This paper uses a life course perspective to explore and understand how an individual’s experiences over their lifetime contribute to the formation of a growing consciousness about their impending retirement. The fieldwork took place in 2016 and was part of a wider mixed methods study about retirement in the UK, which used data from the 1958 birth cohort study (also known as the National Child Development Study). The paper focuses on the qualitative dimension of the study and uses in-depth case studies of four people approaching 60 to consider, in particular, the effects of health, financial resources and employment history on their views on retiring, including the anticipated timing of their exit from the labour market. All four were purposively chosen because they had experienced low pay or poverty during their lifetime and were employed in relatively low paid jobs. State Pension Ages (SPAs) are on the rise in many countries, including the UK, and the authors maintain that it is important to study the working poor, who, even though are more likely to continue working until SPA, are more prone to suffer from poor health, and less likely to be able to put savings aside for their retirement.