The game of Monopoly forces players to deal with the unexpected. The board offers several safe spaces, but it’s mostly packed with dangerous alternatives. Seven is the most commonly rolled number—my friend loved to repeat this stat throughout our games—but players must ready themselves for the worst possible scenario, even if the chances of this happening are low. If they don’t, they face the unfortunate task of choosing what to liquidate to pay off an overwhelming debt.
In Chip Heath and Dan Heath’s book called Decisive, they explain that people are more often wrong than right when it comes to their guesses about the future. The reason? We are naturally overconfident. Instead of preparing our game piece for the likelihood of landing on New York Avenue or Indiana Avenue, we envision the triumph of landing on Free Parking! Our decision-making process is clouded by misguided optimism.
A helpful tool to reverse this trend is offered by researchers J. Edward Russo and Paul J. H. Schoemaker (this is highlighted in a section of Decisive called "Prepare to be Wrong"). They have discovered that when people work backward from a certain future they are better equipped to create explanations for why the event may have happened. This approach is called “prospective hindsight.”
Why does this method work? The Heath brothers explain that prospective hindsight generates more insights "because it forces us to fill in the blanks between today and a certain future event." When we cease to wonder whether an event will or won’t happen, we can focus entirely on the task of considering why a future event would happen. This approach can be used to identify factors that might influence positive outcomes or factors that might lead to negative outcomes.
In Monopoly, the negative factors are easy to spot. You are destined to land on Boardwalk if your dice create the right combination or if you draw the dreaded Community Chess card. There’s not much you can do to withstand either situation besides stocking the appropriate amount of cash and hoping that luck is on your side.
But when prospective hindsight is used in real-life scenarios, we can generate many reasons for why a given situation might happen. Even better, we can identify the factors that pose the greatest threats to our goals and allocate resources to stall these out.