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Mentorship has been repeatedly shown to be a necessary component of successful professional development. However, effective mentorship can be elusive to define insofar as “you know it when you have it,” but it is hard to match the objective qualities of mentorship with the subjective experience of effective and helpful mentoring. This article explores the Collaborative Family Healthcare Association’s mentorship program from the perspective of one mentor and two mentees over the course of a yearlong formal relationship. During the year, both mentees had to navigate significant transitions, including changing jobs and having a baby; these experiences are relevant for many new career professionals.