This paper develops and deploys a theoretical framework for assessing the prospects of a cluster of technologies driving what is often called the digital transformation. There is considerable uncertainty regarding this transformation’s future trajectory, and to understand and bound that uncertainty, we build on Schumpeter’s macro-level theory of economy-wide, technological revolutions and on the work of several scholars who have extended that theory. In this perspective, such revolutions’ trajectories are shaped primarily by the interaction of changes within and between three spheres—technology, organization, and public policy. We enrich this account by identifying the critical problems and the collective choices among competing solutions to those problems that together shape the trajectory of each revolution. We argue that the digital transformation represents a new phase in the wider arc of the information and communication technology revolution—a phase promising much wider deployment—and that the trajectory of this deployment depends on collective choices to be made in the organization and public policy spheres. Combining in a 2 × 2 matrix the two main alternative solutions on offer in each of these two spheres, we identify four scenarios for the future trajectory of the digital transformation: digital authoritarianism, digital oligarchy, digital localism, and digital democracy. We discuss how these scenarios can help us trace and understand the future trajectory of the digital transformation.