This article explores the workplace learning experiences of professional staff at a small private college who changed jobs, primarily due to a departmental reorganization. In many cases, the emerging jobs were ill-defined, and participants found it challenging to be released from the responsibilities of their previous positions. A cultural-historical activity theory (CHAT) analysis explored how these job changers pursued and attained competence in their new jobs. The analysis also exposed the contradictions within an activity system, proposed by CHAT, that shaped participants' on-the-job learning: balancing conflicting expectations and goals, being responsible for multiple, ill-defined roles, managing bureaucratic and technological constraints, and mitigating discrepancies in sense of urgency' and vision across the institution. While individual workers were not resistant to learning their new jobs, their pursuit of the object (competence in the new job) of the activity system was hindered by what seemed to be an organizational or structural resistance to their learning process.