Research relating to mentoring has predominantly been focused on outcomes regarding the mentees. Very little has been explored about the benefits of being a mentor. The minimal research that does take the perspective of the mentor states that there could be wide variety of benefits, which include leadership skills, coping skills, support systems, and broaden of perspective. In this study we examine the relationship between participation in the First Year Mentor Program at Southern Oregon University and the level of different psychological dispositions. We explore the possibility that there may be a difference in these psychological attributes between a general undergraduate population and those enrolled as mentors in the program. We measured dispositions such as hope and life satisfaction as well as possible mediators such as student and faculty support, student engagement, and school experiences. Findings suggest that there are differences as well as complexities within these relationships.