The road-trippers reach Long Island, NY, home of writer Beverly Donofrio. Beverly recounts a long list of personal failures ? getting put in remedial English, a failed thesis, a lost job ? between bouts of reflective laughter. You have to laugh, she tells the road-trippers, and thrive from adversity; take a real look at the opportunities that are presented to you, and say yes as often as you can. From there, the road-trippers head to Detroit, MI, where they encounter one of the renegade artists who is taking back the city. Spoken word poet Airea Dee Matthews urges the road-trippers to find rebirth in collapse. In the mostly abandoned city, the artists of Detroit don't see decay, but possibility. The road-trippers see the decay for themselves when they tour an abandoned building and experience the sense of freedom and energy that drives the artists' push for regeneration. Next, in Chicago, IL, Tele'jon struggles to reconcile his mentors' suggestion that he become a professor with his disillusion with the educational system. After interviewing Professor David Stovall, Tele'jon sees that David shares his concerns about access and privilege, and uses his position to create change. Tele'jon leaves the interview feeling more confident that he'll go to college.