The key question addressed in this chapter is which are the factors enabling longer working life? Four case studies provide empirical support for continued discussion on this issue. They cover different segments of working life: forestry work, public sector work, academics, industrial and service work. We find that enabling and disabling factors differ between trades. The availability of, and motivation to participate in, work-integrated learning is a key factor. Non-formal training and informal learning seem to become more important than formal education. In academia, incentives are embedded in the work itself. Knowledge transfer is generally considered a matter of success. At the individual level, sustained work ability requires relevant competence and adequate health. Obstacles to be overcome include negative attitudes among employers, officials, and the older people themselves. There is a specific need for development of know-how: how to enable older people to stay active in knowledge transfer close to the workplace