Back in my 20s, I became romantically involved with a married coworker. The nightmare lessons of that affair were so intense that I have yet to repeat the mistake.

In my current job I make mistakes all the time. It’s part of the job. It’s unusual for me, and takes getting used to. I’ve never made so many mistakes in my life. The mistakes can cost my boss, the owner, money, if not caught in time. The mistakes center around placing expenses under the wrong job (we have many jobs going on at once) double paying a vendor, or paying a vendor on an estimate quote, rather than paying on an actual invoice. Most vendors are honest and will send money back if overpaid, but I’d guess some haven’t in the past. The mistakes that affect money don’t happen every day, but it happens enough. Most mistakes are caught before they actually affect bottom line, because we have many check in place. Is it a mistake if it’s caught before it makes a real negative impact?

In the past I can only think of two mistake that bother me in my prior 20 years of work.

One, I was working retail, and I said something to a customer that really pissed them off. I wouldn’t even say it was a mistake, but I feel badly the conversation went badly. I pride myself on good customer service. I immediately called my manager (the store manager) and told her what happened, and told her to throw me under the bus if she had to, and to please make the customer happy.

The other, I was on an email train and replied back to the wrong email and wound up sending a response to my partner to the client. That wasn’t a good thing. It didn’t say anything really bad, but I think it ruined the deal. That was when email and the internet were pretty new to me. That will never happen again.

I trusted people and it bit me in the ass BIG TIME. I agreed to buy my company from the previous owner and he essentially dictated all the details of the agreement….take it or leave it including agreeing to having two other key employees as partners. 4 years into taking over I had to fire one partner for allegedly stealing materials from the company and the other very minority partner was complicit in some of these “transactions”. I should have said no partners or no deal. What was I thinking!!??

I tried to fix a $3,000 toner cartridge and ruined it.

@janbb It sounds like it was already ruined…but still I can only imagine the horror you felt when you realized your efforts killed it but good!

Becoming a manager.

Another work-related mistake years ago still haunts my psyche. I touched a pregnant co-worker on her stomach. Never mind that it was a friendly, loving pat which I had expressly asked and received permission to do—I was reported to HR by another employee (who disliked me). I wasn’t cited for sexual harrassment, but I did get a “notation of disapproved behavior” added to my otherwise spotless employee record which led to problems and an earlier-than-planned depature from the company.

It was a horrible, humiliating experience.

Not quitting my last one sooner. My new job is stressful too but at least it’s a 40–50 hour work week and not 50–70

Faxed PHI (private health information) to the wrong number. It went to a beer joint. I had no idea beer joints had fax machines. I self reported myself to the company and got a dressing down. I dial very carefully now.

Trusting the wrong people.

Staying with my last employer for 6 years, trying to succeed at my job and make a difference. After my first week, I knew that the place was incompetently managed and had subpar standards. I should have walked away immediately and not let the place pollute my life and make me physically ill.

Operationally:

I was changing the closing time of the Pacific Stock Exchange to accommodate an early close on the day after Thanksgiving. Some of the time fields were set to Easter Time, some set to Pacific Time. I got the wrong time in one field and the trading system immediately shut down.

Professionally:

The head of Human Resources cam out from New York to meet with staff a week after it was announced we were being taken over. At the meeting, I asked if there were going to be any announcements about layoff packages as a result of the merger, that it was difficult for us to work with such uncertainty.

The HR head called me in about an hour later and said I was disruptive and upsetting, and that I should not have asked any questions. My boss at the time also criticized me for asking questions, and then put it in my performance review. Taught me to keep my mouth shut.

I entered about $5000 worth of incoming stock under the wrong inventory number (transposed two digits), which made a minor hassle of inventory check.

It got sorted, but it was hella awful getting an overzealous dressing-down for something that took about three minutes to figure out.

We later found out the CFO’s wife had just been diagnosed with cancer, so I guess that’s why he was on a short fuse.

@Cruiser Life experience can be such a tough way to learn. I’m guessing that you’d never bought a business until then (really, how many of us do have a reason or opportunity to buy an existing company?) and had to hit the ground running. Now, you know that such transactions need to be negotiations, not take-it-or-leave-it proposals. If you could build a time machine and do it all over again, you’d handle things very differently.

Years and years ago, I accidentally deleted everything on the C drive of a work computer. Twice.

Thank god for Norton Utilities. Saved my ass.

