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In this paper, we examine the phenomenon of representation through the theoretical lens of ambivalence, concentrating on the people involved in representation: representatives. We argue that the theoretical concept of ambivalence can be helpful in analysing and understanding the various tensions environmental and other representatives encounter in their practice. Based on the concepts of “sociological ambivalence”, “ideological dilemma”, and “the organizational centaur”, as well as on insights from social studies of science and sustainability studies, the paper develops a typology of three potential sources of ambivalence: role conflicts, value conflicts, and conflicts between goals and means. In addition, the paper identifies various ways of coping with ambivalence, including the construction of meta-norms, organizational and network support, pragmatism, drawing boundaries for reasonable and acceptable actions, rule bending and discursive negotiation. The paper concludes that the concept of ambivalence adds crucial insights to the positions, practices, and challenges of environmental representatives and notes that ambivalence is not only a matter of tensions and conflicts but can be a source of reflexivity, learning, and agency.