The problem, as Randolph has realized, is that the best way for a young person to build character is for him to attempt something where there is a real and serious possibility of failure. In a high-risk endeavor, whether it’s in business or athletics or the arts, you are more likely to experience colossal defeat than in a low-risk one—but you’re also more likely to achieve real and original success. “The idea of building grit and building self-control is that you get that through failure,” Randolph explained. “And in most highly academic environments in the United States, no one fails anything.”

David Levin says that this is one area where he believes KIPP students have an advantage over their peers at Riverdale. “The day-to-day challenges that our kids go through to obtain an education are very, very different than the day-to-day challenges of the kids who go to Riverdale,” he told me. “As a result, the grit of our students is significantly higher in many respects than the grit of the students who go to Riverdale.”

As Karen Fierst observed, most Riverdale students can see before them a clear path to a certain type of success. They’ll go to college, they’ll graduate, they’ll get well-paying jobs—and if they fall along the way, their families will almost certainly catch them, often well into their twenties or even thirties if necessary. But despite these students’ many advantages, Randolph isn’t convinced that the education they are currently receiving at Riverdale or the support they are receiving at home will provide them with the skills to negotiate the path to the deeper success that Seligman and Peterson hold up as the ultimate product of good character: a happy, meaningful, productive life. Randolph wants his students to succeed, of course—it’s just that he believes that in order for them to do so, they first need to learn how to fail.

13. Discipline

“At KIPP, we’ve always said that character is just as important as academics,” Tom Brunzell was saying. It was six o’clock on a warm Wednesday night in October, and Brunzell was standing at the front of a large auditorium pitching the character report card to an audience of KIPP parents. “We think that even if your children have the academic skills they need—and we’re doing our best to make sure they do—if our young adults grow up and they don’t also have strong character skills, then they don’t have very much. Because we know that character is what keeps people happy and successful and fulfilled.”

Brunzell, who was in his mid-thirties, was the dean of students at KIPP Infinity middle school; it was the third KIPP school in New York City when it opened, in 2005, on one floor of the Roberto Clemente Middle School on West 133rd Street, across from a giant city bus depot. As Infinity’s resident disciplinarian, Brunzell had a very effective stern side, but on this night, he was all smiles, dressed in a pressed button-down shirt and a tie and crisp jeans, looking a little nervous as he clicked his way through the PowerPoint slides on his laptop that were projected on a screen behind him. Brunzell had become the person in the KIPP organization most directly responsible for the character report card; he chaired the monthly meetings of what had come to be called the KIPP/Riverdale character working group. In many ways, though, he was an unusual choice for the job—he had come to KIPP as something of a conscientious objector, an outspoken critic of its system of discipline.

From KIPP’s earliest days, Levin and Feinberg, the founders, were famous—and infamous—for regulating student behavior in direct and often intense ways, prescribing precisely how students should sit and talk and pay attention and walk through the halls. In Sweating the Small Stuff, David Whitman wrote that “paternalistic” schools like KIPP’s “tell students exactly how they are expected to behave, and their behavior is closely monitored, with real rewards for compliance and penalties for noncompliance.” In Jay Mathews’s account of the founding of KIPP, Work Hard. Be Nice, he describes some of Levin’s harsher moments of discipline, like the time Levin caught a student throwing a wadded-up piece of paper. Levin sat the offender on a chair at the front of the class, put a garbage can on the floor in front of him, and told the other students they were free to throw in the garbage any stray pieces of paper they could find—some of which narrowly missed the student. (Mathews says that Levin later regretted that incident.)

When Brunzell arrived at KIPP Infinity, in 2005, he was completing a graduate degree at Bank Street College, a school of education known for its progressive bent. His thesis, which he researched and wrote in his first year and a half working at Infinity, was a thorough critique of the school’s discipline regime. Infinity’s “compliance-based” system “models an atmosphere of punitive dependence,” Brunzell wrote, “which ultimately negates student decision-making.” As a result, he noted, KIPP Infinity students often demonstrated the shallowest kind of good conduct—not contemplating in a deep way the consequences of their actions but ostentatiously behaving well when teachers were watching and then trying to get away with as much as possible as soon as the teachers’ backs were turned.

