This essay elaborates on the notion of risk in relation to democratically challenging situations in education.This refers to situations in which liberal democratic values are potentially challenged, such as in teaching about controversial issues and in moments of expressions of hurtful speech, which can create in teachers an ambivalence for how to act. The essay takes an understanding of risk as holding a plurality, viewing risk as both undesirable and desirable, to be both reduced and embraced. By considering perspectives that implicitly relate to risk in various ways, this essay explores what can be made possible by embracing risk or its reduction in democratically challenging situations. These perspectives envisage tension between different approaches to risk and visualize how risk may be viewed both as possible moments of change and as possible moments of violence. The essay advances the argument that a one-sided approach to risk may thus pose a challenge to the struggle for democracy, arguing instead for a complex approach to risk. Making use of Jonna Bornemark's work on the "paradox of action," the essay proposes the viewing of risk as a paradox, spanning our world of action. The paradox formulates a mutual dependence, in which more is required of one side in one moment and more of the other in the next; neither can be neglected. The essay proposes an approach for teachers: "living the paradox of risk," which is to act in the space between reducing risk and embracing risk in democratically challenging situations.Philosophical Inquiry in Education 2 in society, or does it rather lead to reproducing oppressive power relations? In this essay we highlight the need to maintain these kinds of tensions. With this it follows that we understand liberal democratic values not as ideals to be achieved, but as non-linear qualities to engage in and struggle for, through a responsiveness to processes in the here and now.By putting the notion of risk at the centre of this struggle we explore how different perspectives explicitly or implicitly relate to risk in their responses to democratically challenging situations. A point of departure for this exploration is an understanding of risk as a concept that holds a dual meaningas both undesirable and desirable. As a concept, risk has no agreed upon definition, whether in ordinary usage or in science. Rather it is a concept with multiple definitions (Aven, 2012. See also Renn, 1992. According to Aven, "Some definitions are based on probability, chance or expected values, some on undesirable events or danger, and others on uncertainties" (2012, p. 33). Although its origin is inconclusive and disputed (Oxford English Dictionary, 2021; cf. Aven, 2012), plurality seems in line with the etymology of the word "risk." According to the Oxford English Dictionary (2021), it is suggested that the post-classical Latin resicum, risicum, etc., in the sense of "danger, hazard," ultimately derives from the classical Latin resecãre, meaning "that which cuts," and hence "rock, crag, reef," allu...