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AITA for telling my mom/boss that if she files me as a 1099, I'm filing an SS‑8 with the IRS?

· 3 min read

The Original Drama​

I work for my mom’s small business and, honestly, I act like a normal employee—fixed schedule, supervisor on call, company equipment, all that jazz. The only thing that’s been a real head‑scratcher is her refusal to put me on the official employee roster. Every time I suggest proper paperwork, she calls me “annoying” or “making it complicated.”

Fast‑forward: I quit (or got fired—blame the cosmic irony) in October. Suddenly, my mom’s big revelation: “I’ll file you as a 1099 independent contractor.”

Now, I’m not a freelancer. I don’t own a company, I don’t set my own hours, and I definitely don’t have a “client list.” I’m an employee, and if she misclassifies me, I’ll end up paying the entire tax bill twice—because the IRS will see the red flag and make me pay both the employer’s and employee’s side.

I tried to keep it chill. “If you file me as a 1099, I’ll file an SS‑8 to get the IRS to officially say, ‘Nah, this is an employee.’”
Her reply via email:

“It breaks my heart to see things going in this direction. If you really want to take things to that level, I could mention the years of cash bartending income that was never reported, but I prefer to move forward.”

So, Mom, if you’re going to play the “tax villain,” maybe start by playing the “employee” role.

The Comments – Reddit Style​

“People who want to cheat on taxes are so tiresome. I was married to one.”

Bottom line: Don’t let the IRS come to your house and demand you pay for Mom’s laziness. She’ll feel the heat—literally.

“NTA. I feel like you already know this, but your mom sucks so much you have to question it.”

If Mom’s boss moves, you’re the employee, not the “tax‑fraud suspect.”

“Has she deducted any payroll taxes from your paychecks?”

If your paycheck is a straight‑up “gross” number, Mom’s probably already set you up for a tax nightmare.

“Sure, but OP's mom is trying to pass the employer's tax burden to OP as well.”

Because nothing screams “family business” like double‑taxing your own kid.

“When an employee is misclassified as an independent contractor the proper way to handle it is to file Form SS‑8 and to include Form 8919.”

That’s the IRS’s way of saying, “We’ll do the math, you just pay the tax. No guilt trips.”

“This may not however, result in as much of a tax savings as someone might think.”

Spoiler: You still owe regular income tax. Mom still owes the employer share. It’s a tax tango.

TL;DR​

Mom thinks she can reclassify her employee as a 1099 contractor to dodge payroll taxes. I calmly threatened an SS‑8, and she tried to guilt‑trip me with “cash bartending income” drama. Bottom line: I’m the employee, not a fraudster. If Mom wants to play “tax villain,” she better start paying her side of the bill.