What If You Could Do It All Over? The uncanny allure of our unlived lives.

Joshua Rothman in The New Yorker:

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.

More here.