I was never a paperboy as my mom would not let me. The big Family next door had several routes and I would help out once in a while. That was in the 70's.
Then from 1990-93 I was a Circulation District Manager with the Joliet Herald News. Back then it was an afternoon daily and Morning on Sat and Sunday. I liked the job except for 'crewing' to get new subscribers. I actually rode my bike a few times with a couple of carriers who were having issues with certain customers. I remember one Sun I had a route that the kid who had it was going away for vacation and could not find a sub for that one day. I delivered to a house where there was a broken flower pot on the porch. Sure enough I got a complaint on Monday morning from the Lady at that house complaining the paperboy broke her flower pot. She was speechless when I told her I actually delivered her paper myself and it was already broken when I arrived.

The things I learned while a DM.

1. A route was a whole family commitment not just for the kid.
2. Some kids were awful or lazy carriers and would lie to my face when confronted about problems on their routes.
3. There was no time off for a carrier.
4. People would screw over a kid on collections. I guess they figured they were cheating the paper not knowing the kid had to pay for their paper up front....
5. The Circulation Director I worked for was a dirtbag and would do things to make his circulation numbers look good but ultimately balance the books on the backs of teenage kids. I quit because of this!!!

Max Bryant