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Boss Demands Employees Use Personal Airline Miles For Work Trips, Employee Responds With Petty Genius

by Annie Nguyen
October 13, 2025
in Social Issues

Work travel can sound glamorous until you realize it’s mostly airport food, delayed flights, and long nights away from home. For one frequent flyer, the miles he earned were the only real perk of spending more than half the year on the road. But when a new boss took over, that small reward suddenly came under threat.

After overhearing how many miles his employee had racked up, the boss decided those points “belonged” to the company and wanted them used for business trips. What followed was a perfect mix of clever revenge and professional defiance that turned an unfair demand into a satisfying lesson in boundaries.

A veteran business traveler turns a corporate overreach into one of the most satisfying workplace takedowns ever shared online

Boss Demands Employees Use Personal Airline Miles For Work Trips, Employee Responds With Petty Genius
not the actual photo

'Company requires using our airline miles for work trips?'

Another fun story of an obnoxious boss. As I've mentioned in other posts, I used to travel a lot for business, between 30 and 35 weeks a year.

Our boss was a frequent traveler as well, and taught us the tricks of the trade for accumulating frequently flier miles (and especially status - a really great perk).

Eventually he retired and sold the company to new boss. New Boss overheard that I had over 500,000 Frequent Flyer Miles with my airline (not credit card points),

and said he should implement a new policy that we had to use our personal Frequent Flyer Miles for our business travel, since the company had paid for our trips.

That weekend my wife and I sat down and booked weekend trips all over the country over the next year.

Boston for Clam Chowder? Check. New York City for a Broadway Show? Check. Garlic Fest in Gilroy, CA (a real and delicious thing, BTW)?

Check. By Monday morning, my Airline Frequent Flyer Mile account was down to about 15,000 miles.

Later that week it was time to book a trip and he said I had to use Frequent Flyer Miles. I brought up my account and showed him I didn't...

He asked where they went and when I said I had booked some trips, he demanded I re-deposit the miles.

I pointed out there was a $150 charge per-person and that since it wasn't policy, I wasn't going to pay it.

Pissed, he announced going forward we needed approval for personal use of our personal Frequent Flyer Miles.OK, boss. You bet.

My next step was to spread my flights over any and every airline I could find to prevent accumulating the 20,000 miles required to redeem for a free ticket.

I was on United, Frontier, American, Delta, Northwest, Continental, US Air, Southwest, etc.

At one point I think I booked a trip on the Mrs. Grace L. Ferguson Airline and Storm Door Company

(Google it, it's a Bob Newhart routine, and more true now than when he performed it 60 years ago.)

He eventually figured out what I was up to, and he lost what little patience remained for me.

Then the following (paraphrased) took place.. Boss: "I suppose you think you're a smart guy."

Me: "No, I know I'm a smart guy." Boss: "Don't get cute."

Me: "No, I'm smart. Cute is just a bonus. Look, I see my wife about 10 days a month. I live out of a suitcase.

I know the aircraft evacuation speech by heart. Most of my meals are handed to me throuhg a window.

And thanks to my willingness to do this, you make hundreds of thousands of dollars.

Can you please just let me keep the only perk I get from all this?". Boss thought about it for a bit, grunted, "Fine, keep your miles." and walked away.

Edited to clarify these were Airline Frequent Flyer miles, not credit card points. Sorry about the confusion!

Travel benefits like airline miles, hotel points, and loyalty rewards often sit in a gray area, earned through business travel but accumulated in an employee’s personal account.

According to Forbes and Harvard Business Review, those rewards are typically viewed as the employee’s property unless a company has a written, pre-existing policy stating otherwise.

Employment law experts confirm that in the United States, no company can retroactively claim an employee’s personal reward miles once they’ve been credited to a private account.

Labor attorney Ari Wilkenfeld told Business Insider that “travel points are not a corporate asset unless earned through a company-controlled system or card.” Even if the employer reimbursed the flight, those miles belong to the traveler, not the payer.

For the company to demand their use on future business trips would be legally unenforceable and could violate employee compensation laws.

Historically, only government workers were barred from using miles earned on official travel for personal benefit under the Federal Acquisition Streamlining Act of 1994, but that restriction was lifted in 2002.

The U.S. Office of Government Ethics now explicitly allows federal employees to keep such miles for personal use, noting that they “constitute personal property once credited to an individual’s account”. If even government workers can keep their points, a private employer certainly has no stronger claim.

From a management standpoint, trying to confiscate perks is also a terrible leadership move.

Research from Gallup shows that nearly 57% of employees leave jobs due to poor management or lack of respect for their effort.

Frequent travelers, especially, rely on these small benefits, priority boarding, lounge access, and upgrades, as compensation for long hours away from home. Removing them not only kills morale but can lead to costly turnover.

In this case, the employee’s decision to deplete his miles and scatter his bookings across multiple airlines wasn’t just petty revenge; it was a rational defense against unfair policy.

As workplace consultant Liane Davey points out, “If employers want loyalty, they must first demonstrate fairness.” Travel rewards earned through personal sacrifice belong to the traveler who endured the trip, not to the boss who profited from it.

Here’s what the community had to contribute:

This Reddit users contrasted your boss with their company’s supportive travel perks

Nearly_Pointless − As contrast, the company I used to work for as a frequent traveler helped us to have more pleasant trips

because they knew damn well how hard it is to be gone often.

