Jesse Stoddard

Why Every Kid Needs A Job They Can Quit

Paper Boy Cartoon

My first job was delivering a paper route at around eight years old. As an independent contractor, you were responsible for doing your own prospecting, producing sales, customer service, follow up, and follow-through. You were in charge of your schedule, delivery of the product, and collection of the money.

In situations like these, you are self-employed. In truth, this means you are an entrepreneur, albeit of the most basic kind.

I believe everyone should be an entrepreneur in some shape or form, even if it is while working for other people. It’s more of a mindset, a way of life, a philosophy.

However, in this particular case, I am afraid these descriptions are all over-glorified euphemisms for child slave labor.

At least, that’s what they’d try to call it nowadays.

You see, in those days, and for many, many before them, you could simply pay kids to deliver newspapers to people’s homes directly and therefore keep the price low enough to allow for a healthy profit.

And I miss those times something fierce.

If you are under forty years old, you might not know what a newspaper is. The two words conjoined give it away, but in case you are still confused, it is a print-version of Twitter, Craigslist, and Google or Apple News, combined. Quite ingenious, no?

If you do know what a newspaper is, and you have experienced someone delivering a paper to houses in your neighborhood over the last couple of decades, you probably have a much different impression than what I am remembering.

What you are more likely to have experienced is a middle-aged, balding man with a beer belly who drives a 1978 AMC Concord, a Yugo, or perhaps a 1981 Ford Pinto. He comes at weird times of the day, usually around three in the morning after all the bars have closed. He will stay in his car with the passenger-side window rolled down, slow down a little as he approaches the house, and throw the paper out his window, possibly hitting the sidewalk or the driveway of the home, but more likely getting it stuck in a bush.

To me, this is a deplorable state of affairs.

There is something beautiful about physically holding tangible objects that deliver useful and substantive information without the need for electricity or a screen.

Alas, by the time the greasy man in the Yugo was delivering the papers, they had long fallen from their monopoly on information distribution. There just weren’t enough customers, and the profits made even more challenging to acquire by the many child labor laws.

Therefore, I was one of the lucky ones!

I got in when there was time to really learn some life lessons. I was paid to attend a very novice level of the School of Hard Knocks, which allowed me to graduate to higher levels later on.

I think my mom and dad heard from a neighbor that the older boy that ran the route was moving on to Highschool, or perhaps hiding from the law. Either way, there was a vacancy, and my parents were eager to help me to learn the value of money.

My mom was starting her journey up the corporate ladder as one of the first women to be promoted into higher ranks in the Post Office. It was a lot of work, and she was determined to make it. Both my parents wanted me to learn a good work ethic, and to help me learn how to fend for myself.

My first day on the job was my first meeting with the former paperboy, and my only day of training. He went through the route with me, making me carry the overstuffed, heavy bag, and showing me exactly where to leave every paper.

“Mr. Smith here needs the paper right up against the door on account of his limp. If you don’t tilt it just so, it’ll roll down the stairs, and he will be furious. If you miss this detail one time, you won’t get paid, much less get a tip.”

“Mrs. Jones likes to get her paper two feet out from the door. If you deliver it too close, she will think you are casing the joint, and you will not get your tip.”

“Mr. Johnson never tips. Just throw his paper in the driveway and save a few seconds.”

This went on and on for over an hour. There were so many cul de sacs to visit, and endless houses on the route that my head was spinning.

“Wait, was it Mr. Smith that needed the paper out of the rubber band, or was that Mr. Jonson…” I asked as many confused questions as I could, but was sweating and nervous and couldn’t remember half of what he said.

“No, that was Ms. Edwards. Are you going to remember this? You gotta remember this stuff, kid! The base rate is terrible, so we work for the tips!”

The next day I was on my own, and the clock was ticking.

After school every day, I had to rush to pick up the papers, roll them up with rubber bands, and pack them in my shoulder bag. Then, I’d hustle on down the road. Saturdays and Sundays, I had to get up very early. This paper was seven days a week, and some people seemed to live and die by it.

To make matters worse, Edmonds is a hilly town, and many of the clients lived at the top of those steep hills. In more than one case, there were no other houses on that street that bought the paper. I was reminded of how inefficient it was every time I had to go up those extraordinarily steep and slippery driveways.

It was tough. I nearly quit several times before I even got paid. We got to collect at the end of the month, and we did it in person by knocking on the door.

The first time I went to collect the monthly fees, I was terrified. I had to go up to strangers like a door-to-door salesman and make a new friend. Luckily I could say I was the new paperboy, and I delivered something they liked getting, so I had an in.

Some people left the payment under the doormat. Some left it just inside a screen door. But most of them invited me in. Now that is a sign of the times. It was so healthy back then to be neighborly and allow people, even children, into your home, that it would never have been something to mention.

Today, if an adult invited an unknown child into their house for a cup of tea, they would end up with a search warrant, an ankle bracelet, and their picture up at all the local schools.

