As organizations restructure to increase flexibility, interim management by contractors is increasing as an alternative to employment of `permanent' managers. Interim managers begin their new role on the basis of transactional psychological contracts with their employer Their careers are based on a logic of accumulation of learning across organizations. However, there are also forces that may over time cause the redefinition of the psychological contract, employment relationship and career orientation. Based on an interview survey of 50 interim managers, various metaphors are proposed to assist understanding. Interim managers may be considered, for example, as displaced persons, customers at a dating agency, or hired guns. A number of metaphors are employed to extend understanding of their developing employment relationships and careers. The implications of the findings are examined in relation to predictions concerning 21st-century forms of employment, organization and career.