When you work in IT, you sometimes have to really hold someone’s hand to get them to do things correctly.

What would you do if you had a client in another state who wanted a simple job done, but refused to do it over the phone?

That’s what happened to the IT guy in this story, so he got paid to fly to Chicago, work for a few hours, and then be a tourist for a few days, all on the client’s dime.

Check it out.

All expenses paid vacation? Sure thing!

Ages ago, I was the senior developer for a company that revitalized other companies.

Think of it as a sort of mini Shark Tank; we would find small businesses that had a great idea but were struggling, and we’d help them achieve their goals in exchange for a cut.

This seems like a great job.

Sometimes this meant providing development or engineering talent to get a product off the ground, sometimes it meant providing literal capital, sometimes it meant providing staffing services (support staff and experienced executives were commonplace needs).

We were also a relatively small company, so it wasn’t uncommon for our people to have multiple hats; there was one time when I was working as development lead for one client while acting as interim CTO for another client.

It could be a bit chaotic, but it paid pretty well, was a great experience in a wide variety of things I normally wouldn’t have had, and was usually pretty fun.

Why are some clients always difficult?

So, one Friday afternoon we get a call from a client who was particularly frustrating; a “frequent-flier” if you will.

They seemed to make every thirty-second fix into an insurmountable problem.

I’m going to be intentionally vague about the specific industry the client was in; it’s a tiny industry anyone in their industry would be able to identify them just from the industry and city.

This particular call comes in early in the afternoon: they recently moved things around, and now none of their printers work.

Obviously, it’s mission-critical.

We do some remote troubleshooting, but can’t even get a flicker of life from the device.

We spend an hour or so trying to work through what happened before discovering that there’s a really good reason it won’t work; the cable didn’t reach where they moved it to, so it wasn’t actually plugged in.

Well, that’s about as stereotypical as an IT problem can get, right?

Just plug it in, and you’ll be good to go.

But management says that’s not the solution they want; while it’s totally possible to run a CAT-5 line to the new location, they really want it wireless since that’s the big thing these days.

Wireless printers are pretty easy to configure.

OK, that’s easy too; most of our comparably sized clients had switched to wireless networking for parts of their offices, so we already had the right procedures in place, deployment scripts setup, etc.

All they had to do was plug in the device, which could be very easily acquired at any electronics store, and we could remotely handle everything else in a matter of minutes.

But nope, management dictates that we absolutely have to have a person on-site in the morning to set it up for them.

At this point, it’s very late afternoon on a Friday, and everyone but me and my boss (the CEO) had gone home for the day.

Boss isn’t about to lose his weekend, and work rolls downhill, so I drew the short straw.

We reached out to the client to make sure that they knew what they were asking; they were in Chicago, we were several states away in the midwest, nearing the end of the day on a Friday.

This is going to be very expensive.

If they wanted me to be there by morning, they’d have to pony up for whatever flight we could arrange at short notice, and there was only one flight left that night going from our relatively small airport to Chicago, and the only available seat was in first class.

Additionally, it would be taking off in just under two hours, meaning I wouldn’t have time to get home and pack anything if I was going to make the flight.

They reiterated that it was absolutely crucial that I be there in the morning, and they would happily pay for whatever flight was necessary.

Additionally, I was told that they would have a room pre-booked at the Palmer House (they regularly used a room there for VIPs and such), and I could charge whatever I needed to the room.

Further, they said that if I ended up needing to stay longer than the day, they’d reimburse me for any clothing or essentials I had to purchase since it was so incredibly last-minute.

Cutting it close.

OK, I can live with that.

I get to the airport ten minutes before boarding, make it through the vacant airport, past the TSA checkpoint, and to my gate as they’re closing the door; literally the last person on the last flight of the day.

I arrive in Chicago and shockingly, there is a company car (effectively a limo – literal black car service before Uber was a thing) waiting for me.

He takes me to the hotel, as promised, and hands me an envelope before pulling away from the curb.

The envelope contains a prepaid debit card and a note saying it has $250 on it for “incidentals” but please charge anything I can to the room.

Sweet, was expecting it to be a long weekend in grungy clothes.

Checked in and went to bed.

They are wasting a lot of time here.

The next morning, I show up at their office bright and early.

I sit around for half of the morning before anyone shows up to let me in.

They then show me the new “printer area” which is, as expected, well outside of the area of the office which was originally wired for networking, in what was once a “break area”.

I go “yep, that’s not gonna work with your old wired hub,” run across the street (literally – door to door was one street apart) to the closest electronics store, pick up their shiny new wireless router, run back to their office, plug it in, then get on the closest computer, run through the thirty-second setup, run the script that updates the configs for their quirky, antiquated software so it picks up the “new” printers in the office, and tell the owner that it’s all set up.

Yes, this is really that simple.

He gets this sort of confused look on his face and says “already?”

I respond by pointing out that we did tell them in advance that we could do it remotely if they were willing to actually plug the device in for us, and he finally realizes how silly the call-out was – but now he feels obligated to save face.

I’m instructed that I’m to remain in Chicago until the close of business Monday to ensure there are no issues with the new hardware under actual use; obviously, it’d be fiscally irresponsible to fly me out twice in a week!

Why on earth would they do this?

I ask for clarification; they’re instructing me to stay checked into the fairly expensive hotel, and keep billing things to my room through Monday night?

Yes.

What am I supposed to do with the rest of the weekend?

Is there anything else at their local office that I can fix while I’m here?

No.

Go eat a hot dog and play tourist, just keep my phone handy and make sure I show up at opening time on Monday.

OK, can do!

I go back across the street, pick up a charger for my phone, find a nearby department store and pick up a few changes of cheap clothes, stop by the hotel to drop off my purchases, and spend the rest of the weekend playing tourist.

Chicago is a fun city to be in.

OK, I did a tiny bit of sightseeing and spent most of the time catching up on sleep; but I did ensure to avail myself of room service for every single meal at their expense, before showing up bright and early Monday morning.

I sat in their office for the majority of the workday before the owner came and found me to give me the travel details for my return flight.

He even suggested that I’d done a great job (really, I didn’t do anything but plug a device in!) and should get a drink before heading to the airport and bill it to the room.

As suggested, I went back to the hotel, packed my stuff in my laptop bag, stopped in the bar for a drink (who knew hotels had $100+ drinks?), and headed to the airport.

What a huge waste of money.

All told, they shelled out about $1000 just for the room, probably 2/3 of that in room-service fees, several hundred in transportation to and from the airport, not to mention the flights because they didn’t want to walk across the street, pick up the easily-obtainable piece of hardware, and plug it in.

I got a three-and-a-half-day vacation with first-class travel (one way anyway) halfway across the country for doing just that.

The amount of money some companies are willing to waste is disturbing, but nothing wrong with taking full advantage.

Let’s see what the people in the comments think of this.

Yeah, this guy did everything he was asked.

A lot of money to one person is nothing to many businesses.

Yeah, this type of thing happens a lot.

Yeah, they need a lot of help.

Yup, this worked out well.

Companies waste so much money on stupid things like this.

Never pass up the opportunity to take a free vacation.

If you liked that post, check out this post about a woman who tracked down a contractor who tried to vanish without a trace.