A job is supposed to alleviate boredom? Wow, the 80s were a different time.

I learned at a very young age to never mention out loud that I was bored, or even appear bored. That was part of the reason I read so much.

No, but it’d get you three bucks to go rent a movie.

They both said that before they knew what he was asking for, however, unless "I'm bored" is so commonly followed by a demand for money they knew to expect it. As it stands with the context available to us, they seem to be suggesting that employment itself is the cure for boredom, not any monetary gains therefrom.

I can confirm as a child who had access to and a healthy appreciation for both good books and video games, I was about half as likely to have foisted upon me "something more productive to do" if I was reading than if I was playing video games. The power of burying your nose in a book, not only do you learn something, but people leave you alone.

As a parent myself, the context is very obvious in the first panel with the first speech bubble. It’s always either “I need money” or “Take me somewhere”. Both cases can be solved with a job that earns you money.