Academia consists of implicit norms that are not openly discussed or taught to students. For graduate students, especially students with little to no experience in higher education, these unknown expectations need to be communicated by their mentors—the academic cultural experts. Based on our personal experiences, we identified a set of insights and lessons that encapsulate important critical experiences graduate students may have during their academic journey. We focus on a holistic mentoring relationship in which mentors consider the whole student. We present the perspectives of both mentors and mentees on the lessons learned that included imposter syndrome, identifying strengths, advocating for students, time management, and identifying personal and professional resources. The guidance and support passed down through generations of holistic mentorship can create enduring relationships that go beyond graduate school and well into our professional careers.