This study aims, first, to chronicle the perceived dilemmas of a group of Australian principals whose worklives were preoccupied with school restructuring. Second, relying on empirical data, it develops a typology of dilemmas. This typology then forms the structure for a more detailed discussion of the nature and source of dilemmas encountered by the participating principals. Data were collected and analysed using qualitative methods, based on semi‐structured interviews with 20 Western Australian primary and secondary principals. The findings suggest two main types of dilemmas – general, values‐based personal‐professional dilemmas, called “states of mind”, and specific, practical, organisational dilemmas. It is argued that improving the knowledge base by using empirical studies and developing typologies and conceptual frameworks, is a necessary step in providing closer insights as to how school leaders perceive and manage the most intractable aspects of their worklives. This, is turn, could lead to improvements in leader preparation and training.