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.

There is such a thing as too much sanity

A woman leading a slave rebellion shares a thought: "Too much sanity may be madness. And the maddest of all—to see life as it is and not as it should be."

This is certainly not the first time we’ve come into contact with this idea. Robert Kennedy famously mentioned dreaming of “things that never were and say[ing] ‘why not?’ He was riffing on George Bernard Shaw, I think, so no, this is not an original idea.

But it is worth repeating. Life is too important to accept and submit without thought. To ask why we do something, and why we do not do another thing, is the first step towards all progress. To be willing to ask that question is how we discovered new lands, flew in the sky and to the Moon, and doubled human lifespans in the past two centuries.

This is the greatest plague facing large organizations. The larger they are the harder it is to see what they should be. Because, as in physics, with size they gain inertia and that becomes very hard to halt and change course.

To gain everything, possess nothing

There's a quiet moment between two main characters, who have been rivals for long but are now united against a common enemy. Both are successful ship captains, but one is much more committed to the light lifestyle.

Charles Vane: "All these things. Porcelain. Books. All so goddamned fragile. The energy it must take to maintain it all. And for what?"

Captain Flint: "You have no instinct towards earning for yourself a life more comfortable?"

Vane: “I don't. And had I that instinct I would resist it with every inch of will I could muster. For that is the single most dangerous weapon they possess. The one they tempt. 'Give us your submission, and we will give you the comfort you need.' No, I can think of no measure of comfort worth that price."

I admit, on first glance one might ask what that snippet is doing in a column otherwise about strategy and strategy-making.

But to my mind, there may be no lesson more important than that for a strategist. A strategist must be fully committed to being beyond the seductive lure of status. (Of course, the back-and-forth above is about physical objects, but status is often the coin of the realm amongst strategists.) Personal status may be the death of more strategic minds than all the Four Horsemen put together.

For what it is worth, I've taken that lesson to heart perhaps more than any other. And in so doing I've taken to fight the natural desire to gather physical things and status.

That may sound monastic to some. Abhorrent. But the less weight you carry around this world, the less value you place on stuff and status, the better off you'll be, because you'll be able to speak the truth to the power when the times comes, and without that ability, you will never be the strategist you want to be.