I’m a Southerner. My grandparents on both sides had a very strong “throw nothing away; you might need it later” mentality, and Dad’s pretty dang cheap regardless of all that. So, I certainly understand the “use it ’til it breaks” mentality. I’m like that with my stuff (especially shoes).

But! When you’re running a business, it’s important to update your technology over time. If that ancient tech breaks, nobody will be able to fix it ’cause it’s so old nobody’s being trained on it anymore.

Here’s an example. My last job in 2020 was at a place that made awards — ribbons, trophies, plaques, etc. Everything was ancient, including the building. That wasn’t a big deal with the ribbon-making hot press, but the engraving machine was controlled by a 2001 Dell running WinXP. (The program for the engraver was from the 1980s and was keyboard-only input.)

That old Dell stopped working one day. My boss called in a PC repair guy. He showed up, took one look at the Dell, and said:

Repair Guy: “Wow! I’ve never seen a computer this old before.”

He couldn’t fix it; he didn’t know how. He had to take it away to the office where a much older tech finally fixed it.

I asked [Boss] why she didn’t get a newer PC to run the engraver.

Boss: “New computers don’t have the right connection.”

I told her a custom PC could be built with the needed connector, and it’d be easy enough to install the engraver software. We just needed someone who knew what they were doing. It wouldn’t be THAT difficult to find, honestly, but probably not cheap.

[Boss] wasn’t interested; she wouldn’t even let me finish my sentence.

Boss: “No, the Dell still works.”

Except it didn’t work at that moment, hence being taken away by the repair tech. If the repair company hadn’t been able to fix it, [Boss] would’ve been massively SOL. Engraving was a big part of the business. But [Boss] didn’t even want to consider alternatives for when that Dell bit the dust for good.

I was the plant manager for a manufacturing plant with close to 500 people on the floor. The workforce was stable, but we had the usual openings in the summer for temps or students when the full-time guys wanted time off.

We hired a young kid full-time, the son of a friend of the machine shop foreman. I was encouraging the foremen and supervisors to use the three-month evaluation process to good effect. It’s not that you can’t get rid of people after that; it just makes it easier if you manage it upfront.

Every time I asked how [New Kid] was doing, the answer was, “Great.” Then, one day while I was making my rounds, one of the millwrights asked to speak to me. Sure, no problem. It was about [New Kid].

The millwright, an English tradesman with impeccable trade skills and credentials, had seen [New Kid] struggling with something and asked if he could use some advice. [New Kid] answered:

New Kid: “Why don’t you f*** off and mind your own f****** business?”

He was called into my office for that one, along with the foreman. I explained that [New Kid] had a unique opportunity to work his way into a full apprenticeship as a precision CNC machinist if that’s what he wanted to do, but his attitude needed to change.

That was about two months in. We had a meeting every week after that, and reports of bad behavior and belligerence kept coming in. The last one was from the person who operated the yard crane and the big forklifts; [New Kid] explained to him that he didn’t know how to do his job.

That was it — a week to go and he was out the door. The foreman reported back that the family believed we did this sort of thing deliberately — take young, innocent people, work them hard for three months, and then let them go so we didn’t have to pay severance.

Sigh. I always wondered how people like that end up.

Our company has an engineer who works on software making heart valves at a major pharmaceutical manufacturer. She called me because her computer was making a strange sound. I didn’t work on the help desk at that point, but I was the department admin and tended to get called for these kinds of things before they’d call the help desk. I suggested she reboot and let me know if it happens again. Sure enough, it did. I went into her office, and it turned out — bear in mind that this was in the early 1990s — that her beeper was on vibrate and sitting on top of her steel monitor stand. She was being paged.

A couple of years later, I was on the help desk for real. The same engineer called me and said her keyboard didn’t work. I did basic troubleshooting; I checked the cable and asked what had changed and whether there were any new peripherals added. She said no.

We chatted a little bit more.

Engineer: “I did take the keyboard home to clean it.”

