This article explores the concept of "cleverness" as it is employed by Tanzanian youth to improve their likelihood of succeeding in school. It analyzes the Swahili term "ujanja," which combines cleverness, opportunism, and deception, while it also illustrates an educational anthropologist's ongoing process of familiarization and defamiliarization with this culturally salient concept over many years of fieldwork and engagement with key participants. Specifically, the study draws on interviews with youth participating in a longitudinal study on Mount Kilimanjaro and an extended life history interview with a close friend and research assistant. The interviews reveal the strategies used by some youth to evade peer pressure, thwart sexual advances, and cultivate relationships with school sponsors. The article concludes with a call for greater use of life history methodologies in the study of complex cultural concepts like "cleverness" and of textual forms that elucidate the emotional complexity of narrator/interpreter relationships.