I wrote an article about KIPP and Riverdale and character, drawn from the reporting I did for this book, that was published in the New York Times Magazine in September of 2011. The article produced an unexpected flood of responses from readers, many of whom said they related to Randolph’s ideas about failure and success. Some of them contributed comments on the Times’s website about their own experiences, like “Dave,” who wrote that he had been one of the kids Randolph was talking about, the ones who got high test scores and lots of praise but never developed the grit that came from confronting real challenges. “I’m left now, in my thirties,” Dave wrote, “often wondering how much more I could have accomplished if I wasn’t terrified of failure, and prone to shying away from ventures where my success wasn’t guaranteed.”

Not long after the article was published, and while I was immersed in the research on college persistence, 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 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 millions 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 being 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 that 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’d 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 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. There were a lot of parallels, he wrote, between Jobs’s thoughts on failure and character and the debates that I’d tried to capture in the article. After Jobs’s untimely death, the Stanford speech got a lot of attention, but as it happened, this was a few weeks before he died, and I’d never seen or read it. I clicked the YouTube link the reader had sent and watched Jobs speak, and I soon realized I didn’t know much about his life story. Watching that speech, I learned that in his freshman year, Jobs had dropped out of college—Reed College, in Oregon. 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. In his speech, Jobs explained that dropping out had “been one of the best decisions I ever made.” It even paid off for him, and for Apple, in one very specific way: Freed from course requirements, Jobs sat in on courses that interested him more than his assigned classes had, including one on calligraphy and typography. “I learned about serif and sans serif typefaces, about varying the amount of space between different letter combinations, about what makes great typography great,” Jobs said. “None of this had even a hope of any practical application in my life”—until, of course, a decade later, when he and Steve Wozniak were designing the Macintosh and decided to include, for the first time, creative typography in a personal computer. That flourish helped distinguish the Mac from everything that had come before.

What struck me most about Jobs’s speech, though, was the story he told about his greatest failure: being fired from Apple, the company he created, just after his thirtieth birthday. “What had been the focus of my entire adult life was gone, and it was devastating,” he said. “I was a very public failure.” What he wasn’t able to see at the time, Jobs said, but that became clear later was that the experience of such a dramatic failure allowed him to reorient himself and his work in a way that led to his greatest successes: buying and transforming Pixar, getting married, returning to Apple rejuvenated. As Jobs put it in his speech: “The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything.” That was, I think, exactly what I was looking for in that Columbia dorm room: the lightness of being a beginner.

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. 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 City 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.

2. High-LG Parenting

These days, when I contemplate success and failure, I think less frequently about my own prospects and more often about those of my son, Ellington. I figure I’ve already turned out more or less the way I’m going to turn out. But Ellington? Anything could happen. I started reporting this book right around the time he was born, and it will be published just after his third birthday, so the years I spent working on it coincided almost exactly with the period in his life that neuroscientists tell us is the most critical in a child’s development. The experience of writing the book—and especially encountering the brain research that I wrote about in chapter 1—has profoundly affected the way I think about what it means to be a parent.

When Ellington was born, I was like most anxious parents under the influence of the cognitive hypothesis, worried that he wasn’t going to succeed in life unless I broke out the brain-building flashcards and the Mozart CDs in the maternity ward and then kept bombarding him with them until he got a perfect score on his preschool- admission test. But the brain researchers whose work I had begun to read pointed me in a different direction. Yes, they said, those first few years are critically important in the development of a child’s brain. But the most significant skills he is acquiring during those years aren’t ones that can be taught with flashcards.

It is not as if I suddenly stopped caring about Ellington’s being able to read and write and add and subtract. But I became convinced that those particular skills would come to him sooner or later no matter what I did, simply because he was growing up surrounded by books and had two parents who liked to read and were comfortable with

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