What If You Could Do It All Over?


Once, in another life, I was a tech founder. It was the late nineties, when the Web was young, and everyone was trying to cash in on the dot-com boom. In college, two of my dorm mates and I discovered that we’d each started an Internet company in high school, and we merged them to form a single, teen-age megacorp. For around six hundred dollars a month, we rented office space in the basement of a building in town. We made Web sites and software for an early dating service, an insurance-claims-processing firm, and an online store where customers could “bargain” with a cartoon avatar for overstock goods. I lived large, spending the money I made on tuition, food, and a stereo.

In 1999—our sophomore year—we hit it big. A company that wired mid-tier office buildings with high-speed Internet hired us to build a collaborative work environment for its customers: Slack, avant la lettre. It was a huge project, entrusted to a few college students through some combination of recklessness and charity. We were terrified that we’d taken on work we couldn’t handle but also felt that we were on track to create something innovative. We blew through deadlines and budgets until the C-suite demanded a demo, which we built. Newly confident, we hired our friends, and used our corporate AmEx to expense a “business dinner” at Nobu. Unlike other kids, who were what—socializing?—I had a business card that said “Creative Director.” After midnight, in our darkened office, I nestled my Aeron chair into my IKEA desk, queued up Nine Inch Nails in Winamp, scrolled code, peeped pixels, and entered the matrix. After my client work was done, I’d write short stories for my creative-writing workshops. Often, I slept on the office futon, waking to plunder the vending machine next to the loading dock, where a homeless man lived with his cart.

I liked this entrepreneurial existence—its ambition, its scrappy, near-future velocity. I thought I might move to San Francisco and work in tech. I saw a path, an opening into life. But, as the dot-com bubble burst, our client’s business was acquired by a firm that was acquired by another firm that didn’t want what we’d made. Our invoices went unpaid. It was senior year—a fork in the road. We closed our business and moved out of the office. A few days before graduation, when I went to pay my tuition bill, a girl on the elevator struck up a conversation, then got off at her floor; on my ride down, she stepped on for a second time, and our conversation continued. We started dating, then went to graduate school in English together. We got married, I became a journalist, and we had a son. I now have a life, a world, a story. I’m me, not him—whoever he might have turned out to be.

“The thought that I might have become someone else is so bland that dwelling on it sometimes seems fatuous,” the literary scholar Andrew H. Miller writes, in “On Not Being Someone Else: Tales of Our Unled Lives” (Harvard). Still, phrased the right way, the thought has an insistent, uncanny magnetism. Miller’s book is, among other things, a compendium of expressions of wonder over what might have been. Miller quotes Clifford Geertz, who, in “The Interpretation of Cultures,” wrote that “one of the most significant facts about us may finally be that we all begin with the natural equipment to live a thousand kinds of life but end in the end having lived only one.” He cites the critic William Empson: “There is more in the child than any man has been able to keep.” We have unlived lives for all sorts of reasons: because we make choices; because society constrains us; because events force our hand; most of all, because we are singular individuals, becoming more so with time. “While growth realizes, it narrows,” Miller writes. “Plural possibilities simmer down.” This is painful, but it’s an odd kind of pain—hypothetical, paradoxical. Even as we regret who we haven’t become, we value who we are. We seem to find meaning in what’s never happened. Our self-portraits use a lot of negative space.

For some people, imagining unlived lives is torture, even a gateway to crisis. Miller tells the story of Spencer Brydon, the protagonist of Henry James’s tale “The Jolly Corner.” As a young man, Brydon left America for Europe, where he “followed strange paths and worshiped strange gods,” living as a playboy. Three decades later, he returns to New York, where he takes stock of his peers. Many of them are rich, powerful, or respected; they have built substantial lives. Brydon, who is single and only superficially accomplished, starts to wonder how he would have turned out if he’d stayed. Would he have become a successful businessman? Married his friend Alice, with whom he’s reconnected? He begins to spend his nights prowling the hallways of his childhood home, convinced that the ghost of the man he might have been wanders there. Eventually, he meets a version of himself: an apparitional Brydon, with a forbidding face and two missing fingers, who strides forward in “a rage of personality.” Watching him, Brydon faints. He wakes with his head cradled in Alice’s lap, and realizes that he loves her: better this life than that one!

