This conceptual work seeks to re-examine the organizational ambidexterity concept (the balance between exploitation of current knowledge and exploration of new knowledge) from the temporal sensemaking perspective—constructing and reconstructing the relationship of past, present, and future. Firms compete in a dual environment—technical environment (labor, capital, and input commodities) and institutional environment (symbolic resources, such as legitimacy). Yet, organizational ambidexterity has been largely conceptualized in the technical environment only. I argue that the institutional environment matters, hence symbolic resources (e.g., legitimacy) are substantially invaluable for firms. In this paper, I explore the ambidexterity paradox in which firms reconcile the sensemaking of both their history and future in search of legitimacy (history-based and future-based legitimacy) in the institutional environment. Particularly, I propose two approaches to temporal sensemaking to gain and preserve legitimacy, namely rhetorical history (a means by which firms solidify the past with persuasive strategies) and strategic foresight (heuristic processes to grasp the environmental discontinuities to devise strategies). By underscoring the symbolic resources that firms can strategically capitalize on, this work provides a nuanced understanding of the ambidexterity concept while delineating new future research avenues.