Abstract Despite lacking policies targeting the extension of working life, Chile is the Latin American country that has exhibited the largest increase in the labor force participation rate of people aged 65+ in the last two decades. In this research, following an analytical framework on regulation of endogenous uncertainty and relying on rich qualitative data (life story interviews of 90 older workers aged 60–86, across 21 cities and 6 regions), we approached the complexity of extended working lives in Chile by addressing an unexplored dimension. Specifically, we explore individuals’ agency over their employment trajectories (i.e., both in adulthood and old age) among those who remained active in the labor market after the legal retirement age. Our findings provide strong evidence that extended working lives not only result from precarious social conditions, but are also shaped by complex processes involving both expansive and adaptive individual agency in which people engaged throughout their life course. Therefore, the high exogenous uncertainty in the labor market should not merely be interpreted from the perspective of “precarity,” but also as a scenario that encouraged individuals to behave in a way that led them to engage in the labor force across their lives in accordance with their preferred level of endogenous uncertainty.
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