You Want How Much?

Well, my 2008 is off to a rousing start. I just left my tax preparer’s office. This is the first year that I’ve ever paid someone else to do the paperwork on my taxes, and it turned out to be more painful than doing it myself. I didn’t think that was possible because if you’ve ever filed your own taxes, you know it feels a lot like watching your dog get hit by a car. But sure enough, this was worse. However, I left feeling lucky that the government isn’t looking for me (as far as I know).

They certainly have every right to be looking for me.

It turns out I owe the government a lot of money. A lot of money. And this isn’t an amount that would be considered ‘a lot’ by some people, but ‘a little’ by others. Oprah would consider this a lot of money. Up until the meeting with the tax preparer, I was unaware of this, of course.

The problem arose because the status of my job requires me to pay state and federal income taxes on a quarterly basis, only I have to do so without having my wages and withholdings typed out and mailed to me on a single piece of paper. That means I have to estimate my quarterly payments. For anyone who isn’t a CPA, this is a bad idea.

My wife and I had an opportunity to save a little money this year by filing before January 31, but this put us in a time crunch, so we hurriedly gathered up all of our paperwork and met with a consultant. I handed the nice lady my pay stubs from 2007, as well as my estimated tax statements so that she could figure out our 2008 payment. At about the halfway point of adding the numbers, she shifted her gaze from her computer screen and looked at me as if Cameron Diaz’s brother from There’s Something About Mary had prepared our taxes last year.

“Your 2007 totals were a little off,” she said.

I wasn’t surprised by this news, but when she told me just how far off I was, I’m pretty sure I suffered a stroke. I broke out in a sweat, my legs went numb and my ears started ringing. Given my temporarily-diminished hearing, I couldn’t quite make out her next statement, but I’m pretty sure she said, “A goat could have gotten closer.”

Obviously I never should have attempted to file our taxes without professional help. And if I had thought back to my college days, I would have known that it was a bad idea before getting started. During my time as a semi-declared business major, I had to take a basic accounting class. Things seemed to go fine, but at the end of the semester, my final grade was an H.

After accounting came a semester of finance, which I took through correspondence. If you’ve never done this before, it means you read the book and turn in scheduled assignments, but you don’t attend class. This sounded great, but without a professor to explain the material or to be there when I had questions, it was hard as hell. But I did the assignments, turned them in every week, and at the end of the course I received a letter in the mail that read “Congratulations on completing all of the course work. However, you are not enrolled in this university. Please stop wasting everyone’s time.”

Despite these setbacks, I’ve always done my own taxes since first stepping foot into the “real world.” Believe it or not, it used to be easy. When I didn't have a child, a home or other deductions to itemize, and I had a job that extended me wonderful benefits, like sending me a W-2 every year, filing my taxes wasn’t too complicated.

Now it’s… well, like watching my dog get hit by a car.

So instead of sending our son to college, or feeding him for the next two years, we’ll be paying the government a large sum of money. We’ll also be paying someone to figure this out in the future. Hopefully someone with a slogan that instills the utmost confidence in us that their calculations are accurate. Something like, “Franks and beans!”

That’s someone I would trust with my money.