The tension between the need for critique and its (often unperceived) limits through our given common sense, a tension Charles S. Peirce describes as critical common sense, hasn’t lost its actuality. Vague certainty is one root of this tension, which the paper unfolds by distinguishing two forms: while the first one grounds common sense as a form of life, the second one, self-certainty, represents the purpose of endeavors, and it serves, speaking with Pierre Bourdieu, as a form of distinction (1). As part of an indifference towards power structures of exclusion, vague certainties contribute to what Judith Butlers describes as the violent derealization of others, which is being discussed in the light of the Black Lives Matter and Me Too movement. (Self-)certainty, as is being shown, is not (merely) an epistemological matter, but encompasses the fields of the political and aesthetic. Accordingly, as a crucial part of political critique and practices to counter (self-)certainties, a differentiation of doubting is required – the paper proposes four different kinds: authoritarian, anti-authoritarian, acknowledging and imaginative doubting. They help understand the political struggles of re-realizing formerly derealized positions within society (2). Particularly through imaginative doubting, some shortcomings within Peirce’s notion of the self (and, for that matter, within the pragmatist notion of doubting) are being overcome by showing how to link it to creative processes of abduction, which in turn have consequences for political matters by unsettling implicit consent, or, in the words of Jacques Ranciere, the partition of the sensible (3).