Although the socio-economic and structural contexts of retirement have been the subject of previous research, few studies state explicitly how societal ageism and structural constraints obstruct retired persons' choices or options available in post-retirement life. This study attempts to contribute to the literature of ageing, retirement, and wellbeing in later life in general, by providing real examples of ageism around the time of retirement as structural constraints of old persons. It also illustrates how they consequently reduce the choices of retired persons, and in turn affect their later life. The study draws on data from interviews with 34 retirees aged in their late fifties and sixties in Korea. Within the socio-economic context of ageism around the time of retirement, four options/strategies appear to be available; namely reconciling, complaining and not knowing what to do, finding roles in other activities, and disengaging. Older persons' decisions to continue to work after retirement are often reconciling ones, that is, taken within a context of limited choice and control. Permanent leavers' decisions not to work are also influenced by the limited quality of work available in the labour market. The study concludes by arguing that policies for older persons should take into consideration their diverse expectations and aspirations for their later life, but, at the same time, should remain aware of their constraints within socio-economic contexts.