Long-term unemployment can negatively impact health and well-being, and is a central focus of governments seeking to address poverty and social exclusion. Little is known about how individuals experience programmes aimed at addressing long-term unemployment and consequently the client-centred indicators of ‘success’. In-depth interviews were carried out with 31 long-term unemployed individuals engaged in a ‘life-first’ programme integrating vocational assistance with intensive personal strengths-based support. The participants in this programme faced multiple disadvantages including employment and educational barriers as well as a range of significant personal issues. They equated successful outcomes in the programme with receiving a wealth of psychosocial and practical assistance in addition to vocational support, and having a case manager who approached these issues as a whole. Findings suggest that, in order to provide the best chance of gaining and maintaining employment, programmes should address, in tandem, personal and vocational barriers facing those who are long-term unemployed.