This chapter uncovers how educators constantly exist in a state of flux regarding their own capacity to continue being an educator amidst a challenging university world. As people find themselves thrown into unpredictable situations, they are constantly experiencing their own existential "possibility-for-being' an educator in contrasting modes. In light of Heidegger's notion of human being as "thrown possibility', this chapter presents stories that show various ways educators relate to their own self-possibilities in a university world.