In the literature and popular culture of the United States, autobiographical narratives which tell of rising out of poverty are frequently read as inspiring stories, placed into the highly political discourse of the American Dream. From Benjamin Franklin’s Autobiography in the eighteenth century through J. D. Vance’s much-discussed Hillbilly Elegy (2016), many embrace the notion of success and advancement through personal effort and a bit of good fortune. In essence, they validate the key tenet of faith in the still active Horatio Alger ‘rags to riches’ narrative, in which the key to success lies in merit and not membership in any existing elite. Yet the rather nebulous notion of the Dream can be understood in myriad and contradictory ways, and not all works of transclasse autobiography fit so well into this reading. Tara Westover 2018 memoir, Educated, tells of growing up in a poor, rural, and also in many ways dysfunctional environment, and how a hard-won education opened the doors to escaping a life of poverty, at a superficial level conforming to the meritocratic narrative. More significantly, Westover writes of education broadening her mind and her own sense of self well beyond the harsh intellectual and psychological strictures of her upbringing. In this sense, Westover’s memoir is much more a story of self-discovery than one which neatly fits in to the narrow American Dream ideology of merit-based socioeconomic advancement. This did not prevent it, however, from being appropriated as another inspiring example of how ‘in America, anything is possible’, an interpretation the author herself emphatically rejects. The purpose of this paper is to examine these ideological considerations and in both Vance’s Hillbilly Elegy and Westover’s Educated and place them within a broader spectrum of discourses on the American Dream in more idealistic visions of liberation and fulfilment.