Doing Taxes

Tax time stinks. It really really stinks.

It’s not that my personal taxes are all that complicated (although I do have to mess with freelance income and attempts at writing off business-related expenses the right way). It’s just that I really hate doing taxes. And I’m always consumed by this fear (unfounded, I hope) that I’m going to do something wrong and royally screw things up. That the big bad IRS men are going to come after me because I wrongly wrote off that ream of recycled paper I bought. Scary.

I was fortunate enough that my parents had my taxes done with theirs for a couple of years I had an income. Then I successfully did them on my own. Then, the first year I really had freelance income, I got finished the online filing process and was horrified at how much I owed. More than horrified, really. The number was big enough I had no idea how I was going to pay it! Plus I was worried I’d screwed things up with how to take a deduction for my laptop. And, as I think I may have already mentioned, I was incredibly horrified about how much I owed.

So I took everything to H&R Block and asked for help. And help they did. Wow, that woman came up with things I never would’ve thought of—like the fact I could still write off some of my college expenses, and all sorts of other things I hadn't had a clue about. I walked out of there still owing money, of course, but less than a quarter of what I would’ve owed had I done the taxes myself (even including the cost of hiring her to do them for me).

I was relieved, although I admit at the time I was nervous she’d gotten out of control and taken deductions she shouldn’t have. But I guess that’s what I paid extra for—the guarantee I wouldn’t be penalized for her mistakes.

If you're not sure whether you should do your own taxes, I recommend checking out this MSN article, which can help you figure out the best move.

For a number of reasons, I chose to do my own taxes again for 2006 and 2007. With online programs like Tax Cut (which I keep using because it imports info from the last two years and is accessible from any computer), I can sit on the couch with my laptop and get things taken care of by doing little more than answering questions the program asks and filling in answers.

But as easy as answering those questions may be, the end result this year was still painful—even though I finally got smart and filed estimated taxes, I made more freelance income than I'd expected so I STILL owe a bunch. Maybe that crazy woman who did my taxes two years ago was right when she told me I absolutely should stop doing freelance work. I thought she was rude and she should mind her own business, but when I see how much I owe I wonder if maybe that wacky lady was on to something.

So much for buying a new car right away.

I guess on the bright side, I should be getting a tax rebate this year, right?

Maybe I'd like doing taxes better if I could buy some pets 'n bait while I got my taxes done.

photo: romanlily