April 14, 2025 at 1:55 pm

HR Denied His Vacation Request Until 6 Months In, But The Next Year He Took Nearly Every Month Off

by Heather Hall

HR manager speaking with an employee about paperwork

Pexels/Reddit

Some rules seem fair until you realize they’re only being enforced on you.

What would you do if your employer denied your request for leave, only to approve the same thing for someone else who started at the exact same time?

Would you speak up and risk rocking the boat?

Or would you find a way to play by their rules and still come out on top?

In the following story, one employee finds himself in this very situation and uses the company’s policy to get some time off.

Here’s how it all went down.

Wait 6 months before taking leave, no problem

A few years back, I worked for an entity in the Middle East.

While the salary was low, they gave generous 40 days off, plus public holidays (which were basically 2 Eids that were 5 days each).

With 20 unused days being transferred to the next year

As I worked with locals who were untouchable, the HR would be strict on me. And my boss who was also not a local would just bow down to what they said.

So when a local colleague of mine who started working at the same time as me (in a different department) was allowed to take time off after 3 months, but my 2 days of leave were rejected as I had to work 6 months before accessing leave, I was a bit annoyed.

Six months in, and it aligns perfectly with Ramadan.

Due to everyone fasting, I remember we were able to leave at 1.

He used their policies to his advantage.

So when HR came to ask if I’d be taking a holiday during Ramadan, I saw her panic as I said, ‘Why would I?’ and that I get a week off for Eid after Ramadan.

In the second half of the year, I enjoyed 30 days off (20 of my own, plus 2 Eids).

The better part was my second year. I transferred 20 days, plus my 40 days, plus 2 Eids.

Remember my boss asking for my leave plans for the year and his face dropping when I showed him I take a week off every month of the year, apart from Ramadan, of course- and I still had balance to transfer to the next year.

I found another job midway through my 2nd year.

So, unfortunately, I couldn’t enjoy it as much as I wanted, but at least I got paid out for unused days

Nice! That sounds like it was a great year for him.

Let’s see what the readers over at Reddit have to say.

Most people would do the same.

Take Leave 4 HR Denied His Vacation Request Until 6 Months In, But The Next Year He Took Nearly Every Month Off

As this comment explains, the company doesn’t benefit from this.

Take Leave 3 HR Denied His Vacation Request Until 6 Months In, But The Next Year He Took Nearly Every Month Off

This is so true!

Take Leave 2 HR Denied His Vacation Request Until 6 Months In, But The Next Year He Took Nearly Every Month Off

Probably because they’d be left shorthanded.

Take Leave 1 HR Denied His Vacation Request Until 6 Months In, But The Next Year He Took Nearly Every Month Off

What a well-executed plan!

I wonder how long it took the company to redo that policy when they discovered this was possible.

If you liked this post, check out this story about an employee who got revenge on a co-worker who kept grading their work suspiciously low.

Heather Hall | Contributing Writer, Life & Drama

Heather Hall is a contributing writer for TwistedSifter specializing in internet culture, workplace conflict, and viral customer service stories. With over a decade of editorial experience in digital publishing, Heather excels at curating trending online discussions and providing insightful commentary on the daily dramas that capture the internet's attention.

Since beginning her career in 2011, she has developed deep expertise in SEO-driven digital content, having written for a wide array of publications covering lifestyle, business, and travel. At TwistedSifter, Heather focuses on synthesizing complex social media threads into engaging, highly readable narratives that highlight the human element of viral news.

When she isn’t analyzing the latest internet discourse, Heather is a dedicated mother of three sons who takes family gaming nights entirely too seriously—whether she is dominating in Mario Kart, exploring The Legend of Zelda, or jumping into Roblox.

Connect with Heather on Facebook and LinkedIn.