Henry and the Paper Route — Beverly Cleary

Ten-year-old Henry Huggins wants a paper route, but he has a problem: All applicants must be at least eleven. That doesn't stop Henry. He sets out to show the boss he can do the job, no matter how many obstacles stand in his way.

Unfortunately for Henry, difficulties start cropping up everywhere. His plan to give away a free kitten with each new Journal subscription backfires. And even when he gets a chance to work for an older boy with a paper route, he winds up angering the boy by mounting an all-too-successful ad campaign for the school paper drive. But the final blow comes from the neighborhood's new genius, who moves in and takes over the route Henry was dreaming about. Just when it seems nothing will ever work, the solution to Henry's problems arrives -- in the unexpected form of that little pest Ramona Quimby!