Utilizing the Relational Developmental Systems (RDS) framework, in this chapter, I reflect on my mentoring experiences that shaped both my academic and personal development as a first-generation college student. I describe how RDS elements—holism, interdependence, plasticity, and agency—were evident in my relationships with my mentors and later informed how I mentor others. I describe how being valued beyond my role as a student, participating in reciprocal exchanges, and embracing change within relationships fostered an environment of trust, authenticity, and respect. These qualities contributed to my growth as a mentee while also serving as a foundation for becoming a mentor. I further discuss outcomes and the continuity of mentoring across time, highlighting multigenerational mentoring and the evolution of my enduring relationship with my mentor. Through these reflections, I illustrate mentoring as both deeply personal and profoundly developmental.