This is the second in a series of accounts of various jobs I’ve worked. First story is available in Issue # 1.

Looking back on your own working life, certain jobs stand out among all the others. Sometimes it’s the first job. Going through that initial experience of regimentation or dealing with authority that doesn’t come from family or school is something not easily forgotten.

My first job was nothing like that. I rarely dealt with co-workers and never met or even saw management. Technically, “independent contractor”, rather than employee, was my status. I had an amount of freedom and solitude unmatched in later employment. Of course I’m talking about being a paperboy.


While attending junior high in a tiny Iowa town on the Mississippi River, I noticed that a few of my classmates seemed often to have their own money. They had cool t-shirts of bands and rappers. Large CD collections. These weren’t the children of the wealthier or “important” people in town, but kids that lived a few blocks away from me, whose parents I knew worked decent, but not great, paying jobs. It didn’t take long to discover that these kids, unlike most of us, had a job: delivering the larger, regional newspaper every morning before school.

Even though I already had difficulty getting up for school, it didn’t seem like it would be too hard to get up earlier with money as a motivator. I called the newspaper up and told them I wanted to work for them. The person on the phone told me it would take 30-60 minutes each morning and pay $55 every two weeks. It seemed like a paltry sum to me but I agreed nonetheless. They told me I was to start training tomorrow and gave me the phone number of one of my classmates, who was looking to pass on one of their “routes”.

The next morning, I reluctantly brought my old school Huffy Rangler out of the garage. In small town Iowa, anything that wasn’t an oversized mountain bike was ridiculed. Back in the Chicagoland area, where me and my family were from, lots of kids had the older bikes from the 1980s and would turn them into lowriders. Not here.

Meeting my classmate at a car wash where the bundles of newspapers were delivered each morning, he showed me my new route. It was all a bit confusing. Every house seemed to want their paper in a different spot. The newspaper box, under their welcome mat, between the doors or in a metal box under the kitchen window were just some of the various places that needed to be memorized. Plus, I had to remember which houses got the paper and which did not, as well as which ones only got it on the weekend or just Sunday. Since my dad was a letter carrier for the post office, it seemed like I would be able to do this. Sketching out a map in a notebook and studying it, after a week of training, doing the route became easy.

After some time, the whole thing was very routine. I whipped my bike through alleys and yards, blasting mixtapes full of g-funk and heavy metal made for my waterproof Walkman.The satchel I used to carry the papers soon became weathered and dirty. I was an experienced working man. The news headlines came and went everyday. The Unabomber was caught, Bill Clinton won reelection, the Chicago Bulls keep winning, Tupac is murdered, Iraq is hit with cruise missiles…and on and on.

Eventually the routine started to become smothering. While it was nice to have my own money, it became harder and harder to wake up in the morning. When the weather was bad in the winter, attempting to pedal up driveways and gravel road hills was an exercise in futility. People got their papers late. They started complaining.

One old man in particular would call and complain if his paper was even 10 minutes late. He lived on the outskirts of town, in a small valley surrounded by rocky farmland and thick forest. His house was towards the end of a winding, gravel road which usually had a trace of fog blanketing it in the morning. There were few other houses. Nowadays, this specific area has more development and large homes. The road is paved, some of the farmland has transformed into yards and many of the trees have been fought back and cut down. But in 1996 it was still a picturesque, if eerie, slice of the Driftless Area.

I dreaded delivering to this old man’s home because it required walking into his enclosed and cluttered porch. While we never spoke, he always peered out the windows at me. A part of me thought that one day he would mistake me for a trespasser and strike me down with the thundering clap of the 12 gauge it can be safely assumed he owned. Thankfully, that never happened.

Some people I really enjoyed delivering a paper to. For example, the cop, who lived not far from the old man’s valley. Although I had nothing against him personally (yet), the fact that he was an officer of the law seemed to me enough reason to ruin his day by regularly removing the sports section from his paper.

After about a year, being a paperboy was no longer for me. So I quit. One Sunday morning, in a sleepy haze, the decision was made. My Huffy Wrangler stayed in the garage. My satchel remained hung up in my room, never to be used again. The bundle at the car wash was abandoned. Dozens of angry townspeople called my house, wondering where their Sunday edition was. The newspaper people called me, frustrated and shocked that I would just decide, all of the sudden, to refuse to do my duty. I shrugged.

My first job ended up being also being the first one I quit, without notice.

Originally published on

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