In 1983, Barack decides to become a community organizer. He wants to organize Black folks at the grassroots level, though his ideas are vague. At night, he thinks about the Civil Rights Movement. It makes him think that communities need to be created and nurtured—and during the Civil Rights Movement, there was a lot of nurturing. Barack also thinks that, by organizing, he’ll be able to redeem himself. He spends the months before graduation writing to civil rights organizations, Black elected officials, and tenant rights groups. No one writes back. To pay off his loans, Barack takes a job as a research assistant for a consulting house.
As Barack develops his ideas of what a community organizer does, he also starts to develop his idea of what a community is and how one forms. He makes it clear that communities don’t just arise out of nowhere; rather, they form because people put in the work, together, for a common cause. Not being able to find a job as a community organizer impresses upon Barack how difficult this work might end up being, and it tests how he thinks of himself—especially since he takes a high-paying job that isn’t advancing his values.
Barack is ashamed to be the only Black employee at his level, but the Black secretaries treat him like a son. They seem secretly disappointed that he wants to organize instead, but only the Black security guard says outright that he doesn’t approve. He tells Barack to focus on making money and let the people who are going to make it make it on their own. Barack pays no attention to this, but he sees his dreams disappearing as he’s promoted. One day, Barack’s half sister Auma calls him at his office. She asks to visit and Barack agrees. He excitedly prepares, but several weeks later, Auma calls with the news that their brother David died and she can’t come. Barack wonders who Auma and David are—and who he is if he didn’t cry for his brother.
Being the only research assistant who is Black is a point of shame in part because Barack is made to feel again as though he’s the new kid at Punahou. The support of the secretaries might make this even worse, especially since they don’t approve of his desired life path—he may feel as though he’s letting Black people down by not trying to climb the corporate ladder and increase Black representation in high-level positions. His reaction to David’s death, meanwhile, impresses upon him that he’s totally cut off from half of his family. It’s clearly a big thing for him that he feels no grief, and he sees this as a result of his estrangement.
Barack resigns from his consulting job a few months later and applies again for an organizing job. He works a few odd jobs and is broke within six months. One day, when he attends a talk at Columbia by a speaker proposing establishing economic ties between Africa and Harlem, the speaker and two Marxists lay into a woman who suggests this isn’t possible. Barack feels like the movement is over. Not long after, a Jewish man named Marty Kaufman calls Barack, looking for a trainee to organize in Chicago. Marty is pudgy, unkempt, and insists that Barack must be angry if he wants to organize. He explains that he needs a Black person to help him. Most of his work is with churches, since the unions have so little power anymore—but the churches are notoriously hard to work with.
Seeing people (who are implied to be Black) lay into another Black person impresses upon Barack that the Black community is fracturing and it might be difficult to unite people through organizing. Marty’s interest in Barack begins to push back against this, since he’s organizing in a historically Black part of Chicago. Marty recognizes that many people feel more comfortable talking to someone who looks like them, hence why he’s looking specifically for a Black person—but though he may be correct, he also seems to make the racist assumption that all Black people will naturally be able to connect with each other.
Marty asks what Barack knows about Chicago, and he really only knows about Harold Washington, the recently elected first Black mayor of the city, and that Chicago is highly segregated. Marty affirms that the segregation and polarization mean that not much is getting done. When Barack asks whose fault that is, Marty says it’s not about fault—it’s about whether Harold Washington can harness polarization and do anything. Marty offers Barack the job, and Barack tries to figure out what he thinks of Marty; Marty seems smart and maybe too sure of himself, and he’s white. While Barack sits by the river to think, a boy asks him why the river sometimes runs in different directions. Realizing he’s never noticed the river, Barack packs up and heads for Chicago a week later.
Here, Marty makes the case that when tensions are running high, especially due to racial segregation, politicians have an opportunity to figure out how to harness that energy. Those politicians, like Harold Washington, may have a bunch of very angry or emotional people willing to get out and fight for something better—if the politician in question can get them to mobilize. Barack chooses to go to Chicago when he realizes that he has no ties to New York—in that light, Chicago seems as good a place as any.