Lottery Winner Says Telling Anyone Was the ‘Worst Mistake’ After 10 People a Day Beg For Money —’Even Had A Therapist Try To Rip Me Off’
- Personal Finance
ThePostMaster- 0
- 7 minutes read
People fantasize about hitting the jackpot — quitting their jobs, ghosting the alarm clock, buying that dream mansion, and never setting foot in a breakroom again. But for one Reddit user, the most life-changing moment of all came with a hard crash of reality.
“The worst mistake I ever made was telling people that I had won the lottery.”
That’s how their confessional post began on Reddit’s confessions forum. Not “I blew it all.” Not “I trusted a scam.” Just: I told people. That was the mistake.
Seven years after their win, the original poster said they now bring in just under $800,000 a year through annuity payments and investment profits. At first, they expected support, congratulations, maybe a few celebratory drinks. What they got instead? Constant requests — and not just from the people they were close to.
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“I thought they’d be happy for me,” the poster wrote. “They were happy for me for a minute and then they started to ask me for money.”
Friends. Family. Coworkers. Even the sister of a coworker reached out, asking for rent help. The calls didn’t slow down. “I was literally getting 10 calls a day,” they added. One friend asked for $20,000 to buy an engagement ring for a girlfriend who, the poster later found out, was still seeing other people. The generosity didn’t seem to buy goodwill — only more expectations.
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The Therapist Drove a Porsche. The Winner Drove a Prius.
Just when they thought things couldn’t get more absurd, therapy took a turn. “I even had a therapist try to rip me off by asking me for a cash tip after our sessions,” the winner wrote.
Then came the detail that sealed it: “He said my insurance company wasn’t paying him enough yet he drove a Porsche and I drive the Prius.”
That moment wasn’t an outlier. It became a symbol of how even professionals — people paid to be objective — shifted their behavior once they sensed the money. “It’s ironic that I have more money than I need,” the post continued, “yet I can’t give it away because it brings nothing but problems.”
Reddit Responds with Sympathy, Strategy, and Familiar Stories
The comments offered a mix of empathy, strategy, and lived experience. Several users said they’d never tell a soul if they ever came into serious money. One admitted they’d already set up a quiet inheritance plan for their child, and not even the child knows.
Others shared stories of broken promises and changing dynamics. One commenter described helping their brother through a long legal settlement, with an unspoken promise of gratitude afterward. The settlement came. The thank-you never did. Another user helped a coworker navigate their health insurance plan, was promised breakfast in return, and ended up with nothing but an empty stomach and a changed relationship.
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But one response captured what the original poster seemed unable to say directly: “They don’t want to start over and lose all of them. They want the friends and family to be like they were before.” That line went straight to the emotional center of the story. The money didn’t just change their lifestyle. It changed what people expected from them.
When the Jackpot Comes With a Disclaimer
This isn’t a story about reckless spending. It’s about how quickly good news can become complicated once it spreads. The original poster didn’t want to vanish. They just wanted to celebrate something monumental with people they trusted.
But when generosity turns into obligation, and conversations start sounding like transactions, even financial freedom can start to feel suffocating.
Because sometimes the real cost of a windfall isn’t the money — it’s realizing who treats you differently once they think you have it.
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Image: Shutterstock
