The authors reflect on the creation of the Doctoring program at the UCLA School of Medicine two decades ago. Although Doctoring—at UCLA and other institutions where it has been implemented—has successfully taught large numbers of students psychosocial content and communications skills that are often overlooked in traditional medical school curricula and has had an impact on the larger culture of medical education, the authors believe that its full promise remains unfulfilled. Of the many practical difficulties they encountered in creating and implementing this comprehensive program, the greatest barriers, by far, were cultural. The authors argue that the impact of programs like Doctoring—programs that attempt not only to change the content of what students learn but also to encourage students to think critically and to question fundamental aspects of the way medicine is taught, learned, and practiced—cannot grow unless and until the larger culture of medicine also changes. They offer recommendations for overcoming barriers to improve the next generation of Doctoring and similar programs; these include changing the philosophy behind the selection of medical students, providing far greater resources and support for course faculty, and altering incentives for medical school faculty. They conclude that until major cultural and structural barriers are overcome and the values that Doctoring and like programs attempt to engender become the primary values of the larger culture they seek to change, these programs will continue in fundamental ways to function outside the dominant culture of medicine.