A legacy of leadership is more than a bench, as demonstrated by six Kentucky school superintendents who share a common commitment to providing a resource for continuous professional learning for district superintendents. The six leaders met at the end of their doctorate of education program at Northern Kentucky University in May 2015 to contribute strategies for what they hoped would be an integral part of their leadership legacy in their districts. The six superintendents believe these strategies will find lodging in the hearts and minds of school leaders who, like them, feel compelled to make a significant difference, to matter, and to know their lives count for something more than a bench. They developed a website (www.aspirationalschool.com) that provides overarching strategies and numerous resources to help new and experienced superintendents lead from the head and the heart--to matter and make a difference in the lives of their students. Each focus--strategic planning, effective communication processes, continuous professional learning, innovative instruction, succession planning, and student success during postsecondary education--becomes a professional learning resource for district superintendents. The six leaders present their stories in this article: (1) Strategic Planning: 12 Steps to Success (James Neihof); (2) Effective Communication Processes: A Common Language (Anthony Orr); (3) Continuous Professional Learning: A Focus on the Life Cycle of the Career Educator (J. Robin Cochran); (4) Innovative Instruction: Reimagining the Disney Dream (Buddy Berry); (5) Succession Planning: An Intentional Plan (Ron Livingood); and (6) Successful Post-Secondary Education: Promoting Relationships, Resiliency, and Parental Engagement (Robert Stafford).