My First Job – Your Neighborhood Paperboy

I was inspired to write this post about my very first job after seeing a post on Twitter…

Then I read the post from Ty at Get Rich Quickish. I really enjoyed learning about his background in this way. Seeing what jobs a person has worked in their life tells you a lot about their work ethic, their drive, and their desire. Looking at Ty’s list, I was amazed that they were all side jobs, in addition to his main gig. He’s got a lot of drive, that’s for sure.

It’s a great list and I encourage you to go read Ty’s post on his jobs, called 23 Side Hustles I’ve Done in My Life.

Then here, you can read about my very first job. I will follow up this post with another one about my other jobs, but I enjoyed digging into just my first job so much that I kept writing.

Your Neighborhood Paperboy – Where it all Started

It’s funny how memory works. I can recall very specific things like the nervous feelings I had before I proposed to my wife or funny lines to a favorite movie I haven’t watched in 10 years. But then, I can’t remember what I ate for dinner last night.

That’s what my memory is like when I recall my first job. I don’t remember how old I was, but I remember this crazy guy standing in my driveway offering me a job. He wanted me to be a paperboy.

I had a friend a couple of blocks over and he was a paperboy, at least for a short time. It didn’t last with him. He didn’t want to do it. So I guess he mentioned my name to the crazy guy (his boss). That’s what led this crazy guy to my driveway one afternoon.

I remember this dark color van pulling up to the house, my brother and I were outside playing, and this guy starts talking to us. I know, right? It sounds like the start of some terrible story.

I got this weird vibe from crazy guy, trying to put together what lead him to be talking to me. But then my parents came out and started talking to the guy. They were fine with this guy and made me feel better about the encounter. Before I know it, I was signed up to be a paperboy for this guy.

Crazy guy was desperate to find another local paperboy because my friend had flaked out on him. And I guess that was common, he was always looking for a paperboy, it seemed.

The Paperboy Gig

Anyway, I now had my very own paper route. The gig was great. I had to deliver the daily newspaper (called Newsday) to about 25-30 houses and the Sunday newspaper to about 40 houses. The houses were all within about 5 blocks of my house, an easy bike ride. I knew the streets well already.

This was back in the era of newspapers delivered by kids…the paperboy. Hell, there was a videogame about it…

I had a Huffy bike with a milk crate on the handlebars, secured with bungee cords. I was just like Elliot from the movie E.T. On a normal weekday I could carry all the papers at once, but on Sunday, I could only carry about 7-8 papers at a time so it took longer to deliver. The Sunday paper was so heavy that it would weigh down the front of my bike, making it awkward to ride and steer.

I would deliver the daily paper every afternoon after school and then the Saturday and Sunday papers in the morning. There would be a stack of papers dropped just outside the side door of my house every day.

Most days I would leave the loose paper under a door mat or in a mail slot or inside the weather door on a front porch. If it was raining, all the papers went in a plastic bag. At some point I think I did rubber bands on all the papers to make them easier to throw.

Sometimes I would get a mangled paper. Usually the one on the bottom or top of the stack that was delivered to my house. I would save that paper for the customer who never tipped me. Even then, I knew to make sure my biggest tippers got the best quality.

Newspaper Economics

The newspaper cost $0.35 for the daily and $1.25 for the Sunday back then at retail prices. Delivery cost $3.25 for the entire week or $1.50 for just the Sunday for the pleasure of home delivery from a local kid. At least that’s the best recollection I have.

The way it worked was that I bought the papers for the week from the crazy guy and they were delivered to my house every day. I would deliver the papers every day and then once a week I would knock on each door to collect the fee. And that’s what I would say…knock on the door and say “collect.” Everyone knew what that meant when a young kid was at your front door and said “collect.”

