Sometimes spending a little more can save you from ending up spending way too much!

This guy’s boss asked him to book the cheapest flights for employee business trips, but he didn’t factor in meeting times, hotel costs, and car rental locations.

It became chaos after employees also discovered a clever loophole.

Check out the full story!

Lowest possible fare, lowest possible rate.

Back before cell phones and TSA check points, I was working as an admin assistant.

Ray was my department head and had a great sense of humor.

When I was hired on Ray made sure I understood that I worked for him, even though I would do some office-wide work, he was my boss.

Clint was in charge of another department in our office.

They needed to book flights very often!

Flying from our office to a satellite office for a day or two was common for people in both departments and I was in charge of making standard pre-approved travel arrangements.

If someone needed to change unexpectedly they were supposed to handle those themselves.

Clint seemed unable to understand that.

This is where it gets bad!

At some point Clint decided that he wanted to cut travel costs. “Lowest possible fare, lowest possible rate” for his department.

Lowest possible fares were always the 5 am outbound and 11 pm return flights.

Clint didn’t care.

A couple weeks into this policy Clint is to headed to the satellite office for some in person meetings.

Game on, “lowest possible fare, lowest possible rate.”

Time to give Clint what he wants!

Clint left on the five am flight.

The lowest rate car rental company didn’t keep their cars available at the airport.

Clint had to take the shuttle to their offsite location to pick up his car.

Sadly for Clint, the shuttle didn’t start running until eight, when his first meeting was scheduled to start. (Oops)

This is a problem!

The client refused to reschedule that day, but agreed to the next morning.

At some point it dawned on Clint that he either had to fly home and back or get a room for the night.

He chose to get a room, and of course call me.

One “lowest possible rate” room coming up.

It sounds like a horrible place to stay.

Unsurprisingly, that room didn’t have security on site like he was used to.

It did have little multi-legged friends, if his complaints were true.

The next morning Clint headed out (in the previous day’s suit) only to discover that his car had been broken into overnight.

The police took their time arriving, and by the time they were done, Clint had missed his meeting again.

He found his way around the flights!

Somehow Clint got the client to reschedule again, and he decided to take the flight home and back the next day.

Of course I was kind enough to remember the “lowest possible fare” rule so Clint was booked on the eleven pm flights home and five am return, even though his meeting was midday.

This time the lowest rate car was at the airport so Clint got to skip the shuttle.

Sigh, you can’t win them all.

He had yet to learn his lesson…

At that point Clint’s “lowest possible” policy had already cost the company at least double what a normal trip would have.

Not to mention all the time I had spent calling hotels, motels and car rental companies.

The next day he’s on the five am flight, and makes it to his meeting.

Finally, Clint wised up.

I don’t know when he realized that he didn’t want the “lowest possible fare” at eleven pm.

I do know he decided to take the more expensive, earlier flight home, both days.

Somehow he discovered that he could change that himself.

Clint couldn’t get revenge at OP.

The next time I saw Clint, he tried to fire me.

Too bad, I worked for Ray, who knew (and laughed) about the whole thing.

Clint was furious, but there wasn’t anything he could do.

The company would back Ray, and Ray was backing me.

Things spiraled out of control!

Clint changed the room rate policy, because of his experience, but refused to rescind the lowest fare and lowest rental rate policy.

That was, until accounting let slip that not only had Clint figured out how to take the higher priced earlier flight, he figured out an upgraded seat as well.

Clint found himself with an entire department intentionally missing their five am flights, and rebooking for the more expensive eight am, which somehow only had upgraded seats available every time.

Rental car reservations were missed and more expensive cars were rented.

It got even more expensive.

Meetings that were previously in the office were somehow only available after hours, so clients were taken to dinner.

Dinner included alcohol so rooms were booked at hotels closest to the restaurants, and returning flights scheduled for the next day.

Things finally got better again when the boss realized the damaged!

Less than a month later all lowest price policies were rescinded.

I was allowed to book normally again, and the missed flights, upgraded seats and fancy hotels disappeared.

Dinner meetings remained, but decreased dramatically.

When I left, Clint’s reputation still hadn’t recovered.

GEEZ!

How dumb can a manager be?

Let’s find out what folks on Reddit think about this story.

This user wonders about the long layovers that come with cheaper fares.

This travel agent knows the loophole of cheaper flights.

Exactly! This user knows that Clint was focusing way too much on smaller goals than bigger ones!

This user loves this story!

This user knows exactly how to put it!

It took long enough, but he finally learned his lesson!

If you liked that post, check out this one about an employee that got revenge on HR when they refused to reimburse his travel.