Matt Sheahan was an excellent college student. When he was in his sophomore year, he was on the dean's list and he found how easy it was for him to coast through college. By senior year, he had already had a radio show, a million friends, and credit cards he paid off at the end of each month. He was also one of the few people who came into college with a major and a strong notion of what he wanted to do after college. Then, all his hopes for a good future after college vanished after attending a radio conference wherein he heard the horror stories of how people started their careers. As the end of his college career approached, he still had no idea of what he wanted to do after graduation. In this article, Sheahan shares his struggles of entering the real world after graduation. His mother, Camille Helkowski, a career counselor, also shares her perspectives on guiding college students' and her son's transitions to postcollege life. She also shares how educators can become mentors to college students who are having difficulty adjusting to adulthood. (Contains 3 notes.)