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I’d rather have a simultaneous root canal and colonoscopy than do my taxes. That’s because I have an irrational fear that I’ll be audited and owe thousands of dollars in back taxes, or be sentenced to prison for tax evasion if I make a single mistake.
But after paying out the nose to have a private company file for me last year, and hearing my friends and family members go on about how easy it was for them to do their taxes, I decided to take the plunge myself.
I chose Intuit’s (INTU) TurboTax, as it was the service I was most familiar with. I also didn’t realize that H&R Block (HRB) offered its own online filing option until I sat down to write this article, because like I said, I don’t know much about doing taxes.
After gathering my W2 forms and tracking down my student loan information, I sat down with my laptop on the day after the Super Bowl nursing a buffalo chicken dip and pizza bite-induced hangover and got to it.
TurboTax starts things off by asking if you’re a tax novice or an old pro. If there were an option for “black out when glancing at financial documents,” I would have clicked that. But instead, I chose the novice option. I also signed up for TurboTax’ Plus Benefits for $29.99, as it offered the option to speak with a TurboTax representative if I ran into any trouble (though I didn’t end up taking advantage of it).
The entire process was relatively painless. I entered my personal information, double-checked to make sure everything was correct and answered any questions TurboTax had like whether I was married, had dependents or owned a home.
Filing wasn’t as problem-free as I expected, though. TurboTax provides you with real-time updates that estimate how much you’ll owe or receive from the government and state as you progress through the filing process. It’s a great feature when it says you’ll get money back from Uncle Sam. But it turns into a “Saw-esque” nightmare when it shows that you owe the feds. The problem is the number fluctuates as you move through the filing process.
Watching the ebb and flow of your bank account in real-time doesn’t exactly raise the confidence of a first-time filer. It’s like being told that you’re going to have enough money to pay off your student loans one minute, only to find out you’ll owe double that the next.
TurboTax provides you with the option to turn the feature off, which I eventually did, but I’d much prefer if it were off by default.
I also ran into trouble when it came time to deal with my state taxes. My permanent address is in New Jersey and I work in New York. So at one point, TurboTax asked me to look at the total taxable income I made for both states and eliminate any duplicates.
I was supposed to remove New York from the list, because my address is in New Jersey, but the instructions were too vague, and I clicked through without checking off either state. TurboTax took that to mean that I made double my actual income and the real-time refund tracker briefly showed that I owed $6,000 to the government.
After breaking into a cold sweat, praying to every god I could think of and dry heaving for a solid 27 minutes, I finally figured out that I needed to remove New York from the list of states.
From there it was smooth sailing except for one box I missed dealing with my student loan interest. I ended up owing money to the feds and Jersey, but got a bit back New York. Shortly thereafter, I received confirmation that my payments had gone through, and my taxes were completed.
I’ve always been scared of doing my taxes and was far from confident that I’d be able to file them without having a nervous breakdown when I signed on to TurboTax for the first time. But after running through the process, I can’t imagine going back to an accountant any time soon.
If you’re thinking about trying to file on your own, and are tired of paying someone else to do the work for you, I’d recommend going through with it. It’s scary and will take some time, but in the end you’ll save a few bucks.
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Email Daniel at [email protected]; follow him on Twitter at @DanielHowley.