This essay explicates the role of countersystem analysis as an essential mode of social inquiry. In the process, particular attention is given to the place of negation and the future. One underlying theme is the asymmetry between the negative and the positive features of social activities, the negative being more readily identifiable empirically than the positive. A corollary theme, building on the observations of George Herbert Mead, is: one engages the present through experience; one engages the future through ideas. Furthermore, as Anthony Giddens, Ulrich Beck, and Niklas Luhmann suggest, we in late modernity seem to be facing a future that is more contingent than it was in early modernity. After articulating the foundations of the mode of inquiry we term “countersystem analysis,” we employ Karl Mannheim as a point of departure for critically surveying a constellation of scholars—conservatives as well as reformers—who have relied upon some version of countersystem analysis in addressing the future. Such an orientation serves to advance not only theoretical inquiry but empirical investigation as well.