Many small institutions face difficulties, and the person who bears the brunt of dealing with those challenges is the college president. While each situation is unique, presidents can learn from the experiences of others, and at the very least, commiserate with each other regarding the challenges they face, especially when their institutions are struggling. In this article, the author reflects on his own experience as president of a struggling college over the previous five years, having weathered a two-year period of Southern Association of Colleges and Schools (SACS) probation and facing ongoing financial challenges. He gives advice to presidents of struggling institutions.