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The average worker in industrialised countries is ageing. The baby boomer generation (born 1946–1965) is gradually reaching retirement age. In Canada, the share of workers in the age 55+age group is expected to attain 24% in 2031. There is also a shortage of young workers to replace retirees. Although data suggest that at least one in five older workers suffers from chronic musculoskeletal pain, most will continue working despite pain. Very little is known about the factors contributing to or compromising the likelihood of these workers staying at work with pain.An interpretive descriptive method was used to explore factors associated with staying at work with pain. A transdisciplinary conceptual model was created, based on literature from the fields of work rehabilitation, ergonomics and demographics. Semi-structured individual interviews were conducted. Inclusion criteria were: blue collar workers, musculoskeletal pain (excluding cancer pain) for 6 months or more, and working 28 hours weekly or more. Analysis was performed using themes from the conceptual model; intra- and inter-case analysis was conducted using qualitative data analysis software.Fifteen participants (7 women) were included, ages 55–70. They ranged from self-employed individuals to employees of large organisations, with half of them working in the private sector. Although all participants mentioned the importance of financial factors in their decision to stay at work, they did not generally consider it the main reason. For most, the perception of being useful, having peer recognition and feeling that work contributes to health were essential drivers for staying at work. Flexibility at work was deemed essential by all but took various forms.This study identified, for the first time, both personal and work-related factors associated with working in the presence of pain. These results will help in developing better strategies to keep ageing workers at work.