Most of us aren’t haunted so acutely by the people we might have been. But, perhaps for a morning or a month, our lives can still thrum with the knowledge that it could have been otherwise. “You may find yourself in a beautiful house, with a beautiful wife,” David Byrne sings, in the Talking Heads song “Once in a Lifetime.” “And you may ask yourself, ‘Well, how did I get here?’ ” Maybe you feel suddenly pushed around by your life, and wonder if you could have willed it into a different shape. Perhaps you suddenly remember, as Hilary Mantel did, that you have another self “filed in a drawer of your consciousness, like a short story that wouldn’t work after the opening lines.” Today, your life is irritating, like an ill-fitting garment; you can’t forget it’s there. “You may tell yourself, ‘This is not my beautiful house. . . . This is not my beautiful wife,’ ” Byrne sings.

We may imagine specific unlived lives for ourselves, as artists, or teachers, or tech bros; I have a lawyer friend whose alternate self owns a bar in Red Hook. Or we may just be drawn to possibility itself, as in the poem “The Road Not Taken”: when Robert Frost tells us that choosing one path over the other made “all the difference,” it doesn’t matter what the difference is. Carl Dennis’s poem “The God Who Loves You” tries to make that difference concrete. Dennis poses a question to his protagonist, a middle-aged real-estate agent: “What would have happened / Had you gone to your second choice for college”? A different roommate, a different spouse, a different job: could it all have added up to “a life thirty points above the life you’re living / On any scale of satisfaction”? Only “the god who loves you” knows for sure. It’s an unsettling thought; Dennis suggests that we pity that all-knowing god, “pacing his cloudy bedroom, harassed by alternatives / You’re spared by ignorance.”

Swept up in our real lives, we quickly forget about the unreal ones. Still, there will be moments when, for good or for ill, we feel confronted by our unrealized possibilities; they may even, through their persistence, shape us. Practitioners of mindfulness tell us that we should look away, returning our gaze to the actual, the here and now. But we might have the opposite impulse, as Miller does. He wants us to wander in the hall of mirrors—to let our imagined selves “linger longer and say more.” What can our unreal selves say about our real ones?

Their mere presence in our minds may reveal something about how we live: “Unled lives are a largely modern preoccupation,” Miller writes. It used to be that, for the most part, people lived the life their parents had, or the one that the fates decreed. Today, we try to chart our own courses. The difference is reflected in the stories we tell ourselves. In the Iliad, Achilles chooses between two clearly defined fates, designed by the gods and foretold in advance: he can either fight and die at Troy or live a long, boring life. (In the end, he chooses to fight.) But the world in which we live isn’t so neatly organized. Achilles didn’t have to wonder if he should have been pre-med or pre-law; we make such decisions knowing that they might shape our lives.

Among secular people, the absence of an afterlife raises the stakes. In “Missing Out: In Praise of the Unlived Life,” the psychologist Adam Phillips warns that “once the next life—the better life, the fuller life—has to be in this one, we have a considerable task on our hands.” Given just a single shot at existence, we owe it to ourselves to hit the mark; we must not just survive but thrive. It’s no wonder that for many of us “the story of our lives becomes the story of the lives we were prevented from living.”

It’s likely, Miller thinks, that capitalism, “with its isolation of individuals and its accelerating generation of choices and chances,” has increased the number of our unlived lives. “The elevation of choice as an absolute good, the experience of chance as a strange affront, the increasing number of exciting, stultifying decisions we must make, the review of the past to improve future outcomes”—all these “feed the people we’re not.” Advertisers sell us things by getting us to imagine better versions of ourselves, even though there’s only one life to live: it’s “YOLO + FOMO,” a friend tells Miller, summing up the situation nicely. The nature of work deepens the problem. “Unlike the agricultural and industrial societies that preceded it,” Miller writes, our “professional society” is “made up of specialized careers, ladders of achievement.” You make your choice, forgoing others: year by year, you “clamber up into your future,” thinking back on the ladders unclimbed.

