The Best (Or Worst) Bad Boss Stories Ever

Start Your Own Business Because of a Bad Boss? Join the Club!

Many entrepreneurs, solopreneurs freelancers, independent contractors, small businesspeople, and other self-employed folk start their own business because of a bad boss. Whether it is a string of bad boss experiences or even just one very bad boss, quitting or getting fired and starting your own business is often the result.

Bad bosses come in a surprising variety of shapes: The slave-driver, the jerk, the screamer, the moron, the weirdo, the one who never gives anyone any credit, the manipulator . . . And then what? Sick of being miserable for eight hours a day, or saying the wrong thing at the wrong time, you can’t take it any more and the next thing you know, you’re working for yourself.


It surprises me what a ripe subject this is. It seems like everyone has a bad boss story, or several. Check it out: I have a friend in sales who works for a boss who, once a week, every week, fires someone. Employee morale is of course low, people are constantly in fear of losing their jobs, turnover is a given, and people hate working there.


My first boss was a bad boss. I got a job at an ice cream shop. I was 16. The boss said I needed training, and so had me work for a week – for free. When the week ended, he further informed me that I needed another week of training. I quit during the second free week of labor.

What is Your Bad Boss Story?

I have been hearing a lot of bad boss stories lately. Here are some of the best (or should I say, worst?):

• There was a guy whose wife unexpectedly went into labor three weeks early. He called his office and explained to his boss that he would not be able to make it in for a few days. He was fired for “a lack of commitment to the job.”

• Or how about the woman who worked in food service who got the flu from her son but forced herself to go into work that day anyway because the boss liked “team players.” By midday she clearly needed to go home, on top of the fact that she was contagious. But the boss would not let her leave and made her finish her shift. And yes, most of the rest of the staff got sick that week.

• Or the boss who befriended one woman and, over the next few months, got her to share some secrets about her past employment (private things, nothing illegal). The boss later twisted the info and shared it with his boss in order to ingratiate himself, look like he was on top of things, and get ahead. She was fired and he got a promotion.

• How about the partner in a big law firm who gave the young associate four boxes full of paper – probably 10,00 pages in all – and said it had to be organized and indexed . . . in two days. When the associate showed up two days later, disheveld and exhausted and holding an understandably incomplete index, the boss said, “Good job. I was just testing you.”

• What about the guy who demands everyone work extra hours almost every day but naps every afternoon?

• Or the boss who locks the front door and won’t let people leave at 5:00 (“unless you want to get fired on the spot”) until the team meets their daily quota of sales?

(Do you have a bad boss story? Please share it below.)

Bad Boss Stories: What You Can Do to Make Things Better

So what do you do if you have a bad boss and don’t want to quit, or cannot quit? Here are a few ideas:

1. Do your best. Nothing succeeds like success. Hopefully, the boss will come to realize your value and not want to lose you, or maybe other people in the business notice your commitment. Either way, you will keep your job and some of your sanity if you don’t sink to the boss’s level.

2. Say yes. The bad boss is often an insecure person. To the extent possible, you might want to just try agreeing with her, even if you know she is wrong. In addition, work to figure out what is important to your boss and do that.

3. Speak up. Tell your boss what it is you need and how working together can help the business. Your boss may not listen, but then again, maybe he will.

4. Document. Make sure you keep a log of inappropriate comments and actions; you never know when it might come in handy, in a lawsuit or wrongful termination case for instance. Similarly, document your work and what you do right.

5. Keep your eyes open. This is not your last job, just your current one. Work your network and keep your options open.

6. Become self-employed. The best answer of all!

 Do you have a bad boss story? Share it below!

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