Why Does a Checked Bag Have to Be So Difficult? - This Is Trouble

Why Does a Checked Bag Have to Be So Difficult?

A recent true story out of Yours Troubly’s life in Eastern Europe…

When trying to purchase a bag for my recent trip to Ukraine, the airline I was flying on wouldn’t let me purchase a bag online (I booked through my credit card and the bag wasn’t included). One would think, in 2018, that it would be pretty reasonable to buy a checked bag online.

I tried to email for a week, no response.

Tried to call, was told the queue was 75 people and an hour wait.

So I had my girl call (you know, time is money and all), and she set it all up. The conversation went something like this:

Eastern European airline:

“A checked bag both ways will be $70, we’ll email you the receipt right away.”


“Great, here’s the card.”

Two days later:

Charge for $372.

No receipt emailed.

Two weeks later, on the way home…

At airport:

“Our agent messed up and charged you for an overweight bag. We have no idea why.

Now you must pay $30 more for normal bag.”


“What about that $372? You can’t just apply that?”


“You can try to get it back at your home airport.”



After a bit more prying, I found out it’s because I was a naughty boy. Naturally, when I saw a charge for THREE HUNDRED AND SEVENTY TWO DOLLARS for a checked bag, I decided trying to actually argue with the airline was a moot point.

I’m kinda busy these days—I don’t have hours and hours to time waiting on hold and arguing.

So I disputed $302 of the charge—fair, right—since they said it’d be $70 each way.

I guess that put a “hold” on my bag, and so they made me pay the $30 at the Lviv airport as well.

Ended up being $100 total.

(Then I called my card and disputed the $30, which they gladly granted me as well as 5,000 bonus points—nice chaps).

Anyways, I might be coming across as a complete cheapass, and that’s cool.

It’s not the money, it’s the principles.

This is an example of “American privilege”.

If my girl from Ukraine had used her card, she would have been shit out of luck and had to beg for her money back for WEEKS. It would have taken hours and hours of phone calls, emails, screaming at idiots, and more…and still…

And she’d be lucky if she ever got the money back.


I click a few buttons in an app, or call the nice Citi agents, explain the problem, get money back.

It makes me angry, because I don’t condone companies treating people like this. I look at everything through the lenses of someone like my girlfriend, from a country that doesn’t have as much “privilege” as I do.

Or at least I try.

And it makes my blood fucking boil.


There is nothing I can do.

Except, of course, making more money to make these kind of situations “no big deals” instead of “draining my life savings”.

I’m very fortunate to be where I am today, where I have many times over as much money as I need coming in completely passively, thanks to my niche websites.

To build profitable websites to help give you an “FU fund”, and even as much monthly income as a high-end rental property (multiple thousands), check out the new and improved “Pro Niche Site“.

Kyle Trouble

I'm Kyle "Trouble". I'm a former computer engineer who left the 9-5 in LA at 24 years old and moved to Eastern Europe. I blog about dating, life abroad, and building successful and scalable streams of income.

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