Historic events generate unlived lives. Years from now, we may wonder where we would be if the coronavirus pandemic hadn’t shifted us onto new courses. Sometimes we can see another life opening out to one side, like a freeway exit. Miller recounts the sad history of Jack and Ennis, the cowboys in Annie Proulx’s story “Brokeback Mountain,” who are in love but live in Wyoming in the nineteen-sixties and seventies, and so must hide it. They disagree about how to understand their predicament. Ennis has no “serious hard feelings,” Proulx tells us. “Just a vague sense of getting short-changed.” But Jack, Miller writes, “is haunted by the lives they might have led together, running a little ranch or living in Mexico, somewhere away from civilization and its systematic and personal violence.” Jack tells Ennis, “We could a had a good life together, a fuckin real good life.” The existence he has is spoiled by the one he doesn’t.

It makes sense for Jack to dwell on how things might have turned out in a better world. And yet we can have the same kinds of thoughts even when we’re basically happy with our lives. The philosopher Charles Taylor, who has written much about the history of selfhood, has a theory about why we can’t just accept the way things are: he thinks that sometime toward the end of the eighteenth century two big trends in our self-understanding converged. We learned to think of ourselves as “deep” individuals, with hidden wellsprings of feeling and talent that we owed it to ourselves to find. At the same time, we came to see ourselves objectively—as somewhat interchangeable members of the same species and of a competitive mass society. Subjectivity and objectivity both grew more intense. We came to feel that our lives, pictured from the outside, failed to reflect the vibrancy within.

A whole art form—the novel—has been dedicated to exploring this dynamic. Novelists often show us people who, trapped by circumstances, struggle to live their “real” lives. Such a struggle can be Escher-like; a “real” life is one in which a person no longer yearns to find herself, and yet the work of finding oneself is itself a source of meaning. In Tolstoy’s “Anna Karenina,” Anna, caught in a boring marriage, destroys her life in an attempt to build a more passionate, authentic one with Count Vronsky. All the while, Levin, the novel’s other hero, is so confused about how to live that he longs for the kind of boring, automatic life that Anna left behind. Part of the work of being a modern person seems to be dreaming of alternate lives in which you don’t have to dream of alternate lives. We long to stop longing, but we also wring purpose from that desire.

An “unled” life sounds like one we might wish to lead—shoulda, coulda, woulda. But, while I’m conscious of my unlived lives, I don’t wish to have led one. In fact, as the father of a two-year-old, I find the prospect frightening. In “Midlife: A Philosophical Guide,” the philosopher Kieran Setiya points out that, thanks to the “butterfly effect,” even minor alterations to our pasts would likely have major effects on our presents. If I’d done things just a little bit differently, my son might not exist. Perhaps, in a different life, I’d have a different wife and child. But I love these particular people; I don’t want alternative ones.

“Excuse me, sir. I think you have your cart in front of the horse!”Cartoon by George Booth


I find it easier to imagine different lives for others. My mother grew up in Malaysia, then immigrated to America in the nineteen-seventies, as a college student. In her new country, she went to rock concerts, poetry readings, and law school, becoming an attorney with a distinguished career and achieving the kind of life she’d imagined back home. Even so, she was never really happy; she and my father divorced, and she struggled with depression and loneliness. When I was a teen-ager, we visited Malaysia together. I was astonished to find that the island where she’d spent her childhood was a tropical paradise. Her many cousins and old friends were overjoyed to see her; eating the food, her face lit up. We spent a day with a high-school boyfriend of hers, who ran a small factory (it made refrigerator magnets, as I recall); globalization was transforming the country and raising the standard of living. Would my mother have found contentment if she’d forgone the immigrant struggle? Thinking that she might have, I didn’t worry that, if she’d lived this alternate life, I wouldn’t exist.

