When intern placement veteran Jacqueline Perkins begins counseling students at Florida A&M University (FAMU) about their prospects for getting well-paying, security-related jobs with the federal government, she confronts the 800-pound gorilla in the room--the question of whether a student has been convicted of or pleaded guilty to a misdemeanor. As minor as a misdemeanor conviction or guilty plea appears at first, she says, it can live in government records forever, undermine the job prospects of otherwise stellar candidates and cause major damage to their long-term career aspirations. This article illustrates the importance of character and integrity for students in pursuing opportunities after graduation and discusses what educators can do to address this problem. Former federal prosecutor David P. Baugh said that it is not fair, referring to how misdemeanor offenders are treated. He expresses that it's not just the employment line that narrows when a misdemeanor conviction becomes part of a student or graduate's history. Applying to college and getting campus housing can become complicated as a consequence of having committed a misdemeanor. Perkins advises educators to try simple methods that cost no additional money, such as talking with students more often. She emphasizes that educators should help them understand that there are lessons in life beyond a book.