Tax Debt Horror Stories for Halloween

Who doesn’t love a good scary story? What about tax debt horror stories?

Okay, a lot of people. Even if you enjoy the Halloween season—trick or treating, costumes, and candy—you may not be the kind of person who likes horror movies! But unlike monsters, ghosts, and vampires, some frights are inescapable, no matter how hard you try.

Even if you’re afraid of spiders, you’ll probably run across one someday. If you’re afraid of heights, you may need to reach a high cabinet, clean the gutters, or fly in an airplane. And no matter how scary the IRS can be, if you have tax debt, you’re going to be hearing from them. A lot.

We’ve bravely fought the IRS for years, so they don’t scare us. Unfortunately, your first time dealing with the IRS regarding your tax debt issues can still be as horrifying as a Wes Craven film.

We think it’s time you face your fears. That’s why we’ve collected two scary stories about tax debt just like some of the worst cases our clients have ever dealt with. After each frightening tale, we’ll explain what could have been done to prevent such a gruesome tax debt fate.

2 Tax Debt Horror Stories

Tax Debt Horror Story #1: The Total

By any metric, Gregory wasn’t an organized man. His room was often covered by a thin layer of dirty laundry, his sink was piled with dishes, and his kitchen table swelled with weeks and weeks of mail.

Gregory wasn’t concerned. After all, there are far more important things in life! At least there were, before the day he found the letter from the IRS.


Gregory helplessly searched the opened envelope for another letter, anything that would explain the numbers he’d seen written, a balance apparently associated with him. He knew he’d filed taxes this year. Right? Or was that last year? He knew he must have; he’d find proof of it and clear all this up! All the while, the numbers on the notice seemed to threaten his very existence:


The Tax Debt Lesson

It looks like Gregory is in steep tax debt with the IRS, but could it have been avoided? Even without a few details, we know the answer is yes.

  1. He should have filed his taxes. We’re not criticizing here; lots of people have missed a tax return—or filed after the tax deadline—before. However, if you have to wonder, you’ve probably missed a tax return or two over the years. And filing them
  2. He could hire a tax relief company. When the IRS assesses a debt, that doesn’t mean you’ll end up owing all of it. Filing back tax returns can substantially lower your tax debt.

Tax Debt Horror Story #2: Evader

It started out earnestly enough.

The first year, Arthur had just forgotten. He and his wife, Lilly, had just bought the lake house and they were new to the whole “Airbnb thing.” But considering they only used the house for about a month during the previous year, that 11 months of semi-regular guest rentals was really helping them cover the mortgage—and then some.

Tax season came and went, and the investment property income went unreported. It wasn’t until their third year of side income that Arthur realized what had happened. But it wasn’t like the IRS was knocking on their door or anything; surely they would if there was an issue, right?


The fourth year, Lilly asked. With her work schedule, she usually did a quick pass over the joint returns after Arthur filled them out, and she just hadn’t noticed before. This was the first time Arthur heard the words spoken out loud: “Tax evasion.”

The Tax Debt Lesson

Most people don’t set out to commit tax evasion; it just sort of builds out of one or two omissions. But tax evasion is serious, and there are ways to avoid it.

  1. Arthur should have fixed his error. Mistakes happen, and if you realize you’ve left out an income stream or put down an incorrect number, you can file an amended return to correct the issue. You may even be able to avoid penalties with a first-time abatement!
  2. Lilly and Arthur could have talked about their return. In many joint households, one person handles the bulk of the tax filing. Involving both parties helps, even if it’s just sitting together and reviewing the return together.
  3. They could have saved their income. Estimating your tax obligation is crucial when you have a rental property or work as a contracted employee. If Arthur and Lilly have been saving their estimated taxes, when it’s time to come clean with the IRS, they won’t have dug themselves into a tax debt hole!

Are You Afraid of the IRS?

Your first run-in with tax debt can be scary, but we don’t think you should have to be scared of the IRS. We’ve dispelled the tax monster for thousands of clients, and we can do the same for you.

Now that you’ve faced your worst fears and read our tax debt horror stories, it’s time to face your tax debt head on. We like your chances—do you?

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