Why do girls perform so well academically yet lose ground as professional women? This diminishing number of women up the leadership hierarchy is often referred to as the "leaky pipeline," and attributed to many factors: external ones such as work environments not conducive to work/life balance, and internal ones such as women's own leadership aspirations (Eagly & Carli, 2007). How early does that "leak" begin? Though much research has focused on college-age and adult women, little quantitative analysis has been done with younger girls. The purpose of this research is to study middle school girls to determine whether limiting factors in relation to career opportunities, expectations, and self-beliefs might emerge as early as 10 to 12 years of age. The authors also sought to understand how middle school curricula, programs, and educators might be empowered with specific knowledge to counteract or mitigate these factors. To that end, this research examines what middle schoolers think about careers and what factors may influence their nascent aspirations. Researchers also wanted to know what impact, if any, single-sex environments, here proxied by membership in one organization, the Girl Scouts, might have on young girls' career goals.