Competence in contemporary working life requirements is increasingly aligned with electronically mediated tasks and work roles: i.e. the digitalisation of work. This alignment necessitates workers learning and utilizing the conceptual knowledge and ways of working needed for this work. This knowledge is often distinct from and displaces workers’ existing ways of knowing, which threatens their competence and sense of self. Yet, it can be difficult to access, learn and practice, requiring it to be mediated through interventions making it knowable. For working age adults, this often needs to occur through work activities for efficacy and practical reasons. These worklife learning issues are discussed here from a cultural psychological perspective, drawing on studies of contemporary work and human cognition, considerations for how these forms of knowledge can be made accessible and their processes of knowledge construction be supported. Four key propositions are advanced: i) this knowledge needs to be made accessible to be engaged with and learnt; ii) that can often best occur in work settings iii) workers’ occupational subjectivities need accommodating and iv) electronically-mediated forms and artefacts offer means to make that knowledge accessible and support its learning. Hence, learning, work and digitalisation are reciprocally aligned in promoting both the initial and ongoing development of workers’ capacities.