The different shapes taken on by social entrepreneurship in contemporary society show that social goals are integrated by commercial enterprises and commercial goals are incorporated by organisations with a social mission. Combining a social mission with commercial goals is often presented as a “win-win” situation. In this article we highlight the potential tensions and conflicts created by the conflicting demands and expectations when the institutional non-profit and for-profit logics meet in social entrepreneuring. From this viewpoint, social entrepreneurship is an anomaly which seems difficult to resolve. Despite this we often read descriptions of social entrepreneurs as heroes, which shows how social entrepreneurship is glorified and part of the marketisation of society. This article sets out to present a more complex and problematic picture of practising social entrepreneurship where the obvious “win-win” situations more often appear as “win-lose” and sometimes even as “lose-lose”. From a three-year ethnographic study of an emerging fair-trade enterprise, the concept of disharmony shows that dilemmas are part of everyday life in social entrepreneuring. Instead of posing insoluble conflicts, dilemmas light the way for the individual social entrepreneur. They are managed through temporary rationalisation; finding a way to integrate conflicting demands into the life of a social entrepreneur. Disharmony includes moments of identity struggle, but is also a learning process in which the social entrepreneur tries to understand the difference between what she does and what she actually achieves.