When Kaitlin Driscoll started her teaching career at Santa Teresa High School in San Jose, Calif., she thought that she was ready for the challenge. She had done her student teaching in the same demographically diverse, urban school district that includes Santa Teresa, and she looked forward to teaching English to college-bound freshmen as well as “repeaters”—juniors and seniors who hadn’t yet met their ninth-grade requirements. “This is what I’m meant to do,” she remembers...

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