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Tax and Flu Season Feel the Same

The last time I felt this nauseated, angry and anxious was when I had morning sickness.

I never threw up over homework assignments in high school. Not even when I was a sleep deprived, hormonal, overachiever taking an absurd amount of AP classes. I’m not pregnant, I don’t have the flu, but I am beginning to start to think about possibly getting my taxes together. I’m already having nightmares. I’m convinced that sometime in the distant future, a menacing man in a well-pressed suit will ask to see my work, and if I did my homework wrong, I’ll go to jail.

Courtesy Amblin Entertainment

Courtesy Amblin Entertainment

I’m not even trying to hide any money from the IRS. Quite to the contrary, my ego demands that I declare every penny I earn as a “real artist.” But I’m probably forgetting something important because none of this makes any intuitive sense to me, and I’ve always been pretty bad at worksheets. I am an underpaid freelance everything, so there is a lot of paperwork.

In the below video, the author explains her current tax system.

“I think I could be killed if I don’t pay them.”

Some of this stuff I’m supposed to collect throughout the year, like receipts for…things. Some of it is mailed to me by a motley crew of “employers” and “contractors,” some of whom I don’t remember. Other stuff I’m supposed just to have, I think, like invoices. Maybe? Does insurance matter yet? Can I mail them my insurance card? I don’t have a solid grasp on what separates the forms that matter, from the rest of the nonsense in my mailbox, and my life.

If I get audited, can I bring a character witness?

Marisa Tomei in “My Cousin Vinny” - courtesy 20th century fox

Marisa Tomei in “My Cousin Vinny” – courtesy 20th-century fox

What does auditing entail? Presumably more paperwork, with higher stakes.
The fact that we trust people to keep track of this much paperwork feels like a trap. Have you met people? We’re terrible at this! “Artists” and “freelancers” are ESPECIALLY terrible at this.

Last year I sat down with an accountant to try to create some kind of system. Instead, whatever he said only emboldened my worst instincts. So all year I’ve treated anything remotely “deductible” like I was playing with monopoly money. I think I picked up an expensive dinner bill with my own agent, for no reason.

It's tax deductible right? Via - http://www.thatscoop.com

“It’s tax deductible, right?” Via – http://www.thatscoop.com

I do have a box I’ve been dutifully shoving receipts into, some of which were wet. I have a presumably helpful list of things that I’m allowed to deduct, like “tolls” and “grooming equipment.” Travel seems to matter. Some of the receipts that made it into the box have helpful information on them, like what city I was in and what I bought. A lot of them don’t.

Totally tax ready Via- http://www.cogniview.com

Totally tax ready Via- http://www.cogniview.com

I don’t know how the rest of you are doing this, but I’m confident I’m doing it wrong. Which is scary, because the only thing I know about taxes is that if I do it wrong enough, I’ll go to jail.


So to all the Beautiful Broke Ass freelancers out there who are already overwhelmed with the super hard month to month math, good luck. If anyone wants to write off a drink and talk about it, let me know.

Have a drink with me

#TaxStress

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Kaytlin Bailey

Kaytlin Bailey

Kaytlin Bailey is a stand-up comic. You may have seen her on MTV's Braless, or heard her on SiriusXM radio. She writes for Vice and travels with the CAKE Comedy Tour.