Global megatrends, such as digitalisation, and contemporary crises have highlighted the importance of continuous development and learning in the work context. Learning can be inspiring and motivating but also stressful when generating competence that is not applicable or has poor utilisability. In this study, we approached the ambivalent nature of learning at work from the sustainability perspective. According to the literature, sustainability of learning can consist of four broad aspects: transferability and continuity of learning, well-being, and temporality. We aimed to examine experiences of learning among personnel in three work-life contexts: preventive police work, hospitals, and information and computer technology (ICT). Using theory-driven thematic analysis, we revealed a variety of aspects of sustainability of learning and their different emphases in the three studied contexts. The main finding is that learning and well-being are closely intertwined and temporally framed in sustainability of learning. Based on this finding, we discuss practical implications and future research directions.