The UK governments in recent history have built a strong paternalistic argument describing paid work as an essential route to improve lone parents’ mental and physical well-being. This thesis therefore sets out to explore the question of How does the transition from social assistance benefits into paid work affect the overall subjective well-being of lone mothers and their quality of life? On the impacts of the transitions to work on the well-being of lone parents, some less-researched areas are found when adopting an analytical framework of the Personal Well-being Index (PWI), and they are: quality of relationships, future security, community-connectedness, safety, and leisure. This thesis adopted a qualitative method to fill the gap. In-depth interviews were conducted with some 20 lone mothers with at least one child aged six or under and who had recently returned from social assistance benefits to paid work. Overall, the evidence shows that lone mothers may not be ‘better off’ in work either financially, emotionally, socially or physically. What is clear however, is that they are ‘better-off’ being free from the stigma associated with claiming social assistance benefits. This raises two policy implications. One, the social stigma is being generated and effectively delivered by political tactics to get people off benefits, and it damages the well-being of lone mothers not only during the period of being on benefits, but also for long after their transition. Two, while low out-of-work benefits and sanction regimes are considered as the right measures to encourage claimants to accept a ‘reasonable’ job because it would ultimately benefit their own well-being, it is clear that taking ‘any work’ is not a one-size-fits-all solution. Moving to any type of work in fact carries a great risk that threatens the well-being of the lone mothers, as it can equally be stigmatising, isolating, insecure, and unsafe, and not a route to becoming independent. However, rather it provides good and legitimate reasons for: reducing quality time with children, being unavailable to family and friends, and having leisure time that is informal, irregular, and fragmented, and also for not prioritising their own physical health.