For many organizations, the upcoming retirement of the Baby Boomers and the influx of the younger generations to the workplace will prove to be challenging. In this chapter, we review empirical data on generational differences and provide descriptions of how the average member of the young generation (labeled Generation Me) compares in personality traits and attitudes with the average member of earlier generations. Most changes in generations have occurred gradually over time, in a linear fashion. With increases in self-esteem, narcissism, and the importance of leisure time, expectations for work—life balance, salary, and fulfillment have also increased among the younger generation. The result—a widening gap between what Generation Me expects from the workplace and reality—may explain why there has also been an increase in anxiety and depression over the generations. Implications of these generational differences and suggestions to assist in the management of today's multi-generational workforce are discussed.