Crazy Holiday Stories from Working in Restaurants and Retail

a photo of a Krampus costume, which is mentioned in one of the crazy holiday stories

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The holidays are a crazy time of year for those who work in restaurants and retail. At the very least, the unexpected always happens.

Sometimes, that unexpected experience is embarrassing, and at other times it’s an act of kindness.

More often than not, it’s a lesson learned – something that prepares us for next year’s holiday season.

For today’s blog post, I collected some crazy holiday stories from the TimeForge team. We hope you enjoy them!

Some even come with a kernel of advice that you might find useful as you navigate the rest of the year.

What could possibly go wrong with a Krampus display?

Isla shared a lesson about marketing in retail. “My time in retail middle management was always an adventure, especially during the holidays,” she said. “Eye-catching displays are one of the main ways to boost sales during the busiest shopping season.

One season, our store decided to set up a Krampus display. For those who don’t know, Krampus is a horned, anthropomorphic goat-man in Alpine folklore that scares naughty children during the Christmas season. The employee in charge was very excited about their work and wanted to share this rich European tradition with the masses.”

Sounds pretty innocent, right?

“Unfortunately, to some of our elderly customer base, it was a satanic display of epic proportions that garnered several complaints daily until it was removed.”

The moral of the story?

“Make sure your store displays work for a general audience,” said Isla. You don’t want to unintentionally give your shoppers the wrong impression!

When traveling, it’s better to be safe than sorry

Don, our Software Architect, shared a story about traveling cautiously during the holidays. “When I was in high school, I worked at a nearby Kroger in Mckinney, TX,” he said.

“We had a big December ice/snow storm – at least what you would consider big for North Texas. I figured it wasn’t very safe for me to ride my motorcycle in the ice/snow, so the pharmacist offered to give me a ride home. 

Just a mile from the store, we slid into a ditch and became stuck! I walked back to the store, rode my motorcycle to the stuck car, and freed the car using a tow strap and my motorcycle. It was a wet and cold ride home, but I made it safely.”

(It’s funny that Don actually used his motorcycle to free the stuck car, but I still think he made the right decision playing it safe!)

Years later: remembering a simple act of kindness

Diego, our Support Lead, couldn’t think of a crazy story, but one memory did stand out to him: “Luckily I’ve never had anything too crazy happen during the holidays,” he said. “But I do remember a customer once helping us clean up a table so we could get out early on Christmas Day.”

Weather woes or an opportunity in disguise?

Mike, our Implementations Manager, also shared a weather story. “Back when I was working in grocery, we had a massive snowstorm hit us, and we ended up with a few inches of snow,” he recalled.

“We were in Georgia, so anything more than a millimeter of snow was a reason to shut down the state. I was the only one with a truck, and closest to the store, so I drove through the snow to open up for the day.

Unfortunately, since there was snow, we didn’t have a single customer come in! But it ended up being a great day for organizing the backroom and doing general cleaning tasks.”

The lesson I took from Mike’s story is that it’s always good to have a checklist of tasks to do when things are unexpectedly slow.

Communication during holiday craziness is key

Audrey, our COO, shared a crazy holiday story about her days in retail in 2007. “I remember a particularly rough first day starting a new job at a toy store in the local shopping mall. It was Black Friday (the largest shopping day of the year in the U.S.),” she said.

“I showed up, as instructed, at 4:30 am… and waited. And waited, and waited, and waited. I didn’t have any of the managers’ phone numbers, and my Motorola RAZR didn’t exactly have Google search.

A manager arrived at 6:45 am to open the store and was so excited that I had shown up early. I didn’t correct them about just how early. They probably had no idea that their boss had told me to be there more than two hours earlier.”

Ouch! Better team communication – even just a quick text or call – could have prevented that dip in employee morale.

Audrey continued, “Once the store was open, they handed me an elf costume and told me to ‘get ready to greet people.’ I had mostly worked in restaurants up until that point, so I just assumed that ‘greet people’ meant I should smile and welcome customers to the store.

After a few hours, one of the cashiers helped me understand that I was actually the obnoxiously elfen LP (Loss Prevention). I hadn’t been watching for shoplifters prior to that, so I actually hadn’t been properly performing my job… likely letting merchandise slip out without even realizing it.”

Again, ouch! Reduced margin due to a lack of communication.

“Traffic began to pick up rapidly,” said Audrey. “Shoppers were packed like sardines into each aisle, clambering for the hottest toys.

About halfway through my 12-hour shift, one of the managers explained to me that the nationwide company that owned the toy store was going out of business, so the store was being shut down. Also, more than half of their employees had quit when they received the news. My position was only for a few months, and we were going to be short-handed.”

Yikes! Audrey had no idea she’d signed up for a temp job.

“This meant that on top of Black Friday, they were running a going-out-of-business sale and marketing extreme deals as hard as they could,” said Audrey. “The increased customer traffic paired with the reduced headcount was a recipe for disaster!”

But her crazy holiday season wasn’t all pain and misery.

“It ended up being one of the most fun retail experiences I ever had, and I learned a TON that season,” she explained. “I was running merchandising and training teammates on the cash registers. Wrapping my head around how profit, loss, margin, and labor budget each worked.

I learned some pro tips on payroll processing and how to facilitate camaraderie and culture in the midst of chaos. It was a crucial experience for me.”

The most important lesson Audrey learned from that season’s experience, however, is that during a rush, good leadership overcommunicates.

“It’s good to sound like a broken record,” she said. “It’s good for employees to hear you focus on the same policy, the same process, the same priority. And it’s good to set expectations early, and loudly, and honestly.”

More Holiday Stories and Advice from TimeForge

If you enjoyed reading this blog post, you might also like our Holiday Advice for New Managers. It contains useful tips for getting through the holidays this year.

We also recently published some advice on dealing with no calls and no shows at work.

From all of us here at TimeForge, Happy Holidays! We hope your holiday season crazy in a good way.

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