This article, based on qualitative interviews conducted between 2007-2008 with 12 middle-career educators in the greater Boston area in Massachusetts, details teachers’ career and leadership aspirations in a context of educational change. The findings suggest that teachers who presently are in midcareer struggle with the move toward the principalship, but that generational differences, not the changed educational context, more heavily impact their lack of attraction to the job. Using generational theory, this article offers a critique of the available literature on teachers’ career paths, the principal shortage, generational differences, and the quite different work and leadership expectations of the next generation of school leaders.