When a higher-up demands the “lowest possible fare, lowest possible rate” as a cost-cutting measure, it’s supposed to apply to everyone—including the person who made the rule. A Reddit user explained how that didn’t work out so well for a higher-up named “Clint.” It’s a perfect example of malicious compliance—when someone follows the rules exactly…even when those rules are a terrible idea.
The Reddit user, CatlessBoyMom, posted the story in late 2024, though it happened years earlier. This is the Reader’s Digest condensed version, but you can read the original story here.
Lowest possible fare, lowest possible rate
Back before cell phones and TSA checkpoints, CatlessBoyMom worked as an administrative assistant. Her boss, Ray, had a great sense of humor—and made it very clear she worked for him, even if she occasionally helped the whole office. Clint ran another department.
Travel between offices was common, and CatlessBoyMom handled all the standard bookings. If someone needed to make changes, they were supposed to do it themselves.
Clint…did not grasp that concept.
At some point, Clint decided he was going to save the company money with a new rule: “lowest possible fare, lowest possible rate.”
Which, of course, meant 5 a.m. flights and 11 p.m. returns. So all his employees were getting to the airport before dawn and coming home late at night.
Clint didn’t care.
But a couple of weeks later, Clint had to travel by himself.
Game on.
CatlessBoyMom booked him exactly what he asked for.
Clint took that 5 a.m. flight. The cheapest rental car? Not at the airport. Shuttle required. Shuttle didn’t start running until 8 a.m.—the exact time his meeting started.
Oopsie.
The client refused to meet that day but agreed to the next morning. Clint realized he’d need a hotel—and, naturally, called CatlessBoyMom.
She found him the lowest possible rate.
Which did not include security. It did, however, reportedly include bugs.
The next morning, still in yesterday’s suit, Clint discovered his rental car had been broken into overnight. By the time the police finished up, he’d missed his meeting again.
Impressive.
He somehow got the client to reschedule again, then decided to fly home and come back the next day. CatlessBoyMom, being a team player, followed his rules: 11 p.m. flight home, 5 a.m. flight back. His meeting? Midday.
By now, Clint’s “cost-saving” plan had easily doubled what the trip should have cost—not to mention all the extra time CatlessBoyMom had spent fixing things.
The next day, Clint finally had his meeting.
He also quietly discovered he didn’t actually like the 11 p.m. flight—and rebooked himself onto an earlier (more expensive) one.
Apparently, he’d figured out how to do that all by himself.
The next time CatlessBoyMom saw Clint, he tried to fire her.
Unfortunately for him, she didn’t work for him. She worked for Ray—who knew the whole story and thought it was hilarious.
Clint was not amused.
He updated the hotel policy (shocking), but kept the “lowest fare” rule—until accounting noticed he’d been rebooking himself onto pricier flights…with upgraded seats.
And they just happened to let that slip.
Suddenly, just like that, his entire department started “missing” their 5 a.m. flights, too. Rental reservations were missed. Cars got upgraded. Meetings moved to dinner. Dinner involved drinks. Drinks required hotel stays.
Funny how that works.
Less than a month later, all “lowest possible” policies quietly disappeared.
Travel bookings went back to normal. The chaos stopped. The fancy extras vanished.
Clint’s reputation, however?
Yeah…that didn’t bounce back quite as easily.
The responses
CatlessBoyMom’s post got over 4,000 upvotes—pretty impressive.
Most replies focused on what a jerk Clint was—but also that he clearly learned his lesson. Although CatlessBoyMom did suggest that what Clint did sort of went with the rest of his personality:
[Clint] also thought I should work for him like I did Ray. He would try to give me tasks just about once a week that should have gone to the assistant pool.
I’d take it to Ray. Ray would drop it back on Clint’s desk. Clint would dump it on some poor assistant in the pool, and expect a miracle (because it was now overdue). Lather, rinse, repeat.
A few people shared their own stories of similar malicious compliance, where the boss suddenly had to live with the rules they had made for their underlings and, similar to Clint, it didn’t work out well.
One person who replied, “Bearence,” gave this wise observation:
- A lot of times it’s one person trying to make a name. They don’t expect to be around long enough to feel the ramifications of their stupidity (because they envision themselves rising past it into a higher position) so they don’t really care.
Honestly? Makes sense.
Want to comment on this post? Great! Read this first to help ensure it gets approved.
Want to sponsor a post, write something for Your Mileage May Vary, or put ads on our site? Click here for more info.
Like this post? Please share it! We have plenty more just like it and would love it if you decided to hang around and sign up to get emailed notifications of when we post.
Whether you’ve read our articles before or this is the first time you’re stopping by, we’re really glad you’re here and hope you come back to visit again!
This post first appeared on Your Mileage May Vary
1 comment
A company I worked for tried this a couple times. Once instead of booking me on a flight from the airport closest to my home, they booked me on a flight from an airport 2 hours away “to save money”. To get to that airport, I went to the nearby airport, rented a car one way, and drove to the airport 2 hours away. It cost the rental and 3 hours of my rate to save about $100 on airfare. In another case they booked my return flight to another airport near where I lived, but not the one nearest my home “to save money”. Since the flight got in late at night, the company had to pay a $130 Uber bill to get me home. The travel department (outside contractor) only booked the flights and the hotels under the guidance to save as much money as possible. But they had no responsibility or visibility on the total costs incurred by the employee on the resulting trip.