Entrepreneurial alertness is a psychological aptitude generally associated with aspects of nascent venturing, centered on individuals’ environmental observations, the association of resources, and idea evaluation. A decade following the Tang et al. (2012) consensus construct and scale, critiques remain questioning its utility and unique value to the major conversations in entrepreneurship. Proponents put great emphasis on entrepreneurial alertness’s proven association with opportunity recognition and entrepreneurial actions. Yet, critics suggest it might be an unnecessary step offering little more than a positive association with opportunity recognition in a highly generalized and static way. The purpose of this paper is to address this tension. We do so through a ‘steel man’ approach to these valid concerns. Further, we question the logic of limiting a cognitive construct to a singular event: ‘opportunity recognition’ for a new venture (which we term here, the “Big O”). Drawing on a comprehensive framework inclusive of the full entrepreneurship phenomenon, and integrating insights from cross-cultural psychology, we put forth the case for an ongoing culturally contextualized process perspective towards venturing where individuals are alert to and pursue opportunities (and cope with threats) continuously. This paper provides a new framework for delineating a theoretically grounded “what” and “when” of entrepreneurial alertness.