AbstractPaid employment has been viewed by successive governments in the UK as critical in making transitions out of homelessness, even when combined with problems like substance misuse, criminality or mental ill health. This article presents evidence from a study that sought to subject this belief to critical examination by exploring the relationship between promoting employability and other aspects of resettlement in the lives of a sample of thirty people experiencing homelessness and complex needs. Participants were interviewed twice at six to nine-month intervals to explore their changing motivations and perceptions of housing, work, relationships and hopes for the future.Analysis used ‘pathways’ imagery to locate participants along an integrated pathway to understand how these factors related to one another in the pursuit of resettlement. We conclude that all respondents valued work, but its pursuit depended on the structural obstacles that participants faced. People’s location along a resettlement pathway was determined by their sense of control over circumstances, their success in overcoming barriers and the presence of significant others in their lives, and the pursuit of employment among homeless people needs to take account of progress in their resettlement journeys and the place of work in their aspirations.