Using “think-aloud” responses to scenario-based experiments, this research explores the reasoning individuals use to evaluate and justify the perceived entrepreneurial potential of environmental changes. Building on the notion of external enablers (EEs)—i.e., external changes to the business environment assumed to enable some entrepreneurial pursuits—and the associated framework, this study examines whether and how gradual vs. radical trajectories of EEs lead individuals to perceive different levels of entrepreneurial potential. The analyses of verbalizations reveal that variance in the trajectory of EE causes substantial differences in reasoning profiles and in the cognitive effort devoted to particular facets of reasoning. The findings are largely consistent across regulatory, natural-environmental, and demographic types of EEs. This research provides theoretical interpretations of systematic relationships between EE characteristics and cognitive responses to EEs’ entrepreneurial potential.