This book is based on the professional experiences and research findings of Drs. Litchka, Polka, and Calzi who possess a combined total professional experience of over 100 years as educators in the United States, including over 75 years as public school administrators and over 30 years as chief school officers. The authors have also spent a combined 30 plus years in researching and roles, responsibilities, and stresses of school district leadership. They are committed to appropriately preparing current and aspiring leaders to survive and thrive as superintendents.The authors know the topic of school leadership very well from both the practical “lived experiences” to the various theoretical research conceptual frameworks. This book reflects actual stories collected via their most recent research associated with school district leadership, decision-making, politics, and “living on the horns of dilemmas.”