This paper evaluates the need and prospects for older workers to develop and deploy effective and critical personal epistemologies in order to maintain workplace competence, successfully negotiate work transitions and secure ontological security in their working life. Furthermore, it addresses different ways of reflecting by workers, which types of reflection are appreciated by workplace managers and how these relate to the work situation and other contextual factors. A personal epistemology is an approach to and a practice of learning directed by individuals, often for purposes that are important for them. This seems particularly salient for older workers as both the institutional and brute facts (Searle 1995) that comprise workplace affordances and maturation factors, respectively, may not be supportive of their attempts to maintain competence in their working lives. Instead, as both individual agents and parts of collective actions, the exercise of personal epistemologies premised on critical reflection stands as a means for older workers to understand and respond to the changing requirements of work life. These propositions are introduced and elaborated using a study of older workers' capacities to be critically reflective of their practice and enact workplace change.