Recent research has focused on issues of retention and turnover among K-12 school administrators, yet it fails to address some important complexities in administrator career paths. This article examines three conceptual and methodological issues in the current literature involving administrative turnover: the complexity of role and place in administrators' job transitions, job opportunity and choice open to administrators, and static versus dynamic approaches to assessing administrators' movement and retention. This evaluation includes empirical examples from the authors' study of administrator career paths in Delaware. The authors conclude that these issues have not yet been adequately acknowledged in the literature but that they have significant implications for how administrator career behavior is measured and understood for both research and policy. (Contains 3 notes and 2 tables.)