Mentorship is a critical and necessary practice in the journey of a leader. However, there is a dark side of mentorship that includes misaligned expectations and general negative consequences. In higher education, as with any industry, those who have attained leadership roles are not always models to be followed. It is important for mentees and possible new mentors to recognize all facets of a mentorship relationship and contemplate such issues as: (1) understanding that all leaders are not created equal, nor can all leaders contribute to a successful and fruitful mentor-mentee relationship; (2) learning mentorship-like lessons from a leader with challenges who cannot serve in a mentorship capacity; and (3) remembering to pay it forward and maintaining a commitment to constantly learn, to be open to feedback, and to stay humble.