America's current generation of adolescents promises to be not only one of the country's most complex but also one of the country's largest, rivaling the baby boomer generation in size and consumer power. Understanding the challenges and positive experiences that these students bring with them to college campuses is important for educators as they work to engage students in learning. Exploring the trends that affect students in the nation's high schools provides important insight into how to organize college learning experiences to meet the needs of incoming college students. In this article, the author discusses the educators' challenge and ways to meaningfully engage students with potentially misaligned ambitions, mental health concerns, and high-risk behavior profiles. Higher education faculty and administrators can begin to meet the challenge by taking the time to learn about trends that affect high school students, who are tomorrow's first-year college students. (Contains 9 notes.)