The article addresses the role of the essay in Hannah Arendt’s theorizing. By paying attention to Arendt’s style, we are better able to draw the full conclusions from the well-known fact that she was not a system-builder but took her bearings from concrete experiences. First, the concept of experience—too often taken at face value—is explicated. It is argued that Arendt’s understanding of the concept cannot be reduced to her personal experiences, but must be read against the background of the common world. A crucial dimension in the incorporation of experiences into the Arendtian political theory is the essayistic style of her writings. The essay, as an experimental and tentative platform, provides an indispensable angle to Arendt’s work—even though often overshadowed by “classical” or “narrative” readings. This will be demonstrated in relation to the puzzlement surrounding the controversial concept of “the social.”