Through a mysterious anomaly in the Internet two entries in the TaxGrrrl’s contest for worst tax filing horror story ended up coming to the Tax Update instead. That probably disqualifies them from the free Turbotax copy she’s giving as a prize, so I am reprinting them here.
I was once one of the most powerful men in the country. That entitled me to a limo and a driver. The pay wasn’t so great, but my wife more than made up for it because people just fell over themselves to hire her.
Then the voters of my Podunk state disappointed me and I was out of a job. Of course I’m not going to move back there. One of my very good friends set me up with a great job where I pretended not to be a lobbyist. The pay was good, the work was easy, and I got a car and driver. And the best part: he never 1099′d me, so it was tax-free!
But once you’ve serviced, er served, the public, it’s in your blood. So when I got an offer to work for the President, I was game. But then they tell me I have to pay taxes on the cash, car and driver, even though I never got a 1099. What’s up with that? I was disappointed, needless to say. But the President had somebody tell me I had to act sorry and pay up, so I do. So far, everything’s cool.
Then some woman who got nominated for some “performance officer” job drops out just because she didn’t pay $298 in taxes on her baby sitter. Like it’s 1993 or something. That just cut me off at the knees. What can I do? They tell me I’m toxic and I have to withdraw my name. And now I still have to pay all of these taxes, even though I never got a 1099. Is that right? I’ve never been more disappointed.
If I win the Turbotax, you aren’t sending me a 1099, are you?
You can read the other misdirected entry here.