Progress files represent a major policy initiative involving the use of Personal Development Planning (PDP) aimed at the production of autonomous learners who are capable of planning for their own career and personal futures. The paper is organized in three parts and argues for a more critical approach, which locates PDP as part of broader shifts within educational policy and practice. The first part of the paper explores the lack of conceptual clarity associated with the term PDP. It argues that 'evidence' of 'what works' is unlikely to yield useful knowledge for practitioners as long as this evidence is based on untheorized accounts of PDP. The second part of the paper explores the concept of reflection, which underpins PDP, and argues for greater critical engagement with the conditions of reflection and an understanding of the limitations of reflection. The final part of the paper takes up the broader theme of individualization and returns to the major theme of the paper that the sorts of autonomy that are assumed in the practices of PDP are neither neutral nor an accomplished fact.