From side sewing gigs to questionable uses of office equipment, the workplace hustle looked very different decades ago. Many money-making ideas that seemed normal in the mid-20th century would be instant HR violations in today’s professional world. Here are 18 retro side hustles that simply wouldn’t survive in a modern office.
1. Selling illicit substances from desk to desk
In the 1970s, many workers took advantage of the permitted local laws and took it with them to the workplace.
2. Typing Résumés on Your Office Typewriter
In the 1970s, many workers made extra cash typing résumés for colleagues using office typewriters and paper. Today, that’s a clear misuse of company property.
3. Mini Tailoring Service in the Supply Closet
Employees often hemmed skirts and fixed buttons during lunch breaks, all while using company space as their “studio.” Fire codes and HR policies would shut this down today.
4. Repairing Radios and Small Electronics at Your Desk
In the 1950s and 60s, the office handyman fixed radios, alarm clocks, or fans for a few dollars. Modern workplaces would call this unsafe and disruptive.
5. Developing Photos in the Office Darkroom
Before digital photography, some offices had darkrooms—and employees used them after hours for personal film processing. Today, this equipment doesn’t even exist.
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6. Hosting a Lunchtime Beauty Salon
It wasn’t unusual for someone in the office to style hair, give quick trims, or do makeup touch-ups for extra money. Now workplace liability rules forbid this.
7. Typing College Term Papers for Students
Fast typists made money typing academic papers in the 1970s and 80s. With modern academic integrity rules, and computers, this hustle wouldn’t last.
8. Selling Homemade Baked Goods Without Permits
Coworkers brought pies, fudge, and cookies to sell around the office. Today, most workplaces and local food safety regulations prohibit unlicensed food sales.
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9. Renting Out Your Desk Drawer as “Snack Storage”
Some workers literally charged rent for others to store candy bars or sodas in their desks. Modern offices have shared kitchens and much stricter rules.
10. Polishing Shoes Inside the Office
A surprisingly common side gig in the 1940s, workers polished colleagues’ shoes between meetings. Today’s casual dress codes make this obsolete, and corporate hygiene rules wouldn’t allow it.
11. Making Personal Stationery or Greeting Cards on the Office Printer
Some crafty employees used office printers and paper stock to run a side business making cards and invitations. These days, print tracking software would shut that down.
12. Sewing Custom Aprons, Curtains, or Tablecloths at Work
It wasn’t unusual for employees to bring sewing machines and fabric to the office during slower periods. Now that’s an insurance and noise-control nightmare.
13. Lending Out Office Supplies for a Fee
Workers once “rented” staplers, rulers, or hole punchers to forgetful colleagues. Today, that’s more likely to result in a conversation with HR.
14. Hosting Lunchtime Language Lessons in the Conference Room
Employees are sometimes charged for private lessons in Spanish, French, or shorthand during breaks. Modern workplaces require booking requests and formal approval.
15. Duplicating Personal Flyers or Newsletters on the Office Copier
The 1980s office copier was a goldmine for employees printing church bulletins, club newsletters, or personal flyers. Today’s digital logs catch every page.
16. Selling Handmade Jewelry at Your Desk
Coworkers often displayed handmade bead jewelry or knitted items at work. Modern solicitation policies typically forbid selling personal goods onsite.
17. Catalog Sales at Work (Home Interiors, Tupperware, etc.)
Workers passed around catalogs and collected orders during office hours. Today, companies prohibit sales recruitment and solicitation on the job.
18. Offering Typing or Filing Help for Other Departments…For Cash
Some employees earned side income assisting coworkers or other departments off the books. This would violate modern payroll and compliance rules.
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Looking back, it’s almost unbelievable how casual and creative workplace side hustles once were. What seemed perfectly normal in a 1950s or 1970s office would trigger a dozen approvals, HR emails, and compliance checklists today.
But that’s what makes these retro gigs so fun to revisit: they remind us just how much the workplace has evolved, and how resourceful people have always been when it comes to earning a little extra on the side. If you loved this content, check out 35 Vintage Photos of the Early to the Mid-1970s, or 40 Vintage Photos of the Early 1990s That Capture the Era.
