When I read this passage, I thought immediately of Jeremy with his Jack Kerouac affinity. Then I thought this applies to many Zed Omegas plus a whole lot of folks where choosing something uncertain often means dropping away from the safe route they’d been on. Here’s a rare first-person account in what otherwise is a mostly journalistic tone in How Children Succeed: Grit, Curiousity, and the Hidden Power of Character, by Paul Tough of dropping out of college at 18: 

“I found myself wondering anew about my decision to drop out. Why had I done it? I dug through a box of old papers from that era, looking for clues, and I discovered a letter that I’d almost forgotten, a long exegesis of my decision to quit that I wrote in my Columbia dorm room over Thanksgiving weekend that freshman fall. It was eight pages long, single spaced—and, to give you an idea of the technological age we’re talking about, it was written not only in longhand but in cursive. I pulled out the letter—it had a couple of coffee stains, but it was still legible—sat down in my office, took a long deep breath, and reread it. It was, as you can imagine, pretty embarrassing. There is no soul more overwrought than that of an eighteen-year-old trying to make a life-changing decision. But I was glad I had found the letter, and despite its moments of adolescent insufferability, I felt a good deal of compassion for my conflicted younger self.

I had been a high-achieving student in high school, with good grades and good standardized-test scores. I arrived at college excited but confused, lost on a campus and in a city where I didn’t know a soul. I was glad to be in New York but less glad to be sitting in lecture halls. Even in high school, while I was being such a responsible student, I had felt grave doubts about my relationship with formal education. I had a rebellious streak—I was a teenage Kerouac reader—and like million of high-school rebels before me, I was convinced that what I was learning in the classroom didn’t really matter, man. And on that November day at Columbia, I decided I had finally had enough. “I have been educated for fifteen years and three months, which is 84 percent of my life,” I wrote, with characteristic precision (for the record, I was counting from the first day of nursery school). “Going to school is all I know. Education is a game, and let’s face it: I’m good at it. I know the rules; I know how to perform all the required tasks. I even know how to win. But I’m sick of the game. I want to cash in my chips.”

It is always hard, the eighteen-year-old me wrote, to quit doing something everyone tells you you’re good at in order to do something you’ve never tried before. But that was precisely what I felt I needed: to do something uncertain, unsafe; something I didn’t know if I could succeed at. The specific trial I fixed upon for myself was a long journey, an odyssey of sorts: I would take some of the money I was about to spend on my next semester’s tuition, buy a touring bicycle and a tent, and pedal my way, alone, from Atlanta to Halifax, sleeping in state parks and the backyards of strangers. It was an odd idea. I’d never been on a long bicycle trip before, and I never been on even a short one by myself. I’d never been to the American South. I wasn’t particularly good at talking to strangers. But I somehow felt compelled to subject myself to this mission. I had a notion that I might learn more along the road than I would on campus. “This may be a total failure, a flop, a disaster of gargantuan proportions,” I wrote. “It may be the most irresponsible thing I’ll ever do. But it may be the most responsible.”

A couple of days after the New York Times Magazine story on KIPP and Riverdale [schools] came out, a reader sent me an e-mail message saying he thought I should watch the commencement address that Steve Jobs gave at Stanford University in 2005…. And believe me, if decades after you drop out of college, you’re still trying to justify your decision, there’s nothing more reassuring than finding out that one of the most successful and creative businessmen of modern times did the same thing. And what’s more, that he had no regrets.

… A month or so after writing my dropout letter, I did, indeed, drop out. I bought a bike and a tent and a Coleman stove and a one-way plane ticket to Atlanta, and from there I bicycled to Halifax, through many rainstorms, flat tires, and strange encounters. It took me two months, and at the end of the journey, I felt it was the best thing I’d ever done. I gave college another try a few months later, back in my native Canada—McGill University, in fact, where a decade or so later Michael Meaney would begin to discover such amazing things about rat mothers and their licking habits [integral research included earlier in the book]. And then three semesters after that, I dropped out again to take an internship at Harper’s Magazine. This time, the dropping-out stuck. I never went back to college, never got a BA, and, haltingly, I began a career as a magazine editor and a journalist. I didn’t go on to found Apple, or even NeXT (Jobs’s failed computer company), and in fact, I continued for the next two decades to struggle with some of the same questions I had been wrestling with in that dorm room—Should I do something I’m good at or something I love? Take a chance or play it safe?—until on another fall morning, twenty-four years after dropping out of Columbia, I found myself dropping out of another esteemed New York institution, the New York Times, again without much of a safety net. This time, the strange adventure I set out on was not to pedal a bicycle halfway across the country; it was to write a book. This one.”