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Embarrassing Moments at Work


8 Most Mortifying Career Moments

By Tiffany Miller

Nightmares of showing up to a board meeting naked don’t come close to some real life slip-ups. Imagine getting so nervous meeting Morgan Freeman that you called him Mr. Seamen. It happened to an LA photographer. At least he laughed about it.

Here are some other embarrassing moments at work:

Assistant Photo Editor, New York

Sarah got her first job working on the website at a major car magazine, not knowing one thing about cars.

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Not only was she unfamiliar with cars, “I didn’t even drive,” she said.

That led to obvious problems. The first happened when Sarah was asked to create a photo gallery of parts on a Mercedes.

“I was supposed to put a grill in the gallery. So I thought tailgate, you know, a BBQ,” she said.

That obviously wasn’t the right choice and she figured it out as soon as she heard her boss scream her name
“He gave me a book on car parts and I never messed anything up again,” she said.

TV Producer, New York City

Stephanie was a producing a morning show segment with Robert Verdi – the TV stylist who always wears sunglasses on his bald head. The call time was 4 a.m. — too early to get any kind of decent sleep. And, apparently, her outfit-selecting judgment wasn’t at its best that early hour.

“The sundress and cowboy boots I’d worn out a few days earlier seemed like a good idea,” she said.

But Stephanie wasn’t ready for the Verdi critique.

“That’s a lot of boob first thing in the morning,” he said, laughing.

And, it was in front of the entire crew and her boss.

“I just stood there. Silent,” she said. “I had nothing to cover myself up with and had to work with him for the rest of the day.”

Research Assistant, Cleveland

Gina had an extra hard night out partying, but she knew she couldn’t afford to call in sick.

“My boss could smell a lie a mile away,” she said.

So the work-hard, play-hard research assistant dragged herself into the lab at 8 a.m. that Friday morning. She said, “I couldn’t believe my luck when my boss told me he’d be out all afternoon with a medical appointment.” It sounded like a much-needed nap might be possible.

Gina decided to lock herself in the back room after her boss left to catch a few Z’s. She was sure she wouldn’t be caught because she had the key to the door. Plus, she set the alarm on her cell phone. Her plan was flawless.

Soon enough, though, she was startled awake.

“My boss’s doctor was out so he came back. He found another key. Talk about mortifying,” she said.

Accountant, New York

Lauren was coming home from a very late night during tax season, catching a cab back to her downtown apartment. She was wearing a peacoat and a dress, conservative enough for her mostly male office.

“It certainly wasn’t revealing,” she said.

But apparently the cab driver felt differently.

“He asked me if I’d been “walking all night’,” she said.

She said it was embarrassing “for about a second,” but she just thought it was funny the next morning. Lauren decided to tell her boss the story for a good laugh. He thought it was hilarious and now tells the tale to every new client that comes into the office.

Sales Assistant, Philadelphia

Five years ago Jess was just out of college, working her first full-time job at a large ad agency. Her boss was the detail-oriented type who loved creating new processes.

“He’d scream at me for stapling incorrectly. His expectations were impossible,” she said.

So when her oh-so-perfect boss made a major grammar flub, typing ‘their’ instead of ‘they’re’ in an email, Jess couldn’t resist making fun of him. She shot off a note to a few of the other sales assistants that pointed out the error — enjoying a little revenge.

Everyone received the message just fine, including her boss. She had hit reply-all.

Law Student, San Francisco

Kara was clerking at a law firm while finishing up her last year in law school.

“I was hoping they’d be so impressed they’d hire me when I graduated,” she said. Apparently she impressed them in other ways. Kara came out of a meeting with several senior-level attorneys when she realized more than one button had come loose on her once-conservative top.

“I was totally spilling out. No one had the balls to let me know,” she said. Somehow Kara lived through it and actually got a job after graduation.

“Maybe it worked for me,” she said.

Starbucks Barista, Seattle

Starbucks baristas are vigorously trained to make drinks perfectly every single time. Bridget was new, but fairly confident with her skills, when Starbucks CEO Howard Schultz popped in line for his double short extra short nonfat latte. She started feeling really nervous and didn’t pay close attention to his special request. Extra short means light on the milk. She filled the cup up to the top, handed it to Howard and heard, “Is this my drink? It was supposed to be extra short.”

Uh-oh. Sorry, Mr. Starbucks.

Bridget offered to remake his latte but he just grinned patiently, said “Thank you” and walked away. No complaints and Bridget kept her job.

Crime Reporter, Chicago

As a crime reporter for a daily newspaper in Chicago, Jane is a stickler for facts. She’s known for her confidence and bold questions at press conferences. So when the entertainment reporter came down with the flu, she wasn’t too nervous about taking on a fluff piece and interviewing the cast of the movie Rent. Unfortunately, she didn’t have time to do much research.

“I asked Idina Menzel what it was like doing Idina Menzel’s makeup,” she said. “I had no idea she was the star.”

Jane thought no one would find her out, but apparently her editor was friendly with another reporter there for an interview.

“The entire staff heard about it,” she said. Mortified? Yes. It’s no surprise that Jane sticks to the crime beat now.

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