Social entrepreneurship seems commonly related to two different missions. On the one hand it is about making profits and surviving in a market context, and on the other hand there is a social mission. This study focuses on tensions of multiple identities from the social enterprise perspective in the form of a fair-trade company emphasizing the social mission of human rights issues, albeit challenged by the business assignment. The purpose of this article is to elaborate on the connection between identity dilemmas and the tensions of social entrepreneurship from the perspective of entrepreneuring. The dilemmas presented in this article arose from an attempt to dissolve an anomaly that a social entrepreneur perceived. In these situations she found herself to be in a deadlock position between the non-profit and the for-profit logic. Moving between these logics creates opportunities as well as dilemmas for the social entrepreneur. Choosing one of the logics, in which the dilemma is re-constructed as an opportunity, seems to be a way to move on, until another dilemma arises. Hence, becoming an entrepreneur involves a process of negotiating one’s Self from the different expectations and making identity adjustments in relation to the different logics.