Students attending suburban and rural schools face obstacles that make dropping out of school a viable option for them. The need for schools to find strategies that will keep students in school is critical. One strategy that is successful in keeping student interested in school is participation in sports. As the leaders of sports' teams, coaches provide the necessary mentoring that can positively guide a student's decision to stay in school. In this qualitative naturalistic inquiry, three coaches were interviewed. Each of the respondents were significantly influenced by their families and certain "mentors" that they had as they were in school; crediting them for molding their professional philosophy. The respondents used their life experiences as a guide in their professional careers to relate with their students and athletes.