In an era of metrification and managerialism there is widespread acceptance that a lack of Aboriginal wellbeing reflects a culture of welfare dependency. But Indigenous wellbeing is more complex than simple equations suggesting "getting off welfare" will achieve betterment. There is no one-size-fits-all solution to issues of Indigenous disadvantage. Social work literature establishes that moral, social, and political aspects of working the social are in tension with technical and rational aspects. This paper draws on Charles Wright Mills's concept of the "sociological imagination" to render an historical, social-structural, and biographical account of addressing wellbeing within West Australian Kimberley Aboriginal communities since the 1970s. Highlighting the actualities of community as shaped by time, place, and interaction, an argument is made for developing a social work imagination that researches "what is happening here" through ethnographic approaches that consider the intersectioning of history, biographies, and social systems. Without such local knowledge and engagement, effective social policy cannot be enacted from the centre.