Scholars have alluded to the dynamic and often transient nature of meaningfulness, exhibiting perplexing features such as variations across the course of one day or fluctuations across the tenure of a seemingly enriched and meaningful job (Bailey & Madden, 2017a; Lepisto & Pratt, 2017). However, theorizing has lagged in providing a nuanced account of this temporal nature and how it impacts individuals and organizations, underscoring the need for a holistic understanding of the ebb and flow of meaningfulness in the workplace context. Our paper aims to bridge this gap by advancing theorizing around the dynamic processes of what makes and sustains meaningfulness at work. In our theorizing of meaningful work, we draw inspiration from the emerging understanding that meaningfulness is not a static experience but rather characterized by paradoxes and a dynamic negotiation process. We develop a theoretical model that illuminates the dynamics of meaningful work by detailing the three phases of aspiring, enacting, and regaining meaningfulness that is driven by the foundational meanings people derive from work and their ability to pursue such meanings through the employee-employer exchange relations and their interlinking mechanisms. We offer a set of propositions and delineate methodological recommendations that open new avenues for fruitful research in meaningful work and its dynamic processes.