A computer scientist by training, Bezos wanted a systematic way to analyze his decision—an algorithm of sorts for reaching a sound conclusion. And he finally came up with it. As he explained in a 2001 interview:
I wanted to project myself forward to age 80 and say, “Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have.” I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision.[22]
Bezos anticipated a boldness regret, then made avoiding it in the future the impetus for his behavior in the present. The Regret Minimization Framework was a wise move for him, and it’s a useful mental model for the rest of us. Anticipating our regrets, we’ve seen, can improve our health, help us become billionaires, and earn the affection of survey-distributing college librarians. It is a powerful medicine.
But it should come with a warning label.
THE DOWNSIDE OF ANTICIPATION
To understand how anticipated regrets can go sideways, let me invite you to ride a subway, buy a microwave oven, exchange a Powerball ticket, and take a standardized test.
Imagine it’s the morning rush hour and you’re racing to catch a subway train to work. On your way to the station, your shoe comes untied because in your earlier rush you tied it so hastily. You find an empty patch of sidewalk, stop for a minute, retie your shoe, and move on. As you arrive on the subway platform, you see your train pull away. Drat! If only you hadn’t stopped to fix your laces, you would have made your train.
How much regret would you anticipate experiencing from missing the train by one minute?
And a related question: How much regret would you expect to experience if instead you missed the train by five minutes?
According to Daniel Gilbert of Harvard University, who led a group of researchers who conducted experiments about this very issue at a subway station in Cambridge, Massachusetts, most people forecast that they’ll suffer much greater regret from the one-minute miss than the five-minute miss. Yet in reality, the amount of regret people actually endure is about the same in both situations, and it turns out to be not very much at all.
One problem with using anticipated regrets as a decision-making tool is that we’re pretty bad at predicting the intensity and duration of our emotions.[23] And we’re particularly inept at predicting regret. We often overestimate how negative we’ll feel and underestimate our capacity to cope or balm our feelings with At Leasts. As Gilbert and his colleagues write, anticipated regret “can be a bit of a boogeyman, looking larger in prospect than it actually stands in experience.” We’re like bumbling meteorologists who keep （mis）predicting rain. As a result, the researchers say, “decision makers who pay to avoid future regrets may be buying emotional insurance that they do not actually need.”[24]
Overestimating regret has another consequence: it can cloud our decisions. Suppose that after waiting a bit, you’ve boarded the next train and made it to work. After a productive morning, you take a lunch break and walk to a nearby electronics store to purchase a countertop microwave oven for your apartment. After a brief conversation with the salesperson, you narrow the options to two.
Both ovens are the same size, deliver the same power, and offer the same features. They appear identical except in two respects. The first microwave is from a well-known brand; the second is from a generic brand. And the first microwave costs $149, while the second costs $109.
Which do you choose?
When Itamar Simonson of Stanford University conducted an experiment like this, he found that consumers split about fifty-fifty. Half chose the more expensive name brand; half chose the less expensive generic brand.
But then he introduced a wrinkle. He told buyers that shortly after they made their decision, he’d reveal how an independent consumer magazine rated the two choices. With that promise in the air, the buyers grew cautious. More people—two-thirds, in fact—selected the name brand. People anticipated greater regret if they departed from the status quo （opting for the recognized brand） and then learned it was the wrong decision.[25] So, to bypass that unpleasant sensation, the buyers played it safe. They became less concerned with making the smarter choice and tried to make the less regrettable choice—and those aren’t always the same.