Recent efforts emphasize the roles that privilege and elite education play in shaping affluent youths’ identities. Despite various backgrounds, the common qualities shared among the eight adolescents showcased in this book lead them to form particular understandings of self, others, and the world around them that serve as means for them to negotiate their privilege. These self-understandings are crucial for them to feel more at ease with being privileged, foster a positive sense of self, and reduce the negative feelings associated with their advantages – thus managing expectations for future success. Offering an intimate and comprehensive view of affluent adolescents’ inner lives and understandings, Negotiating Privilege and Identity in Educational Contexts explores these qualities and provides an important alternative perspective on privilege and how privilege works. The case studies in this volume explore different settings and lived experiences of eight privileged adolescents who, influenced by various sources, actively construct and cultivate their own privilege. Their stories address a wide range of issues relevant to the study of adolescence and the various social class factors that mediate adolescents’ educational experiences and identities.