Job #3: Paper Boy – Age 12 – 1976
If lawn mowing was steady work and snow shoveling was a hustle, being a paper boy was my first taste of logistics. Not the clean, bar-coded Amazon Prime kind, but the raw, analog grind of a twelve-year-old hauling dead trees and ink around Baltimore. It was me against gravity, me against time, and me against a sack of newspapers that weighed as much as I did.
I delivered the evening and Sunday editions of The Baltimore Sun. Weekdays meant hoofing it after school, lugging a canvas sack over my shoulder until the straps dug trenches in my skin. Sundays were a different animal. The paper was so bloated with ads and inserts it had to be split into two deliveries. Saturday brought the “lite” version, coupons and comics and recipes and what not, and then Sunday was the real monster, a brick of newsprint so heavy it could throw out your back before puberty even hit.
My route wasn’t in Hampden, the working-class row house neighborhood where I lived. Nope, the Sun decided to export me north into Roland Park, where Baltimore’s money slept behind manicured hedges and polished doors. Delivering there was like sneaking into another dimension. Their sidewalks were longer, their porches were bigger, and their expectations were sharper. You didn’t just toss the paper on their lawn and run. It had to land neat, dry, and close to the door. These people didn’t want news, they wanted service.
I had a secret weapon: my skateboard. Most paper boys trudged along, dragging their sacks like condemned men. I bombed those quiet Roland Park streets on four urethane wheels, bag swinging, firing newspapers at porches like some wild-eyed twelve-year-old courier of doom. The skateboard cut my route time in half, but it also meant I lived on the edge of catastrophe. Baltimore sidewalks are war zones. Cracks, tree roots, uneven seams --- each one a landmine that could stop the board dead and send me flying, papers scattering like confetti at a parade.
There was one hill in particular, a long, steep plunge that made or broke the route. At the top, the choice was yours: bail and walk it like a coward, or drop in and trust your legs not to shake apart. I usually chose the latter. Controlling the board with a hundred pounds of newspaper strapped to me was lunacy. The trick was to keep just enough speed to stay balanced, but not so much that you overshot the porch or rocketed into the intersection like a human missile. When I stuck the landing --- paper thudding perfectly against the door --- it felt like Olympic gold. When I missed, I perfected the art of the sheepish apology.
Collecting money was its own side hustle. Some Roland Park families tipped like I was delivering lost treasure, folding crisp bills into my hand with a smile, “keep the change”. Others treated me like I was running a scam, digging through couch cushions to scrape together exact change, their suspicion hanging in the air like stale cigar smoke.
And then came the jackpot. One afternoon, a customer opened the door, a guy in his thirties, and casually asked if I liked comic books. “Yes!” I blurted out, my twelve-year-old brain already racing. He told me he had a couple of boxes he didn’t want anymore. Free. I nearly levitated. The only problem was logistics again --- I was on my skateboard. No way to haul boxes. So the next day I returned with my dad, and we loaded them into the car.
It was a gold mine. Spiderman, Hulk, Thor, Iron Man, Batman, The Archies, G.I. Joe, dusty westerns, psychedelic side stories, and dozens I’d never seen before. Hours and hours of stories poured into my lap. It was like the universe had expanded overnight, and my paper route had opened the wormhole.
The job wasn’t glamorous. It was hard work and balancing acts, skateboard wheels rattling, newspapers cutting into my shoulder, and that constant gamble with gravity. But it was also freedom. Twelve years old, bombing down Roland Park hills at sunset with the news of the world slung across my chest. And on that one perfect day, it was more than just cash in my pocket. It was the day the paper route didn’t just deliver the Sun --- it delivered me into what would become the multiverse.
