The dynamic mother-daughter relationship can be loving and supportive at best as well as contentious and tragic. It is a relationship predicated on maternal instinct which can provide direction and support for deep insight into notions of womanhood, personal and political philosophies. However, in providing this guidance, ironically this same maternal guidance can act to stifle the growth of an adolescent daughter as she transitions into womanhood. Jamaica Kincaid’s ‘Annie John’ can be seen as an exemplar of this transition. Annie (...) has to contend with not only her mother’s maternal pressure on her to conform, but she must also adhere to cultural expectations of a creolized culture predicated on both Africana and British understandings of femininity, social expectations, womanhood, and etiquette. This challenges Annie’s own emerging philosophy and desire for independence and self-definition. As discussed in this paper, success can be achieved outside and beyond the mother-daughter dynamic once a daughter has had the opportunity to consider, realize, defy the hypocrisy of being encouraged to be independent whilst being forced to follow one’s mother’s notion of womanhood. In a valiant attempt to avoid the tragedy of replicating her mother’s own flaws, Annie John’s personal growth was no easy feat and created at times a contentious dynamic. However, this journey not only facilitated her success and independence so that she could travel beyond the shores of Antigua, it demonstrated an independence of thought that African Caribbean creolized women must experience in order to realize their own success. (shrink)