Obama recounts her high school life at Whitney M. Young High School, whilst reflecting on her parents sacrifices, ensuring that their children had the best education possible and privileges like other children. In this chapter, the author starts by informing the readers about her mother’s decision to work, which was not only a change of routine but also a financial boost to the family (Obama 52). Her high school experience is stated as being "designed as a kind of equal-opportunity nirvana, meant to draw high-performing students of all colors” (Obama 53). The environment and students at Whitney M. Young High School, who mostly came from privileged and well-connected families, made Michelle question her abilities. The author states "Am I good enough” was “a question that dogged me through my first month” (Obama 53). To fit in, she strategized on keeping quiet and simply observing her classmates. Michelle kept wondering whether children from the south side of Chicago were smart like their northern peers, and as the author puts it, “the truth is I didn’t know. I had no idea whether we were smart like them” (Obama 54). This made Michelle doubt her background and her self-belief.  

Subsequently, Michelle recounts her trip to school from the south side to Jackson Park Highlands and Hyde Park “following the curve of Lake Michigan north toward downtown” (Obama 54). During her trip to school, the author watched women and men in smart outfits going to work with a sense of self-importance. Importantly, Obama’s discovery of an African American elite, comprising of doctors and lawyers gave her a glimpse of the “apparatus of privilege and connection” (Obama 55). Children from affluent African American families had an opportunity to travel internationally, a privilege that Michelle lacked.  

In this chapter, the author shows her parents sacrifice to ensure both Michele and Craig got quality education and privileges. For instance, Michelle’s father deteriorating health did not prevent him from driving twelve hours to Princeton University to watch one of Craig's games, did her [Michelle] parents low financial status hinder them from paying for her trip to France. According to Michelle, “we were their investment, me and Craig. Everything went into us” (Obama 56). Parental guidance also helped in building Michelle's confidence and fighting the feeling of being not enough within herself. She worked hard to prove to the college counselor that she deserved a chance to join Princeton (Obama 60). Ultimately, her [Michelle] parents’ investment had finally paid off when she got an admission letter to Princeton University.