At first, I was pretty lousy. I could smile, but other than that, I said the wrong things and didn’t get much by way of tips.

Over the weeks, months, and changing of the seasons, I got better and better. I got a bike and built the muscles in my legs enough to get up the steepest hills and speed up my delivery times. I mastered where to put the paper for each client.

I even got the idea to hit up other homes along the route to get more business and ask for referrals from my existing client base.

The most significant improvement, however, was the increase in tips.

Getting generous tips was an art and science. The science part was pretty straightforward; deliver on-time, in the right place, offer consistent service with a smile, and be extremely friendly and jovial. You also had to know the best time to go in to collect the fee. All of this could be passed from one paperboy to the next, or be written down and codified.

The art side, however, required finesse and mastery. There was a Kung Fu to it. You needed to read each individual client and figure out what they liked about getting their newspaper and how it impacted their life and family. You had to know how to show industriousness to those that were Republicans. And yet, you’d also demonstrate your bleeding heart to the Democrats.

You had to show an interest, be smart, and if all else failed, put some ash and soot on your face and sing “It’s a Hard Knock Life” from the musical Annie.

Yup, when I was eight, nine, and ten, I was exposed to more adult discussions than the average kid. Every dinner time was an in-depth discussion about business, politics, and the human psyche with my parents. As an only child, you are expected to do more because you are their only hope for the future.

Besides, mom and dad always talked shop to help them blow off steam, whether it was the bureaucracy of the Postal Service or one of their dreams to start their own business.

All of it made me better.

I remember a sweet little old lady that used to invite me in a lot more often than just collection time. I politely declined most days, but when it came to getting paid, I finally had to accept.

The old lady loved to talk and tell the same stories over and over. She made me very strong tea, and I would sit politely and listen to her ramblings. Eventually, she would start repeating herself, which was a cue for me to attempt to escape.

“Mrs. Johnson, thank you so much for the tea. I am so sorry, but I really gotta go. I have to visit my other customers.”

“Oh, but you haven’t had cookies yet. You must have cookies. I made them myself.”

The cookies were way too sweet. As in, sugar-overload sweet. And some were doughy and undercooked. And some were burnt.

“Now, where was I—Oh, yes…”

…And she would start her story over from the beginning.

Finally, after an hour or two, when I could get one leg outside the door, she would give me my tip.

A shiny quarter.

By the way, I wasn’t Laura Engels’ adopted brother Albert from Little House on the Prairie, and this wasn’t 1885. This was somewhere around 1985 to 1987, so a shiny quarter wasn’t like getting twenty bucks today. Still, in those years, it could get me one-third of the way toward buying a comic book, which is probably what I wanted more than anything else.

One particularly terrible winter, the snowstorms blasted us with a vengeance. By the way, you might not remember this, but we used to get snow in the Pacific Northwest during December. We occasionally got what was termed a “white Christmas.” I know, I know, crazy talk, right? If you are trying to picture it and you live in the northwest, just think of our current Februarys.

At first, I did a decent job of delivering the papers. After a couple of weeks, however, it became harder and harder. The snow accumulated, and I began to lose motivation.

It was the first time in my life that I experienced the concept of being underpaid what I was worth. I realized that I could design my own future. Well, maybe as a young kid, I didn’t think of it that way exactly, but at least I knew that if I could make money one way, I might find other ways to make even more money.

The storms made delivering the paper horrendous. Then, the powers that be called us and said something that put my little brain over the edge.

“There is a special edition that needs to be delivered on Christmas Eve.”

Hold the phone! Shut the front door!

I was only a child! Christmas vacation is a fundamental human right. No way was I going to do that.

My parents and I debated this for a while. There was virtue in doing one’s duty. One must finish what one starts, fulfill promises, and all of that. Only I never signed up for this, I never promised I’d even still be doing this, and I already “finished” in that I had done it for longer than the last kid had.

I was apprehensive about letting my folks down. I was worried I had failed at fending for myself and having a good work ethic.

And then my mom did something incredible. She drove me around the neighborhood, and we got the papers delivered in time for dinner. We did it as a team. She bailed me out. After all, what is family for?

We came home and curled up by the fire in sleeping bags on the floor. It was a breezy old house, and on cold winter nights, there was nowhere better than right next to that blazing fire.

Dad arrived home from working overtime, delivering mail for the Post Office, which required about twenty times more work than I was doing, delivering to far more homes every single day.

And he told me very clearly many times to get a good education and not to deliver mail for a living. Yet, in a way, here I was, starting to walk in his footsteps.

Nonetheless, it was going to be a wonderful Christmas Eve surrounded by snow, a warm fire, a loving family, and soon even Santa Claus. I could almost hear the reindeer trotting on the roof, the sleigh bumping our chimney, when…

The telephone rang.

“Jesse, we have a special edition of the paper that needs to be delivered on Christmas, before eight o’clock in the morning.”

“I quit.”

And on that day, either an entrepreneur or a bum was born.

Picture of Jesse Stoddard

Jesse Stoddard


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