Globalization, social media, ever-increasing computing power, and the proliferation of low-cost advanced technologies have created a level of worldwide complexity and rapid change never before seen. To remain competitive in this environment, the US Department of Defense and our coalition allies must identify new ways to empower our forces. In this paper, we assert that part of that solution includes increased investments in our Human Dimension. Specifically, we argue that military personnel require an expanded set of competencies, higher levels of nuanced skills such as critical thinking and emotional intelligence, and more efficient and agile pathways to expertise, and that achieving these outcomes depends, at least in part, on revising the military learning enterprise. Towards this end, we outline a vision for the future of military learning, painting a picture of the “art of the possible� and proposing a roadmap that outlines five enabling conditions needed to achieve this future vision. The conditions include: (1) Cultivate ubiquitous learner-centric, technology-enabled instruction; (2) Build upon the foundations of data-driven learning; (3) Foster a learning culture at the organizational level; (4) Encourage and empower social learning; and (5) Draw upon deliberate practices and the evidence-based body-of-knowledge from learning science. Enacting any one of these conditions will pose significant challenges, and particular science or technology gaps associated with each condition create additional hurdles. Nonetheless, we argue that the time is right, in terms of understanding and demand, to take action. One major step in that direction is to agree upon a shared grand strategy, that is a vision for our Human Dimension and the military learning system that empowers it. That is the professional dialog this paper attempts to help inform and encourage.