When I was in college (when newspapers still had wide circulation), for two summers, my friend Bill and I got the best job ever. We were "summer district managers" for a newspaper that delivered to a very large area. It was one of the largest circulation newspapers in the country.
It was supposed to be like a management internship for college kids, but the office we worked out of used us simply to get their papers delivered. They gave us a van, paid us something like $10 an hour for 8 hours a day (which was a lot at the time), and then sent us out with the van and thousands of newspapers to cover all the paper routes they couldn't fill during the summer when kids went on vacation. In addition to the hourly wage, they also paid us by the newspaper (and I think we were delivering more than a thousand newspapers a day), and we got to keep whatever tips we could collect. We'd just leave envelopes every two weeks with instructions to leave the money in their mailbox or under their mat. Most people actually complied, amazingly, so once every two weeks, we'd take longer and collect our money. Even if we didn't collect from every single house, we were still rolling in cash because we were delivering a boat load of newspapers. Still, at the end of the summer, Bill decided we were going to collect from everyone who hadn't paid us in a few months, because there was no way he was going to leave any money on the table, and he started ringing doorbells at 5 a.m. I am surprised we didn't get killed.
We'd show up before 4 a.m., grab the newspapers, and one of us would starting driving toward our first neighborhood while the other was in the back of the van stuffing newspapers into bags. The routes were all over the place, but we had it down to a science. It would take us a few hours and then we were done for the day. We didn't have show up for the actual "management" internship. We'd just head to the beach.
On some of the routes, we'd drive down the street tossing the newspapers from the window of the van. We got a lot of complaints -- the paper wasn't on their stoop, etc. We'd get little slips with the complaints and we were supposed to correct it, but we didn't care. One person complained a bunch of times and Bill just cancelled the newspaper on them. I feel guilty thinking back (even if I am laughing). It may have been the best job I have ever had.