Vocational pathways to Higher Education have a key role in opening teacher education to under-represented groups but bring with them particular challenges. Teacher educators need to address the challenges faced by these learners, of not only connecting their learning but also challenging their knowledge, and doing so in an invested work environment. This paper shares my experiences as a teacher educator working with two groups of Indigenous and non-Indigenous para-professional pre-service teachers in remote and urban Central Australia. I identify four key role-shifting challenges individuals face in developing their professional practice and locate them in two interdependent areas: social sphere challenges arising out of the situated learning setting of professional experience, and those occurring in the personal sphere of professional identity. I suggest that the new ways of mentoring and the development of student’s reflexive capacity needed to address these challenges can best be mobilised by re-positioning the role of professional identity at the centre of both professional experience and academic learning.