The postcommunist concept of transition, as it was in use during the 1990s and early 2000s, is analyzed from the viewpoint of its intellectual prehistory. The concept is partly contrasted with alternative notions, partly relocated to its antithesis of communist ideology, where “transition” actually was an established concept. Via Hegel and Lenin, the concept’s logic of asymmetry and negativity is theoretically demonstrated. One thesis is that radical versions of teleological postcommunist transitology have unconsciously reproduced an essentially communist conceptualization of change that may generate new ideological biases and misconceptions. The reconstruction of the dialectics between communist and postcommunist transitology indicates and responds to a need for historical reflexivity.