Me: *Curious* “How did you clean it?”

Engineer: “I put it in the bathtub with soapy water.”

The procurement manager at our small company abruptly had to accelerate his retirement by a few years due to health concerns. At the same time, his assistant, who had been training to be his replacement, had to move across the country to help out family, seeking out a new job out west at the same time.

We were left scrambling a bit to find a new procurement manager. Some of our other employees knew enough to keep things running in the short-term, but everyone who knew the system was either already in a vital role and didn’t really have the bandwidth to take on more responsibilities, or was happy where they were and declined a shift into the new role. So, we posted the job on some outside job boards.

I was thus rather surprised when one of the receptionists from our front office applied for the position. Looking at her CV, her only jobs had been working as a receptionist and a tutor, with nothing in procurement or supply chain management. But, after consulting with my boss, we decided to give her an interview anyway. Everyone has to start somewhere, and maybe she would end up being a good fit for the role that we could promote internally.

The very moment that I walked into the room for our interview, before I even had a chance to approach my chair, [Receptionist] launched into a rapid-fire description of an idea she had for a marketing campaign for our product. A, that is not what the procurement manager position covers, and B, that is not something I, as part of Human Resources, would cover. I tried to get a word in edgewise as I sat down, to try and clarify what position she was interviewing for, but she just talked right over me, meandering her way through this marketing campaign idea, through an idea for renovations we should make to our office, to pitching the idea of issuing everyone company credit cards. None of these things were related at all to the procurement manager position.

Finally, she wound down enough that I was able to explain that the position was for a procurement manager, with the responsibilities of evaluating the quality and pricing of the various parts we needed, timing our restocks, and trying to source new suppliers if needed. Three times during this explanation, [Receptionist] broke in with, “Oh, but I think I should…” and then circled back to her marketing idea or talked about how employee morale was something she would focus on.

Finally, after fifteen minutes of getting absolutely nowhere, I gave her the typical ending pleasantries. I thanked her for her time and told her that I didn’t feel she would be a good fit for this role but that she should keep her eye out for other postings. Meanwhile, I was making a mental note to talk to our customer service manager to find out if [Receptionist] was steamrolling people who tried to call us the way she had been steamrolling me. (She wasn’t, as it turns out, at least not before this.)

To my slight surprise, she gave me a big smile and a cheery “Okay!” and bounced out of my office.

It turns out, she had apparently completely tuned me out when I told her she wasn’t a good fit for the role, and she started telling everyone about how she was a shoo-in for the job. Thus, when our actual new procurement manager was hired, she threw a massive fit, storming into my boss’s office to scream about how I had “promised” her the job, how this hire was nepotism (the new procurement manager’s name rhymed with the name of our Chief Finance Officer, which was apparently enough for [Receptionist] to determine that they were related), and how she was going to stage a walk-out if we didn’t give her the role.

She had two back-to-back no-shows when we didn’t give in to her demands, and she ended up being let go after she came in and proceeded to scream at the first customer who called in about how she was being mistreated.

I am doing some design work for a company that manufactures apparel for schools and sports programs, mostly recreating low-resolution logos into more usable vector files. After several months of paying regularly, they develop a large back debt, and I tell them I can’t do any more until they catch up.

About four months later, they contact me. I’m surprised to hear from them.

Client: “Hi! I believe we owe you money. [Amount], correct?”

Me: “Actually, it’s [larger amount], but yes. Great to hear from you.”

Client: “Great! Well, how about we give you 3% ownership of our new company we’re just starting? We’ll need a lot of work done.”

The client outlines what the work would be, from branding to a complete online store, and they mention a fee they would pay for my work.

Client: “We’ve got a lot of capital set aside to get everything going and get this off the ground. We’re very excited about where this can go. How’s that sound?”

Me: “Why don’t we get caught up on what you owe me now before we go any further?”

Client: “Oh, we don’t have the money to pay you right now, but think of the potential!”

I declined their offer. I’m still waiting for payment.