In Honor of National Boss Day: Bad-Boss Stories

Oct. 16 is Boss's Day. What better way to celebrate this occasion than with stories about some of the worst bosses of our lives.

In Honor of National Boss Day: Bad-Boss Stories Photo (cc) by Trenten Kelley Photography

When you walk into work today, you might want to give your boss a special smile. Oct. 16 is Boss’s Day or National Boss Day, an unofficial observance in offices and factories across the land.

Patricia Bays Haroski, who worked at State Farm Insurance in Deerfield, Ill., came up with the idea in 1958, says Oct. 16 was her dad’s birthday.

Haroski’s purpose was to designate a day to show appreciation for her boss and other bosses. She also hoped to improve the relationship between employees and supervisors.

Good luck with that. In honor of this special day, we’ve assembled a bunch of bad-boss stories from Money Talks News writers and sources across the Web. Unfortunately, not every manager is a gem who values his or her workers, and some are downright vile.

From MTN writer Marilyn Lewis

This is a story from the dark ages. I mean really long ago. My first real journalism job was at a weekly newspaper that shall remain nameless. I was paid $400 a month. We had an all-female staff, something unusual back then. The staff was me and another woman. We killed ourselves covering every meeting and every bit of news imaginable. Very long hours. After about a year of this, I asked the publisher for a raise. I was thinking something along the lines of maybe $20 more a month.

“No dice,” he said. “Sorry.”

“Wait a minute,” I said. “You know you could never get a guy to work for this kind of money.”

Sure, he said, good-naturedly. “Why do you think I only hire women?”

From AOL Jobs

The worst boss was this guy who as soon as he started to talk to you he would scratch his crotch. This was made worse by the fact that I worked in the Santa’s Workshop. Belynda P.

A recent entry on

Today, I went to work at my job as a secretary. I had been given the task to file my boss’s collection of Playboy magazines alphabetically by name of the centerfold. There was one for every month from the years of 1980 until now.

Another doozy from Marilyn Lewis

I was ill-suited to be a waitress but all my friends were making good tips so I thought, “How hard can it be?” I landed a lunch job at a fancy European restaurant that catered to the city power brokers. White linen tablecloths, many forks and knives, fresh flowers. That kind of thing.

You were supposed to only put things down on the table to the diner’s right and pick up only from the left. Or was it pick up from the right and put down on the left? Anyway, you had to carry this small round tray wherever you went. Empty or full, you never put it down, was the instruction.

The chef was a temperamental Eastern European guy. Famous in town as an artiste. He hung over everyone in this big hot kitchen with many huge copper pots all simmering with various cream-filled dishes. He yelled constantly, barking, criticizing, demanding. Everyone was jumpy. Most of all, me.

Mid-lunch rush on my first or maybe second day, I thought I was holding my head above water when the maitre d’ sends me to the kitchen for a bunch of water glasses. I trot in and, as instructed, hoist a heavy tray of stemware so it’s balanced on one hand and start to move toward the doors into the dining room.

From behind me, without warning, the chef screams at someone — not me: “No! Not like that!” I jumped. The tray tilted, then tipped, then crashed to the floor of the kitchen, loudly shattering every glass. I tried to clean it up but someone shooed me out of the kitchen.

At the end of the shift I was counting my tips when the chef, who hadn’t spoken to me since he’d hired me, walked past me and, without stopping or looking at me, said in passing: “I don’t need to tell you that you’re fired, do I?”


The boss with personal conflicts

Jane from Winchester wrote that her boss came into a meeting with his wife, and then “proceeded to scream at her and tell her what a moron she was” in front of everyone.

Here’s one of mine

Years ago I worked in a newsroom where the reporters’ assignments were written in a book on a desk. When you arrived at work, you checked the book to see what you would be doing that day. One day my assignment in the book was to remind one of the editors to call about the status of her drapes. Apparently she was having them cleaned or shortened.

I told her I didn’t think it was appropriate to give me assignments that had nothing to do with my job.

Later a boss higher on the food chain took me to an empty room, backed me up against a wall and screamed that if he assigned me to sweep the $#&@ floor, I would sweep the $#&@ floor. (Yes, he used that word.)

A similar tale from Reader’s Digest

My boss was a real gentleman.

Although it wasn’t my job, he once made me mow the lawn around our office building. I was wearing a dress and high heels.—Tamara T., Nebraska

Another bad-boss story from my past

This didn’t happen to me, but I once had a boss who was utterly heartless when a co-worker began making mistakes at work that were totally out of character for her. It was soon determined that she was diabetic, which was the likely cause of her mistakes. Nevertheless, the heartless wonder put her on probation.

Bosses of the world, do you recognize yourself in any of these stories? That might explain the shortage of gifts on this special day designed to salute you. It’s not too late to make amends.

Do you have any bad boss stories to share? Let us know on our Facebook page.

Karen Datko
Karen Datko
A veteran of three decades in the newspaper business, I moved to online writing and editing in 2007, specializing in personal finance. I'm frugal but not cheap, have zero debt and paid ... More

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