Women from rural, low-income backgrounds holding positions within the academy are the exception and not the rule. Most women faculty in the academy are from urban/suburban areas and middle-and upper-income family backgrounds. As women faculty who do not represent this norm, our primary goal with this article is to focus on the unique barriers we experienced as girls from rural, low-income areas in K-12 schools that influenced the possibilities for successfully transitioning to and engaging with higher education. We employed a qualitative duoethnographic and narrative research design to respond to the research questions, and we generated our data through semi-structured, critical, ethnographic dialogic conversations. Our duoethnographicnarrative analyses revealed six major themes: (1) independence and other benefits of having a working-class mom; (2) crashing into middle-class norms and expectations; (3) lucking and falling into college; (4) fish out of water; (5) overcompensating, playing middle class, walking on eggshells, and pushing back; and (6) transitioning from a working-class kid to a working class academic, which we discuss in relation to our own educational attainment.