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Introduction Mentorship, a supportive relationship that actively provides knowledge and insight, has many benefits. Although not extensively studied, medical students pursuing various specialties have diverse experiences with mentorship. Objective To understand how mentorship impacts medical student decisions involving rotation choices, residency programs, field of practice, interest in research, and career trajectory. Methods We hypothesized that effective mentor-mentee relationships would strongly impact medical students' decisions. Distributed to fourth-year osteopathic medical students at a single medical school, this study used a survey design to assess mentorship's impact on their aforementioned decisions. Results Sixty-one students responded to this survey. Fifty-nine percent of respondents said they did not receive enough mentorship in medical school while 63.9% of respondents said their quality of mentorship was good/very good. Most survey respondents strongly agreed/agreed that the amount and quality of mentorship impacted their decisions involving rotation choices, residency programs, field of practice, and career trajectory. Qualitative data analysis led to the emergence of three themes: students pursuing primary care had positive mentorship experiences as compared to students pursuing non-primary care careers, female students stated they did not receive enough mentorship, and a majority of students cited the lack of formal mentorship as an area of improvement. Conclusions Our study demonstrates the profound impact mentorship has on a medical student's career. Respondents believed their mentorship experiences strongly impacted their decisions involving rotation choices, residency programs, field of practice, and career trajectory. Participants also believed availability in the amount and quality of mentorship could be improved. The perceived lack in the amount and quality of mentorship may have negative implications on medical students' career prospects.