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The original was posted on /r/maliciouscompliance by /u/danieldonnr on 2023-07-06 06:29:30+00:00.
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 balance was down to about 15,000 miles.
Later that week it was time to book a trip and he said I had to use miles. I brought up my account and showed him I didn’t have enough miles. 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 were to reserve miles for approved vacations only. 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 Grace 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…