After her school wins the coveted United States National Secondary Education Award, a school principal embarks upon an educational odyssey. The principal discovers that the reasons for winning the award are a sham! As her school falls apart, she begins to reflect on the stagnant school organization and the ineffective prescriptions for improvement. She wonders why as a democratic nation, American schools do not model the practice of democracy for students. The principal begins her quest to unearth the flaws in her own thinking about the way schools work in her quest to create more democratic schools. Endeavoring to understand how systems really work, the principal puts her new ideas into practice and shares with the reader the lessons learned from past practices. This book presents a guide for principals in the form of rules that suggest that educational leaders must ask themselves why they do what they do. It also takes readers through a series of vignettes focused on how principals can practice democracy in the schoolhouse, while challenging themselves and their school community.