Although the pace of digital transformation (DT) has been accelerating in more organizations, there is still much uncertainty about the ways organizations can achieve the intended outcomes from such efforts. Rather than just focusing on the transformation outcomes, our paper suggests that a more fruitful approach is to conceptualize DT as a journey that is often faced with contradictory tensions. We adopt paradox theory to explain the dynamics through which organizations can manage these tensions while driving their DT efforts. Drawing on extensive review of the DT literature and pre-existing research cases of three organizations’ experiences with the DT process, we developed the concept of DT pathways. DT pathways are the varied journeys experienced by organizations as they make strategic shifts, leveraging digital technology and evolving the organization’s business model. We show how DT pathways emerge as organizations adopt different DT strategic intent, actions, and responses to a range of paradoxical tensions. We outline three potential pathways— virtuous, moderate virtuous, and vicious DT pathways—and their attending predictive propositions that may serve as a guide for managers and researchers involved in DT efforts and research.