Rather than anticipating an issue or proactively addressing it, college and university administrators often find themselves in the position of reacting to recent laws or court decisions. This paper examines an issue ripe for proactive thought; an issue not yet directly considered in court cases: free speech and the student employee. In the development of First Amendment free speech jurisprudence on public college campuses, which cases and legal theories apply depends on whether the person claiming free speech violations is an employee or a student. A question not yet answered by the United States Supreme Court as it relates to the public higher education setting is: what if the person is both? Further, which standards apply and what are the differences in those standards? Although arguably addressed in the K-12 setting and in the private sector, but yet somewhat hypothetical for public colleges and universities, as student activism and campus student employment increases, the question is an important one for which to seek answers for the student affairs administrator. This paper reviews the legal basis for First Amendment free speech and then presents some practical ways to approach student/ employee speech.