Being a professional means incorporating special knowledge and dealing with it concerning problems with a high potential for innovation (see a.o. Hitzler, 1994). This knowledge has different dimensions: “technical knowledge” refers to the ability to create professional application routines; “process knowledge” describes being firm with interaction routines and organizational constellations; and carrying “Interpretation knowledge” as subjective relevance, rules and perspectives, which is highly important for acting out as a professional (Bogner & Menz, 2002). This last type of knowledge, as a kind of implicit subconscious knowledge, concerns job routines as well as decision-making in uncertain situations (Meuser & Nagel, 2010). In that sense professional school leaders must be flexible, perform situated leadership and deal with given structures in the context of their own professional approach. They find themselves on the top of their school’s organization chart and mainly manage the daily business at the school, while at the same time have to deal with political relevancies. On the one hand they have as professionals the freedom to innovate, and on the other hand, they are bound to social institutions. Concerning these demands one can link being a professional school leader to having an entrepreneurial self, which refers to a certain kind of perspective or world view rather than the position at the labor market (Klinge, 2016). In the classical sense, being entrepreneurial means “creative destruction” to form something new (Schumpeter, 1947), being open-minded and being brave in acting, and walking towards opportunities in a vast field of social relations (Bude, 2000). Thus, based on the above, the main purpose of this paper is to discuss the link of uncertainty management in professional school leading and the entrepreneurial self. This was accomplished through a qualitative research methodology, reconstructing implicit knowledge of school leaders. The empirical material was gained through expert-interviews in the “SHaRP” Project (Brauckmann, 2016) and interpreted in a secondary analysis through the documentary method (Bohnsack, Pfaff, & Weller W., 2010) . Our findings confirm this link between being a school leader and entrepreneurship: while one type of school principal sees school management as a burdensome bureaucracy, the other type sees it as opportunistic entrepreneurial acting and being a “self-made man”.