Career paths, career development and participation in adult learning are to a large extent dependent on learning experiences and labour-market entrance in early life stages. However, within the group of people with relative weak educational and vocational background variance was found in terms of how people perceive their situation and how they describe, plan and realise their career. Based on narrative interviews with low-qualified adults, the presented study describes individual circumstances and approaches to lifelong learning and career development. Based on the concept of enacted career, the article shows how the differences in the perceptions of career and learning can be understood as contextualised action. The article shows inner resources and external constraints have potential influence on the educational and career development in this group. The discussion focuses on consequences for career counselling and guidance.