Regret to the Rescue: How To Be Brave When You Don’t Feel Brave

Brave decisions are the stepping stones between where we are and where we want to go. But what do you do when you need to make a brave decision—to make that phone call, to ask that question, to accept or reject that promotion—and your bravery is M.I.A.?

A while back, a junior investment banker told his boss about an idea for a new business. “I think it would be a better idea,” his boss said, “for somebody who didn’t already have a great job.”

The junior banker then asked himself: When I’m 80 years old, how will I feel about this?  In answer to his own question, Jeff Bezos famously concluded: “It might sting to leave this good job and not make that kind of money again.  But I know for a fact, I have this idea, and if I don’t try it, I’m going to regret it.”

With this question, Bezos tapped into the power of something called “anticipatory regret.”In their now famous experiments, Daniel Kahneman and Amos Tversky discovered that simply anticipating the regret we might feel later is why we irrationally cling to tanking investments instead of cutting our losses (what if it goes back up!), and why we experience FOMO (tomorrow’s Instagram feed will be more than I can bear!).

But in a bit of psychological judo, Bezos turned the power of anticipated regret back on itself. Instead of focusing on the regret of possibly missing out on a lucrative banking career like his boss imagined, Bezos anticipated an even bigger regret of not pursuing his idea and being cursed to forever wonder what if?

Almost every seemingly “courageous” thing I do is spurred on at some point by anticipatory regret.  Every time I prepare to step on stage in front of hundreds or thousands of complete strangers, periodic waves of anxiety wash over me.  But that fear is always overpowered by my fear of how I’ll feel later about myself if I don’t walk onto that stage.

Before walking into a crowd of Spanish-speakers (a daily occurrence living in Puerto Rico) I feel a surge of anxiety thinking about the moments of awkwardness and vulnerability I’m about to endure. But after quickly imagining how much I will later regret pretending to be on a phone call during my kid’s entire basketball practice, or driving home from the grocery store without the bread and milk I specifically went there to buy; I open the car door, square my shoulders, and march into the fray pretending like I’m comfortable and confident.

A few moments later, something magical happens.

After clicking lock on the minivan’s key fob, my pretend confidence begins morphing into something like real confidence.  After hearing my hotel room door latch shut behind me as I begin trekking down to the ballroom where I’ll be speaking, my anxiety starts giving way to excitement. In some strange spell of mental alchemy, I must do this slowly becomes I want to do this.

I imagine Jeff Bezos sipped on that same neuro-cocktail of nervous energy mixed with excitement as he watched the skyscape of Manhattan slowly recede in his rearview mirror, inching toward his destiny in Seattle.

And that’s the point.  Anticipatory regret is not about creating a semi-permanent state of fear where you spend your days pinballing from one imagined fear to the next.  It’s about giving your bravery a jump-start, a little boost to push you over the finish lineof your next brave decision.