This paper seeks to highlight and discuss two related issues pertaining to female entrepreneurs using recent Irish research. The first strand of the argument seeks to critically evaluate aspects of EU and Irish enterprise policy and its impact on female self-employed entrepreneurs. The European Union aims to become the most competitive and dynamic knowledge-based economy in the world and this involves moving up the value chain through the development of more technologically orientated industries where women are minority stakeholders (either as owners or employees). It is implicit in this policy that all participants will have acquired a high level of technical skills and literacy and this may place female entrepreneurs at a significant disadvantage. A second strand seeks to link the well-trodden debate on gender disadvantage in the labour market to disadvantages as female entrepreneurs. The paper argues that the issues which drive women from the labour market and into self-employment negatively impacts upon their performance as self-employed entrepreneurs -- out of the frying pan and into the fire. This argument relies on the international literature for support, which suggests that females, moving from the labour market to self-employment, often do not have the business acumen and skill-set to make that transition successfully. It is arguable therefore that female self-employed entrepreneurs in Ireland may be doubly disadvantaged. In the first place, the skill-set that they have acquired through employment lacks critical business acumen. Secondly, the sectors to which they migrate are predominantly low-tech services with limited growth potential. This paper argues that economic policies and enterprise support policies contribute to the perpetuation of disadvantages faced by many female entrepreneurs. The paper is based on research findings carried out in the Dublin region.