Sport management seems like a glamorous career path. Many students believe if they do well in classes and graduate, they will be the next general manager of the New York Yankees or athletic director of a major Division I intercollegiate athletic department. While sport management professors hope that every student has the potential to succeed, it is incumbent upon faculty members and students to have a realistic expectation of their career options and a true understanding of what it takes to be successful. This article leads a fictitious student and faculty member through four years of the student’s educational adventure in sport management with special attention being given to what students can undertake to best prepare them for the future and improve their chances of landing the right job. This case study demonstrates the value of a comprehensive sport management education and what students can do to set themselves apart from their competition in the job market.