Various versions of existential philosophy ask for meaning in view to the radical freedom and loneliness of humankind. They can be considered as a countermovement to modernity, by addressing the discomfort with one’s own existence. “Philosophical faith”, as Jaspers describes, attempts to protect thought and life from nihilism and demands seriousness and truthfulness in thought. The relationship to transcendence protects us from restrictive worldviews and opens us to unpredictable reality, thus becoming the core of philosophical belief. Transcendence opens up an open, indeterminable reality and counteracts rigid worldviews. Existence and transcendence are, thus, related, yet transcendence remains unobtainable. If it becomes rigid, it loses its power. Those who fail to experience borderline situations run the risk of missing themselves and of genuine philosophizing. This is a contradictory task of philosophical thinking.