This study is focused on exploring decision-making and leadership in two urban principalships. The study is focused on reflections from a former principalship in Baltimore City and the influences from the former experience that influence leadership and decision-making in the present context within a District of Columbia Public School. In his work studying school culture Bryk (2010) supports the idea that leadership is the driver of change in successful school improvement efforts. The study uses Bryk’s framework as a foundation for the reflections on challenges related to Bryk’s five essential supports for school improvement. The goal of this study is to seek a greater understanding of decision-making and leadership actions within an urban school principalship in order to inform current practice. Leadership as the driver of change as an essential component of school success has piqued my interest in reflecting on and understanding my leadership practices. Study of reflections on my leadership as a tool for further developing skill and practice could be a valuable resource for other school leaders within the field.