This article reports representative findings regarding the careers of school principals in Germany. Almost a third of teachers already thought about applying for a position as a school principal but decided otherwise, not only because they fear stress and strain, but also because they are content with their current pedagogical work. School principals choose their career first and foremost to widen their creative scope and to gain more responsibility and autonomy. Despite a high level of overall job satisfaction, one fifth of school principals in Germany has a turnover intention. The findings are discussed against the backdrop of the virulent shortage of school principals.