This article, based on the 18th Annual Bill McWilliams Memorial Lecture, explores the concept of ‘civil courage’ and its role in the future of probation work. The reader is invited temporarily to suspend their justifiable cynicism about the politics of probation and to examine how ‘nostalgia’ – the recollection of past good – can be used to build future cultures and identities that are recognisably ‘probation work’, regardless of the organisational environment in which they are located. Drawing on recent research projects, the work of others and the emergence of the Probation Institute, I suggest that probation workers engage with courage in what has been termed ‘edgework’ in other contexts. Controlling the boundary between order and chaos through voluntarily testing one's values, knowledge and skills to their limits and thus experiencing the satisfaction of success in the face of predicted failure, may be one characteristic of courageous probation work.