My mother was young when she moved across the world; once we’re rooted in adulthood, even much smaller shifts can seem inconceivable. My lawyer friend, who has a wife and two children, hates his job and is always talking about leaving it so that he can pursue an entirely different profession, but he simply can’t figure out how to make the switch. I feel for him. Having clambered up his ladder, he won’t easily get down. But I also want to tell him what Jean-Paul Sartre said about the allure of imaginary lives:

A man commits himself and draws his own portrait, outside of which there is nothing. No doubt this thought may seem harsh. . . . But on the other hand, it helps people to understand that reality alone counts, and that dreams, expectations, and hopes only serve to define a man as a broken dream, aborted hopes, and futile expectations.

Sartre thought we should focus on what we have done and will do, rather than on what we might have done or could do. He pointed out that we often take too narrow a census of our actions. An artist, he maintains, is not to be “judged solely by his works of art, for a thousand other things also help to define him.” We do more than we give ourselves credit for; our real lives are richer than we think. This is why, if you keep a diary, you may feel more satisfied with the life you live.

And yet you may still wonder at the particular shape of that life; all stories have turning points, and it’s hard not to fixate on them. Sartre advanced those ideas in a lecture called “Existentialism Is a Humanism,” which he delivered in Paris in 1945, when he was only locally famous. On arriving at the venue, he discovered that he would have to push through a brawling crowd that had gathered in a sort of mini-riot. (“Probably some communists demonstrating against me,” he speculated, according to Annie Cohen-Solal’s “Sartre: A Life.”) He considered leaving the event but then decided to press on, spending fifteen minutes making his way to the front, receiving a few kicks and blows along the way. The lecture was a sensation and made Sartre an international superstar. That might not have happened if he’d decided, reasonably, to leave.

Like facets in a jewel, such moments seem to put our lives into prismatic relief. They make us feel the precariousness and the specificity of the way things are. In “The Post-Birthday World,” Lionel Shriver builds a whole novel around this conceit: its chapters alternate between two time lines, one in which Irina, its protagonist, didn’t kiss her husband’s friend, and another in which she did. (In the first time line, she often thinks back on the moment of the almost-kiss—an instant when her happy life hung in the balance.) The same essential premise animates countless popular narratives, from rom-coms like “Sliding Doors” to sci-fi series like “Devs.” And yet the premise is irrational: in truth, our lives have infinite facets, and, for any given outcome, the turning points we isolate are necessary but not sufficient. The butterfly effect works in reverse: Sartre had to give his lecture, and my wife had to step into my elevator not just once but twice, and yet many other, unremembered things also had to happen—in fact, everything had to go a certain way.

Often, these stories serve a didactic purpose; they provoke thoughts that bind us to our lives. They suggest that we should be grateful for what’s actual—that we should sink deeper into the life we have, rather than dreaming of the lives we don’t. But my mother, being unhappy, and restless by nature, thought often of her unled lives. Sometimes she seemed lost in them, or misled by them. She dreamed, in particular, of quitting her job and running a farm stand. And so, the summer after I graduated from college, she moved out of the D.C. suburbs and into a remote little house in the Virginia countryside, two hours away, near the Blue Ridge.

It was a second emigration. Her commute was punishing; unsettled and lonely, she grew isolated and drank too much. A few years later, she had a profoundly disabling stroke. Little of the person she was remains. Today, she lives in a nursing home, where, strangely, she seems content. Not long after the stroke, I made one last visit to her house, to clear it out before it sold. I took a photo of her vegetable garden, gone to seed—the closest she ever came to living the life she’d pictured.

What we could have, should have, or would have done—these kinds of thoughts follow an if-then logic. But we’re also drawn to alternative selves that hover on the edge of sense. Miller recounts how, when the musician Melissa Etheridge and her partner decided to have children, they faced a decision: for their sperm donor, they considered one of two friends, David Crosby or Brad Pitt. They chose Crosby. “My teen-agers now are, like, ‘I could have had Brad Pitt,’ ” Etheridge later said. “ ‘I could’ve been amazingly handsome.’ ” Miller shares a joke recorded by the philosopher Ted Cohen, about a man named Lev: “If I were the Czar, I would be richer than the Czar,” Lev tells a friend. “How could that be?” the friend asks. “Well,” Lev says, “if I were the Czar, on the side I would give Hebrew lessons.” If I’m the Czar, or Brad Pitt’s son, am I still me? The idea that I, myself, could also be someone else seems to exploit a loophole in language. The words make a sentence without making sense. And yet the senselessness of the wish to be someone else may be part of the wish. We want the world to be more porous and lambent than it is.

