Not much is said about why the narrator wants to go out West and live "on the road". The fact that he leaves everything he has to go out to the West with just $50 in his pocket says a lot about his character; he is a daring, care free individual who has the will to survive and hunger for adventure. The narrator spent almost half of his money on a bus from Newburgh to Chicago, which was not the smartest decision, since he had just begun what would be a long trajectory. His actions led me to assume that he is the type of person that struggles to begin with something, but once he has begun, everything becomes easier. Also the fact that he asked for rides shows that he is a humble person who is not always caring about what people think of his social status.