In this article, the concept of introducing and analytically using the concept of dilemmatic space in an educational context offers a potential to elucidate and deepen the understanding of the complexity of teachers’ everyday practise in work. Traditional ways of looking upon dilemmas is that they are related to specific situations where people react to conflicting values, obligations or commitments, ending up in situations where there often is no right way to act. However, the idea of a dilemmatic space, introduced by Honig (1996), offers a more complex understanding of dilemmas and their positioning and relations. Instead of being considered as specific events or situations, dilemmas are regarded as ever-present in peoples’ living space, as in a dilemmatic space. As seen as a relational category wherein one object is related to another(s), the spatial dimensions of dilemmatic space highlight the dynamics of dilemmas and dilemmatic spaces. These dynamics are important to recognize, for instance in relations to changeable boundaries of the space or issues dealt with that conjure up the dilemmas both on an individual and social level. These changing conditions of values, decision, responsibility and authority change the rules for relations, negotiations, and positioning, and thus the boundaries for the dilemmatic space and the dilemmas. In this article, the theoretical base for the idea of dilemmatic space is elaborated and connected to conditions for teachers’ work. Some conclusions are that new concepts force us to challenge pre-conceptions and involve us in new kinds of sense making processes. As such, the idea of dilemmatic space offers a broad theoretical framework to conceptualise dilemmas as well as the complexity of the educational contexts.