I’ve done my taxes on my own using TurboTax, from the comfort of my own home, for the last 8 years. The software stores all of my old documents for me and welcomes me and guides me kindly and simply through questions which I can do on my own schedule (or at 3am). Even with a small business return to file, I never paid more than $100. My favorite feature of TurboTax is the “audit risk meter.” Upon completion, the software gives me an audit risk score, and as long as my arrow stays in the green section, I’m golden. (Knock on wood, spit three times over my shoulder.)

Another prime feature in Turbo Tax is the running tally of what you owe or your return in the sidebar at all times. This is critical for playing with deductions to play the “what if …then how much” game of numeric experimentation.

When I was younger, I had my dad’s CPA friend, Ricky file my taxes. But the last time he did it, he missed a prime deduction, which turned my refund into a payment. I forgave him; he was just diagnosed with Parkinson’s Disease. We spent 3 1/2 hours on talk therapy in between feeding him a few numbers for my taxes. When we were done, I thought I may have earned some credit for independent study towards an imaginary psychologist degree.

My master opus of taxes was directed by Mr. Taxman. I wish I was being funny here, but this was actually what he called himself, with a Website to match: Mr.Taxman.com. Who goes to someone with that name? He came highly recommended by an intelligent and trusted friend. [Side note, this is also the friend who suggested we get alcoholic drinks out of fishbowls at Brother Jimmy’s. After this fishbowl of drunk-sauce, I did one of those “twist my ankle in wedge sandals” moves and broke my foot.]

Mr. Taxman’s office was within his red-wallpapered apartment in an Upper West Side Classic 6. I didn’t know what that meant, but he told me when I seemed unimpressed. He was overweight, sweating through his white button down and was the kind of bald with tufts of hair on the sides, like a Muppet. He had leftover mustard on the corners of his mouth and I pointed them out and he laughed it off, saying he was too busy to go out for lunch so he ate at his desk.

We went through my numbers and after an hour, he told me I owed the IRS $15,000! I was appalled.

“How could this be possible? I am a single mother! What can we do? Can’t we deduct more?” I started screaming, outraged. He’s a CPA; aren’t they supposed to make it so I don’t have to pay? Isn’t that what I pay him for?

“Do you travel for work?” He asked.

“Yes, of course,” I said. I got excited. Now we’re getting somewhere. He kept on with the questions; forcing me to approximate numbers, and when they weren’t high enough, he suggested a higher number. I told him I didn’t have receipts, he said not to worry; he had less than a one percent audit rate. I would have liked to see this in a visual illustration Turbo-Tax style with a meter because after all his clicking on the calculator and flirting in between sips of Dr. Brown’s Root Beer, he said, “OK! I did it. Now you’re getting $5,000 back!”

I thought this was a joke but quickly realized this must be his method. He must make you feel devastated by how much you owe the IRS and then he says, “Let me work my magic numbers genius” and now ka-ching, the register drawer has swung open in your favor. From red to black in just a few finger dances on the calculator.

I almost hugged him when I left, but sweaty, bald, mustard CPA isn’t my flavor. My euphoria lasted for a few short months when I got the dreaded audit letter from the IRS. This is one of life’s truly “OH SHIT MOMENTS” just behind unplanned pregnancy. At first, I ignored their letters and notifications thinking I could run from the IRS, but you cannot outrun them any faster than you can outrun a bullet. Within a few weeks, they seized my wages at work. In retrospect, I should have contacted Mr. Taxman, but I was so angry, scared, confused, and figured I had to handle this one on my own.

On the day of the audit with my agent, I dressed in a form-fitted, but conservative, slightly low-cut black shirt dress and high heels. My hair was perfect, my makeup, immaculate; I can’t say I looked any worse than on my wedding day. I was anti-Feminist all the way and wanted to use any inch of my sexuality on the IRS man; I prayed wouldn’t be gay.

I got there and the machine-man refused to even make eye contact. No handshake, no glances at the wasted push-up bra cleavage. I have had more intense conversations with my toilet while puking during a hangover. My decade of experience of bullshitting on the job and winning clients with smiles and schmoozes was futile here. I had no game. He wanted receipts and documentations and nothing of which I had.

I walked out of the office with a bill for $15,000.

The moral of the story: Turbo-Tax or bust.