Housekeepers have extremely difficult—and often thankless—jobs. It can be physically taxing, and these brave people are often underpaid to do the work around strangers’ homes that others don’t want to do. Housekeeper Cara Simmons understood this all too well…
Cara did her job for years without ever enjoying a day off, even when it began to take a serious toll on her physical health. Still, her positive spirit never diminished. One day, she was tasked with an otherwise ordinary housekeeping assignment—and it ended up changing her life!
Cara Simmons of Cleveland, Ohio, was a 36-year-old single mother of three who made ends meet as a housekeeper. She worked so hard that she never took a single day off, let alone went on vacation.
Unfortunately, this routine caused Cara to be hospitalized more than once. The stress gave her stomach ulcers, and she still had trouble paying rent. However, Cara pressed on, giving her all to every assignment for her family.
Her children loved and appreciated her dearly, and her employer—a housekeeping services company called Maid Brite—was especially impressed by Cara’s work ethic.
Things were definitely tough, but what Cara didn’t know was that she was about to get the assignment of a lifetime. On a day that seemed like any other, Maid Brite sent Cara to a “very important” client’s home…
As soon as Cara arrived, she was greeted by a woman who introduced herself as Madeline Blue. She explained that, although the house was already cleaned, Cara was still needed for some work.
Madeline said she was hired by the owners of the house to organize a large party that would take place that evening. She hired Cara to assist her in preparing everything. It sounded reasonable, so Cara took on her first task: meeting the world-renowned chef—Manny Slomovits—who would prepare an extravagant six-course meal for the event.
Cara’s work had only begun. Her first assignment was to taste—and evaluate—every dish for the event. This was not something Cara was used to, but as a dutiful employee, she agreed. She was a little wary, of course.
Making conversation as he presented the extravagant meal, Manny asked Cara what her favorite food was. Cara immediately replied “spaghetti”; that was her kids’ favorite food, after all. It was clear that she always put their happiness before her own.
The meal that the chef had prepared was a far cry from spaghetti. Cara was asked to taste a South African Tristan lobster—which was worth somewhere between $400 and $500—as well as lobster tail and quail egg with basil oil.
The rest of the meal consisted of an assortment of gourmet dishes that featured $4,000 white truffles and even edible gold. Sweet chocolate treats topped off the dessert menu. This party was certainly going to be fancy!
The meal was delicious, and incredibly expensive. Madeline then returned and asked if Cara could answer the door. That was when she came face-to-face with two men who arrived for the party’s reflexology station…
Then, Madeline made an odd request: the men needed to warm up their hands before the party started, or else they’d get cramps. Would Cara allow them to give her a massage? While it was unusual, Cara was happy to oblige. It was her job, after all!
It must have been a surreal experience for the hardworking housekeeper, and she expressed disbelief about how easy her workload was. “I think it’s my birthday,” she joked as the therapists worked their magic.
Little did Cara know how much more was in store for her. Next, Madeline took her upstairs to a bedroom, where she explained that she was trying to clean out a closet by getting rid of an assortment of designer clothes…
That was where Cara was supposed to come in: she was told that she could take whatever she wanted for herself, including designer heels, a beautiful gold watch, and even a stunning jade necklace!
After that unusual shopping spree, Cara answered the door to find a delivery man with a large box. Madeline asked her to open it, and what Cara found in there was shocking…
Somehow, Cara’s own belongings were in that box! Obviously, this was extremely unusual. She’d never even been to this house before, so how—and why—would her very own stuff be sent there?
Cara started to get suspicious, and perhaps even a bit worried. The delivery man arrived with an even bigger box, but he wouldn’t answer Cara when she asked him where they came from.
After being pressed, however, the delivery man explained that the items were for “the woman who lives in this house, Ms. Simmons.” To Cara’s utter shock, Madeline said, “Yeah, Ms. Simmons is my boss.”
Cara was supposed to be cleaning this house—so why was she being treated so nicely? She soon learned she was on a webseries called Prank It Fwd, which improves people’s lives in highly unexpected ways. Once they introduced themselves, they had one more surprise for Cara.
