This happened about thirty years ago. I worked at an IT Consulting company for about two years. In October, they lost their primary contract with a large state department that kept most of their 100-plus employees working and generating income.

Suddenly, there were a bunch of consultants out of billable work and on the bench, and the company scrambled to find new gigs for us. Some were able to be placed immediately, while they had more trouble finding work for others with more specialized skills, like me. The company kept us on at full salary and offered us training in other skills, which I took advantage of.

Come December, the holiday party season started. We had a nice lavish party on a weekend in a brand-new luxury hotel that had just opened recently. Obviously, the party had been paid for before the contract loss.

There were the usual drinks and dancing and food, and there were prize giveaways via random numbers. The grand prize was an all-expenses-paid weekend at the hotel. I was attending with my girlfriend, and I happened to have the winning ticket for the grand prize. Sweet!

I went up, and the woman from Human Resources giving out the prizes had a sour look on her face. I didn’t think much about it. My girlfriend and I were stoked about this opportunity for a mini stay-cation.

I came in for work the following Monday and was immediately called into the boss’s office. I was thinking they had finally found a new client for me, but no. They were letting me go due to no work. I wasn’t the only one let go that day. It sucked that it was right before the holidays, and I was slated to go back to California over the holidays to see family.

It looked to me like the Human Resources lady wanted to ask for the prize back since I was no longer going to be an employee, but she didn’t have the guts to ask. (I’d have politely declined.) But at least I knew why she had a sour look on her face at the party when I won.

I took the time off for the holidays, and when I got back, I found a new client on my own within a week. My girlfriend and I used the prize as a way of celebrating my new career as an independent IT consultant.

I worked for a company that sold domain names. Despite having multiple different wordings on our site explaining this, I would get one of these kinds of calls every day.

Caller: “Yeah, I bought a domain name from you guys.”

Me: “Thank you, sir. What issues were you having with it?”

Caller: “Well, I type my address and there’s no website.”

Me: “Have you linked your site to the domain name yet?”

Caller: “What is that supposed to mean? Where the h*** is my website?”

Me: “We don’t make the website for you, sir. We just sell you the website name.”

Caller: “That’s bulls***! I paid for my website. Where is it?”

Me: “You need to either make the website yourself or pay a web designer to make it for you, sir.”

Caller: “So, I just paid all that money, and I don’t get a website?”

Me: “Sir, you paid us $4.99. You can’t expect someone to make a website for that little money.”

Caller: “I wouldn’t have bothered with this website bulls*** if I’d known I had to do it myself! You’re all crooks!” *Click*

Caller: “I’ve forgotten my password.”

Me: “No worries. We can reset that for you.”

We go through the security and reset process.

Me: “Okay, we have a selection of security questions you can choose, like, ‘What is your favorite sports team?’ or, ‘What town were you born in?’”

Caller: “Hmm, I don’t like those. Can I make my own?”

Me: “Of course.”

Caller: “I want my question to be, ‘What is today’s date?’”

Me: “I… I can certainly set that up for you, sir, but I would recommend something else.”

Caller: “No, I will remember it. Please make that my security question.”

After one more suggestion to try something else, we go ahead and make the change. I am not allowed to suggest or know the answer to the security question, so I can’t make any more comments. I leave some notes in his account for the next person he calls with an issue.

I am told he actually did call back the next day. His complaint?

Caller: “My answer to the security question isn’t working! It was working fine yesterday!”

I worked at an investment company, but when one of their subsidiaries needed me full-time, I was transferred there. That was no problem as it was better for me to be able to focus 100% on a project with reasonable deadlines. After a few months, the parent company decided to sell the subsidiary.

It has now been over a year since the sale, which brings us to today’s email discussion.

Parent Company: “Hello! We need help developing an IT solution for our new holding, [product].”

Me: “Hi! I would love to help you, but unfortunately, I don’t have the time as I am busy with my current job. I wish you the best of luck with [product].”

Parent Company: “What do you say? I’m your boss! We need to resolve this ASAP!”

Me: “I am no longer employed by you, as I was moved down to the subsidiary, where I am now employed. But since I worked for you for six years, I can produce a quote, so I can help you outside of my current working hours while you look for a person who can take over the project.”

Parent Company: “I don’t know what to call this… We can’t go on like this. We have to help each other. It’s not okay that if I ask you for a favor, you want to start sending invoices. We must help each other!”

Me: “I do know that what you’re trying to make me do is called slavery. That is, work without pay, which I agree is not okay. No, thanks.”

I support the faculty at a major university. I am upgrading a professor’s laptop from OS X 10.6 to 10.7.

Professor: “I’m very excited to use the new OS!”

It’s rare to see someone so enthusiastic about a relatively minor upgrade, but I’m not about to discourage passion about tech!

As soon as it boots up, he immediately begins poking the screen with this finger. After a few seconds, he stops.

Professor: “Wait, doesn’t Lion have a touchscreen like an iPad?”