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This paper explores freedom and its constraints as perceived by owner-managers.• Freedom is defined as the opportunity to choose. The concept of 'choice' combines ideas from the three literatures used in this paper: discussion of freedom by philosophers, studies of managerial work and behaviour and writings about owner-managers and entrepreneurs.• Owner-managers' perceptions of freedom and its constraints are illustrated and analysed through qualitative data obtained in Finland from four in-depth interviews and twenty-four essays.• The perceptions of these owner-managers imply that freedom in managerial work has many aspects. The constraints perceived vary except that the importance of profitability is highlighted by all those studied.• One of the primary aims of this paper is to help owner-managers to understand and appraise how they see and do their jobs. The research discussed here is of Finnish owner-managers. However, there seems no reason to think that the conclusions are not applicable in other countries.