As long as you're thinking, "That shouldn't have happened or I shouldn't have done that," you're locked in a struggle against reality. Many people pour years of energy into useless "shouldn't haves." The angry ones endlessly repeat that their ex-spouses shouldn't have left them, their parents shouldn't have overfed them, or their bosses shouldn't have made them wear uncomfortable chipmunk costumes in 90-degree heat. Even drearier are the sad ones, who forever drone some version of "If only." If only they'd married Sebastian, or gotten that promotion, or heeded the label's advice not to operate heavy machinery, they would be happy campers instead of les misérables.
I call this unproductive regret. People use it to avoid scary or difficult action; instead of telling the story of the past in a useful way, they use it as their excuse for staying wretched. If you're prone to unproductive regret, please hear this: Everyone agrees with you. That thing you regret? It really, really, really shouldn't have happened. But. It. Did. If you enjoy being miserable, by all means, continue to rail against this fact. If you'd rather be happy, prune the "shouldn't haves" from your mental story, and move on to...
2. Separate Regret's Basic Ingredients
Of the four basic emotions—sad, mad, glad, and scared—regret is a mixture of the first two. Your particular situation may involve enormous sadness and a little anger ("My father died before I ever met him. Damn cruel fate!") or enormous anger with a side of sadness ("Why, why, why did I get a haircut from a stylist who was actively smoking a bong?"). Whatever the proportions, some regretters feel sadness but resist feeling anger; others acknowledge outrage but not sorrow. Denying either component will get you stuck in bitter, unproductive regret.
Considering anger and sadness separately makes both more useful. Right now, think of something you regret. With that something in mind, finish this sentence: "I'm sad that __________." Repeat until you run out of sad things related to that particular regret. For example, if your regret is contracting Lyme disease, you might say, "I'm sad that I feel awful." "I'm sad I can no longer ride my pogo stick." "I'm sad that the woods don't feel safe to me anymore."
When you've fully itemized your sadness, make another list, beginning each sentence with the phrase, "I'm angry at ________." For example, "I'm angry at my body for being sick." "I'm angry at God for creating ticks." "I'm angry at the entire town of Lyme, Connecticut, for which this $#@* disease was named." Write down all the causes for your rage, even if they're irrational.
Once you have a clear list of your sorrows and outrages, you can move on to step 3, where you'll work both angles to transform unproductive regret into the productive kind. This is extraordinarily useful but also profoundly uncomfortable because the only way out of painful emotion is through.
3. Grieve What is Irrevocably Lost
Sorrow is a natural reaction to losing anything significant: a dream, a possession, an opportunity. Productive grief passes through you in waves, which feel horrific, but which steadily erode your sadness. The crushing mountain of sorrow eventually becomes a boulder on your back, then a rock in your pocket, then a pebble in your shoe, then nothing at all—not because circumstances change but because you become strong enough to handle reality with ease.
You're finished grieving when you see someone gaining what you regret losing and feel only joy for them—maybe even secret gratitude that circumstances forced you to enlarge your own capacity for joy (this is how I feel about people who don't have a kid with Down syndrome). If your sadness stops evaporating, if a certain amount of it just isn't budging, simply grieving may not be enough. Regret is telling you to seek out a part of whatever you've lost.
4. Reclaim the Essence of Your Dreams
You can't change the fact that you binged your way up to 300 pounds, or lost a winning lottery ticket, or spent decades in celibacy rather than celebration. But you can reclaim the essential experiences you missed: loving your own healthy body, enjoying abundance, feeling glorious passion. In this moment, resolve that you'll find ways to reclaim the essence of anything you can't stop grieving.
Jenny's big regret was that one disastrous gymnastics meet had tanked her chances to make the Olympic team. When I asked her what she would've gotten from the Olympics, she said, "Pride, excitement, world-class competition, attention." Once she'd articulated these essentials, Jenny found herself gravitating toward a job in television, which provided all of them. Now, she says, her life is so exciting that she virtually never thinks about the Olympics. Instead of sidelining her, regret became just one more springboard.
I've been coaching long enough to brazenly promise that if you decide to reclaim the essence of anything you regret losing, you'll find it—often sooner than you think, in ways you would never have expected.