This qualitative narrative explores the psychological burden and spiritual challenges faced by a summer camp director through a reflective, first-person account. The author employs autoethnographic methodology, documenting midnight observations and personal experiences while overseeing 800 children and staff at Camp Ramah in Ojai. The study reveals the profound responsibility inherent in youth supervision, examining instances of self-harm, substance abuse, and adolescent crisis management within a Jewish educational context. Through literary analysis incorporating Salinger's "Catcher in the Rye" and Talmudic interpretations of divine responsibility, the author conceptualizes his role as a protective "catcher" for vulnerable youth. The research identifies the paradoxical nature of caregiving, wherein those charged with preventing others from "falling" may themselves require support systems. Key findings indicate that effective youth leadership necessitates recognition of one's own limitations and the cultivation of community support networks. The study concludes that sustainable caregiving requires acknowledgment of the caregiver's vulnerability, drawing on Jewish theological concepts of collective responsibility and the necessity of mutual support systems. This work contributes to understanding the psychological dimensions of youth work and the intersection of spiritual leadership with crisis intervention in educational settings.