In this article, the author interviewed five former colleagues who were retired special education administrators about their careers and perspectives during the spring of 2012. They all worked for a regional education agency in Pennsylvania. The interviews revealed many challenges, from physical exhaustion to a changing organizational culture. Yet, in spite of these challenges, those interviewed sought feedback and guidance from mentors, reflected on their experiences, and searched for ways to support their teachers and staffs even as their programs grew and their responsibilities increased. Replacing education administrators, whether in special or general education, is challenging due to many factors, including long hours, insufficient salary, and a lack of support. The biggest challenge, however, may be the disinterest of Gen X educators in traditional administrative positions. As the number of retiring education administrators increases, it is crucial that school districts and regional education agencies implement strategies to more effectively recruit or retain them.