This study expands the scope of trans* studies by examining how trans* identity continues to impact life long after the intense changes of initial social and medical transition have subsided. While a growing body of interdisciplinary literature explores trans* identity development and early medical transition, less information is available from either the academic or popular press about the life-long consequences and challenges of a trans* identity. Drawing on thirty semi-structured interviews, I contribute a much-needed theoretically grounded empirical case study that builds upon earlier research by using a life course perspective and employing concepts from identity theory and an intersectional analysis. I find that significant challenges remain in areas including family, dating, work, healthcare, eldercare, and end-of-life decisions. Furthermore, the challenges trans* people face and the resources they have for managing those challenges are powerfully shaped by the embodied capital they possess and simultaneously held identities such as race, ethnicity, class, sex, and gender.