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The transition from high school to college can be very difficult for many students. The authors believe that students can advocate on their own behalf by educating themselves on challenges they may potentially face, as well as establishing realistic educational and social goals. Concurrently, parents can assist their children by becoming more aware of the transition issues, and learning how to help anticipate transitions. This paper will acquaint the reader with three key transitional challenges new college students face, as well as offer an approach to productive interactions with both students and their parents. As evidenced in steadily improving persistence rates, the University of Pittsburgh has found by educating new students and parents in realistically anticipating first year challenges, students are able to produc- tively work through their freshman year university experience. [ABSTRACT FROM AUTHOR]