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Filing your taxes on paper in 2019: How hard could it be?

Daniel Howley
Technology Editor

I’m terrified of doing my taxes. Every year in early January, when my W2s come in the mail, and I start seeing ads for tax preparation services, a chill runs down my spine. I’ve never been audited, and I’ve only owed money to the federal or state government twice, but I’m paralyzed with fear of the IRS nonetheless.

So what better way to get over my fear of taxes than to make doing them as hard as possible. That’s right, rather than hiring an accountant or using TurboTax, I decided to try my hand at doing my taxes the old-fashioned way: With a pen and paper.

It didn’t go well.

In fact, it went so poorly that I ended up filing my taxes through TurboTax, because I was thousands of dollars off by my initial calculations.

There’s a reason e-filing your taxes is easier.

I’m bad at math

I’m a writer, or so I like to tell people. And while there are certainly plenty of wordsmiths who know their way around a calculator, I’m not one of them. In other words, I’m terrible at math.

My cousin, a math teacher, tried to help teach me when I was a kid, as did my own math teachers, but I took to it like a duck to an airplane propeller.

All of that is to say, I was immediately intimidated by the sheer amount of numbers on my tax worksheet. Surprisingly, though, I spent the majority of my time filling out my 1040 simply by plugging in information from my own W4.

But when it came time to figure out my tax computation worksheet, I hit a brick wall. It turns out, if you put a decimal point in the wrong place while calculating your taxes, you’ll get wildly inaccurate results.

My calculations showed that I was getting more than $11,000 back from the federal government alone.

Naturally, when I saw that number, I began planning out where my wife and I would go on vacation, and what kind of TV I was going to buy.

But, my far more intelligent, and kind producer Ned Ehrbar saw the preposterous amount of cash I was due, and figured I must have made a mistake. After moving the decimal and recalculating, I found that I was only getting back north of $200.

That’s a heck of a change, but hey, at least I didn’t owe anything.

Once that error came to light, I realized that if I was going to file my taxes and avoid ending up in manacles at a federal prison, I should just file my taxes on TurboTax.

Moral of the story?

Never let me do your taxes.