This article focuses on preparation and access to the superintendency and is based on a research study conducted in 2010 that included data gathered from four recently retired, reputationally successful superintendents. While intended to examine career pathways that best prepare future superintendents, the study revealed that specific positions did not impact participants' preparation for the position as much as their broad and diverse experiences and the people they met who served as mentors and sponsors. Additionally, findings from the study indicated that such experiences only prepared superintendents for success because they built on critical personal qualities and skills individuals already possessed including vision, commitment, ability to build relationships, a strong work ethic, genuine concern for their work and for other people, and courage.