Indiana recently gained status as a national leader in educational reform. At the same time, a record number of superintendents retired, with 62 retirements in 2012 and 2013, representing 21% of superintendents in the state. The purpose of this study was to explore factors influencing superintendents' decisions to retire during this time. Quantitative survey methodology was used to gather data directly from retiring superintendents over two years with 28 participants. Analysis of responses revealed that school funding issues, including Indiana's new voucher program and its impacts on education funding, were the highest-rated issues influencing participants' retirement decisions. This research advances our understanding of the superintendency in today's school reform climate and identifies factors potentially affecting longevity in the position.