Mentoring for me has been a journey of sharing. I learned from wonderful mentors and mentees. The pathways into and within academia are varied, and our perceptions, expectations, and presumptions about those pathways are diverse. Mentoring cannot be just a transmission of knowledge and skills, because a mentor’s experience and training is only a part of the journey. What the mentee brings to the journey is equally important, in some ways more important. The lessons I have learned from mentoring relationships convince me that I can serve best when I know there is much I do not know but I want to learn; I listen to who I am actually with and appreciate their narrative and insights; I can be in the moment while still holding a vision of a possible future; I problem-solve together with my mentees, side by side in real life circumstances both inside and outside of the academy, and I can make myself available spontaneously whenever needed. Mentoring is idiographic: we are participating in the creation of an individual story. In that process we must be willing to deconstruct “best practices” and co-construct “success.” Mentoring is similar to midwifery: the outcome is not our child, but we do all we can to understand the person, the context, the connections and facilitate the creation of the person who is coming into the world. This chapter shares practices and anecdotes from that perspective.