The increase in female-headed households is one of the most significant post-war realities in Sri Lanka. In Northern Sri Lanka, many women are left in a fragile balance between being primary earners while also being the main caregivers within families. This has had wider implications for Sri Lanka’s overall economic development where women remain on the outskirts of the country’s development and many struggle to come out of poverty. This paper aims to examine the main barriers to economic empowerment experienced by female-headed households in Northern Sri Lanka. The paper argues that the failure of women to take part more actively in Sri Lanka’s economic growth is a result of various, often deep-rooted, structural constraints, rather than restrictions inherent in the choices of the woman. In turn, this paper argues that for post-conflict initiatives to be relevant to the realities of female-headed households, they must question gender issues and how it intersects with other aspects of marginality such as class, ethnicity, caste, social values, and disability.