In this article a framework is presented to understand the changing character of individual learning processes and of educational practices related to work and employment. Based on two research projects – a research on women’s biographical learning in relation to work and a European research on the socio-economic integration of young adults – a perspective of transitional learning is developed. It is argued that nowadays individual learning processes can be understood as processes of transitional learning aimed at creating meaningful connections between individual life and society via work and adult education. This interpretation, together with the changing educational landscape, calls for a reconsideration of the interventionist role of the adult educator. In order to stimulate and support these learning processes, guidance, training and counselling are becoming reflexive activities in need of interpretive professionals.