Using metaphors of nets, trenches, sink holes and cisterns, this book shows instances of the obstacles that hinder academic success for our children. The purpose of this book is to bring an awareness of what is broken in our educational system by looking at leadership and reform efforts in the midst of relationships, sustainability of reform efforts in economic unpredictability, the impact on the future workforce, and what is needed to overcome obstacles. A second purpose is to engage educators, in particular leadership, in thought provoking conversations around building the trusting relationships amongst stakeholders that is necessary for effective, transformative and successful school districts. The book introduces three case studies of three school districts that, in the form of short vignettes, share stories of how relationships can impact the climate and culture of a district. This book will contribute significantly to the establishment of trusting relationships that empower educational leaders to work through reform efforts for the good of their communities and help future leaders persevere and not fall into despair in their leadership journey, but instead learn along the way.