The article moves from the impact of digitalisation on the international labour market to the importance of lifelong learning measures in countering the negative externalities arising from technological progress, such as labour fragmentation, obsolescence of traditional and repetitive jobs, and skill mismatch. It aims to provide insights regarding the latest efforts in implementing models for continuous training of workers in the current legal framework by carrying out an analysis of remarkable practical experiences and emphasising the different approaches to upskilling and reskilling of the working-age population. By taking into account the idea of an “individual right to continuous training” implemented both by legislative interventions and collective bargaining, this study highlights some of the best practices concerning lifelong learning that could be adopted to counter the growing polarisation between high and low qualified workers. In the final part, the study mainly aims to provide the basis for a discussion regarding effectiveness and scope of the examined measures. In this respect, it also suggests the importance of social safeguards not embedded into employment contracts alone but guaranteed by the labour market itself and applied to the whole labour force. In particular, it stresses the need to strengthen workers’ employability throughout their working life to counter involuntary unemployment, highlighting the importance and topicality of the theory of transitional labour markets (TLM).