Paperboy by Vince Vawter

In the heat of the summer of 1959 in Memphis, a boy takes over his friend's paper route for one month. While delivering and collecting on the route, he learns a lot about his neighborhood, the world around him, and about himself.

This is - hands down - the best book I've read in recent history. I can't stop thinking about it. The kid (we don't learn his name until close to the end) suffers with a stutter, so he's typically afraid to speak in public, especially to strangers. But this new responsibility encourages him to try some coping mechanisms and to practice, practice, practice.

By making routine, regular trips around the neighborhood, he gets a glimpse of the day-to-day in households other than his own. He begins to understand privilege, race, and responsibility. Good and bad things happen, and when his buddy returns at month's end, our hero is a little different than he was previously. You will be too.