March 5, 2026 at 9:48 pm

Retiring Military Officer Who Rarely Missed Work Asked For Time To Move His Family, So When His Power Hungry Boss Said No, He Took All His Medical Leave And HR Made Him Accept It

by Benjamin Cottrell

older military officer

Pexels/Reddit

Sometimes the fastest way to lose a good worker is to remind them they’re just a number.

So when a dedicated military officer nearing retirement requested a little flexibility to relocate his family, his promotion-hungry boss denied it.

What he didn’t realize was he had just authorized a masterclass in strategic compliance.

Keep reading for the full story.

Alright, game on.

As a military officer, it was required to apply to retire 12 months out from your retirement date. I was in what I would call a mid-level manager job.

He considered his team very good at what they did.

I had about 40 employees and we had a $500M annual budget for our program. My team was really great with very professional and competent people and rarely any issues.

We performed really well. They would come to me with their issues and over time I saw patterns and we would fix them.

This ended up benefitting the company a great deal.

For instance, one issue we solved saved the organization $64M over a four year period. We had a lot of other smaller wins (a few million here and there), but that was a biggie.

But for whatever reason, his boss was still a total monster.

My boss, who was bucking for General, was a jerk. For lots of reasons, but just a sour and unhappy person.

So as this officer’s retirement grew nearer, he started to plan a relocation.

About 7 months from my retirement in the following spring we decided to move my spouse and kids to my home town to be able to start the new school year.

We had a house and just needed to move and get set up.

But when he asked his boss for time off, it didn’t go well.

I asked for three weeks and the boss would only give me two weeks.

That only gave us a week and a half to get my family settled after the four day drive with kids, animals, etc.

Plus the furniture and everything arrived just two days before I had to be on a plane back. So I was salty.

That’s when this officer decided to go lethal.

Game on! I was prior enlisted and knew how to play the game by the book.

It is important to note that I only missed about ten days of work in 23 years due to illness.

All of his good ideas suddenly stopped flowing.

Two things happened. No more multimillion dollar savings ideas that made the boss look good came out of my office and it was time for me to take care of stuff I neglected over the years.

In regular meetings, when asked where the next savings was going to come from, it was always crickets.

But that wasn’t the only thing he did.

I knew I needed surgery for an injury I had and had some other medical issues I had been neglecting due to work and just life.

I planned to take care of all that post retirement, as it would give me time to recover and figure out what I would do for a living because we couldn’t survive on just retirement.

Since my boss wouldn’t let me get my family settled, it was time to take care of all my medical issues.

It was time to start making appointments en masse!

I made medical appointments to get checked out for all my issues. I had two procedures that had me out of work for a week each.

But the cherry on top was I got surgery the day before Thanksgiving and the doctor had me on convalescent leave for 4 weeks.

This really cost the boss big time, so he tried to go to HR, but it backfired.

When you are on leave like that, you have to have a form signed by your boss and it indicates the address where you will be taking that time to recover. Of course I used my hometown address so my wife could help me recover.

Boss was ticked and tried to deny the leave. It went to our version of HR and they said he had to allow it.

That made him even more ticked.

Luckily, it all worked out for the officer in the end.

In the end, I got to spend the holidays with my family across the country and only had about three weeks left on the job before taking my terminal leave (that he could not deny) when I returned.

I didn’t want a ceremony or anything, I just rode off into the sunset.

This boss should gave just kept his jerk mouth shut.

What did Reddit think?

Some people just don’t deserve good fortune in their career.

Screenshot 2026 02 07 at 12.00.39 PM Retiring Military Officer Who Rarely Missed Work Asked For Time To Move His Family, So When His Power Hungry Boss Said No, He Took All His Medical Leave And HR Made Him Accept It

This commenter knows someone else who would appreciate this story.

Screenshot 2026 02 07 at 12.01.15 PM Retiring Military Officer Who Rarely Missed Work Asked For Time To Move His Family, So When His Power Hungry Boss Said No, He Took All His Medical Leave And HR Made Him Accept It

We can only hope the boss changed his horrible ways after this.

Screenshot 2026 02 07 at 12.02.07 PM Retiring Military Officer Who Rarely Missed Work Asked For Time To Move His Family, So When His Power Hungry Boss Said No, He Took All His Medical Leave And HR Made Him Accept It

This user wouldn’t have hesitated to use up all the company time they needed to address medical concerns.

Screenshot 2026 02 07 at 12.02.38 PM Retiring Military Officer Who Rarely Missed Work Asked For Time To Move His Family, So When His Power Hungry Boss Said No, He Took All His Medical Leave And HR Made Him Accept It

This boss learned a valuable lesson that you can only control so much, especially once HR gets involved.

Thought that was satisfying? Check out what this employee did when their manager refused to pay for their time while they were traveling for business.