17 Strange Side Hustles That Were Totally Normal Back in the Day
From ice cutters to snake oil salesmen, these quirky side hustles from the past were once vital to daily life. They offer a fascinating glimpse into a world where innovation and necessity sparked strange but essential careers.
- Alyana Aguja
- 5 min read

In the past, bizarre side hustles were the pillar of daily existence, keeping things moving in a world without modern amenities. From the devoted milkman bringing dairy to the sidewalks and backstreets, to the eccentric snake oil salesman hawking dubious remedies, these jobs were a necessary, though odd, component of the past. Now, they are a captivating reminder of how necessity brings about innovation and resilience, the way we existed prior to technology’s reign.
1. Lamp Lighter
Image from Wikipedia
Before electric lights illuminated the streets, lamp lighters were vital to city life. They patrolled the streets every evening, lighting gas lamps and keeping cities well-illuminated after dark. They smothered the flames come morning, forming a vital night-time routine for safety and convenience.
2. Ice Cutter
Image from Gone Jobs - WordPress.com
Before the invention of refrigeration, ice cutters cut blocks of ice from frozen rivers or lakes and stored them in ice houses during winter. They were sold to households and industries for the rest of the year. It was a labor-intensive job that kept food chilled in an electric refrigerator-less world.
3. Canoe Postman
Image from Pinterest
In rural areas of America, particularly during the early 20th century, individuals used canoe postmen to deliver mail where there were no roads. Paddling along rivers and lakes, they delivered letters and packages to outlying communities. It was a vital service for residents far from the postal centers.
4. Chimney Sweep
Image from Mr Soot
In the 1800s, chimney sweeps were a common side hustle, especially in London, where most homes had coal fires. These workers would climb inside chimneys to clear soot and debris, preventing dangerous fires. It was a dirty job, but one that kept homes safe and warm during the cold months.
5. Typewriter Repairman
Image from Los Angeles Times
Typewriters were once the go-to instrument for writers, journalists, and businesspeople. Fixing them was a valuable skill, and numerous individuals operated small establishments providing speedy repairs to broken typewriters. This hustle declined with the advent of computers but was once an integral service in each office.
6. Rag Picker
Image from Procurement Magazine
Before recycling became common, rag pickers used to walk around cities, picking up pieces of fabric, paper, and other useless materials. These would be sold to paper mills or utilized in the production of rags for industrial cleaning. It might seem odd now, but it was once a significant waste management job.
7. Switchboard Operator
Image from Wikipedia
Before computerized technology, individuals used to work as switchboard operators, physically transferring calls by inserting wires in a switchboard. The work demanded speed and accuracy, as operators had to direct telephone calls to the right place. The advent of automated systems phased this rush out in the long run.
8. Milkman
Image from Drink Milk in Glass Bottles
The milkman was a common figure in neighborhoods across the land, delivering fresh dairy goods to front doors daily. Prior to supermarkets being prevalent, this hustle provided families with a way to obtain daily necessities without ever having to step foot outside the house. The milkman’s extinction came about with refrigeration and the advent of grocery stores.
9. Snake Oil Salesman
Image from The Conversation
While it rings of a hoax now, snake oil salesmen used to roam the streets selling questionable “medicinal” remedies. Posing as miracle cures, they promised to cure everything from arthritis to dermatitis. For all their deception, these peddlers were surprisingly effective in an unregulated world.
10. Trolley Operator
Image from Volunteer
Streetcar operators were indispensable in urban centers prior to the automobile’s heyday. They moved streetcars from fixed routes to get people where they needed to go. Operators ran the whole deal, driving and taking fares in many cases. The invention of buses and motorcars spelled this hustle’s decline.
11. Hurdy-Gurdy Player
Image from Wikipedia
Hurdy-gurdy musicians were street performers who performed on a hand-cranked instrument to entertain people as they walked by. This performance was a widespread side business in Europe and the United States throughout the 18th and 19th centuries. These musicians commonly survived through tips and donations, which helped fill the cultural climate of the times.
12. Fish Monger
Image from Whole Foods Market
Fishmongers were common in pre-refrigeration food markets when selling fish from a stall or even from door to door. They’d make great efforts to get fresh fish to consumers, making it a demanding but necessary job in the food supply chain. Fishmongers were once a respected part of coastal city communities.
13. Milk Carton Salesman
Image from Fast Company
Prior to boxed milk’s popularity, numerous individuals were milk carton salespeople. They went door to door, selling milk and other dairy products directly to homes, frequently filling glass bottles from big milk tanks. This side business declined as contemporary convenience stores became the sellers of dairy products.
14. Soap Maker
Image from Pittsburgh Magazine
During an era of non-mass-produced soaps, local soap makers would produce soap bars for the communities where they lived. They generally made use of fats, lye, and ash to produce simple cleaning agents. Soap making was a business and an art, and most individuals depended on it for their hygiene purposes.
15. Window Washer
Image from Skyscraper Window Cleaning
Prior to the invention of skyscrapers, window washers were a common sight in city life, washing storefronts, houses, and offices. Window washers employed long poles and buckets of water to clean windows, keeping businesses looking their best. This hustle gradually gave way to high-rise building maintenance as cities became taller.
16. Street Sweeper
Image from Wikidata
Street sweepers were workers employed to sweep city streets by hand, picking up trash with brooms or small carts. Although city sanitation departments utilize machines today, previously, this was a necessary job to keep cities clean. It was a physically demanding hustle that served to keep public areas clean.
17. Fender Repairman
Image from Key Collision Center
Before the widespread popularity of bumper cars, fender men were a requirement for owning an automobile. Every time a car’s fender was dented, owners would take the car to one of these handymen, who would beat out the dents and make the car good as new again. This gig gradually became extinct as body repair shops came on the scene.