This article explores the ambiguity of social work, which acts as a mediator between the individual citizen and the state by exerting both compassion and control. When dealing with managerialism, social work usually adopts two different perspectives, namely one of acceptance and reproduction of the managerial logic and another one of resistance to managerialism. Nonetheless, the author puts forward an alternative proposal to these approaches which conceive social work as a powerful change agent that leaves no room for ambiguity. Thus, social workers should adopt an ironic perspective by embracing ambiguity and by becoming aware of both the significance and limitations of their field. The author also proposes three metaphors by means of which social workers can understand the notion of irony and visualize different facets of their field, namely the social worker as a trickster, as Columbus and as a happy Sisyphus.