According to the Center for American Progress, women make up 52% of all professional-level jobs, however, they only make up 14.6% of executive officers, 8.1% of top salary earners, and only 4.6% of Fortune 500 CEOs. Considering this disparity in leadership, it brings to question if women are generally taking on leadership throughout their lives. The purpose of this study was to examine how mentorship affects first-time female freshmen’s willingness to take on leadership opportunities. Data were collected from three mentees and three mentors through an initial interest survey, semi-structured personal interviews, and the 3D Wisdom Scale Assessment. Data were analyzed using a ground theory approach which consisted of open, axial, and selective coding; leading to a discursive set of theoretical propositions. Interviews focused on the mentee’s experience through the mentorship program, and the mentor’s perspective of the mentorship program on their mentees. Additionally, the 3D Wisdom Scale developed was utilized to evaluate growth in wisdom dimensions which directly correlated to personal construct corollaries. The findings of the study included: 1) The mentees and mentors expressed growth in their self-esteem and self-confidence. This increase in self-awareness led to a willingness to take risk and face potential failure; 2) Leadership development took place on several levels; 3) The mentees had a realization of the impact of their gender; 4) Two-thirds of the mentees showed a substantial understanding and practice in all three of respective corollaries; and 5) The mentees and mentors displayed general development and growth. The substantive theory that emerged from this grounded theory study was: ‘Through proper mentorship, a first-time female freshman’s’ self-esteem and willingness to take on leadership opportunities will increase.’ Unlike the majority of upperclassmen who have had a mentor, all of the freshmen participating never had a mentor prior to their participation in the program. Mentors played a substantial role in the development of these freshmen and their willingness to take on leadership opportunities. Recommendations for further research include a longitudinal study examining if these freshmen continue to involve themselves in leadership opportunities throughout their college career.