Cash & Coupling: Aww, My Tax-Filing’s All Grown Up!

There was a time in my life when I actually looked forward to tax season. Like most people, I had taxes withheld from each paycheck, so that when tax time rolled around each year, I was guaranteed a nice little refund. I’d collect my W-2s, spend an hour or so filling out paperwork on a cold February afternoon, and voila: a few weeks later I’d have a check from the government I’d quickly blow on impractical shoes, a haircut and half a month’s rent. If I was feeling really responsible, I might sock away half the refund for a “rainy day,” which for my 20-something, job-hopping self meant impetuously quitting a boring job without having another lined up, because, Hey! I’m rich! I just got my tax refund, which is basically the same thing as winning the lottery!

Then I grew up. Well, if you can consider having expensive car problems and student loan payments from graduate school as “growing up.” Suddenly, I had real — and immediate — expenses swallowing up my tax refund. No more impractical shoes for me when I was drowning in debt. By the time I finally got my finances together, I had started freelancing to supplement my full-time income. Now when tax season rolled around, I actually owed the government some money (most freelancers don’t have taxes withheld from their paychecks and wind up paying Uncle Sam in one lump sum). Luckily, I still got a refund on taxes paid through my full-time gig, but a lot of that refund was just going back to the IRS to cover what I owed on the freelance front. It’s now been two-and-half years since I made the leap to full-time freelancing, which means, you guessed it: no more tax refunds at all. These days, I have a special savings account into which I make sure to deposit 30 percent of each paycheck so that when tax season rolls around, I have the funds to cover my butt. Growing up, it turns out, is kind of overrated.

Becoming a full-time freelancer isn’t the only recent change I’ve made that affects my taxes. Last year, I also got hitched, which means this is the first time I’m filing as a married person. And my husband, it turns out, has very complicated taxes. Before our wedding he sold a bunch of stock he’d had for most of his life, fearing another drop in the market and wanting to make sure our nest egg was safe and we had money set aside to eventually buy a home. Also, we decided to pay off the remainder of my student loans before starting a new life together. Because he sold all that stock, he has tons of paperwork to go through and extra taxes to pay this year. In addition, there are receipts for charity donations to file, certain deductions to be found, and a seemingly endless stream of stuff I can’t even begin to understand. Suddenly, it’s all so … complicated.

Luckily, Drew, my husband is pretty good with numbers. I never would have guessed it when I first met him. He went to art school and makes short films and designs baby clothes for fun. But his dad’s a CPA and I guess something must have rubbed off on him. After getting a little high from selling his stocks last year, he’s even reinvested a bit in the market and does his own version of day-trading, sometimes waking up at the crack of dawn to watch the market for a couple hours before he goes to work. Hearing him talk about the market, and now watching him work on our taxes has been an introduction to a side of him I didn’t realize existed. I knew him as this sweet, funny, often-neurotic creative type. That’s who I thought I was marrying. But he’s more than that, and I have to say I’m relieved. While it’s not exactly the good-time-Drew with whom I fell in love, it’s a practical side that’s definitely necessary in a marriage where finances dictate so much of a couple’s stability, if not indirectly affecting their happiness.

All that said, we’re only days away from the Apr. 15 deadline and Drew is still nowhere near finishing our taxes. If I were filing my own, I’d have finished them six weeks ago and sent a check off immediately. But Drew’s still searching for paperwork he needs to finish; we still have file folders laid out all over the desk I work from at home; and he’s still calling his father and brother on a near-daily basis asking for advice on things I don’t really grasp. I wish I could wave a magic wand and be done with all this tax business. It’s spring, the weather is beautiful and I’m ready to have my husband back. But, of course, it’s not just his taxes he’s working on. They’re our taxes now. He may be the one doing the legwork, but he’s doing it for the both of us. So this year, as annoying as it is, tax season is a reminder of how marriage works. We’re a team now and we work best when each of us takes responsibility for things we excel at (or at least excel at more than the other). So Drew does our taxes and I … well, I mix the cocktails. Hey, it works for us.

Photo: iStockphoto

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