This paper addresses women in entrepreneurial activities within a family context. The starting point is two classic Swedish novels, Carl Johan Love Almqvist’s Why Not! A Picture out of Life (1839) and Hjalmar Bergman’s The Head of the Firm (1924). The field of entrepreneurship has grown substantially over the last two decades and there is an increasing interest in exploring how family issues influence entrepreneurship as well as how entrepreneurial activities impact business families (Chrisman, Chua & Steier, 2003; Cliff and Aldrich, 2003). In this paper, our aim is to generate ‘novel’ knowledge about gender and identity dynamics in relation to women entrepreneurship in a family context. Women play an important direct and indirect role in entrepreneurial activities, but there is still a need for research on women in entrepreneurship and family contexts (Brush, 1992; Nelton, 1998; Danes and Olsen, 2003; Sharma, 2004). In a family context, relevant work on female entrepreneurs often concentrates on the role of co-entrepreneurs or copreneurs (e.g., de Bruin & Lewis, 2006). Recently, entrepreneurship researchers have argued to take into account the ‘everydayness’ of entrepreneurship (Steyaert and Katz, 2004), family and household contexts (e.g., Aldrich, & Cliff, 2003) and its social context (e.g., Davidsson, 2003). This takes on particular importance with regard to women in entrepreneurship; as such a perspective will draw attention to the ‘more silent feminine personal end’ of entrepreneurship (Bird & Brush, 2002: 57).