Understanding how best to assist mature-aged workers (i.e. those over 45) maintain their employability across extended working lives, and what workplaces, educational institutions and government agencies can do to sustain that employability, is now central to many countries' national social and economic goals. In most countries with advanced industrial economies and those aspiring to develop such economies, mature age workers are now likely to need to engage in longer productive working lives and, potentially, engage increasingly in more demanding kinds of employment such as professional, managerial, executive, and technical work. As a case study, this paper discusses interviews with mature-aged Singaporean workers, some of whom are also employers, about how sustaining their employability should be realized. First, it describes something of the current circumstances (i.e. constraints and opportunities) for workers aged over 45 in Singapore through accounts of their experiences in workplaces and educational institutions. Second, it advances views that can inform policies and practices to improve workplace practices and also the provision of lifelong learning (e.g. CET) in both Singaporean workplaces and educational institutions. In all, it argues that both workplace and educational provisions need to support mature age workers in ways that are commensurate with their skills, confidence, and capacities to progress. Yet, beyond what workplaces and educational institutions can provide, the active and pro-active (i.e. agentic) engagement of these mature aged workers is also essential.