My grandfather worked four jobs. He was a fireman, a handyman, a substitute teacher, and a housepainter. With those jobs, he was able to put four children through college. That’s where he spent all his money, because he knew that education was the best way to get ahead in life. (This was before Instagram and sex tapes.)

“Protect your brain!” he always told me. “Because it’s all you got! Your brain is your ticket to wherever you want to go.” (I think he might have been Ms. Frizzle from “The Magic School Bus.”)

It was definitely my ticket out of Staten Island, because it got me into a Catholic high school called Regis,1 which would change the course of the rest of my life. I was extremely lucky to get accepted to Regis, because (a) it’s one of the best high schools in the country and (b) it’s free. For Catholics in New York, Regis is almost like the Watchtower building for Jehovah’s Witnesses. Tens of thousands of kids apply for a hundred and twenty spots in each class. To this day, if a Catholic mother hears that I went to Regis, she will grab my face and say, “God bless! What a wonderful place!”

The only catch was that Regis was in Manhattan. So on a good day it took me an hour and a half each way to get there.

I took a bus, then a ferry, then a subway—which, when you type it into Google Maps, looks like you’re emigrating from China to San Francisco in the eighteen-forties.

But no one complained about the commute, because it was a free high school, and we all felt insanely grateful to be there. As my grandfather reminded me, “If you don’t want to make the trip, there are plenty of kids who would take your place!” Then he’d say, “By the way, did you hear about the boy who stuck his head out the bus window and hit a telephone pole and his head ripped clean off his body? Protect your brain!”

Initially, my parents were very worried about their overweight, dirty-blond, gap-toothed fourteen-year-old commuting alone into New York City and taking the subway home late at night. (My freshman photo is a real “Come and get it!” to subway pedophiles.) Like many of the kids at Regis, I was book smart and street illiterate. There was a nickname for New York in the nineteen-thirties that I always loved: the Wonder City. And for most of us, coming from the suburbs and suddenly being in the middle of Manhattan with no adult supervision after school ended, New York was a wonder city on every level.

Some of my friends used this freedom to do actual fun things, like taking Ecstasy and sneaking into clubs like the Limelight (a deconsecrated church where you could dance on the altar) or Tunnel (which seemed to get shut down once a month because someone O.D.’d or got stabbed). Police referred to Tunnel as “an open-air drug supermarket.” (Which today is just a Walmart.)

I was way too afraid to try drugs, because, again, my brain was all I had! So I enjoyed the nerdier perks of being in Manhattan, like seeing a David Lynch movie that never would have played on Staten Island. Or sneaking into a private club to watch poets pay tribute to Robert Giroux, one of the founders of the publishing house Farrar, Straus & Giroux. You know, crazy teen-age high jinks!

I wasn’t always so squeaky clean, though. Occasionally, I would sign out of school under the guise of visiting a nearby museum, but would instead run off to play billiards at a local pool hall, like one of the troubled teens in “The Music Man.” Or my friend Milosz and I would go to the Knitting Factory or a performance-art space called ABC No Rio. We’d share a forty of malt liquor and watch a twelve-person band called the World / Inferno Friendship Society perform punk-klezmer songs about Weimar Germany, Paul Robeson, and the Austro-Hungarian actor Peter Lorre. The closest thing we had to that on Staten Island was a waiter who sang “That’s amore! ” And, one time, my friend Pete and I went to an Italian restaurant downtown and ordered “one glass of red wine, please!” And they brought it! One glass of red wine for two out-of-control teens. Then we stumbled home, flying from the wine but also terrified because we thought “The Blair Witch Project” was real and the witch was coming for us next. (Did I mention that we were book smart?)

I got to meet the most intimidating and sophisticated girls in the world. Girls who attended fancy neighboring schools with names like Marymount, Chapin, Spence, and Nightingale—names that just sounded rich. We would have high-school dances and somehow persuade them to attend, and I felt like a way chubbier Jay Gatsby faking a cultured air to mask my Staten Island-bootlegger upbringing. (That’s still how I feel ninety-five per cent of the time.)

All my friends and I would hang out for hours after school, because no one wanted to go home. The adventure of the city was so much more exciting than anything waiting for us in the outer boroughs. It was like a slightly more grown-up version of “The Goonies.” Only, our treasure? Was knowledge. And our Sloth? Was a guy on the subway who looked like Sloth. And look at that . . . he’s unzipping his pants. “Hey-y-y, you guy-y-y-ys!!!”

The upside of having an hour-and-a-half commute is that you can get a lot of homework done on the way home. (And on the way to school in the morning you can cram for all the tests you didn’t study for the night before.) There were also many days when homework and studying were disregarded in favor of extremely juvenile and dangerous behavior. Like doing “dips” on the chain-link ropes between two moving subway cars. Or seeing who could run across all four subway tracks to the platform on the other side without “touching the third rail” and “dying.” Or tying your friend’s hands to the subway pole and then “pantsing” him so that he was naked and couldn’t pull up his pants. And then, if a stranger on the train tried to help him, you’d yell, “He’s touching that kid!” Really smart, cool stuff like that.

There were scarier moments, like when a group of older, much stronger teen-agers followed us off the train late one night, jumped us, and broke my friend Pete’s nose. Or the time when I was standing on the corner of Houston and Bowery and watched a man step into the street and get hit at full speed by a city bus, and his body basically exploded in front of me. That was very, very disturbing, and I can still close my eyes and picture pieces of him lying on Houston Street. But it’s also New York, so fifteen minutes later you just move on with your day.

I was always on edge when I travelled home alone late at night. I was very conscious of never smiling, because I was afraid that if I smiled someone would punch me. I actively tried to look sad, and, in keeping with my living-in-my-head approach to life, I would invent awful things that had happened to me to tell a robber so that he would feel guilty and then not rob me. Like, I expected a robber to say, “I’m so sorry, Colin. I was going to steal your ten dollars, but after hearing that your cat killed your sister I cannot in good conscience take your money. In fact, here’s five dollars from me. In memory of your sister, Noxzema.”