Since the concept of the teacher seems to be, that she or he is the one who owns knowledge—in contrast to students who don’t—it is understandable that teachers have doubts creating a situation out of those usual boundaries. In this chapter, it is argued that if we want to teach adequately for the post digital age, we have to embrace doubt. Doubt is a force that falls out of the usual teleological approach of teaching, because we don’t exactly know the outcome. This theoretical approach translates into practice—or better: is in itself a practical approach—because since one does not know which outcome an educational situation will have, he/she has improvise, embrace doubt, and deny classical power structures.