In this essay I attempt to offer a theological assessment of the resignation of pope Benedict, and this in view of the fact that he for more than fifty years, since Vatican II until today, as a theologian and a Church leader, has been fundamentally determining the history and profile of the Roman Catholic Church. I wager on the concept of ‘cognitive dissonance’ to explain why the pope resigned, indicating that a massive clash occurred between the theological ideas Joseph Ratzinger holds about Christian faith and the Church, and the actual situation in which both Christian faith and the Church find themselves. For Ratzinger, Christian faith is in the first instance about conversion, and the Church is called to be a beacon of light and truth, calling the fallen modern world to conversion. It is the same Church, however, which is weakened by sexual and financial scandals, and which is losing at a steady pace public authority. In my analysis, it is precisely because the Church closed in on itself to protect itself from a world perceived as inimical, that it forgot that it is in need of conversion itself, before it can call the world to convert. It is the lack of openness and dialogue, both within the Church and of the Church with the world, which has caused this forgetfulness of conversion and rendered the Church ill-fit and isolated in view of its calling. Stepping down as pope was the way for Pope Benedict to bring about dissonance reduction. It would seem, however, that especially Pope Francis’ words and deeds to realize a more humble, poorer and dialogical Church, offers a more appropriate way to effectively reduce the cognitive dissonance at hand.