Over the last few years, I have found myself with opportunities to make more personal decisions at a higher rate than ever before. There are three reasons for this:

  • I have more autonomy over my professional life than I did while I was in the military
  • My wife and I are now empty-nesters with far fewer demands on our daily family life
  • With the slower pace of my professional life, I have had more time to identify forks in the road even, especially when they are over the horizon 

As you might imagine, most decisions are rather mundane, but some have been monumental. Regardless of where decisions fall on that spectrum, the weight of making them can feel immense, even when it need not be. I tend to overthink and overanalyze just about every situation to minimize uncertainty and maximize the likelihood that I made the right decision. For those monumental decisions, I have begun to refer to my decision-making process as “Forecasting Regret.” Simply put, it amounts to envisioning the negative outcomes of each potential course of action and weighing each potential result against the other, immediately dismissing the alternatives that would potentially lead me to experience the greatest level of regret down the road. 

Regret is not an emotion I have experienced often as I tend not to second guess myself after the fact. Even if I was one to second-guess myself, I have found that forecasting potential regret before choosing a path heads that type of self-doubt off at the pass. Rather than being consumed by the need to make a decision, taking a moment to anticipate how we might feel about that decision after we make it is critical to increasing the likelihood that we are about to make the right one. When we do so, It’s not enough to base our forecasted feelings only on the short term. We must also consider the long-term implications, good and bad. By forecasting how we might potentially regret a decision, we can ensure our ultimate choice aligns with our personal values and long-term goals. Here are a few steps:

  1. Remind Ourselves of Our Core Values and Goals: Before diving into the specifics of a decision, it is important that we ground ourselves in our core values and long-term goals as a means of holding ourselves accountable.
  2. Consider Possible Outcomes: For each option under consideration, outline the best and worst-case scenarios. For this drill, I recommend focusing on the worst cases as the objective here is to address the potential regret associated with those negative outcomes.
  3. Engage in Mental Simulation: Imagine ourselves in the future, having already made the decision. Reflect on how we might feel about it, factually and emotionally. 
  4. Apply the 10/10/10 Rule: This rule involves evaluating how we will feel about the decision in 10 minutes, 10 months, and 10 years. What might feel right when looking through the 10-minute-later lens often feels differently when reflecting from a 10-month or 10-year later perspective. If those time horizons don’t work for you, tailor your own. Note: I did not create the 10/10/10 Rule.
  5. Seek External Perspectives: Because our personal biases can cloud our judgment, consulting with others who have faced similar decisions can provide valuable insights.

I will give you a recent example. Earlier this year, my wife and I made an offer on a condo. We were elated when the seller accepted it, but soon after we learned that some issues in the construction of the condo gave us reason for pause. We consulted with structural engineers, did lots of legal and safety research, and talked with friends and family. All of this left us believing there was an equal chance that this was either a show-stopper or nothing to worry about. We asked ourselves which potential scenario would be more regrettable:

  • Scenario One – Buy the condo anyway: Proceed with the plan only to learn that the structural damage was so significant that a substantial homeowners association assessment was required and/or that in 10 years the condo was worth less than our offering price due to the safety concerns.
  • Scenario Two – Pull back the offer: Quickly cancel the offer on the condo only to learn that there was nothing to be concerned about in the first place and that in 10 years the condo doubled in value and realize we lost this once-in-a-lifetime opportunity.

We decided that Scenario One would have left us with far more regret than Scenario Two, so we pulled back the offer and haven’t thought twice about it. There has been no second-guessing. Forecasted regret was nullified. 

  • How might the process of forecasting regret change the way you approach decision-making?
  • What specific strategies or tools, such as the 10/10/10 rule or mental simulations, would be most effective for you in forecasting regret?
  • Can you identify a past situation where forecasting regret might have led you to a different decision?

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