Rebuilding Rob

As WordPress continues to recycle old prompts, I pulled another prompt from The Coffee Monsterz Co to respond to today

What was the first way you earned money?

The very first job I ever had was delivering papers for The Detroit News. We had a unique setup in my neighborhood: a house on one of the main roads bordering my subdivision served as a “paper station.” The News had worked out a deal with a local family to use their place as a hub where they’d drop off bundles for the dozen or so carriers in the area.

Every day after school, I’d head over to pick up my route. The “bulk” of the job literally depended on the day of the week. We’d check in with the manager, who would tell us the count for the day. Wednesdays, Saturdays, and Sundays were the heavy hitters because of the “fillers”—the midweek sales flyers and Sunday comics—that we had to manually insert ourselves.

There was a specific kind of relief when you’d walk in and the manager would say, “50s. No filler.” That was a good day. It meant the papers were thin, light, and easy to load onto a bike. (Or into a car, if you were an older kid with a “motor route.”)

The $1.65 Subscription

Back in the late ’80s, a weekly subscription ran just $1.65. I remember people being absolutely shocked when the price “drastically” jumped to $1.95. Today, you can’t buy a single daily issue for less than two dollars, and they’re half the size they used to be.

Because this was the ’80s—pre-internet and pre-smartphone—being the paper boy meant you held the keys to the neighborhood’s information. People were genuinely waiting by the door for that “thwack” on the porch. If I was late, they didn’t just check Twitter; they had to wait in silence with their coffee. That’s why the “Christmas tips” were so generous—I was their connection to the world.

The best part of the job, of course, was collecting. If you did a good job—getting the paper to the door dry, on time, and convenient for that first cup of morning coffee—the tips were great. Christmas tips were the real “unexpected wins.

365 Days of Grit

Paper routes were a lesson in consistency. You worked every single day. It was only an hour or two of labor, but you worked through holidays, rain, wind, sleet, and snow. You know the drill.

Looking back at the time invested versus the profit after paying the weekly bill, it might have been the best hourly money I’ve ever made. In fact, unless I was selling drugs, I don’t think I could have topped those wages as a junior high kid.

Lessons from the Route

There’s a lot of nostalgia for how simple life was then, but it was also a masterclass in business. I learned about overhead and profit margins: we’d get a bill for the papers we “bought” from the News, and anything we collected beyond that was ours.

It wasn’t all easy money, though. There were days I was sick and had to scramble to find a friend to cover the route for a flat $20. And then there was the time I got bitten by a dog—nothing drastic, and the dog had its shots, but it’s one of those rites of passage you just expect as a paper boy.

The Best Part?

This was completely tax-free money. Or, at least, our routes were such a small blip on the IRS’s proverbial radar that they didn’t care. It would be a couple more years before I discovered the reality of income tax while working stock at a local convenience store.

But for those few years in the neighborhood, it was just me, my bike, and the “50s—no filler” days.

Today’s post is inspired by the WordPress Daily Prompt. While I’ve taken the topic in my own direction for the Road to 1,000 Days, you can find more responses to today’s prompt HERE.

Thanks for stopping by Rebuilding Rob. Be sure to like 👍, comment, and subscribe below. It’s greatly appreciated! Also, feel free to follow me on social media and check out my recent posts!

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AI art created with Google Gemini.

The article “The Paper Station: My First Taste of the Hustle” first appeared on Rebuilding Rob.