I had moved from successful businesswoman to therapist and was doing fine. Then suddenly, at age 50, I was tripped up from an unexpected source—deep, unresolved feelings of confusion and pain surrounding my lost opportunity to become a biological mother. In this paper, I will examine both other women’s and my own ambivalence over issues of motherhood and track how those issues affect female identity. I will show how psychoanalytic training provided me the holding environment and safe relational home from which to deal with this sensitive part of my identity. Finally, I will examine, from an experience-near perspective, how concepts of complexity, intersubjective systems, and relational theories and new attitudes changed my organizing principles, and discuss the intersubjective implications of working with patients when the analyst integrates authenticity and self-disclosure into the therapeutic relationship.