Affiliate Disclosure: Some of the links on this page are affiliate links, which means we may receive a commission if you decide to buy a product or service we recommend.
The only thing worse than a mistake is a mistake that sinks you into debt or saps a month’s income in a split-second. So please learn from these brave pioneers of financial disaster. Their mistakes are your cautionary tale.
1. Dodging the Tax Man
Just like any problem, ignoring the Internal Revenue Service will not make your tax obligations go away. One debtor went to the bank one day to find all his accounts completely drained.
Uncle Sam always collects his debts and doesn’t always offer a payment plan. Pay your taxes. Your elected officials have lots of worthwhile plans for your money, they promise!
2. Buying a Nightmare Home
One homebuyer thought they did their due diligence. Unfortunately, they didn’t detect mold, electrical and plumbing flaws, water damage, and even bats in the attic. Few financial mistakes are as costly as buying a nightmare home.
3. The American Muscle Money Pit
Note to self: I won’t dive into Jay Leno’s hobbies if I don’t have Jay Leno’s money. Car restoration is not a venture for those making less than $40,000 annually, as one naïve would-be mechanic found out.
The burnt-out gearhead said they were “OK giving up my time and labor but severely underestimated how expensive a total restoration would be.”
4. Foregoing Dental Insurance (and the Dentist)
So long as you break out the Crest twice a day, floss a couple of times a month, and lay off the sweets, you can skip the dentist appointments and forego dental insurance, right?
Wrong. One “anti-dentite” (thanks, Seinfeld) paid so much out of their own pocket for dental work that they could have bought the dentist’s office. Go to the dentist, and get dental insurance.
5. Over-Shopping at the Grocery Store
It doesn’t matter that you shop at Walmart instead of Whole Foods. If you’re spending money on groceries that go bad before you cook them, you’re consistently throwing money down the drain. Better to pay more at Whole Foods for ingredients you’ll use than to pay half-price at Walmart to throw the food out.
6. Turn Down a Scholarship? That’s Bold.
Ironically, turning down a full scholarship from Notre Dame is what you’d expect from someone who would never get a full scholarship to Notre Dame. From Fighting Irish to fighting to get out of debt in the span of one terrible decision.
The short-sighted student got their Master of Business as anticipated but said their education cost “$60k more than it needed to.”
7. Leaving the Court Date Off the iPhone Calendar
One forgetful no-shower let their court date slip by. Forty-five days in jail and two years of probation later, they are a religious calendar user who will never forget the most expensive missed appointment they ever had.
8. Doing the Right Thing
One responsible Samaritan rues the day they struck a parked car with their vehicle, left a note, and ended up paying $180 out of pocket for repairs. If they had a do-over, they would have skipped the note-writing and pocketed the $180. We don’t know if we would recommend that! Dishonesty always costs more.
9. Marrying the Wrong Person
A spouse can be far more than a life companion. The wrong husband or wife can be an albatross on your credit score, the cause of a monthly bank statement that’s always in the red, and the ball and chain that prevents you from reaching your financial dreams. Marriage can be liberating, or it can be a financial prison. Choose wisely before slipping the ring on.
10. Sandwiching While Driving
True story (as far as we can tell). One guy was making a sandwich while driving, caused a violent collision, and now faces $30,000 in medical bills (and likely higher insurance premiums). Most expensive ham and Swiss ever.
Siblings and Widow Fight Over Inheritance of Childhood Home, but Deed Settles Dispute Once and For All
After the unfortunate loss of their father, a gripping family saga unfolds as three siblings find themselves entangled with conflicting desires over their family’s home. While certain siblings are determined to honor their father’s legacy by offering his widow a portion of the inheritance, others grapple with a profound dilemma.
He Receives Inheritance From Biological Mother but Also Feels Entitled to Stepmother’s Estate, Sparking Controversy
When a woman’s stepson inherits a windfall, she strives for what’s fair while planning her estate. But her husband’s disapproval sparks a thrilling twist, forcing her to question her choice.
Retired Couple Keeps Their Millions a Secret; After Needy Family Discovers Wealth Unwanted Financial Demands Follow
A couple worked tirelessly and embraced frugality to amass a substantial retirement nest egg. As they approached semi-retirement, they were confronted by financially irresponsible relatives seeking assistance.
She Buys Nephews’ Lottery Tickets for Fundraiser, After Hitting the Jackpot They Demand a Refund
When a woman and her boyfriend hit the jackpot in the Christmas lottery, jealously quickly forms. The boyfriend’s sister and her sons, who sold them the winning tickets, demand a slice of the windfall. This unexpected demand ignites a heated battle, leaving the couple with doubts about their decision.
She Buys Nephews’ Lottery Tickets for Fundraiser, After Hitting the Jackpot They Demand a Refund
Greedy Sister Snatches Largest Diamond Inheritance, but Has Meltdown Over Diamond’s Real Worth
Bound by love for their fashionable mother, two sisters face an unexpected divide when it’s time to distribute her inheritance. While both seemingly receive an equal share, one sister soon discovers a hidden truth that shatters their relationship.
Greedy Sister Snatches Largest Diamond Inheritance, but Has Meltdown Over Diamond’s Real Worth