In this study, we analyzed the experiences of an educational leadership doctoral student and aspirant to the professoriate (protégé) and an educational leadership professor (mentor) during our two-year mentoring relationship. Collaborative autoethnography was employed, and our analysis relied primarily upon a process-oriented model of mentoring. Four main themes emerged: (a) reciprocal trust, (b) experiential learning, (c) stability and change, and (d) mutual benefit. Our relationship also was marked by several critical features, and we described the timing and sequence of the socialization experience. This productive mentoring relationship offers a detailed model for doctoral students and faculty members who wish to pursue a similar relationship. From our research, we also contribute to the broader mentoring literature, in which previous researchers have rarely delved simultaneously into mentor and protégé experiences. Scholars who study mentoring will gain from insights into the manner in which anticipatory socialization unfolds, as well as critical features that emerge and evolve in the process.