This perspectives article written under the sponsorship of the Commission on Change and Innovation in Dental Education (CCI) of the American Dental Education Association (ADEA) summarizes data on the numbers of women and persons of color earning the D.D.S./D.M.D. degrees and entering the U.S. dentistry profession in the first decade of the twenty-first century and examines job factors of importance to recent graduates of doctoral programs in other academic disciplines that may have relevance for planning recruitment and retention strategies within academic dentistry. The characteristics and expectations of Generation X faculty are explored: who are they and what do they want from the academic workplace? The article describes the culture clash that often occurs when Gen Xers encounter policies and practices that were designed by and for prior generations (e.g., Traditionalists and Boomers) who filled the ranks of dental school faculty in the 1970s, 1980s, and 1990s. Recommendations for rethinking academic employment systems in ways that might make the university workplace more attractive to Generation X are described.