In this chapter, I explore my complex and personal journey of mentorship as a Black woman navigating the racialized and gendered landscape of academia. Drawing on Black Feminist epistemologies and Standpoint theory, the chapter distinguishes between mentors and role models, emphasizing that true mentorship requires relational proximity, trust, and reciprocity. I recount both affirming and traumatic mentoring experiences—ranging from exploitation and betrayal to long-standing, transformative relationships—and reflect on how social position, cultural identity, and institutional power dynamics shape access to mentoring. Central themes include the politics of visibility, the burden of the Strong Black Woman (SBW) ideal, the significance of race and gender in mentor-mentee dynamics, gatekeeping and the importance of honesty, trust, and clearly defined expectations in mentoring relationships. The chapter concludes with practical lessons learned from both positive and negative encounters, offering insights for current and aspiring mentors and mentees committed to fostering equitable and empowering academic spaces.