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How are risk orientations shaped in the sphere of work beyond proximate structuring institutions? In the absence of clear organizational imperatives or institutional supports, what provides the broad contours of a workable imaginary? Using interview data from small business owners in Argentina, I show that the form and content of generational memories of crisis influence the uptake of entrepreneurial discourse and apprehensions of economic risk. Older business owners draw upon their collective memory of the 2001–2002 economic crisis to engage in a process of adversarial personification that posits the macroeconomy as a cunning enemy and positions them as strategic actors. Conversely, younger small business owners—who did not live through these economic shocks as small business owners—draw upon the entrepreneurial ethos that they collectively cultivate through generational communities of practice to engage in a process of empowered distancing that minimizes the severity of economic crisis. Using Kenneth Burke’s theoretical schema to identify grammars of motive and action, I show how older business owners deploy a generationally shared narrative to develop a conceptualization of economic agency that does not derive from the entrepreneurial ethos. By arguing that collective memory generates economic subject positions, this article demonstrates that the “use value” of collective memory lies not only in its uptake by politicians, journalists, and activists engaged in political projects, but also in the everyday ways that economic actors use narratives about the past to develop strategies of risk management in the present.