This paper explores mentoring and mentorship at the beginning and ending of one's career path and the role of mentoring in the process. It frames the mentoring and leadership discussion using the lens of a first year teacher in a LaSallian elementary school in Browning, Montana, on the Blackfeet Indian Reservation. Topics examined in this paper are garnered around the questions of who are your mentors and of how do they help you. Mentoring is a complex endeavor propelled mainly by love and care. In our examination of mentoring practice, we explore the behaviors, relationships, leadership styles, personality, individual gifts, and learning styles which create the cornerstone of the formation of mentoring. Mentoring begins and ends with exploring and validating each individual's gifts of love, joy, peace, patience, kindness, goodness, gentleness and self-control, whereby mentors provide presence, encouragement and accountability for the journey.