Tax Preparation Horror Stories for Halloween

It’s time to get spooky. Tax preparation horror stories spooky.

Halloween has to be one of the most spirit holidays of the year around Edge Financial; we love seeing people go all out and have some fun. We even have an annual costume contest and face painting for the whole family!

Halloween is also a time to reflect on what scares us. Goblins, ghosts, and witches may not frighten us as much as heights or spiders. (Spiders are scary year-round.) For many of our clients, one of the scariest things is tax season. Seriously.

Getting your tax return filed is something you should be proud of, so it pains us to know fear keeps thousands of people from filing their taxes until the last minute—or after the tax deadline!

The only way we can dispel these fears is by facing them head on.

Today, we’re sharing two tax preparation horror stories like the ones we hear every day from our clients—and much like your noisy friend who yells, “Don’t go in there!” at the movies, we’ll explain how each horrifying ending could have been avoided.

Tax Preparation Horror Stories for Halloween


Melissa’s bag was already on her lap when she saw her computer’s clock strike 5 p.m.

She must have set a startup record for fastest office exit, offering only a few distracted “Goodnights!” to her coworkers, who had already read on the team message board that she’d be missing their monthly happy hour to “handle some personal business.”

That personal business was waiting for her on her kitchen table as she walked through her apartment’s front door. A stack of papers, files, and receipts nearly three inches thick!


Melissa’s new Etsy shop was mostly responsible; she was in her wooden ornament business for the long haul, but she’d never filed taxes for an LLC before. And she certainly never thought dotting the i’s and crossing the t’s would take too long, so she’d waited until the last minute to start.

As the clock ticked on, Melissa realized how wrong she was. She didn’t even notice what time it was until about five minutes to midnight. That’s when it dawned on her: She was going to miss the tax deadline.

The Moral of the Story

Melissa could have avoided her horrific fate—missing the tax deadline and accruing penalties that will now affect her small business—a few different ways.

  1. She could have started filing her taxes sooner. When you own a small business, you need to allot extra time to file. It helps to break down the process into small chunks (think 30 minutes) you can complete when you have time.
  2. She could have filed for an extension. This won’t save you if you owe the IRS money, but if you don’t, that extra six months can help a lot.
  3. She could have hired a tax preparer. This was Melissa’s first time filing for her business; a tax prep company would be a smart investment to ensure she files an error-free tax return.


Marcus wasn’t an organized guy. He’d never claimed to be.

But he was never reminded of his Type B tendencies more than during tax season. However, by some stroke of luck, he would routinely get his taxes filed every single year—just under the deadline—and never have an issue.

In early June, Marcus’s luck ran out.


It was during his usual biweekly stroll back from his mailbox when he spotted the envelope. Relatively plain looking, it stood out among the dozens of brightly colored letters and grocery bargain advertisements. The moment he tore open the side of the envelope and slid out its contents, his Type B personality switched to Type A.

Marcus had been audited.

The Moral of the Story

Even without knowing exactly why Marcus was audited, it probably could have been avoided. Here are a few ways he could have prevented the IRS audit.

  1. He should have been more organized. When organization isn’t your forte, it’s easy to lose track of receipts, tax forms, and run the risk of filing an incomplete return. Fortunately, “organization” doesn’t have to be extreme. Even a single file, pile, or inbox folder will make your work easier.
  2. He could have hired a tax prep service. Marcus clearly doesn’t love taxes and paperwork, so an easy solution would be to hire someone who does! A tax preparation company would have spotted what he didn’t, and if he was still audited, could defend him during the IRS audit process.

Tax Preparation Horror Stories: Face Your Tax Fears!

We may be experts at the tax preparation arts, but that doesn’t mean they should be scary to everyone who isn’t. All it takes is a few good lessons, and you’ll be able to bravely file a tax return you can be proud of. We think these tax preparation horror stories can help.

If you’re still afraid, don’t be. We’ve dispelled the tax monster for thousands of clients over the years, and we can do it for you, too. With that option on the table, filing taxes isn’t so scary anymore, huh?


Ready to get started?