This chapter argues that career practitioners may perpetuate social inequalities by not reflecting critically on how they themselves potentially take part in the reproduction of dominant discourses when they navigate and handle some of the typical challenges in career guidance practice. These include, for example, the tension between helping individuals follow their dreams and be ‘realistic’ or the one between staying true to the person-centred approach to guidance and following policy targets and guidelines. Reflexivity is made relevant by the dominance of neoliberal discourse in institutional practices, which potentially masks social inequalities as it resonates with traditional humanistic goals of career guidance. In this regard, reflexivity invites practitioners to critically reflect and unpack the reflexive nature of their actions—i.e., both the way in which their actions are embedded in dominant ideologies, which inform guidance practice, and in the way these actions potentially reproduce the very same ideologies. These challenges are explored in the context of Serbia through interviews with a group of career practitioners from this country.