Human development involves numerous interactions between the individual and social typecasts, family values, cultural traditions, media stereotypes, and a variety of external sources placing normative values and expectations on human development. These interactions can provide strong gender role typecasting, especially in developing adolescents, and sets boundaries for social interaction, support, and peer group associations (Hall-Lande, Eisenberg, Christenson, & Sztainer, 2007). One critical phase of development occurs between pre-pubescence and adolescence (Greenfield, Keller, Fuligni, & Maynard, 2003). The focus of this study is on female adolescent development and the effects of social/parental stressors utilized to force conformity and describe appropriate gender expectations to achieve essentials for success. The presence of gender role stressors during development will be utilized to establish the existence and effects of gender role conflict. The manifestation of Gender Role Conflict (GRC) occurs when external perceptions, gained through parental or social influences, formalize within developing females and creates incongruence between individual goals and social forces pressures acting on the developmental process (Hoffman, 2006a). Female adolescence provides a challenge to individual awareness or submission to social compliance when forming developmental pathways to adulthood. All women do not necessarily experience gender role stress during adolescence development. However, for those who do, gender role related stress creates varied levels of dissonance between personal determination and social context (Fine, 2011). GRC is the resultant stresses which often mark the difference between successful developmental achievements or confounding socially prescribed developmental attitudes with unresolved conflict and elevated stress (Small & Memmo, 2004). This study will examine gender role conflict as it develops from intra-familial stress, social structure, and regional cultural influences and the resultant negative effect in achieving individuation, positive sense of self, and attainment of life goals (Hertzman, 2002). Stress has the potential to develop positive or negative connotations during development. However, this study focuses on the negative aspects of stress related gender role conflict and the long term effects on development (Dickerson, 2004). The researcher will utilize qualitative comparative case study design to examine the development of, or effects from parental, social, and cultural influences on adolescent female development and goal achievement (Martin & Fabes, 2009). The experiences of adult women who currently occupy gender variant career fields will be examined in order to identify the personal or social influences that affected career decisions. This research is not a study of career fields. Rather, it is a study of women who by career choice have broken career related social stereotypes and were more likely to have experienced gender role stress during development (Worell & Goodheart, 2006). Social and familial developmental expectations are primarily predicated on gender role assignment as specified by birth sex (Fine, 2011). The resultant developmental gender role conflict emerges when external developmental influences are not congruent with individual values or goals (Allison & Schultz, 2004). Gender role preconceptions, as determined by birth sex alone, have been framed without regard to individual differences or consideration of the developing female’s self-expression or experience as she matures (Barnett, Biener, & Baruch, 1997). As such, the adolescent female is unwittingly placed in narrowly defined categories formed by societal and familial influences without regard to her individual characteristics or her voice (Anthony, Holmes, & Wood, 2007). The experiences of adult women as related to adolescent development, parental or social influences apparent, and/or existence of GRC prior to entering gender variant career fields will be obtained and discussed within this dissertation.