Time’s Arrow has been widely debated in scientific and philosophical circles, yet this theoretical construct is relatively nascent in the social and behavioral sciences. More specifically, we may have much to discover from this lens when viewed in the context of organizational learning. The purpose of this article is to extend this research through an interdisciplinary framework of philosophy, history of science, and organizational learning by focusing specifically on critical reflection as an irreversible process. Returning to Epicurus’s original investigation of time, this paper argues for an ontology that links irreversible processes with Prigogine’s description of the Arrow of Time. Furthermore, defining critical reflection as an irreversible process then leads to an epistemological framework that helps describe change over time during organizational learning processes.