u/DruncleMuncle — reddlx

I worked for a small company where employees could plan and book their own travel, but there were some guidelines. One of them was "Always select the least expensive option for flights, do not book based on convenience."

After a particular trip, I picked a flight that was an additional $50 so I could get home earlier on a Friday. Problem was I was travelling with a co-worker who followed the rules, and when we submitted our expenses, I was asked why I took an earlier and more expensive flight, instead of spending 3 hours at the airport after our last meeting. I was given a warning.

Well, my boss and I had to go to a conference in London. Since we were flying from the US, we decided to piggyback on some client meetings. We left our home airport, spent two nights in Amsterdam, and then 5 days in London. My boss would never book his own travel, so I had to do it for him.

On the way home, there was a direct flight to our home airport, but it was an extra $250, so I booked a flight that put us through JFK and instead of landing home around 1 PM, we landed at 5 PM.

Enter my malicious compliance: I booked the less expensive trip, and we had a 4-hour layover on a Friday afternoon. My boss was pissed because he had an hour drive from our airport, so he had to cancel a date night with his wife.

He asked why I booked this flight instead of something that got us in earlier, and I explained the policy. Monday morning, we had a chat with HR about using "best judgment" when it comes to booking.

Oh, the kicker was that because of my status with the airline, I got an upgrade on both flights and was able to stretch out. Boss? Not so much.