Costly Mistakes: People Open Up about Their Biggest Financial Mess-ups and Failures

By: Stephen Thompson | Last updated: Nov 11, 2023

We’ve all been there: making a stupid mistake that costs us money. But some of us have learned these expensive lessons the hard way. Reddit asked users to share their “biggest idiot tax” experience and the mindless ways they have lost money. 

Guess what? The ways people have lost money due to being stupid range from absurd to downright cringeworthy. Thankfully, INSIDER has compiled a list of these stories. Although we can’t attest to every one, they are entertaining and relatable. Get ready to cringe, laugh, and perhaps learn something about dodging costly mistakes in the future!

Passport Fiasco: A Tale of Impulse and Ignorance by SecondSingles

Spontaneity can be bliss, but it can also be disastrous, as Reddit user SecondSingles learned the hard way. Perhaps they were feeling too adventurous and decided to book a last-minute flight on impulse, only to realize the next day they had bought a non-refundable ticket—plus their ticket had expired. 

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Source: Getty Images

This is a typical facepalm moment! So instead of jet-setting off to their dream destination, they were left with a non-refundable ticket and an expired passport. Too sad if you ask us. However, lesson learned: Don’t be like this user and blow your hard-earned cash on a silly mistake! 

The 8-Year Internship: How One Person Lost $250K in Salary by Sticking Around

Tell us, what’s worse than staying in an unpaid internship for years? Well, staying in a paid one for eight years and missing out on hundreds of thousands of dollars. That’s exactly what one Reddit user did, starting at their internship job in 2008, at the peak of the recession when job offers were scarce. 

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Source: Getty Images

This user, of course, accepted a low hourly rate, hoping to make up for it as time went on. But sadly, after several years, they discovered they were underpaid by 30-40% compared to average hourly wage. Despite trying to agree on a raise with the firm, they were guilt-tripped and gaslighted. Luckily, they found a new job that paid what they deserved. 

The $1,500 Mistake: How A Couple Paid For a Service They Never Used

Sometimes, alack of oversight can lead to a big financial blunder. That happened to Bostaevski, who discovered that he had been paying for a Dropbox business account for 20 months—a service he had never used. 

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Source: Pexels

Bostaevski’s wife has signed up for the account to research the Dropbox business model, intending to cancel it a few days later. Unfortunately, she forgot. The couple was unaware of the $75 monthly charge until it had added up to a whopping $1,500. Lesson learned: Keep a closer eye on your bank statements and always cancel your subscriptions for unused services. 

The Fat Fax: Paying for a Year Gym Membership with a Broken Leg

They say that laughter is the best medicine, but it doesn’t do much for an unused gym membership. Reddit user Rubyface made the silly mistake of signing up for a gym with a discount for autopay, only to break her leg soon after. 

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Source: Pexels

Despite being unable to use the gym for over a year, she kept paying for it, hoping to use it once she was healed. But time passed and the gym membership remained unused. Rubyface dubbed this mistake her “fat fax.”

Love in the Time of Canceled Flights: Paying For Your Ex-Boyfriend’s Vacation

Ah, love. It makes us do some pretty funny things. Like paying for part of a vacation we didn’t even go on. That’s the mistake this Reddit user made. Initially, she wanted to cancel her plane ticket for a trip with her now ex-boyfriend. But she mistakenly canceled the entire booking. 

Source: Klaus Vesfelt

Feeling remorseful, she offered to split the rebooking costs of last-minute flights for her ex-boyfriend, who was stranded at the airport. This decision ended up costing her over $400. But it was worth it to ease her conscience, right?

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When Pride Costs $1,500: An Exemplary Tale of Ignoring Good Advice

Lendergle thought he knew better when his wife warned him not to lean a lawn chair against their rental car. But his stubbornness ended up costing him big time. The lawn chair slid sideways, leaving a two-foot scratch down to the bare metal. 

Source: Getty Images

Thanks to lost rental revenue and a costly paint job, the resulting scratch led to a $1,500 bill. It truly is an “idiot tax” he knows he deserves, as his wife keeps warning him for years to pay attention. Don’t be like Lendergle—always listen carefully to your partner. 

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Zach Matthew's Mistake of Being a Gallant Gentleman

He thought he was being a chivalrous hero by helping his friend back her mom’s Expedition out of a crowded parking lot. Little did he know it would lead to a costly mistake that would haunt him for years. 

Source: Pinterest

Within a few seconds, Zach manages to hit not one, but two cars, racking up $800 in repair costs. As a broke 17-year-old making just $7.50 per hour, it blew his bank account! 

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Catwallada's Mindless Money Mishap

Who goes to the ATM being sleep-deprived? Well, this Reddit user does. In a funny moment of sleep-deprived forgetfulness, Catwallada went to the ATM and left $10 in the machine after withdrawing her cash. How does one explain this? 

Source: Getty Images

Although it seemed like a tiny mistake when it happened, it turned out to be costly and funny. Trust us, this is a true “idiot tax.”

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From High Hopes to Hard Liquor: A $1,000 Concert Catastrophe

This has to be the most hilarious “idiot tax” tale on the list. For this Reddit user, it was supposed to be the concert of a lifetime. In fact, he shelled out nearly $1,000 for a pair of tickets, hoping to have the best seats in the house. 

Source: Pinterest

Shortly after arriving, things took a turn for the worse. This user let loose with $50 worth of hard liquor and was wheeled out of the venue in a drunken haze before the concert started. His hopes were crushed, leaving him with an empty wallet and regrets. 

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A Costly Textbook Trap

Imagine renting a textbook for a class, then finding it useless. And then when you think it couldn’t get any worse, you go on an extended family vacation, forgetting to return the book. Well, for this Reddit user, the mistake cost them a $100 late fee! 

Source: Getty Images

But wait, that’s not all! The cherry on top? The textbook is soon to be outdated because, obviously, the laws of nature change every few years. Don’t fall into the same trap. Enlighten yourself on textbook options and always double-check the need for your books before spending your hard-earned money.

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