The relational approach to psychotherapy, furthered by the analyst's use of the transference-countertransference paradigm, can create the gateway to explore and understand patients' internal barriers to growth. The analysis can then help patients to achieve a more integrated self-view that allows them to enjoy success and fulfillment in both their private and their public lives. Even as they strive for their own self-definition, women hold onto old relational ties. In this paper, two case examples are used to elucidate the complex relationships that women have with their earliest caregivers. The cases demonstrate how women remain fixed in early familial internalizations and identifications, and find themselves repeating patterns of self-sabotage that impede their success.