Women and men are still segregated into different occupations. There has been a marked underrepresentation of women in science and technology fields for many years, despite some increases in the number of women earning undergraduate and graduate degrees in science. The notion of possible selves can be applied broadly to the problem of why the tendency for young women and men to sort themselves (or at least allow themselves to be sorted) into different occupations is so persistent. This chapter discusses the ways in which societies' gendered expectations may affect the possible selves that women and men develop. The idea of adult education as transformative, as an opportunity to alter one's fundamental view of oneself and the world, and as a vehicle for change in possible selves, particularly for women, is also explored.