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Michelle’s grief leads to a fight with Craig over the choice of a casket for their father. Soon, however, Michelle reflects that Suzanne’s and her father’s deaths carry a lesson: life is short. She starts exploring her career options in earnest. Michelle’s mother once briefly worked for Art Sussman, a lawyer for the University of Chicago. He introduces Michelle to Susan Sher, a city hall lawyer, who in turn introduces her to Valerie Jarrett. Jarrett served on the staff of Chicago’s first Black mayor, Harold Washington, and now works for Mayor Richard M. Daley, son of Richard J. Daley, who had been Chicago’s mayor during the tumultuous 1960s. Valerie impresses both Michelle and, later, Barack, with her knowledge of Chicago politics and her conviction that there is room within the system to do good things and to advocate for the interests of the Black community, even under a mayor whose family name is synonymous with old-school, white Chicago politics.
Barack is in a good mood after taking the bar exam. Although Michelle passed only on her second attempt, she and Barack are confident he passed on his first. At a celebratory dinner, Barack professes his love for Michelle but repeats his arguments against marriage. Michelle tries to control her anger, but when a waiter lifts the lid on the dessert tray to reveal a ring, she realizes that Barack has pranked her. When he proposes on one knee, she accepts. Soon, they visit Kenya, so he can introduce her to his Granny Sarah. Michelle feels strangely out of place as an African American in Africa, but Granny Sarah makes her feel welcomed and loved.
During the next year, Michelle works for Valerie Jarrett, as a citywide representative of the mayor’s office. Michelle is inspired by the skill and confidence with which Valerie and Susan Sher juggle their careers and their responsibilities as single mothers. Barack, meanwhile, does voter registration work in the Chicago area, for a national organization called Project VOTE! At Michelle and Barack’s wedding, in October of 1992, Michelle’s high school friend Santita Jackson, now a professional singer, performs “You and I,” from the Stevie Wonder album Southside gave Michelle decades ago.
After the honeymoon in California, there is both good and bad news. The good news: Barack’s voter registration work has helped Bill Clinton to win the presidency and Carol Moseley Braun to win her U.S. Senate race, making her the first Black woman elected to the Senate. The African American vote in Chicago has mattered. The bad news: Barack has been neglecting a book project he was under contract for, and the publisher has now canceled the contract and wants the advance back.
Barack announces that he is heading off to a cabin for a couple of months, to finish the book, so he can sell it to some other publisher. The cabin is nine thousand miles away, in Bali. Michelle is left to wonder whether she will be able to have both a career, like Mary on the Mary Tyler Moore Show, and a settled home life, like her mother—a Black version of June Cleaver on Leave It to Beaver. The question is still unanswered when Barack returns home with a nearly finished first draft and a contract with a new publisher. Michelle says good-bye to city hall and plans to look for work in the nonprofit sector. The Obamas buy a condo in Hyde Park.
This section continues to explore the motif of connection to the Black community as part of becoming. When Michelle visits Art Sussman at the University of Chicago to explore job prospects, she admits that she’s never been on the campus despite its proximity to her home. The university’s elite nature did not make it a welcoming place for the surrounding Black community, and despite Marian’s former brief employment there, the Robinsons felt that the Ivy League was more likely to accept their gifted Black children. As an adult with an impressive professional background, Michelle realizes that she may be in a unique position to bridge the gap between local Black students and the university’s insular reputation. She begins to understand further the value of different perspectives, a theme that will reappear when she is First Lady. Michelle also experiences surprising revelations about Blackness when she travels to Kenya with Barack. Though she hadn’t expected to fit in, she anticipated feeling a deeper connection to her ancestral roots. Instead, she feels foreign and disconnected from both Africa and America. The experience enriches her journey of becoming as she comes to understand elements of being Black that she hadn’t previously considered.
Michelle’s struggle with bias against politics also resurfaces in these chapters. Despite her father’s tireless efforts to uplift the Black community through his work as Democratic precinct chair, Michelle has been left with the impression that politics is a tool used to oppress Black people and keep them from accessing the machine that’s designed to uplift the rest of the country. Valerie Jarrett, however, holds views that are much aligned with Barack’s, and she helps Michelle understand that working at City Hall is a good way to serve overlooked neighborhoods. Though Barack worries that Michelle will become discouraged under the potentially narrow focus of Mayor Daley’s administration, they both have faith in Michelle’s abilities to work hard and produce results. Michelle also sees how Barack’s efforts for Project VOTE! have resulted in the successful election of President Bill Clinton and the first Black female senator, Carol Moseley Braun. Michelle learns to have some faith in the political system and its ability to serve Black Americans, and her leap from law to government becomes her largest swerve so far.