May 3, 2026 at 11:24 am

The Ultimate Power Trip: Why a Boss Denied Her Employee’s Dream Trip Only to Take Her Own Family to the Exact Same Spot

by Benjamin Cottrell

woman yelling at her phone

Shutterstock

There’s a special kind of rage that only comes from watching your boss do the exact thing they told you that you couldn’t do.

One employee had her Grand Canyon vacation denied during a work trip because her boss claimed she’d already be “off” while working long conference days.

But the boss’ full audacity was revealed just 48 hours later.

Keep reading for the full story.

I’ve had it with my boss

My boss holds my vacation requests for hostage.

I missed booking a cruise because it took her 3 weeks to approve the days.

Her boss made very clear that she didn’t consider these requests a priority.

I put in a request, spoke to her 4 times about it. The 4th time was on a Friday before her vacation.

She left without approving.

But that wasn’t even the worst of it.

The worst though was when I was on a company work trip to Las Vegas.

I arrived on Sunday night.

We were expected to work until Thursday night.

So when the employee put in yet another request, her boss denied it.

I asked to take off that Friday and a few days the following week so that my hubby & I could go to the Grand Canyon/Sedona.

She said no because I “would be off Mon to Thu.”

I pointed out I would be working (& they were long days).

On the trip, I was waking back from an event with my boss and another director.

Then the full scope of her hypocrisy became evident.

The director asked my boss if her family was with her.

She said, “My husband is here and my daughter is arriving tonight. We’re going to the Grand Canyon since we’re here.”

The other director knew about my request.

He just looked away because he thought I might explode.

What an absolute nightmare of a boss.

What did Reddit think of all this?

It’s time to stop asking for permission from this terrible boss.

Screenshot 2026 04 10 at 12.45.49 PM The Ultimate Power Trip: Why a Boss Denied Her Employee’s Dream Trip Only to Take Her Own Family to the Exact Same Spot

The more direct she is, the better.

Screenshot 2026 04 10 at 12.46.57 PM The Ultimate Power Trip: Why a Boss Denied Her Employee’s Dream Trip Only to Take Her Own Family to the Exact Same Spot

Sometimes a boss’ boss has to step in when they’re being particularly unreasonable.

Screenshot 2026 04 10 at 12.47.29 PM The Ultimate Power Trip: Why a Boss Denied Her Employee’s Dream Trip Only to Take Her Own Family to the Exact Same Spot

Time-off requests work quite differently in other countries.

Screenshot 2026 04 10 at 12.48.09 PM The Ultimate Power Trip: Why a Boss Denied Her Employee’s Dream Trip Only to Take Her Own Family to the Exact Same Spot

This boss was a hypocrite with a capital H.

If you enjoyed this post, check out this story about a construction manager who was barking up the wrong tree with his “get back to work” demand.

Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.