May 22, 2026 at 5:55 pm

A Boss’s Ultimatum Over Approved Vacation Led to an Unexpected Resignation

by Michael Levanduski

Workers arguing

Shutterstock

Having a job is very important, but it is also essential to ensure that you are able to live your life. That is why a good work-life balance is considered essential for just about everyone.

What would you do if you arranged to have several days off from work around Christmas, and you even managed to get people to cover your shifts, but then your boss said you would be fired if you didn’t come in those days?

That is what happened to the drilling rig worker in this story, so he told his boss that he should consider the day before he wanted to leave his last day on the job.

The boss didn’t believe him.

Keep reading to see what happens when he runs into a former coworker after starting a new job.

Fired if I don’t work that day, made it my last day.

A few years back I worked on a relief crew on a drilling rig.

The rig ran 24 hours a day with three shifts. Crews worked 6 days and then 2 days off.

My crew would replace a working crew so they could have their 2 days off so we worked mornings 2 days, then afternoons and then nights.

I bet it was a nightmare to try to schedule all of this.

It was common to find someone to take a shift if you wanted an extra day off but the replacement had to have the same abilities.

A crew had a driller, Derrickhand, motorman, chainhand, and floorhand.

People started as floorhand and as they learned they would work their way up with more responsibility and more pay.

This makes sense. That might help to ensure they have proper coverage at all times.

Sometimes when someone changed companies they might take a lower position so it was common to have someone with derrickhand capabilities working motor or chain.

In September my wife asked about the chances of getting off for Christmas.

I checked the calendar and my days off fell on December 24 and 25. Done deal! I have it scheduled off. Then I decided to sweeten the pot.

I found a guy who would work December 22 and 23 for me. Also found one who would work the 26 and 27.

It is going to be a great Christmas this year.

I took this to my driller who agreed they could work for me.

With my 6 days off I could drive 400 miles to visit family. Things looked pretty sweet, too sweet.

The other guys on my crew were in the same position, so they all tried to find replacements and two were successful.

Not everyone can have time off; that is the downside of jobs like this.

Unfortunately, the driller only had 3 other guys on the rig who could work for him and none of them wanted to help.

He got mad and said since he couldn’t get the time off none of us could have it off.

I reminded him that he had already approved my time and he said that was canceled and if I didn’t work on Dec 23 then I was a run off MF (fired).

I told him fine, I will work the 23rd but that will be my last day of work. Consider this my 3 month notice.

I wonder if they don’t really believe him that he would quit.

At work, nothing much was said for the next few weeks.

Outside of work I was networking and found another job I could start the first week of January.

All was set. At the end of my shift on the 23rd I emptied my work locker and said my goodbyes.

The driller barely acknowledged me.

Great, everything is working out for the best.

Went home and drove to see family the next day. Spent a relaxing week there and then came back to start my new job.

About the end of January I went to a friend’s birthday party. There I saw one of my old crew.

The driller must be delusional. He is never coming back.

He asked me when I was going to go back to work. The driller thought I was just sulking around and would come crawling back soon.

He never hired a replacement and they had been working short handed for over a month.

I said he better hire somebody. I wasn’t playing games and when I said I quit I meant it.

It is always funny when someone in management doesn’t believe that an employee would ever quit or be willing to stand up to them. The worker in this story clearly had plenty of options available, so he had no reason to put up with a terrible boss.

If you enjoyed this story, check out this post about a carpenter who was shocked to find the police waiting for him after his last day of work.

Read on to see what the people in the comments have to say about the story.

It looks like the manager really thought he had the upper hand.

Comment 5 74 A Boss’s Ultimatum Over Approved Vacation Led to an Unexpected Resignation

The manager was just too lazy to find a replacement.

Comment 4 75 A Boss’s Ultimatum Over Approved Vacation Led to an Unexpected Resignation

He gave his manager way more than enough notice to get the time off.

Comment 3 76 A Boss’s Ultimatum Over Approved Vacation Led to an Unexpected Resignation

This is really how time away notifications should be handled.

Comment 2 77 A Boss’s Ultimatum Over Approved Vacation Led to an Unexpected Resignation

Make it make sense. This manager is an idiot.

Comment 1 77 A Boss’s Ultimatum Over Approved Vacation Led to an Unexpected Resignation

Some managers have it in their heads that the job is the most important thing in everyone’s lives. They just can’t believe it when that turns out not to be true. Odd that the boss couldn’t give him 6 days off, but still held the job open three months later.