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As a preteen I built my bank account, my résumé and my character in a sadly bygone way.

The sullen teenage captain of the newspaper substation, dressed in an oversized flannel shirt, a zip-up sweatshirt and a black stocking cap to combat the cold, glared at me. If the station was heated, we didn’t feel it. 

“Don’t just stand there looking stupid,” he said, adding insult to frostbite injury. It was 4 a.m., and I was barely awake as I paused from stuffing inserts into the Sunday paper. I had to keep blinking to keep my eyes open.

This was the inglorious side of my first job: a paper route on Milwaukee’s Northwest Side. It was 1993, a time when it was still possible for 12-year-olds such as myself to find part-time work.

Aside from an occasional babysitting gig and a modest allowance, I had no source of fun money, so I thought a route would be my key to big bucks and financial independence. Working a few hours delivering daily papers after school and on Sunday mornings would leave me plenty of time to do homework and watch TV.

So, on a crisp fall afternoon, I took my career into my own hands and called the circulation department of The Milwaukee Journal. Was I in luck! The kid down the street, a couple grades ahead of me, had decided to give up his route.

I don’t recall any orientation or on-the-job training. I had to learn on my own, a character-building sort of baptism by fire. The newspaper seemed to have a lot of faith that its young carriers would succeed.

The job was a breeze for the first few days. Papers were dropped off at my home, and all my subscribers were within three blocks. I stuffed the papers into my oversized canvas bag (which looked pretty snazzy), and the leaves were soon crunching under my sneakers.

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It all seemed pretty grand until I received my first check – around $8. And it wasn’t until then that I learned I had to collect subscription charges from several customers – some tipped, some didn’t – and turn the money in to the Journal.

Still, I enjoyed the routine. Even waking up at 3 a.m. to deliver the thick Sunday papers from the car driven by my dad wasn’t too bad – at first. Watching the sunrise when we finished the route was a nice perk, and Dad and I worked well together, joking around. Then winter struck, subzero temperatures set in and the arguments began. After several hours, we’d arrive home irritable, hungry and exhausted, our coats and hands stained with ink. During Mass, I’d often nod off, only to be shaken awake during the sign of peace.

But Christmastime and the early December delivery of the Journal calendar made up for the dreaded Sunday mornings. Most customers tipped handsomely during the holiday season – $10 here, $20 there – and my $250 or so total was a king’s ransom for a junior high schooler. I’d like to say I saved my earnings for college or shrewdly invested in Microsoft or some other future behemoth. But I spent most of it on YM magazines, granny dresses and Salt-N-Pepa cassette tapes. 

In January 1995, the Journal announced it was merging with the morning Milwaukee Sentinel, and among the big changes would be a new carrier age requirement of 18. After more than a year of hellish Sunday mornings, though, I was ready to quit anyway.

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More than two decades later, I appreciate my father sacrificing his Sunday mornings to haul me around on my route. We can chuckle about it now, but at the time I’m surprised Dad didn’t dump my papers on a curb somewhere and make me deliver them all myself, considering all of the whining and guff I gave him.

I also look back on the work itself fondly. I enjoyed the independence of delivering during the week, and the route taught me skills such as time management I still use today as a freelance writer. There seem to be so few opportunities for preteens today to earn a little spending money of their own.

My generation was the last group of kids to march down neighborhood streets, newspaper bags slung over their shoulders.


“The Paper Route” appears in the September 2018 issue of Milwaukee Magazine.

Find it on newsstands beginning September 3, or buy a copy at milwaukeemag.com/shop.

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