Many years ago, my cousin and I wanted to book a family holiday. We wanted to try something new and visit a country none of us had ever been to. For reasons unnecessary to this story, we couldn’t use our local travel agent. So, we headed into the next town, where there are two travel agencies on the same street corner. We randomly picked one. Both ladies working had customers, so we sat down to wait.

The first lady was putting together a trip for an older lady and was trying to book a night at a specific hotel. No matter what she tried, the system wouldn’t let her book the hotel. She asked the second lady for help. No dice.

Then she called the corporate helpline. The shop was part of a chain like TUI or Thomas Cook. It turned out they didn’t have a contract with that particular hotel; that’s why she couldn’t book it. Instead of finding another one, she started to argue with the person she had called. For several minutes, she went through variations of:

Travel Agent #1: “I don’t understand why it doesn’t work.”

Pause.

Travel Agent #1: “Can you book it for me?”

Pause.

Travel Agent #1: “Can you add it to the system?”

Pause.

Travel Agent #1: “Why can’t I book this hotel?”

Etc.

Meanwhile, the other lady was putting together a honeymoon trip for a young couple. They wanted to spend a few days in the Maldives. After looking at beach resorts for a while, they asked about the tides since they wanted to go snorkelling. Now, I know that the Maldives has two high tides per day, but in Germany, we are used to one a day.

The travel agent lady looked confused.

Travel Agent #2: “Tides? Why?”

Couple: “Well, if the high tide is very early or late during our stay, we might not be able to go snorkelling.”

Travel Agent #2: “Let me check.”

She then went over to her colleague and asked in a whisper:

Travel Agent #2: “Do you know what tides are?”

Her colleague looked equally confused and said no. So, she went back to the couple.

Travel Agent #2: “It’s going to be fine.”

At that point, my cousin and I looked at each other, got up, left, and walked into the other agency next door. There, we were set up with a lady who was actually from the country we wanted to travel to, and she was able to put together a fabulous trip.

I am writing this as I am sitting on the balcony of the same hotel she recommended all those years ago, looking at the full moon over Sutomore Beach and enjoying my fourth holiday in beautiful Montenegro.

This is the story of when I was “that” caller.

When I started working at this company, to work remotely, we needed to log in to the company VPN through two-step authentication: first, a random code generated by a key fob, followed by a personal password. A few years later, the method was changed to using a single passphrase composed of the random code followed by the personal password.

Three years after the method was changed, and countless times I have used it with no issues, I get back from my vacation, try to log in to the VPN, and it doesn’t work. Frustrated, I call IT, wait in the queue for a good twenty minutes, and when the agent picks up, I relay the problem:

Me: “So, I am just back from vacation, I am entering the random code, and it keeps failing.”

Agent: “Sir, you need to enter the random code AND your password at the same time.”

I quickly realize my brain fart and apologize.

Me: “Oh! I am sorry! I am wasting your time with something I have been doing in the wrong way… I am really being that caller this time!”

Agent: *Laughing.* “Don’t worry, it sounds like you had one h*** of a vacation if you managed to forget this much about work. Have a good day!”

We both hang up, chuckling.

When I was sixteen, I worked at a hockey rink in the Toronto area. I had a customer and their family (obviously tourists) leaving after skating, making some small talk and telling me about their vacation.

Tourist Dad: “Yeah, we’re gonna drive to the next spot now.”

Me: “Oh, where is that?”

I was thinking they were going to say a neighbourhood in the city or another nearby region, which is why I almost choked when they said:

Tourist Dad: “Mount Whistler.”

Me: “Whistler… as in… British Columbia?”

Tourist Dad: “Yeah. You know the way?”

Me: “To… the airport?”

Tourist Dad: “What? No! To Mount Whistler! We’re driving!”

Me: “That’s a long drive!”

Tourist Dad: “Can’t be that far. It’s still in Canada. Now, you know the way or not?!”

Me: “Well, yeah, okay, when you leave the parking garage, you turn left…”

Tourist Dad: “Left, uh huh…”

Me: “Drive five blocks, and you’ll see the sign to the highway; also left.”

Tourist Dad: “Five blocks, left again, uh huh…”

Me: “Then you turn to the on-ramp for going west…”

Tourist Dad: “On-ramp for west, uh huh…”

Me: “…And then keep going for about four-and-a-half thousand kilometres.”

Tourist Dad: “What’s a kilometre?”

Me: “A little more than half a mile.”

Tourist Dad: “Okay, great, thanks!”

They piled into their car and headed for the highway. I often wonder how far they got…

My boss’s boss comes over to me, working away at my desk:

Big Boss: “You booked off two weeks in the middle of September?”

Me: “That’s right?!”

Big Boss: “And [Boss] approved that? Two weeks all at once?”

Me: “Yes! I finished the big project over the summer, and I’m taking a break.”

Big Boss: “He should have run it by me and HR. We can’t approve your vacation.”

Me: “Uh… why?”

Big Boss: “Nobody can cover you.”

Me: “Well then, you need to figure it out, as flights have been bought and hotels have been booked. I’m going.”

Big Boss: “Then we may have to fire you.”

Me: “So you can’t survive without me for TWO WEEKS… but you’re prepared to survive without me FOREVER?!”

[Big Boss] tried to backpedal when he realized his threat was not going to work, but it was too late, and I told him I had to get back to work. I later told my own boss about it, who told me not to worry. He also told me that [Big Boss] was prone to making baseless threats like that just to make himself feel big, but that every time he tried to actually fire someone, the CEO (Big Boss’s dad) would always override him. How sad…

I work for a tech company in Seattle. I’ve had some vacation in the calendar since March, and it’s now the start of Fall.

Boss: “I need you to move your vacation days. We have a major client meeting and—”

Me: “—Not happening. I’m going hunting in Montana.”

Boss: “You can go a week later, it’s not that hard to—”

Me: “—It is that hard to.”

Boss: *Sighs.* “What would it take to move your vacation?”

Me: “Hmm, let’s say $15,000.”

Boss: *Looks shocked but maintains his composure.* “How do you figure?”

Me: “$1500 for out-of-state hunting license and tags, $4000 I have to pay the outfitter even if I don’t show. Another $5500+ to reschedule with another outfitter if I do get to go.”

Boss: “That leaves $4,000.”

Me: “Travel, tips and incidentals, and cost of my time to scramble and reschedule everything. And mental anguish.”

My vacation was not cancelled.