Her so-called “boss’s house” was actually a present to Cara and her family! It went above and beyond her wildest hopes and dreams, and she thanked the pranksters with tears of joy. However, she wasn’t the only struggling single mom who saw a surprise interaction flip the script on her life.
Tanna Marino of Cypress, Texas, was a mother to four children and the wife of a firefighter. She was a small-town girl, and her family was always the most important thing in her life.
Tanna worked long hours as an appliance technician at a company called Mr. Appliance. She liked her job, but money was always tight, and she wasn’t able to spend nearly enough time with her children. Then, one day she got an unusual phone call…
On the other end of the phone was a television scout asking Tanna if she’d like to star in a reality television show pilot. Tanna was stunned at the proposal, and even after asking for details of the show, she was still on the fence…
The scout didn’t reveal much about the show other than the fact it was called Don’t Quit Your Day Job. After weighing the pros and cons, Tanna figured this might be a chance to earn some extra income the family very much needed.
Tanna agreed to do the show, and when she showed up for filming on the first day, she met the camera crew who was going to follow her around while she went about her business. She was also to train a new employee named Faith Brown.
To Tanna, Faith came across as someone who normally worked an office job. She was wearing thick makeup, jewelry, and long acrylic nails. Even though she was dressed slightly out of character for a such a hands-on job, Tanna welcomed her aboard.
It was immediately apparent Faith didn’t have much experience in the field, but Tanna was patient and walked her through her routine. The cameras rolled the whole time, and Tanna concluded the reality show was about training odd new hires.
For several days, the two women made house calls together, and Tanna explained to Faith how to handle every issue. Faith and Tanna were getting along great, and Tanna even brought Faith to her house one afternoon to meet her family.
Faith met all four of Tanna’s kids, as well as her husband Michael. Faith was so touched by how welcoming every member of the family was, but after the delightful evening, Tanna admitted to Faith something very personal.
She confided in Faith that even though she and Michael had jobs, money was incredibly tight. She would more than likely need to get a second job for supplemental income. This would mean spending even more time away from her kids. This broke Faith’s heart.
Hearing Tanna’s struggle to stay active in her children’s lives brought up memories of Faith’s own father who was significantly absent in her life, as well. Now, it was finally time for the mother of four to know exactly what the reality show was about.
After Don’t Quit Your Day Job wrapped up the employee training part of the show, the crew told Tanna she’d be visiting Faith’s home for the final segment. However, when Tanna showed up later that afternoon, Faith had short blonde hair — and looked completely different.
She introduced herself as Dina Dwyer-Owens, the CEO of the corporation that owns Mr. Appliance! She had spent the last several days in disguise alongside Tanna, learning from her and finding out what life was like on the front lines of the job.
The television crew informed Tanna there was no show called Don’t Quit Your Day Job. It was actually a show called Undercover Boss, where bosses worked alongside their employees while incognito to learn about what day-to-day life was like.
Dina was impressed by Tanna’s work ethic, so first, the CEO granted Tanna $5,000 to spearhead a “Women in the Trades” program to assist women who were learning a trade.
Next, Dina set up a $10,000 scholarship fund so Tanna and Michael could start saving for their children’s college education. Tanna was in tears at Dina’s generosity, but that wasn’t even the biggest shock…
As Tanna was choking back tears, the CEO presented the mother with one more gift: a check for $25,000! Tanna was so shocked she nearly fainted! Dina said the money was a personal gift from her.
The whole reason Dina was interested in appearing on Undercover Boss was so she could explore the inner workings of the company as a regular employee and not as the boss. Luckily, Tanna exemplified all of the qualities Dina was looking for in an employee, and she rewarded her for all of them!
It must have been such an interesting experience for both women during the course of filming. Dina was able to see how Mr. Appliance operated from a completely different perspective, and Tanna was able to help a “new employee” gain valuable experience!
Tanna couldn’t believe how generous Dina was after filming wrapped. She thought she was simply showing a new employee the ropes, but that couldn’t have been farther from the truth. For more on this inspirational story, check out the video below.