Extracted from a larger study of the educational evaluation profession, this qualitative analysis explores how evaluator identity is shaped with constant reference to political economy, knowledge work, and personal history. Interviews with 24 social scientists who conduct or have conducted evaluations as a major part of their careers examined how they came to recognize themselves as adept evaluators. The paper explores four adaptations to program evaluation—higher education faculty who define themselves as academic entrepreneurs whose work is largely funded by evaluation contracts; post-academics who seek intellectual freedom beyond the university; professional evaluators who perceive themselves as intimately connected to contract research organizations; and layover evaluators who are waiting for the next career move. The paper concludes with a discussion of implications for the professional development and academic training of future program evaluators.