Though Brunzell was calling into question some of the fundamental elements of the KIPP tradition, he received a surprisingly encouraging response from both Levin and Joseph Negron, the young principal of Infinity, which in its first year achieved remarkable results, even by KIPP standards. The school opened with just a fifth- grade class, recruited from the housing projects and bodegas of West Harlem and Washington Heights and chosen by random lottery. Only 24 percent of the incoming students had passed the state’s fourth-grade English test at their previous public schools; just 35 percent had mastered the fourth-grade math standards. But after a year at KIPP, 81 percent passed the fifth-grade English test and 99 percent passed the fifth-grade math test. And yet, Negron told me, he agreed with Brunzell that things at Infinity weren’t quite right that first year. “We had kids who were doing the right thing for the wrong reasons,” he said. “We didn’t have that many student issues, and we had good results, which was great. But we just didn’t feel like we were the type of school where we were creating happy and fulfilled lives.”

When I met Brunzell, in the fall of 2010, he had been at KIPP Infinity for more than five years, and over that time Infinity had changed, partly in response to his criticisms. Punishments were less severe and of shorter duration, and discipline conversations between students and administrators, though still often intense, were conducted less publicly and with more emphasis on making sure students felt heard and respected. The character report card was, for Brunzell, a critical part of those reforms, providing a different structure for conversations about behavior, one that allowed for deeper reflection and, potentially, more growth.

At the same time, Brunzell had tempered some of his original critique. He told me he had come to appreciate some of the elements of the KIPP behavior-modification system that had once struck him as overly authoritarian. One example was SLANT, a set of classroom habits that KIPP students were drilled on at the beginning of fifth grade, their first year at KIPP. For Brunzell, SLANT, which stands for Sit up, Listen, Ask questions, Nod, and Track the speaker with your eyes, was a useful way to teach code-switching, the ability, highly prized at KIPP and at many other low-income urban schools, to recognize and accurately perform the behaviors appropriate to each different cultural setting. It’s okay to be street on the street, according to the theory of code-switching, but if you’re in a museum or a college interview or a nice restaurant, you need to know exactly how to act or you’re going to miss out on important opportunities. “At KIPP, we are teaching the professional code of behavior, the college code of behavior, the cultural-dominant code of behavior,” Brunzell said, “and we have to teach that every moment of the day.”

This is an area where KIPP’s teachers and Riverdale’s diverged especially sharply. K. C. Cohen, the Riverdale guidance counselor, told me that over the course of the school year, she had perceived a growing disagreement between the two schools over certain indicators on the character report card. It wasn’t that she and other Riverdale teachers valued strengths like self-control less than the folks at KIPP did, she said. It was just that they were beginning to realize that they might define those strengths differently. “If you’re showing self-control at KIPP, for example, you sit up straight and you track the teachers,” she explained. “Here, you can sit in a ball in your chair, and no one cares. We don’t care if you lie on the floor.”

As we spoke in her office, Cohen read through the list of twenty-four indicators on KIPP’s character report card and mentioned a few others that she thought would resonate differently at each school. “Take ‘Student is polite to adults and peers,’” she said (an indicator for self-control). “That’s great, but at Riverdale, kids come up to me and pat me on the back and say, ‘Hey, K.C.!’ And that’s okay. At KIPP, though, teachers are always Mr. This and Mrs. That. There’s a sort of formality.” It’s the confusing thing about code-switching: the kids who are actually part of the dominant culture don’t necessarily act like it at school—or perhaps it is more accurate to say that at a school like Riverdale, slouching and wearing your shirt untucked and goofing around with teachers is dominant-culture behavior.

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