unusual.

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