Abstract Background Proposals to extend working lives are a frequent policy response to increasing older populations and associated pressures on state pension systems. However, all the consequences of a later retirement age are as yet unknown, with the perspectives of people potentially the first cohort of workers encouraged to remain in the workforce under-explored. Methods We conducted exploratory semi-structured interviews with 22 people aged between 51 and 63 in service industry occupations in Ireland. Falling just above low-income thresholds, this group were asked about their preparations for retirement, their views on continuing to work beyond anticipated retirement age and what measures, if any, can be implemented to facilitate working later in life. A thematic analysis was performed to provide a rich and detailed account of the perspectives of older workers as they approached retirement age. Results We found a general acceptance of working later in life, however this was contingent on several factors. The overarching enabler was continuing in good health with financial status a key underpinning motivator. For participants with insecure housing, patchwork employment histories and inadequate pension provisions, there was an impetus to continue working to generate savings before retirement. Often with less secure employment trajectories than previous generations, a leisurely retirement lifestyle was a diminishing prospect for our study participants. Working in multi-generational workplaces with the opportunity to shift to mentor roles was welcomed. As retirement approaches, measures such as reducing working hours while protecting existing welfare benefits would encourage people to remain in work for longer. Conclusion The complex and individual nature of continuing to work beyond expected retirement age requires flexible policy responses. An individualised approach to retirement which recognises the increasingly diverse nature of employment over the life-course is needed. This research contributes to advancing knowledge on how the choices of older workers can be facilitated in the context of our rapidly growing older population.