A Friday Chat About Taxes

Do them!

MEGAN: Hi! I’m over-caffeinated and ready to CHAT IT UP.

NICOLE: I haven’t had my caffeine yet but I am also ready to CHAT! Let’s do it! Happy Friday!

MEGAN: Happy Friday to you too! I honestly consider it a miracle that we make it to the end of the week, so I am feeling very #blessed to be able to talk to you. Also, in an hour or so, I’m going to sit down with my accountant and, ugh, skldjflksd, do my taxes.

NICOLE: Good on you for getting them done early! Will it be the kind of thing where you have one meeting and then two weeks later you get a huge envelope in the mail with your taxes, along with a blue Post-it arrow pointing towards the amount you have to pay?

MEGAN: Sadly, no, because I LOVE the Post-it arrow. It feels very adult, like I’m signing the deed to a house or something. I believe I’m Skyping with an accountant from Brass Taxes. We will have the one meeting, they’ll ask me some questions about my estimates for expenses and then I will “digitally sign” a bunch of crap. Then I’ll pay a lot of money. Where are you in your tax journey?

NICOLE: Despite my being anxious that I was too late to set up a tax convo with my CPA, she is less anxious about that. Today I’m going to scan and email my old tax returns at her request. Then, if I understand it correctly, she’s going to ask me for a bunch of stuff (1099s, deductions, etc.) and then we’ll have a meeting. Later, my taxes will arrive completed. Then I’ll pay a lot of money. Or maybe not, depending on how good my estimated taxes were this year!

MEGAN: I need to get on that estimated tax train, I think. On Monday, I sat down and tried to do my own taxes because hey, why not. I did them twice in Turbo Tax just for “fun” and the number that I owed was QUITE LARGE, mostly because I sort of forgot about being on unemployment for a portion of this year and subsequently forgot about the fact that I didn’t pay taxes on that money. So! Hopefully my accountant is good.

NICOLE: Are unemployment taxes taken out of unemployment benefits? I guess they must be.

MEGAN: That is a very good question. The way that I understood it was that I had the option to have taxes withheld from my unemployment benefits and I didn’t do that because unemployment in New York is about $425 a week. This is like, the third time, I had been on unemployment in my career thus far, and I’m pretty sure that every time, I panicked, decided not to have them take taxes out and then been mad at myself when tax season rolled around.

NICOLE: It makes sense, though. You need to pay your rent and utilities first, and you can pay your taxes out of the money you earn when you’re employed again. Or, if that scenario doesn’t pan out, you can also pay your taxes in installments. Etc.

MEGAN: Yeah, and also, $425 is…not a lot of money. It’s not NOT a lot of money, it’s obviously better than nothing and I am grateful and glad, but something about taking the additional hit from having my taxes taken out of it made me feel bad. So I didn’t! And now I have to pay!

But it’s fine.

NICOLE: It’s interesting that we should feel grateful for a system that takes what it wants out of our paychecks (without consulting us) and then pays us what it wants when we’re unemployed (again without consulting us), but I get it. Also if we don’t like our taxes or our social safety net we’re supposed to vote, right?

MEGAN: LOL VOTING. Yes. If we don’t like what’s happening, we’re supposed to vote. And yeah, feeling “grateful” is kind of weird! But that’s how systems like this gaslight you, right?

NICOLE: The tax tables and unemployment benefits are all public information, so it’s not like they’re saying one thing and doing another. But the information is so complicated. I should in theory be able to do my taxes myself. But I can’t — and it’s not because I can’t do math.

MEGAN: Right?!? I was convinced that I could do my taxes by myself, even though they feel “complicated” because of all the 1099s, but when I sat down to actually do it, I was worried that I’d somehow screw it up so bad that the IRS would come for me.

NICOLE: Me too. Or that I’d end up paying way more than I needed to because I didn’t understand the questions on the form.

MEGAN: THE QUESTIONS. Turbo Tax also makes it very easy for you, like it’s dumbed down to the point where your hand is being held the entire time and still, I found myself wondering if I was just bad at reading comprehension or if this was really just Too Much.

NICOLE: I’m trying to remember the article where I read this, but there was some cautionary tale about a self-employed individual claiming a teacher supply deduction because he taught the occasional writing course, but that deduction only applies to full-time K-12 teachers. Or something. Of course, the tax software just asked “are you a teacher?” and he clicked “yes.”

MEGAN: Yes! The tax software is quite vague. Like, “Do you have a home office?” leads to “Do you have a space in your home that you do work specifically and only work?” which leads to “If this space is in your bedroom, maybe it counts, but if it’s your couch, it definitely doesn’t also if it’s in the laundry room and the washing machine happens to be there, well sorry bud.” You end up not trusting yourself.

NICOLE: Remember how I told you the other day that I ate lunch at a table, not at my desk? Gotta keep that home office pure. Except my “home office” is so small that I barely have any deductible space — plus I just realized that sometimes I watch TV at my standing desk, which probably ruins everything.

MEGAN: Here’s a thought — what if you got rid of your bed! And your couch! And your bookshelves! Just kidding, please don’t do that.

NICOLE: Plenty of people have bookshelves in their offices! And couches! (If they’re at a certain level of employment that grants them an entire office, not just a cube!) Also, plenty of people watch YouTube or Amazon or Netflix at their desks, even during working hours, or they take lunch at their desk and watch videos, or… look, everyone else gets to use their desk for multiple things, why can’t we?

MEGAN: We deserve it. We really do.

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