Both previous studies and theoretical standpoints suggest that contemporary changes in work will lead to increasing conflicts between the VET system and the labour market. Their coordination to ensure that the knowledge acquired in educational and training environment accords with the working capability demanded at work is increasingly challenging. In order to sustain their employability, individuals have to adjust to changes in work through work- based learning. The aim of the paper is to explain mid-level workers’ learning and adaptation pattern. Empirical data will be used to present and explain a model of worker adaptation. Three types of adaptation can be identified: passive adaptation, related to the learning of technical skills; flexible adaptation, related to the acquisition of general skills and competencies; and transgressive adaptation, related to the attainment of transgressive capabilities and a redefinition of work identity. In the paper, I am going to argue that the meaning of work and the work identity associated with it constitute a “space of values”, the locus of employees’ learning, development of work-related capabilities and mobility. The methodological approach to the research question has been a constructive one, with the employees’ perspective taken as the central element. Therefore, a qualitative methodology is employed, based on empirical data gathered mainly through open individual interviews with employees.