Lessons Learned From a Paper Route

The paperboy is an American icon. We’re all familiar with the image of a young scamp on foot or pedaling a bike, delivering the morning paper and learning the value of a dollar. My paper route taught me much different lessons, ones which still drive how I approach my work decades later.

Dana Ross
3 min readFeb 16, 2016

My route had me delivering a free advertising supplement for a suburban newspaper. If you’re in the Chicago area, you might know it as a certain Daily newspaper. Every week, my dad & I picked up a couple hundred bound papers from our contact and an equal number of red plastic bags. I spent a lot of Tuesday nights listening to R.E.M. or Rush and stuffing papers into bags. Wednesday after school, I slung a bag of papers over my shoulder and dropped one on the porch of every address on my list.

How did you get on the list? Everybody was on the list. How did you get off the list? Call the paper threatening to sue if they dumped another stupid paper on your porch and maybe they’d take you off the list. I wish I could say I had an idyllic relationship with my “customers”.

I made fifteen cents a paper. 200 papers was a couple hours of work, but $30 in my pocket before taxes. These were the days before widespread Internet access. Today, I’d be building websites or something. Back then, this was one of the few jobs available to a fourteen year old.

One fateful day

Part of the deal was every week someone from the newspaper drove around our territories to make sure we did our job. They assumed a certain number of papers were brought inside before they checked. But if it looked like you didn’t deliver enough of them, they wouldn’t pay. And one time, that’s exactly what happened.

The manager of a local store called up the paper. Someone dumped a pile of newspapers in little red bags behind his store, and he wanted to know when someone was coming to pick them up. The store was on my route, and only a couple blocks from my house. And by the time their driver verified my route, they didn’t see any papers anywhere. I was chastised and went unpaid for a week.

I never found out who dumped the papers. Supposedly everyone else’s route was verified. So either another paper carrier found a way to cheat & not get caught, someone was saving up their unwanted papers to make a statement, or the whole thing was a lie and my boss wanted a way to get out of paying me for the week.

Lessons learned

I gave up on the paper route after that. My Dad kept doing it for some reason, and gave me the paychecks no matter how many times I refused. But there was no point working for someone who could just arbitrarily take away my money for the week, especially after I worked hard for it. I wouldn’t be surprised if what they did was illegal, but I was fourteen so who was going to stand up for me?

That experience taught me about respecting myself at work, a lesson I’ve had to re-learn a couple times since then. But, it’s an important lesson. And anybody who would do that to someone isn’t worth respecting, whether they’re your boss or not.

It would be years before I learned of the Principle of Charity, but I certainly understood it that day. Never go into a situation assuming you know everything going on. If someone sounds irrational, or crazy, or like they’re outright lying to you, assume there’s something else going on until you’re proven otherwise. English might not be their first language. They may be having a bad day, and aren’t expressing themselves clearly. Or, let’s be honest, they may actually be trying to pull a fast one. Human beings are quick to judge, but we owe it to those around us to slow down and make sure we’re acting justly.

I guess it’s water under the bridge at this point. The newspaper is still around, and I’m doing better than ever. But every once in a while, I think back to this terrible experience and chuckle. I’m certainly glad my kid will grow up in a world with more opportunities for a young teen to make an honest buck, maybe even as their own boss. And I’m proud to have helped create that world.



Dana Ross

Building the web since 1996. Full-stack developer, but love front-end tech. I also socialize feral and abused cats.