Early career principals in Jewish day school are frequently unprepared for the role, contributing to attrition in school leadership. This narrative study explores the socialization of ten Jewish day school principals in the first three years of their first position. These leaders have similar feelings of being overwhelmed and unprepared as principals in other school contexts. They also experienced stress factors unique to Jewish day schools, exacerbating the challenges of socializing into their new role. In response, principals seek support structures within and outside of the school. Conscious cultivation of support may contribute significantly to principal retention.