Introduction: Finding ways to improve communication and self-reflection skills is an important element of medical education and continuing professional development. This study examines the relationship between self-reflection and educational outcomes. Methods: We correlate performance in a preclinical course that focuses on self-reflection as it relates to contextual elements of patient care (Human Context of Health Care), with educational measures such as overall grade point average, clinical clerkship scores, and Medical College Admission Test (MCAT) scores. Results: Student performance in Human Context of Health Care correlated with MCAT-Verbal scores, MCAT-writing sample scores, clerkship grades, and overall medical school grade point average (R = 0.3; p < 0.001). Conclusion: Writing and selfreflection skills are often neglected in undergraduate medical curricula. Our findings suggest that these skills are important and correlate with recognized long-term educational outcomes.