Despite their academic training, most anthropologists do not work in tenure-track positions in departments of anthropology. While some systematic data indicate where these anthropologists are employed, we know less about their experiences or what led them to work outside the academy. This paper discusses examples of divergent career paths among the special issue contributors and analyzes key themes in their papers. While their histories vary generationally, our authors share commonalities. Many mastered cross-over skills that prepared them to work collaboratively and to apply anthropological insights and methods in research and community settings. Some perceived stigma and barriers to communicating with traditional academic colleagues. Others merged theory and practice to develop pedagogical reforms. Drawing on lessons as mentors in training programs and advocates in our own careers, we recommend that practitioners' narratives be used to re-imagine career options, revise training programs, and increase visibility for applied careers across the anthropological community.