What If You Could Do It All Over?

What If You Could Do It All Over?

The uncanny(ˌənˈkanē) allure(əˈlo͝or) of our unlived lives.

By Joshua Rothman

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(dätˈkäm) boom. In college, two of my dorm(dôrm) 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(ˈmeɡə). 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(inˈSHo͝orəns)-claims-processing firm, and an online store where customers could “bargain(ˈbärɡən)” with a cartoon(kärˈto͞on) avatar(ˈavəˌtär) for overstock goods. I lived large, spending the money I made on tuition(t(y)o͞oˈiSH(ə)n), food, and a stereo(ˈsterēō).

I liked this entrepreneurial(ˌäntrəprəˈnərēəl) existence—its ambition(amˈbiSH(ə)n), its scrappy(ˈskrapē), near-future velocity(vəˈläsədē). 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(ˈbəb(ə)l) 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(ˈinˌvois) went unpaid. It was senior(ˈsēnyər) 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(ˈeləˌvādər) struck up a conversation, then got off at her floor; on my ride(rīd) 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.