Get a New Perspective on Your Regrets

The soundtrack to my road trip fantasy always begins with the Allman Brothers’ “Ramblin’ Man.” In my imagination, the camera pans down to a glistening Winnebago cresting a hill on a clear blue July morning, everyone in my big family laughing, free as the clichéd wind as we sluice down narrow lanes and merge onto interstates crisscrossing the country. No school. No bosses. No deadlines. No editors. No watches. No cocktail parties. Back to nature.

Strike that. Back to my nature: the great outdoors as imagined first by a boy ill at ease in a wooden classroom chair, then a man who never felt quite like himself in a suit and tie, and eventually a writer who would channel Sal Paradise as he drove headlong into the narrative future.

I had indulged in this cross-country daydream on maybe one or two (thousand) wintry occasions over the past four decades. But the lamentable reality was clear: with seven kids spanning a generationwide 19 years, the logistics of any July-August escape from civilization was as unrealistic as my adolescent dreams of taking Marilyn Monroe to the prom. And so each summer since the late ’70s, rather than commandeering some behemoth and schlepping my brood across the Plains and over the Rockies as I had daydreamed, my family and I found ourselves marooned—happily, I should add—on a narrow barrier island in North Carolina, where we sardined ourselves into a small beach cottage a hundred yards from the Atlantic Ocean.

Not in a Winnebago cruising down Big Sur.

I have tried hard—shoulder-to-the-wheel hard—to avoid regrets in this life, a life swimming with undeserved, lucky grace. But this interstate dream has tailgated me through the decades, my heart still rising like the high Sierras when I see a lumbering motor home in the rearview mirror, then sinking like the Grand Canyon as the driver passes me with a toot and a wave.

This is the point in many essays when the weather-beaten wilderness guide is supposed to offer younger trailblazers some sage advice about not being afraid to live their dreams. You know—living in the moment, blah, blah, blah.

But after all those kids and all those summers parked on the same barrier island—not tearing up the highway behind the wheel of my fantasy Winnebago—I finally realized that while carpe diem makes the kind of good inspirational message that sells magazines, and the Serenity Prayer offers a fine antidote for sour grapes, both are dead ends on the road out of regret.

I arrived at that rueful truth a few summers ago when, early one dark and windless morning, alone on the upper deck of our little beach cottage, I watched the thick, dark stalactite of a waterspout reach down from threatening heavens to touch the sea, stirring up an inverted mushroom cloud of roiling ocean below. It was a magnificent and malevolent sight.

There was no time to run and, with the cottage perched above the sand on eight-foot stilts, no basement in which to hide. The waterborne tornado was either going to blow us to kingdom come—or it wasn’t.

In that elemental, humbling moment, instantly full of regrets far deeper than the missed opportunity for a cross-country romp, it was clear that none of us, not a single living organism on this beach, would have any special dispensation with the heavens—or the sea. No notion of being “self-actualized” would lift us above our fate. No half-baked idea of karma would save us.

In fact, there was nothing to do but stand on the deck and face the storm. Having no answer to the oncoming twister and churning seas, I could only take on the riptides of remorse in my belly: a thousand regrets at my failures as a teacher, as a writer, as a citizen of the world; a deep sorrow at not being a better father; heartbreak at not being a more adoring husband.

Alone in the depths of my fears and self-reproach, an unexpected calm washed over me—a preternatural stillness in the path of the ominous funnel cloud.

I saw then that regret offers a rare opportunity to be a better human being, a humbled cousin to the skimmers soaring just above the swells, the sand sharks below, the prehistoric sand fleas burrowing deeper with each crashing wave. I saw how regret chastened me. I saw how regret brought its own unexpected satisfactions, pointing out its own surprising pathways to salvation.

And a few minutes—or millennia—later, when the waterspout had passed by without incident and dissipated, I counted my blessings and raced over the dune, diving into the glistening Atlantic and towing behind me regrets as large as that mythical Winnebago, with a bumper sticker just below the ladder: Carpe Desiderium. Seize the Regret.

Since that day, I count my regrets every morning like a call to prayer. I howl and hiss into the great maw of the universe over my disappointments, real and imagined; and yes, I still carp on and on about that elusive cross-country romp.

And I promise to do better.

Then, like every creature that roams the earth or sea, I get back to the real work, to the keyboard, the classroom, the kitchen, the backyard, noting the wind, the currents, the scent, hunting and pecking, staving off the ceaseless hunger for one more day.