As an administrator of a program intended to help retain students at Syracuse University, the author found herself in an ironic position this past August. She was presenting a workshop to parents of incoming first-year students about what they could expect from their sons and daughters during the first semester of college. It was ironic because within days of the workshop, she was making the trek from Syracuse to southern New York to drop her own daughter at a small private school and sitting through the same presentation that she had just given. In this article, the author shares her experience in helping her daughter go through the process of taking some important steps toward a change that could prove to be a difficult transition in the first semester of college. The lessons she learned from this experience are described.