I had a Free Press route starting the day before my 11th birthday and kept it going, no ****, until the summer of my 16th birthday, when I switched to hourly jobs.
It was a Free Press route, early morning gig. The platonic ideal was up at 5am and on the road to deliver within ten or fifteen minutes. Actually, it was more like up around 615am and maybe out in half an hour. Too many days I got home with only a razor thin margin to get showered and dressed to catch the bus to school. Too many of those times my mom had to drive me for missing the bus because I dawdled too much on the route. She was not happy about it.
All seven of us kids had routes. Our house was were Paper Dropoff Central because three of us were paperboys at any given time, and there would be a couple other kids in the neighborhood with routes. So we'd walk out to the front porch and there were the paper bundles. I don't know how my dad arranged that, but we didn't realize how good we had it.
Nowadays, kids don't deliver papers. I'm not even sure they're allowed to anymore. Now it's adults driving cars who deliver papers. We get the Trib and the NYTimes delivered on Saturday and Sunday. Our "paperboy" lives in Des Plaines—I know because the end-of-year tip envelope we get gets mailed there. Des Plaines is half an hour away by car even when the Kennedy is not under construction. And the Kennedy is under heavy construction right now.
I know it's end of year when two things happen, even beyond the envelope: (1) the paper gets delivered all the way to my front door instead of on the walkway near the front fence; and (2) it comes around 7am instead of the usual 830am or 9am. Then, after the first of the year, everything reverts back to "normal". Imagine that.