Miller quotes the poem “Veracruz,” by George Stanley, in full. It opens by the sea in Mexico, where Stanley is walking on an esplanade. He thinks of how his father once walked on a similar esplanade in Cuba. Step by step, he imagines alternative lives for his father and for himself. What if his dad had moved to San Francisco and “married / not my mother, but her brother, whom he truly loved”? What if his father had transformed himself into a woman, and Stanley had been the child of his father and his uncle? Maybe he would have been born female, and “grown up in San Francisco as a girl, / a tall, serious girl.” If all that had happened, then today, walking by the sea in Mexico, he might be able to meet a sailor, have an affair, and “give birth at last to my son—the boy / I love.”

“Veracruz” reminds me of the people I know who believe in past lives, and of stories like the one David Lynch tells in “Twin Peaks,” in which people seem to step between alternate lives without knowing it. Such stories satisfy us deeply because they reconcile contrary ideas we have about ourselves and our souls. On the one hand, we understand that we could have turned out any number of ways; we know that we aren’t the only possible versions of ourselves. But, on the other, we feel that there is some fundamental light within us—a filament that burns, with its own special character, from birth to death. We want to think that, whoever we might have been, we would have burned with the same light. At the end of “Veracruz,” the poet comes home to the same son. It’s as though my mother became a different kind of person, finding happiness in her garden while she could; and I, having moved to San Francisco, became a coder with a business plan and a head full of algorithms; and still, when our eyes met over Skype, we were us.

This vision seems impossible. As Sartre says, we are who we are. But isn’t the negative space in a portrait part of that portrait? In the sense that our unled lives have been imagined by us, and are part of us, they are real; to know what someone isn’t—what she might have been, what she’s dreamed of being—this is to know someone intimately. When we first meet people, we know them as they are, but, with time, we perceive the auras of possibility that surround them. Miller describes the emotion this experience evokes as “beauty and heartbreak together.”

The novel I think of whenever I have this feeling is Virginia Woolf’s “To the Lighthouse.” Mrs. Ramsay, its central character, is the mother of eight children; the linchpin of her family, she is immersed in the practicalities of her crowded, communal life. Still, even as she attends to the particulars—the morning’s excursion, the evening’s dinner—she senses that they are only placeholders, or handles with which she can grasp something bigger. The details of life seem to her both worthy of attention and somehow arbitrary; the meaning of the whole feels tied up in its elusiveness. One night, she is sitting at dinner, surrounded by her children and her guests. She listens to her husband talking about poetry and philosophy; she watches her children whisper some private joke. (She can’t know that two of them will die: a daughter in childbirth, a son in the First World War.) Then she softens her focus. “She looked at the window in which the candle flames burnt brighter now that the panes were black,” Woolf writes, “and looking at that outside the voices came to her very strangely, as if they were voices at a service in a cathedral.” In this inner quiet, lines of poetry sound:

And all the lives we ever lived and all the lives to beAre full of trees and changing leaves.

Mrs. Ramsay isn’t quite sure what these lines mean, and doesn’t know if she invented them, has just heard them, or is remembering them. Still, Woolf writes, “like music, the words seemed to be spoken by her own voice, outside her self, saying quite easily and naturally what had been in her mind the whole evening while she said different things.” We all dwell in the here and now; we all have actual selves, actual lives. But what are they? Selves and lives have penumbras and possibilities—that’s what’s unique about them. They are always changing, and so are always new; they refuse to stand still. We live in anticipation of their meaning, which will inevitably exceed what can be known or said. Much must be left unsaid, unseen, unlived. ♦