In this chapter, we present a perspective on the professionalisation of students in higher vocational education, which relates their life orientation to professional and societal values and beliefs. In a teaching programme at HU UAS Utrecht, inspired by Biesta’s notion of a pedagogy of interruption, students are prompted to articulate personal answers to philosophical and existential questions about the good life and doing good work, to prepare them for becoming reflective professionals. The concept of life orientation primarily draws on the narrative philosophies of Ricoeur and Taylor. These two philosophers relate ethics to identity, and describe how answers to moral and existential questions are a part of identity formation. Dialogical Self Theory helps us to understand how personal values interfere with professional and societal beliefs. We present two cases about a critical professional situation which bring students to reflection, and show how students’ life orientations influence their professional decisions within different contexts.