@Love_my_doggie I worked at this company for 14 years and the choice I had was to buy the company with said partners who also worked at the company who are also key employees, or get paid triple six figures and continue working for the old owner who none of us wanted around anymore. It was a no-brainer. At that time I truly believed these 2 partners to be as dedicated as I to growing the business and would never have suspected that greed would consume them the way it did. In a matter of months I will have 100% ownership…the way it should have been from the get go.

Years ago, I used to work at a bakery. If kids came in with their parents, we could give out free cookies if they asked. One day, while it was very busy, a mom walked up with her daughter and asked if she could have a cookie. But she informed me that the kind didn’t matter, as long as it wasn’t peanut butter because her daughter had a really bad peanut allergy. I don’t know if I heard incorrectly and thought she asked for a peanut butter cookie or what… but I ended up giving the girl a freakin’ peanut butter cookie. Luckily, the little girl (somewhere around 4) was very aware of her allergy and only took a nibble of it after they’d wandered off and then informed her mom. Who informed my boss. Who informed me… and I almost started bawling. I felt like a complete moron, and I was so scared that I had hurt the little girl and sent her into anaphylactic shock or something. The mom came back and luckily wasn’t livid because she could see how upset I was, and she wanted to let me know that her daughter was okay.

Even now, just thinking about it is enough to recall the feeling in the moment. Ugh.

I was working on an experimental fuel controller for one of my test vehicles. I needed to do something with the electronics and removed the controller leaving the fuel feed line in place so it would be easy to reinstall. Since I was the only one working on it I left the keys in the ignition and did not both to put up a “Do Not Start” sign.
That evening one of the maintenance people decided to move it so he could clean the floor. He turned the key and, Whoosh! Fire!
When I came in to work the next morning the vehicle was charred and covered in white dust from the fire extinguishers. Oops!

There are two that tie for the worst:

#1. One of the tasks as a reservations manager at a Chicago hotel was to load sales contracts into the reservation system. This was back in the days of DOS, and it was a time-consuming process. The incoming contracts were kept in date-of-stay arrival order until loaded.

Unfortunately, a city-wide event was announced for a date almost a year away, so it was placed near the bottom of the pile. One of the sales reps booked a large block of rooms. By the time I got to that contract, most of the room inventory had already been booked. I was sick about it, and immediately went to the general manager and director of sales.

Fortunately, both were experienced and level-headed. The team brain-stormed on how to resolve the problem as quickly as possible. We got it rectified within a few weeks, but it took a tremendous amount of effort as well as a good dose of figurative self-flagellation from me.

The only positive aspect of this situation was working together with a plan so that it never occurred again. And it didn’t.

#2. When the company was sold almost a decade a go, a new president was brought in. He hired an outside company to do a thorough study on was was working, what wasn’t etc. Frankly, it was desperately needed.

The final result was that the dept. I worked for would probably keep the same amount of people, but be restructured. I would have stayed and taken a demotion, but a life-style change resulted in my accepting the severance package instead.

A co-worker and friend outside of work was informed that his dept. was to be eliminated. Since he had worked in my dept. before, he had a wife and two young children to support, and that I trusted him, I asked to meet with him. With the promise he would keep it a secret until officially announced, I gave him a heads-up on the opportunity.

A few days later, one of my direct reports came to me to ask if the rumor was true. My friend had told his direct report about the job opening in case he was interested. That guy ran into my employee over the weekend and asked her about it. I wasn’t about to lie to her; she was asked to keep it under wraps. Of course, the word got out quickly.

I had already told my supervisor what transpired. Her response was, “When a secret is shared with another, it is no longer a secret.” It was a valid life lesson.

It worked out alright during the few months I was asked to stay on. I just felt really bad for the four people who reported to me. Their jobs were secure and were ready to move to move on to reporting for their new supervisor (my boss, who accepted a demotion). Who wouldn’t?

While it sorted itself out, as it usually does, the frustration those employees went through wasn’t worth the risk in the name of an attempt to help out a friend.

I worked for a mail/phone order photography company 25 years ago. I shipped $60,000 worth of Polaroid film to some thieves.

Polaroid film was a commodity back then – it was easy to sell – lots of people had Polaroid cameras. You could turn a garage full of Polaroid into a stack of cash really fast.

The credit card company had confirmed we were shipping to the card holder’s home and the account was 10+ years old.

Well, that was a tough lesson. The credit card company did not tell us the card holder’s home address had been changed 48 hours before the order.

VISA didn’t care, the credit card’s bank did not care. Their contracts left us holding the (empty) bag.

I got the Secret Service involved (yes, really!) because it was an interstate commerce thing and they sent an agent out in a UPS uniform to make a delivery.

The fraudsters sent a child (not legally accountable) to answer the door.