To win, position. To position, OODA: Observe → Orient → Decide → Act.

Despite what my enemies tell you, I am not the enemy.

Between 3:52 and 6:15 pm today, I played 2 games of Catan with friends I met a couple of weeks ago. One guy clearly saw me as a threat, so he tried to stifle me. He missed the importance of rallying others (i.e. an embargo against the leading player), so he failed.

He observed correctly, but he failed to orient. (To orient is to figure out what your observation actually means. He saw I was a threat: Observing. He missed that the answer was rallying others against me: poor Orienting.)

Almost all skillful game behavior is about positioning. Positioning means observe and orient, then repeat (and repeat…) before you decide and act.

Chess: Literally “Proving It”

Most high-level chess matches end in resignation, not checkmate. In these situations, chess is not played to win, but played to superior position.

At the highest levels, a player sometimes resigns before your average (ie 1500-rated) chess player even understands why. It’s not even “Player A is now ahead by a knight.” It’s “Player A would be ahead by either a knight or two pawns in 4 moves and they both know it.”

High-level positional chess games are almost incomprehensible to your average observer, just as a fighter pilot saying “Is the humidity 45% or 46%?” wouldn’t mean anything to me. I don’t even know if humidity is relevant to a fighter pilot! That’s the point.

Even better for me and my point and the puns in this post: in chess, they literally call the process of someone playing an advantage to its victorious end “proving it.” The positioning is the game; the proof is execution. 

OODA? Ooh! Duh!

Speaking of fighter pilots (“What a segue! This guy can really write!”), in the early 1970s, US Air Force Colonel John Boyd established the OODA loop as a decision-making framework for his pilots.

In an OODA loop, one Observes, Orients, Decides, then Acts.

Four moves. Three are about positioning.

Pair the OODA loop with my favorite fighter pilot quote (“How many fighter pilots does this guy know?”): 

• “A superior pilot uses his superior judgment to avoid situations which require the use of his superior skill.”

The process becomes:

1. Get good enough at the skills, so
2. you understand how the skills work, and therefore
3. don’t have to use the skills anymore, because
4. you’re dodging the danger.

(Can you imagine how much of a fighter pilot’s practice is Observing and Orienting? Reminds me of my brother-in-law!)

The Games Behind the Pokerface

In The Count of Monte Cristo (my current tome; spoilers incoming), our hero escapes from prison and is picked up by a nearby boat. The prison fires off a cannon shot. Immediately, the boat’s captain asks, “What does that cannon mean?”

Our Hero calmly states, “A prisoner has escaped from the Chateau d’If [prison], and they are firing the alarm gun.” 

Our Hero’s nonchalance convinces the captain that Our Hero isn’t the escapee. Your average person might feign ignorance. But Our Hero – by his claimed background – would know what the cannon means. This move may appear more dangerous, but it’s much safer.

Our Hero’s OODA loop is beautifully speedy: not only does he observe and orient quickly, but he also decides and acts speedily, all while not appearing to be doing so.

This approach is also true for game experts. Many poker players win games in ways you don’t even realize they’re playing:

• Getting invited to the softest games
• Table selection
• Position at a table relative to both good and bad players
• Talking with fellow players before any cards are dealt to learn their psychology and therefore their leaks.

Stop Acting

(Note to self: find some subtle way to mention to the reader that this section title has a double meaning.)

I am quite skilled at a particular tactic my mother describes as “Baffle them with bullshit.” It’s all Acting, and no OOD. I recognize the pattern → Act. It lacks… a certain elegance.

Relaxing and contemplating (Observe and Orient) have historically been my weaknesses.

To be fair, it’s live Observe and Orient that’s my weakness. I’ve stored plenty through years of preparation, which is why those around me say I’m skilled at games. But Pattern-Match → Act is just stored OO at hyperspeed. In known scenarios, this works. Live execution in novel territory is a different animal.

My poker game has won thousands of dollars despite my complete lack of poker face.

I wish I could install an old turntable in my brain. It would Observe, then Orient, then Observe again… until sufficiently positioned, then Decide and Act. The beauty of the turntable: it’s stuck in the OO grooves (“Ooooooooooo”). I’d have to thunk it on the side to shake it into DA.

As my new Catan group improves at the game, each player will develop our own approach. My Catan-enemy will either improve at his orientation or continue being shot down.

It’s like that key rule everyone knows in the game of real estate: Position, Position, Position.