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Chapter 34 of 66

“Wanna bet?” redux

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were missing made me feel good about myself, reinforcing my routine change.

Ideally, we wouldn’t compare ourselves with others or get a good feeling when the comparison favors us. We might adopt the mindful practices of Buddhist monks, observing the flow of inner thoughts, emotions, and bodily sensations without judging them as good or bad at all.

That’s a great goal, and I’m all for a regular mindful practice. It will, the research indicates, help improve quality of life and is worth pursuing. But getting all the way there is a tall order if we don’t want to quit our day jobs and move to Tibet. It works against the way our brains evolved, against our competitive drive. As a parallel practice, the more practical and immediate solution is to work with what we’ve got, using that comparison to strengthen our focus on accuracy and truthseeking. Plus, we won’t have to give up our lives and find a remote mountaintop to live on.

We need a mindset shift. We need a plan to develop a more productive habit of mind. That starts in deliberative mind and requires foresight and practice, but if it takes hold, it can become an established habit, running automatically and changing the way we reflexively think.

We can get to this mindset shift by behaving as if we have something at risk when we sort outcomes into the luck and skill buckets, because we do have a lot at risk on that fielding decision. Thinking in bets is a smart way to start building habits that achieve our long-term goals.

“Wanna bet?” redux

Treating outcome fielding as a bet can accomplish the mindset shift necessary to reshape habit. If someone challenged us to a meaningful bet on how we fielded an outcome, we would find ourselves quickly moving beyond self-serving bias. If we wanted to win that bet, we wouldn’t reflexively field bad outcomes as all luck or good ones as all skill. (If you walked into a poker room and threw around words like “always” and “never,” you’d soon find yourself challenged to a bunch of bets. It’s easy to win a bet against someone who takes extreme positions.)

Imagine getting into an accident at an intersection after losing control of your car on a patch of ice you couldn’t see. Your first thought would likely be that you got unlucky. But what if you had to bet on that?

Depending on the details, there would be a lot of alternatives to just plain bad luck you would now consider. Based on the weather, maybe you could have anticipated some ice on the road. Maybe you were driving too fast for the weather conditions. Once the car started sliding, maybe you could have steered differently or maybe you pumped the brakes when you shouldn’t have. Maybe you could have taken a safer route, choosing a main road that would have been salted. Maybe you should have kept the Mustang in the garage and taken the Suburban.

Some of the reasons we come up with may be easy to discount. And some may not. The key is that in explicitly recognizing that the way we field an outcome is a bet, we consider a greater number of alternative causes more seriously than we otherwise would have. That is truthseeking.

This is what Phil Ivey does.

The prospect of a bet makes us examine and refine our beliefs, in this case the belief about whether luck or skill was the main influence in the way things turned out. Betting on what we believe makes us take a closer look by making explicit what is already implicit: we have a great deal at risk in assessing why anything turned out the way it did. That sure sounds like a bet worth taking seriously.

When we treat outcome fielding as a bet, it pushes us to field outcomes more objectively into the appropriate buckets because that is how bets are won. Winning feels good. Winning is a positive update to our personal narrative. Winning is a reward. With enough practice, reinforced by the reward of feeling good about ourselves, thinking of fielding outcomes as bets will become a habit of mind.

Thinking in bets triggers a more open-minded exploration of alternative hypotheses, of reasons supporting conclusions opposite to the routine of self-serving bias. We are more likely to explore the opposite side of an argument more often and more seriously—and that will move us closer to the truth of the matter.

Thinking in bets also triggers perspective taking, leveraging the difference between how we field our own outcomes versus others’ outcomes to get closer to the objective truth. We know we tend to discount

the success of our peers and place responsibility firmly on their shoulders for their failures. A good strategy for figuring out which way to bet would be to imagine if that outcome had happened to us. If a competitor closes a big sale, we know about our tendency to discount their skill. But if we imagine that we had been the one who closed the sale, we are more likely to find the things to give them credit for, that they did well and that we can learn from. Likewise, when we close the big sale, let’s spare a little of the self-congratulations and, instead, examine that great result the way we’d examine it if it happened to someone else. We’ll be more likely to find the things we could have done even better and identify those factors that we had no control over. Perspective taking gets us closer to the truth because that truth generally lies in the middle of the way we field outcomes for ourselves and the way we field them for others. By taking someone else’s perspective, we are more likely to land in that middle ground.

Once we start actively training ourselves in testing alternative hypotheses and perspective taking, it becomes clear that outcomes are rarely 100% luck or 100% skill. This means that when new information comes in, we have options beyond unquestioned confirmation or reversal.

We can modify our beliefs along a spectrum because we know it is a spectrum, not a choice between opposites without middle ground.

This makes us more compassionate, both toward ourselves and others.

Treating outcome fielding as bets constantly reminds us outcomes are rarely attributable to a single cause and there is almost always uncertainty in figuring out the various causes. Identifying a negative outcome doesn’t have the same personal sting if you turn it into a positive by finding things to learn from it. You don’t have to be on the defensive side of every negative outcome because you can recognize, in addition to things you can improve, things you did well and things outside your control. You realize that not knowing is okay.

Certainly, in exchange for losing the fear of taking blame for bad outcomes, you also lose the unadulterated high of claiming good outcomes were 100% skill. That’s a trade you should take. Remember, losing feels about twice as bad as winning feels good; being wrong feels about twice as bad as being right feels good. We are in a better place when we don’t have to live at the edges. Euphoria or misery, with no choices in between, is not a very self-compassionate way to live.