This qualitative study examined the subjective experience of school counseling interns (N = 26) with and without teaching experience. Non-teachers acknowledged a steep learning curve as they adjusted to the school and teacher cultures, but relied on personal qualities and counselor training as they moved successfully into competence. Teachers reported challenges related to altered roles, less structure and control in their work, and unfamiliar ways of relating within the formerly familiar school culture. Findings have implications for preparatory curriculum, challenge assumptions about what teachers and non-teachers bring to the field, and suggest that the groups would benefit from differential guidance during their transition into the profession.