The _Essay discusses the relation between surveillance and imagination. It unfolds the argument that surveillance as a form of (political) oppression is necessarily centering on a decisionistic act of the individual who has to opt for deviant or conformist behavior under conditions of obvious social and political surveillance. Today, however, especially due to processes of an ongoing digitalization, surveillance is becoming a mode of self-expression, experiencing a shift towards its habituation and normalization within social reality. This development marks a clear difference from the classic habituation of surveillance as estranged, governmental practice. What seems to remain intact with regard to contemporary concepts of surveillance is the importance of the view and the meaning of surveillance as a politics of the image and the imaginary.