Mature workers have been at the centre of policies aimed at encouraging higher workforce participation, longer working life and enhanced savings for retirement. Low mature age workforce participation rates reflect labour market withdrawal in the face of multiple barriers to participation for many. Their apparent voluntary joblessness conceals the fact that mature workers endure longer periods of unemployment, discrimination, redundancy and other barriers to employment (hence the drift to 'early retirement'). The policy dilemma is not just about addressing discrimination barriers, access to appropriate retraining or skills enhancement for mature workers, but what this tells us about lifelong learning as a means of managing and mitigating risk. The mismatch between work opportunities/skills shortages and the low education and skills base of many mature workers, means it is simplistic to think that working longer might be a short term way to address skills shortages; without an enormous investment in the current ageing cohort. Drawing on Transitional Labour Market (TLM) theory and European reform agendas, this article argues that the link between investment in lifelong education/ skills training and stronger labour market participation needs attention; not just for current cohorts of excluded or underemployed mature workers but to position strategically for future generations.