Background: Demographics are changing on a global scale. In the United States, an aging population continues to work, either by preference or because of insufficient resources to retire. Of even greater importance, a younger generation, referred to as the Millennial Generation, will soon predominate in the workforce and even now accounts for nearly 100% of resident physicians. By the year 2020, there will be 5 generations in the workplace. Methods: This paper defines and details the characteristics of the 5 generations and examines how the vision, attitudes, values, and expectations of the most recent generations will reshape the workforce and graduate medical education. Results: The need for change is imminent to educate the next generation of physicians. Among the changes necessary to adapt to the multigenerational challenges ahead are adopting mobile devices as preferred communication tools; using social networking sites to recruit residents; adding games, simulations, and interactive videos to the curriculum to engage students; breaking down departmental silos and forming learning teams that come from different specialties; developing benchmarks and milestones to measure progress; extending the social learning ecosystem beyond the resident years; embracing diversity as the norm for both practice and learning; and providing both coaching and mentoring. Conclusion: For decades, resident physicians have shown commitment, tenacity, and selflessness while shouldering the dual responsibility of patient care and the pursuit of their own education and skills development. Resident engagement has been shown to drive change in undergraduate medical education and in the learning and performance of their teachers. The latter is evidence of reverse mentoring that will be a major factor for improvement in this digital age. We have only to embrace this opportunity to the benefit of our patients, our learners, and ourselves