During the 90’s before internet travel booking, our company has an in-house travel department as we had that many people traveling.

Our agent had great relationships with several airlines and hotel chains.

We frequently got 1st Class upgrades and room perks due to her negotiation skills. We kept all mileage and hotel perks to boot.

She was absolutely adored by all of us traveling and the CEO personally gave her bonuses quarterly because of her efforts.

He also had near zero turnover in his sales, tech and engineering groups who did the bulk of traveling.

He damn well knew who kept the dollars flowing into the company.

While this group bonded over the sanctity of miles, sharing tales of flashy rental car perks and boss battles

newhunter18 − I swear we worked for the same guy. My boss was a complete d__k about travel.

And it's true, if you're spending your entire life traveling, the miles are the one perk that comes out of it. Anyone who takes that away is just a d__k.

Plethorian − I spent 10 years on the road. Eventually I got permanent President's Circle status at Hertz.

When a team went on-site for an implementation, I'd show up in amazing cars

- brand new convertible sports cars, Camaros, Challengers, Mercedes, a top-end Cadillac CTS with 7 miles on the odometer - you get the idea.

I got the nicest car on the lot, no matter what level car I reserved. The rental car bus would drop me off at my car.

When I brought the car back, an agent would drive me to the airport check-in in the car. My superiors were pissed at this, but there was nothing they could...

I wasn't paying any extra, it was just a perk of traveling so much for so long.

I still contend that the Cadillac CTS rental at corporate for a meeting, followed by the Mercedes in Las Vegas contributed to my firing. Oh well.

One commenter recounted shutting down a similar mile-grab with a sharp retort

[Reddit User] − I had an employer try and force me to use miles that I had earned before starting with them.

When I told my supervisor, full stop, that I wasn't going to use MY miles to pay for a trip that

THEY were requiring me to go on, his response was "Well, it's obvious that you don't care about this company."

I responded with "That's not true, I care about this company about as much as you care about me."

Another cited the 2002 federal law change freeing government workers’ miles

[Reddit User] − Your boss might have worked for the federal government or a nonprofit that was funded by the federal govt. ,

or maybe he had just heard about it, because that was the law until 2002. I worked for a nonprofit funded by federal dollars and traveled internationally,

racking up many miles, but was required to use them for more business travel.

The fiscal 2002 Defense Authorization bill, signed into law in December, included a provision allowing civil service,

military and Foreign Service employees to use frequent flier miles obtained on government travel for personal use.

Prior to the law's passage, federal employees were not allowed to use their frequent flier miles

because the 1994 Federal Acquisition Streamlining Act (Public Law 103-355) prohibited them from accepting promotional items,

including frequent flier miles, they received while traveling at the government's expense.

One folk griped about companies hoarding miles via booking agencies

vrtigo1 − My company just goes straight for the jugular and forces us to use their travel booking company so they get the miles directly.

At least we still pay directly, so we still get the credit card points. The ironic thing is that even though they get the miles for the trips we book,

we could get much better pricing if we didn't have to use their designated travel service so they'd actually probably end up spending less on travel if they'd just let...

And this user  cheered an employee who refused a similar rule

Twuggy − Heard another story like this. 'Employees must use their own miles' type rule.

As travelling to other locations was not part of their job description the person just outright refused. The company brought in HR who sided with the employee.

These Redditors loved the Bob Newhart nod and suggested more festival trips

Conscious_Teabag − You should also look into the artichoke festival. It’s nearby and it’s artichokes like you’ve never seen them before.

Also the Bacon Festival at the Monterey Fairgrounds is AMAZING. but yeah the garlic festival is pretty cool, try the garlic ice cream!

We were stationed nearby when my husband was a Marine and it was so fun exploring the cities nearby!

PrudentDamage600 − In reality, when he bought the company, none of the mileage you held actually belonged to the new company.

It was being held in your possession and there were no requirements when earned. They were not any of the assets purchased by the new owners.

Xibby − The first company I had to travel for issued me a company card and we had an official company travel agency for dealing with company travel.

Boss says you need to travel, call agent, you’ll have your tickets, hotel, and rental car booked. Just fill in the expense report on your corporate card.

I quickly learned the ins and outs and what would be approved expense wise

and when other colleagues in my department had to travel with they just got to ride on my corporate card. The catch?

Miles went to the corporate pool because it’s a corporate card. As a lowely p__n I don’t get any miles benefits.

Miles from corporate cards went to executives, maybe if you travel enough you get executive lounge access or a first class upgrade if an airline gives it to you.

The benefit... the one time I ran into a weather related event I called the emergency travel line as soon as we could turn on cell phones,

and my two coworkers and I had hotel, rental car, and rebooked flights by the time we got down the jetway, while everyone else was swarming the customer service desk.

We got to go to a decent hotel and got to b__ around Arizona state parks in a rented SUV for a couple days on the company’s dime.

Every employer since has been expense travel... so pay for it yourself and get reimbursed. And since it’s your card (and finances) your card perks are yours.

Generally get a one airline ticket out of rewards miles generated by business travel theses days. The position of OP’s employer seems dubious.

Sometimes, the best revenge isn’t breaking the rules; it’s following them so precisely that the rulemaker ends up grounded.

Would you have drained your miles too, or taken the fight straight to HR? One thing’s for sure: this story proves that a good sense of humor and a well-timed plane ticket can be the ultimate career survival skill.

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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