It is important for sports administration programs to prepare students for career entry and transition into productive roles within their new jobs upon graduation. However, even the best academic curricula for those entering a profession may be inadequate for preparing students for early success in their careers. Not only do academic curricula lack the ability to train students for problem solving and independent thinking, they lack the ability to provide context, reducing transfer of knowledge to practice. The purpose of this article is to provide instructors in sports administration programs background information related to the transition graduates may face when entering the job market. The underlying assumption is that if instructors better understand the process of job entry and transition, they can better prepare students to embark on their careers. Included are discussions of professional preparation programs, the expectation gap held by new employees, job role transition, and organizational socialization.