The concept of “self-esteem” plays a crucial but at the same time ambivalent role in contemporary educational discourse. On the one hand high self-esteem is put forward as a solution for educational problems. On the other hand philosophers of education argued that the concept of “self-esteem” is not doing justice to educational situations and thus an unjustified transfer of a psychological concept to the sphere of education. The paper at hand asks for the concept of “selfhood” that lies behind the different approaches to “self-esteem”. What is the “self ” we are esteeming? The paper formulates a philosophical reflection on the presuppositions inherent in both the “standard view” on self-esteem as well as in the criticism on it. Both proceed, as I want to show, from a one-sided and thus simplified concept of what it means to be a “self ”. I will argue that a phenomenological approach to “selfhood” can be helpful in order to gain a better understanding of the role of the “self” in education.