July 4, 2025 at 5:47 pm

He Tried To Tell His Company Their Travel Rules Made Things More Expensive, But When They Didn’t Listen He Took Advantage Of Their Cluelessness

by Ashley Ashbee

Plane taking off

Pexels/Reddit

A lot of workplace policies aren’t fully thought through, either because the people making the decision haven’t bothered to research or because they’re just so oblivious to how the real world works.

Decide which camp you think this story falls into.

The details are below.

You want me to wait until the last minute to book my hotel? Deal.

I work remotely for a small company (~100 employees) and based on my contract, I have to return to the office for a week 4 times a year.

The last time I went back up was in November.

In the contract, it’s laid out that my employer pays 100% of hotel and gas/airfare.

Normally this is an extremely uneventful routine.

It’s a mid-sized Midwestern city with not much to do, so it is what it is.

The office had an odd solution to a pseudo-problem.

A few months before I went back up we had our financial audit and one thing that was pointed out to our accounting department was a lack of controls on purchasing.

The way it used to be was every manager/supervisor had a company credit card with a $1,500 balance and as long as we stayed under that limit, we didn’t have to do any kind of purchase orders.

After our audit, my accounting team decided to make purchase orders 100% of their focus.

Going forward, it doesn’t matter what it was, what the situation was, if you didn’t have an approved purchase order you could not make the transaction.

All this happened in early October as I was trying to book my hotel for my on site week in November.

Normally I have freedom in choosing when I go onsite, but I was requested to go that specific week by my CEO and CFO as we were launching some strategic planning and they wanted me onsite.

So I put the purchase order in for the hotel and I don’t hear anything back.

I forget about it for a couple weeks then remember mid October that I still don’t have a hotel room booked.

When I initially made the request it was about $550 for 4 nights.

Looking again in mid October it was now up to $700 for 4 nights.

I look around and noticed that same week I’m supposed to go up there’s a concert in the same city followed by a big college sporting event in that town.

I send an email to my accounting folks that I need to book a hotel, rates are going up, room availability is going down, yadda yadda yadda.

I get a tersely worded email back saying that everyone has different priorities and my purchase order will be addressed once all the ones before it are done.

She warned them!

So I sit back and wait and keep checking every other day and keep seeing prices go up.

I send a weekly email asking if it’s approved yet and I keep getting absolute silence back.

Finally a week before I email my accounting team with the CFO included saying if I don’t book a room that day, there wouldn’t be any left and I wouldn’t be able to make it up for the strategic planning work.

About 30 minutes later I get back an email that says word for word: “You are authorized to reserve a hotel room for 4 nights.”

Cool. That $550 room is now $1,200.

I book it and move on with my life and don’t think any of it.

Last week, I got around to uploading my credit card receipts and submitted my expense report which included that $1,200 hotel stay.

I got a call from my CFO today just exploding on me, furious about where the hell did I stay that cost that much and what was I thinking.

I very calm just forwarded the original purchase order and all the emails I sent saying that prices were rising.

I had dead silence on the phone as he read through the email chains and just said “For **** sake!” then hung up.

At the end of the day all supervisors got an email that the purchase order system was being shutdown until they could figure out how to manage it better.

Here is what people are saying.

That’s what you took from this?

Screenshot 2025 06 13 at 4.40.07 AM He Tried To Tell His Company Their Travel Rules Made Things More Expensive, But When They Didnt Listen He Took Advantage Of Their Cluelessness

Exactly. You don’t make your business clunky just for the sake of it.

Screenshot 2025 06 13 at 4.40.21 AM He Tried To Tell His Company Their Travel Rules Made Things More Expensive, But When They Didnt Listen He Took Advantage Of Their Cluelessness

I don’t think it’s a matter of trust, but more a matter of competence.

Screenshot 2025 06 13 at 4.40.33 AM He Tried To Tell His Company Their Travel Rules Made Things More Expensive, But When They Didnt Listen He Took Advantage Of Their Cluelessness

I’m sure you are in the majority.

Screenshot 2025 06 13 at 4.41.03 AM He Tried To Tell His Company Their Travel Rules Made Things More Expensive, But When They Didnt Listen He Took Advantage Of Their Cluelessness

Excellent way to feel better about this.

Screenshot 2025 06 13 at 4.41.47 AM He Tried To Tell His Company Their Travel Rules Made Things More Expensive, But When They Didnt Listen He Took Advantage Of Their Cluelessness

I wonder what other genius policies these people have come up with.

Sounds like shutting it down was a good idea.

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