Contemporary analyses of work and unemployment need to place psychological findings in the context of society, culture, and gender in understanding the meanings of paid and unpaid work for men and for women. The Australian Psychological Society discussion paper (in this issue) takes a comprehensive view of the literature and places it in the contemporary Australian social context, but fails to consider the extent to which socially constructed gender roles affect individuals' relationships with work. This paper complements the discussion paper by examining men's relationships with work and unemployment from a gendered perspective. Given the centrality of paid work to men's sense of self, there is surprisingly little psychological research on the extent to which patterns of paid and unpaid work, and discrepancies between desired and actual patterns of employment, interact with gender roles and expectations to affect men's physical and emotional wellbeing. This is particularly a concern, given structural changes in patterns of employment. Increasingly, men need to juggle the traditional view that a real man provides financially for his family with contemporary definitions of masculinity that emphasise egalitarianism and flexibility, in the context of rapid changes to work and family structures. The challenge for men is to find new ways of defining themselves and their sense of self-worth, other than exclusively through paid work.