I would start collecting for the week on Thursday when I delivered the papers and would usually finish by Saturday. I would knock on the door every day until they answered the door and paid me. I remember some people telling me that they would get me next week and I’d say okay. I had a couple houses that would go up to 3 weeks before they paid me. Usually that meant a bigger tip, so I was okay with it.

Being in New York (I grew up on Long Island), we had a culture of tipping. I didn’t know this, of course, until I was older, but New Yorkers generally tip for everything…

• Got a guy who mows your lawn…tip him.
• Got a mailman you know by name…tip him (at Christmas).
• Got garbage men who always take that extra can of trash…tip them (at Christmas).
• Got a paperboy who doesn’t toss your paper in the bushes…tip him.

It was just part of what you did. Now, that doesn’t mean that everyone tipped me, but many people did. It was common. Most customers rounded up the weekly fee of $3.25 to $4.00, some would go up to $5.00. The Sunday paper was the same where customers would usually give me $2.00 or $2.50.

I remember at some point that the paper prices went up, I think $0.25 for each service. So the weekly paper went from $3.25 to $3.50 and the Sunday went from $1.50 to $1.75. This cut into my profits from tips immediately because my customers continued rounding up to the nearest dollar amount and screwed me out of $0.25 each week. That was my first experience with lost wages. I got used to those tips and the lost wages meant buying less baseball cards or Italian ices. Bastards!

I would write down in a little ledger book who paid me and exactly what they paid. I could track how much a particular customer paid me in tips or see if they ever paid a tip.

I remember being at a friend’s house one time a town over. He had a paper route, too. We were hanging out one day at his house and were going to walk to the stationary store (sort of like a convenience store that had office products, cards, candy, etc). My friend didn’t have any money so we stopped to collect at a few of his customers on our way to the store. He marked it down in his book and we were off to buy more baseball cards and other junk.

Overall, I recall clearing about $30 per week. That was a king’s ransom in my time at my age. I was rolling in the money. That breaks down to making about $0.13 to $0.17 per paper that I delivered.

My goal each week was to collect enough in fees to first pay off my weekly charge for buying the papers. After that, all other collections were mine, my profit.

Looking back, the margins weren’t great, but what did I know. Plus, back then we didn’t know this internet thing was coming.

Lessons Learned

I learned a great deal from my first job. I learned what it meant to be responsible for something every day. The newspapers never stopped.

I learned how to handle money and that good customer service could mean more money.

I learned to smile and be polite to my customers, it was the friendly thing to do, but it also could mean more money. You learn a lot when you live off of tips.

I learned that punctuality counts…being on time is just as important as where you put the paper.

I learned that 30 bucks can buy a lot of baseball cards. I mean…A LOT.

Post Script

Funny thing about the “crazy guy” who was my first boss. My parents got to know him well and they liked him. He turned out to be a great guy. I was a kid, what did I know. In fact, my parents had him and his wife over for dinner a few times.

After me, my older sister got a paper route, just a few blocks away from mine. My younger brother took over my route when I quit.

Then later, after we had all quit and moved on, my mom actually started delivering the paper. She didn’t have a cool bike with a milk crate like me, so she used the family van. She delivered something like 100-200 daily papers. She was a stay at home mom and the schedule of this gig was a great one for her. I remember helping her many times. The best was helping on Sunday because she would stop at the bakery on the way home. I can still taste the warm end of the bread or a roll that I ate on the drive home…delicious!

Of course now we don’t see a paperboy anymore. Hell, most people don’t see a newspaper anymore. That interwebs thing really took off and stuck around. I guess it wasn’t the fad that the news industry thought it would be.

I loved my first job. What was your first job? Tell me about it in the comments. I would love to see what you did to get started in the working world.

Follow me on Twitter as well for more ramblings.

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About Brian Stephens

Brian is on a journey from massive debt to real estate mogul. Join him as he stumbles and fails on his way towards long term success. Debt isn't pretty and turning it around won't be either. His primary goal here is to tell the story and network with like minded people who want financial independence through real estate investing.

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