With an ageing population, comes an increase in our working lives, so the necessity to motivate and retain older workers becomes more pertinent. Lower turnover intentions and successful ageing at work have been linked to being proactive, but what drives this behaviour amongst older workers is less understood. This research explores the values and motives stimulating proactivity amongst working professionals aged 50–60 (seven males and seven females). Semi-structured interviews were analysed using template analysis. Understanding these motivational factors enables organisations to create conditions that promote proactive behaviour among older workers. The study identifies four distinct clusters that elucidate how proactivity is triggered among older workers. The findings indicate that both achievement motives and intrinsically driven proactivity were present among all participants. However, the value orientations that inform proactive endeavours diverged across the different clusters. Implications for theory and practice are provided.