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Michelle becomes the founding director of a new organization, Public Allies, that places talented young people in apprenticeship positions in the nonprofit sector. After three years, thanks in part to support Michelle and Barack line up through their various Chicago connections, the organization is on sound financial footing. A tip from Art Sussman leads Michelle to a job at the University of Chicago, with better pay and better health insurance. She becomes an associate dean with a focus on community relations. One of her tasks is to find ways to connect students to volunteer opportunities in the surrounding neighborhood.
Barack works for a public interest law firm, mostly on voting-rights and employment discrimination cases. He also teaches a class at the University of Chicago Law School and occasionally runs community-organizing workshops. Working at night in a book-strewn space he and Michelle call “the Hole,” Barack has finished his book, Dreams of My Father. A scandal involving a sitting member of the Chicago statehouse creates an opening for Barack to run for the Illinois state senate. Although Michelle doesn’t care for politics and predicts that the experience will grind Barack down, she isn’t prepared to veto the idea. When Barack wins his race and takes his seat as an Illinois legislator, it turns out that despite all the expected challenges, the work suits him.
Both Barack and Michelle, however, suffer more loss and grief. Barack’s mother is diagnosed with cancer and dies before Barack is able to fly to Honolulu to say good-bye. Michelle suffers a miscarriage. After failed attempts to conceive again, the Obamas turn to in vitro fertilization (IVF). Their first daughter, Malia, is born on the Fourth of July.
Michelle negotiates a half-time return to her job as an associate dean, but even with the help of a highly capable babysitter, she feels badly overextended. Barack, after being reelected to the state senate, decides to challenge an incumbent Democratic U.S. Congressman for his seat in the primary election. A Christmastime visit with Barack’s grandmother “Toot” in Hawaii is interrupted by news from Springfield (Illinois’s capital) of an abruptly scheduled vote on a major crime bill. When Malia is too sick with an ear infection to fly back home and Barack chooses to stay with his family, his opponent blasts him for being away at a critical time. Barack’s donor and endorsement support dwindles, and he loses badly in the spring primary.
After a single round of IVF, the Obamas welcome Sasha into the family, but soon, the departure of the beloved babysitter forces Michelle to reassess her work situation. Fortunately, the new president of the University of Chicago Medical Center is willing to hire her as the director of community outreach, knowing that she will need flexibility to deal with her responsibilities as a mother. With a full-time salary, she will be able pay for more help at home. By now, George W. Bush is president, and America has been through the 9/11 attacks. Barack is thinking of running for the U.S. Senate, but Michelle is losing her patience with him: he is away too much and habitually comes home later at night than promised. A couples therapist helps the Obamas make some adjustments. For Michelle, the adjustments will include a morning workout routine with a friend, and at night a fixed dinnertime and bedtime, whether Barack is home or not.
These chapters largely explore the theme of harmony versus chaos. Michelle is content and excited in her new job at Public Allies, and Barack has struck a balance between being a lawyer, teacher, organizer, and author. Though their next career changes require more shifts and some physical distance, their ambitions are aligned. Barack’s time away from home in the state capital allows him to throw himself into his work as a state senator and Michelle to transition into a more prominent position at the University of Chicago. Their Friday night dinners allow them time to reconnect and continue to plan for the future. Their difficulties in conceiving a child, however, are a chaotic twist. Once IVF helps them finally achieve the family they’d planned for, as the children grow older, Michelle struggles to keep a reasonable home life schedule. Barack’s job demands and relaxed attitude about time create chaos for his family as they attempt to eat dinner together and see him before the children’s bedtime. Michelle’s decision to keep a schedule and let Barack hold himself to it is a fresh attempt at harmony in the household.
The conflict between work and family obligations also intensifies as the Obamas become parents. After Malia’s birth, Michelle finds it increasingly difficult to balance her home and work life even with the help of a caring babysitter. While running for U.S. Congress, Barack’s decision to stay with his wife and sick child in Hawaii and miss an important state senate vote on a gun control bill gives his opponents ammunition to discredit him in the media, and he ultimately loses the race. Shortly after Sasha is born, their babysitter leaves and Michelle is faced with the difficult decision of whether or not to return to work. She calls up her own experiences during the times her mother stayed home to take care of the family and their needs, and she likes the idea of devoting time and energy only to the home without allowing work to compete with it. When an exciting new job opportunity causes her to reevaluate, however, she decides to ask for the flexibility she needs as a mother. Michelle’s new higher salary allows her to outsource some of the home duties and allows her to spend more time with her children when she isn’t at work, thus allowing Michelle to strike the balance she needs to succeed as both mother and professional.