Pick your one or two best gambling decisions throughout your life. Pick them before reading on. Take however much time you need. This blogpost will be here when you get back.

This post has been inspired by my recent reading of Annie Duke’s books, “Thinking in Bets” and “Quit.” I wrote about these books last week. I’m not sure which book spoke about this topic. I read them more or less concurrently as audiobooks checked out from the library, and they’ve both been returned.

Had I answered this question before I read Duke’s works, I probably would have chosen that night in 2001, following comped tickets to the Espys at the MGM Grand in Las Vegas, where I hit a $100,000 royal flush followed a half-hour later by Shirley, my wife at the time, hitting one for $400,000. That was my biggest score ever (so far!), and indirectly led to my “Million Dollar Video Poker” autobiography, while also making others believe I was a strong player. 

Today, that evening wouldn’t make my top ten in terms of gambling decisions.

That night represents my best result — not my best decision. Your result combines your decision-making and your luck. So that was my luckiest night. But probably not my best decision. By the time that evening came along, I knew the MGM Grand system could and had already made the decision to put in as many hours as I could before either the games were removed — or I was. That night was part of an earlier decision (which may well be among my best ones), but there was nothing special about gambling that night — other than the lucky result. I was not a better player one day after that night compared to my skill level the day before. But the score convinced others that I was an expert.

Another good decision concerned getting ready for a series of promotions — including how much to play, starting when, and what deception to use to make the play last longer. Less than a week before I arrived, they removed the game I planned to play. What I planned didn’t translate to the best remaining game. So, all that planning came to naught. Still, the decisions I made getting ready for the play were excellent. The fact that the game was removed prior to me being able to implement the play doesn’t mean my decisions were faulty in the least.

Annie Duke muses that when most people think about their best decisions, they almost always pick ones that turned out well. They are not separating the decision itself, which they can control completely, with the amount of luck that arose while implementing the decision, over which they have much less control. The result itself is very loosely correlated with the quality of the decision.

They say, “Luck favors the well prepared,” and I tend to agree. Making good decisions to put yourself in position to win is an important part of the winning process. Still, when you draw two cards to three aces, it’s largely luck that determines whether that 2-in-47 fourth ace comes in this time. And some days you’re dealt three aces more often than usual. Sometimes less. You have no control over that.

Keep making good decisions. Good results will usually turn up over time, with lucky and unlucky swings along the way.

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Bob Dancer

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