James' World 2

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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 Websites 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.

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