With April 15th less than two months away, I can’t express how much I hate this time of year. Ever since I began freelancing I’ve always dreaded the first half of the year - and I’m sure a large percentage of freelancers can sympathize with my feelings.

When it comes to my annual income taxes, I do things the hard way. I know, I’m supposed to set money Aside each month (specifically for taxes), and pay my taxes quarterly. Well, I seldom do that. Instead, I use my personal savings to pay Uncle Sam, or I’ll cram once I know my tax bill and get the payment to the IRS by the deadline. For the most part, I haven’t had any trouble paying the bill. I’ve always had enough write-offs, and I’ve never experienced real “payment shock.” And to help matters, I file jointly with my husband, which I think reduces what I would have owed. I get anxious around tax time every year…but it always turns out well. But I don’t know if I’ll be as fortunate this year.

Aside from the fact that my income increased in 2008, my husband and I started a new business, which will likely increase our tax bill. We didn’t have any large office or business expenses. And the home improvements we made last year put a dent in our savings. So basically, I’m relying on the write-offs we get for paying mortgage interest, medical expenses and having a home office. Lets just hope it’s enough….