March 14, 2025 at 7:49 pm

Boss’ Strict Expense Report Rules Made Travel More Difficult, So One Employee Followed Them To The Letter And Cost The Company Even More Money

by Benjamin Cottrell

women calculating expenses

Getty/Reddit

In the world of corporate expenses, perception often matters more than the actual numbers.

When one boss fixated on “acting like an owner”, one employee decided to stop cutting costs and start playing by the unspoken rules instead.

And it was a heck of a lot more expensive!

Read on for this tale of malicious compliance!

Nitpicking Expense Report

My Fortune 500 employer didn’t have a formal travel policy, but my boss made up her own arbitrary rules.

She once told me I didn’t “act like an owner” because I bought ice cream at the airport, claiming she knew I wouldn’t spend my own money on airport ice cream.

The boss went through line by line, criticizing each expense.

I explained that I could have ordered the three-meat BBQ plate but instead ordered the two-meat plate and got ice cream.

Another time, she told me my expense reports “looked different than everybody else’s.”

She was right — I expensed public transit receipts when the company would have paid for town cars.

She also told me I could never expense breakfast if I started the day at home, even if I took a 5:30 AM flight and wasn’t hungry that early.

So the employee started following the boss’ instructions.

So I started taking town cars and flying out the night before for all trips.

I’d sleep in at the hotel, eat great hotel breakfasts, and expense it all.

My expense reports looked like everybody else’s, and she stopped complaining.

Her nitpicking ended up costing the company $300+ more for all work trips.

The boss got what she wanted — just at a much higher cost.

What did Reddit think?

It’s a crazy idea that some bosses actually want you to spend more money on a company trip!

reddit comment

Some bosses really do care about their employees’ well-being!

reddit comment

On the other hand, some management can be pretty clueless of what employees need on a lengthy company trip.

reddit comment

She thought she was enforcing better spending, but all she did was guarantee her employee full advantage of the system.

This boss probably just should have left well enough alone.

If you liked that post, check out this one about an employee that got revenge on HR when they refused to reimburse his travel.