Secularization poses serious challenges for religiously affiliated schools. Catholic schools in the Netherlands find themselves embarrassed regarding their educational endeavor because they are unable or lack the inspiration to talk about this subject in religious terms. This article aims to explore new ways of overcoming this embarrassment. Firstly, an overview is presented of the current situa­tion and of the embarrassment of Catholic schools, in terms of their problematic choice of actions. Based on a critical-dialogical convergence of theological and pedagogical considerations, a Catholic vi­sion on the educational endeavor is subsequently developed that is understood in terms of interrup­tion, the other, and transcendence. From this vision of the educational endeavor, new strategies are presented – at the community level of Catholic schools, and at the individual level of teachers, school leaders, and governors – to promote an openness to receiving new, unexpected insights and possibili­ties. The receipt of these insights and possibilities is closely related to an awareness of transcendence, in both a secular and a religious sense. The initial findings of recent empirical research on the impact of these strategies are presented.