How did Obama confront and solve the problems he was facing in Chapter 5?

In Chapter 5, Obama recounts the aftermath of this realization and his time at Occidental College, located outside of Los Angeles. At the start of the chapter, Obama describes himself as being drunk one night after a party and listening to a record by blues singer Billie Holiday. Obama had an argument with his good friend Regina and was thinking over whether what she said to him was true. During his last few years of high school, Obama did drugs and lived life with no clear goals in mind. He belonged in "the club of disaffection" and learned to "laugh at the world’s ongoing folly and see through all the hypocrisy and bullshit and cheap moralism" (94). Obama noticed with bitterness that the black and poor friends in this club ended up in jail, while his white friends seemed to do fine.

Obama realized that there was a pattern to the criticisms--"Look at yourself before you pass judgment. Don’t make someone else clean up your mess. It’s not about you"(110)--directed at him by whites and African Americans in his life. Obama had been living out of fear and acceptance of the idea that all the high expectations others had of him were somehow associated with whiteness. Obama imagined Regina's grandmother, Toot, and Lolo's grandmother demanding that he do better and be like them in his determination to succeed in the face of challenges. "My identity might begin with the fact of my race," Obama realized, "but it didn’t, couldn’t, end there" (111).