The purpose of this action research study was to explore and identify how reliability and resilience are evident in the daily lives of principals in an urban school district. The study was structured according to Stringer's (2007) action research methodology. This action research employs a design that follows a cycle of inquiry. Data collection included interviews, artifacts, observations, regional meetings and district leadership meetings. The final phase of reflection allowed for new learning about the organizational environment that may result in potential change. One major outcome of this study was the reduction in stress on both principals as evidenced by an increase in their well-being. Conclusions of this study include the importance of informing and including principals in decisions that are made centrally and the significance of providing them autonomy to make mindful decisions as they understand the complexities of their buildings more than central office.