This article explores the experiences of men in non-traditional occupations. In particular it focuses on the dynamics of career entry, career orientation (namely, a preference for intrinsic or extrinsic rewards) and the possible existence, nature and consequences of role strain. Four occupational groups are examined: nurses, cabin crew, librarians and primary school teachers. The results suggest that men fall into three main categories: seekers (who actively chose the ‘female’ occupation), ‘finders’ (who did not actively seek a non-traditional career but who found the occupation in the process of making general career decisions) and settlers (who actively chose the occupation, often as a result of dissatisfaction with a more ‘masculine’ job, and who then settled in their non-traditional career). Settlers, in particular, are associated with a more intrinsic career orientation and express a desire to remain close to occupational and professional practice. Role strain is prevalent in men's experiences in their non-traditional career. The potential sources of such role strain and the implications for career aspirations and career choices are explored.