Headship transitions in U.S. independent schools represent critical organizational events that affect multiple school constituencies, including faculty, staff, and students. With recent projections forecasting a high level of impending headship transitions in independent schools, this paper seeks to capture how second-year U.S. independent school heads (n = 16) describe their transition experiences in order to provide insights into how boards, heads, and school communities can provide meaningful supports for their incoming school leaders. Further recommendations for practice and research are also provided.