Adult educators employed in steel mill career development programs offer the field a unique glimpse into the relationship between context and career trajectories. This article explores the lives of these adult educators against the backdrop of contemporary theories of career development, situated learning, and continuing professional development as a function of career identity. In particular, this article reports on a study that examined how teachers reflected on their practice and the implications this may have for the development of their professional identity. The specific questions this research addressed included: How did the teachers acquire the knowledge they feel they need to teach in the classroom or work in an adult education setting? How do they come to see themselves as adult educators? What does this mean to them? To what extent does reflection on practice lead to the development of identity as adult educators? Evidence suggests that although the field of adult education has explored career paths of its members in numerous contexts and theorized about how these elements come together, it has yet to describe, much less theorize, the path of those who locate themselves within and contribute to the practice of adult education outside of the mainstream.