Purpose: The purpose of this paper is to explore Thomas Pynchon's novel Against the Day as a symptomatology of organization and examine the (un)easy relationship between the novel and organization. Design/methodology/approach: The novel is explored through three interrelated readings: first, the novel is considered as a representation of the gruesome nature of capitalist ordering; Second, the novel's textual strategies are examined to consider its co-implication and knotting into the very logic of organization it abhors; Third, the novel is read as a search for other spaces haunting the broken machine of capitalist organizing. Findings: The paper shows how Pynchon's writing and critique of capitalist organizing occupies an indeterminate space characterised by the ambivalence of ambivalence, where deciding upon its final meaning is a reductivist strategy ill suited to this complex text. Instead the novel functions through a complex process of displacement and emplacement. Originality/value: Theoretically, the paper extends further the understanding of the relationship between literature and organization, challenging reductivist readings of this relationship to explore how the novel simultaneously emplaces and displaces the reader so that critique, as well as convention, are thoroughly unsettled.