Strategic wisdom from pirates

What 'Black Sails' can teach about strategy

I know it's a show. I get that. It's not even a fiction so much as a fiction built on top of another fiction (a prequel to Robert Louis Stevenson's Treasure Island). That makes Black Sails (on Starz) something of a double lie.

Still. It is humans at conflict. Competing, killing, duels for advantage. To win. While it is only on-screen in two dimensions, aren’t these scenarios the starter's pistol for all strategy? Zero-sum contests for some indivisible prize. Maybe though it’s fake, it's fiction, or double fiction even, maybe there's really something here to pay attention to.

I've had some spare time on my hands lately, and so I re-watched the entirety of the four seasons. Yep, that's a lot of time. A lot of time to watch these cascading competitions, and there were several moments that stuck out to me as worth thinking through beyond the screen.

Sail into the storm

There's a moment where one captain sets a trap for another by stranding a ship in the middle of the sea. When the pursued captain stops out of curiosity, the pursuer advances into attack position. Because the pursuer has the favorable winds, the pursued captain is put to a choice: surrender, or fight from a disadvantaged spot.

The pursued captain makes a third option—he sees a storm and sails straight into it. By doing so he knows he may be headed into a “ship-killer,” but his pursuer will not risk the same storm.

There are at least two real takeaways from this fake scenario. The first is to deny your adversary the ability to dictate your choice. To break out from the straightjacket your adversary wants to place upon you. The second is to have the courage to do that which no one else would. To find another way, even if no one would take that way. To change the game by doing that which others will not.

Mind the trendline

There's a moment with Captain Flint, a key character on the show, where he tells a close confidant: "All warfare is the same. Two questions are of paramount importance. Who was my opponent yesterday and who is he today? Answer those two questions and there is very little he can hide from you."

I could not agree more. Perhaps this is the part Sun Tzu left out. The problem with "know yourself” and "know your adversary" is that it doesn't include depth. Or past. Or history. Or what came before. All those must matter. Seeing what's in front of you is important, but knowing what came before seems just as, if not more important.

It provides you a pathway. Plot two points (more if you're lucky, but two will do) and you can spot what may come next and where your conflict may be headed.