This paper explores the notion of “power” prevalent in Václav Havel’s understanding of the post-totalitarian regime. With this notion of power, which is “seeping” in nature, rather than rooted solely in an individual agent’s actions, the role of the individual in the formation of the political “we” becomes a central issue. The starting point is Havel’s well-known example of “the greengrocer,” that illustrate how Havel pictures the way out of the post-totalitarian regime as one in which individuals move from living a lie to living in truth. I show how Havel’s talk about truth and authenticity, and his emphasis on a life in truth (which may appear judgemental, naive and cliché-like) is best understood. The wrong way to understand this is simply to say that people who merely obeyed that government, as the greengrocer did, are to be held accountable because they did not put up a fight against their oppressor. Such an understanding goes wrong because it fails to take into account the complexity of the relationship between power and language. In contrast to this, I argue that the central issue here is not that particular agents are to be held responsible for countersigning messages that they think are false. More precisely, I argue that the moral difficulty here is that the greengrocer’s deeds, which appear as countersignatures of the regime, are possible because the messages conveyed are “innocent” on the surface, in a “literal” sense. The moral dimension of the greengrocer’s actions, aiming to shed light on the complex relation between the government and the individual, is revealed as located in a field of tension between inherited sense and new projections. This, in turn, can help us to see the real nature of the transition Havel’s grocer undergoes when he moves from living a lie to living in truth. It is not a matter of negating a false statement or utterance, nor of replacing it with a true one. It is a matter of realising that the responsibility for meaning is, ultimately, ours – and that the way in which he, the grocer, is one of us is something that has to be earned.