This article elaborates a deceptively simple suggestion made by Hegel (philosophy is the activity of thinking things over). It relates Hegel's suggestion above all to Dewey's stress on looking back, looking around, and looking ahead. In this endeavor the article touches upon two seemingly contradictory facets of philosophical thought—the autonomy and heteronomy of such thought (on the one hand, the apparent capacity of philosophy not only to transcend its time and place but also to unfold according to its own immanent logic and, on the other hand, the manifest entanglement of philosophy with historical circumstances) (West 1989, 7–8). To a greater extent, however, the article focuses on the dramatic character of philosophical efforts to think things over, once again. The drive to think things over is frequently rooted in historical crises, in experiential conflicts. The actuality of philosophy cannot be adequately understood apart from such dramas and conflicts, ones taking place far outside the studies and classrooms of thinkers.