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The team got into a surprisingly passionate discussion about jobs that are much tougher than people realize, and it all started with one simple question: What was the hardest job you ever had?
Eddie went first, immediately flashing back to the warehouse where he worked for his dad. He remembered long days hauling streetlights, loading trucks, and driving forklifts before he was even old enough to truly appreciate how dangerous that probably was. The warehouse crew, a pair of guys he described as reformed gang members, practically adopted him and even let him drive the forklift. They brought in a cousin once who told such wild Chicago gang stories that Eddie is pretty sure the guy was hiding out in Texas. It was an unforgettable time, but also a brutally hard job. Bobby thought back to his early years working golf course maintenance, which required waking up before sunrise to mow greens and weed-eat acres of grass before most people’s alarms went off. But the job he said he learned the most from was waiting tables. Nothing teaches patience, humility, and adaptability quite like dealing with customers from every walk of life: good, bad, strange, picky, and everything in between. Lunchbox insisted his toughest job was the one that looked easiest on paper: corralling shopping carts at Sam’s Club. His location sat at the top of a hill, and every single customer parked at the bottom. He spent eight hours a day in scorching Texas heat pushing carts uphill, the asphalt radiating heat like a stovetop. Miserable, he said, and not the breeze people assume.
From there, the show moved into a list of the official jobs ranked as harder than most people think. At the top: caregivers. Whether caring for aging adults or people with major health needs, the emotional toll, the physical responsibilities, and the heartbreak of loss make the job far heavier than outsiders realize. Customer-facing jobs came next—anything involving constant interaction with the public. Everyone on the show had experience in retail or food service, and they all agreed: dealing with people all day, every day can be rewarding, but it absolutely wears you down at times. Paramedics and EMTs also made the list, roles that require not just courage but a massive emotional shield. The team agreed these professionals have to become somewhat numb to trauma simply to stay effective, even if that sounds harsh. Their ability to stay steady when everything around them is chaos is exactly what people need in a crisis.
Construction work, especially roofing, was another unanimously tough one. Bobby recalled cleaning up roofing jobs where shingles rained down nonstop and the heat made everything feel twice as difficult. The team agreed that anyone who works on a roof in summer deserves serious respect. Teachers were next, and the room quickly got spirited. Lunchbox argued they have it easy with air conditioning, desks, and worksheets. Everyone else pushed back immediately, pointing out how challenging teaching truly is when done well. Managing kids, adapting lessons, dealing with parents, and doing it all with a limited budget is no small task. Good teachers, they said, absolutely earn their reputation as some of the hardest workers out there. Raymundo chimed in about his time as a call-center operator, over a hundred calls a day, many involving upset customers, and the constant pressure to upsell. Even he admitted he bailed on most tech issues and sent callers straight to another department.
Delivery drivers made the list too. Lunchbox brought up his time delivering catering orders for Jason’s Deli, lugging giant containers of iced tea, trays of food, and supplies across hospitals, often without receiving a tip. Today’s delivery drivers have a different challenge: tipping depends entirely on blind generosity from strangers who don’t even see them. The final job on the list was wedding photographers and videographers. Lunchbox dismissed it as “easy money,” but the rest of the room pushed back, pointing out that capturing someone’s biggest life moment, perfectly, under pressure, with no do-overs, isn’t simple at all. Plus, everyone else gets to enjoy the party while the photographer works in the background trying to get everything just right.