With the central players in the United Kingdom policy debate on pensions schemes and funding advocating an extension to the average working life (or, more precisely, a rise in the age of ceasing work), this paper reports the findings of qualitative interviews with men and women at or approaching state pension age that examined what motivated some people to continue to work after that age. By exploring their work histories and orientations to work, the paper shows that people from different social and occupational backgrounds not only conceive work and retirement in different ways but also have contrasting opportunities to continue in occupations after retirement age. Their attitudes and the opportunities they encounter shape the decisions they make at state pension age. Distinctions are drawn between those who articulated an identity as a ‘worker’ and those who defined themselves as ‘professionals and creatives’, and within those categories, between the employed and self-employed. The paper elucidates the tensions between individuals' normative expectations of retirement, their desire for autonomy and flexibility in later life, and the financial and occupational reality of life after state pension age. We argue that understanding the different cultural meanings of work and retirement for different types of worker has implications for the design and implementation of policies to extend working life.