The Best Lesson I Learned From Doing My Taxes

by The Hairpin

The year I worked as a freelancer was the worst, because they TOOK my money at the end of it. I was so confused, like, “There is literally no way I could have predicted this would occur!” I was on someone’s payroll the next year, but I had been so scarred that I nervously also paid my quarterly “estimated income tax” on the freelance income that had ceased to exist. So then I got my normal return AND my EIC return, and it was twice the free money!!! Is wrong somehow? So that’s how I learned I basically don’t even have a brain, just a giant face-shaped goldfish bowl on my shoulders, with one sad, dumb goldfish swimming back and forth. — Anonymous

So I figured out a couple of years ago that nothing really bad happens if you mail your taxes a day or two late. Is that stupid? Am I the only one who sort of thought that if you tried to mail your 1099 any time past 11:59 p.m. on April 15, the mailbox/your brain would instantly explode/incinerate? Like there’s some sort of spiritual punishment and/or IRS Special Ops SWAT Team waiting to strike? OK, maybe I was. It actually turns out that the IRS just calculates whatever the late payment penalty is and then sends you another bill. Which is irritating in its own way. But still. Figuring out that the IRS doesn’t have some supernatural powers sort of chilled me out about taxes a little. — Simone Eastman

The first time I did my taxes I was working a ridiculously low-paying nonprofit job, so it took me two minutes and I got a $500 return that I spent on a last-minute trip to a music festival. I learned that that sort of thing is best not shared with my parents. — Angela Serratore

I totally have a guy who lies on all your forms and gets you more back than you basically made, and I used him two years ago but have been so scared of an audit ever since that I can barely sleep. All my friends still use him, though, because they’re greedy assholes.

Also, doing my taxes makes me feel like an idiot for not having any sort of retirement/IRA/401K or anything. I will be poor when I die. — Anonymous (a.k.a. Living in Fear of Audits)

I haven’t ever learned anything from doing my taxes, because each year I send everything late and sloppily to a faceless attorney in the city I grew up in, and then they send me a bill so large I’m not even going to say what ballpark it’s in. And then when they email me follow-up questions (“Ms. Zimmerman, can you please sign your name on the orange sheet we sent you 19 weeks ago?”), I try to respond so quickly that I “make it up to them.” Because if I’m so up-to-date on the computer, how could I possibly be as stupid as I seem from the way I handle everything else? So I guess instead of “I haven’t ever learned anything,” it’s “I learned to convince myself that tax people respect me because of the speed at which I email.” Ha. Anyway, how do I do taxes? — Edith Zimmerman

I do a fair amount of freelance work, so I can deduct a lot of expenses from my taxes. That’s great, but it also requires me to figure out everything I’ve spent in those categories. Which in turn involves lots of receipts and bank statements and such, and can be a gargantuan task if you save it all up until the last minute, which I obviously do because why would I ever deal with taxes unless I absolutely had to? So for years, when I couldn’t put it off any longer, I’d force myself to spend one very crabby Saturday afternoon wrangling my year’s worth of receipts.

That is, until a few years back, when I had a breakthrough. You see, I’d just finished reading Eat, Pray, Love (I know! I had to! For work!), and one thing she said that resonated with me at the time was the whole “I will not harbor unhealthy thoughts anymore” bit. So I was working on keeping those pissy little ships of pessimism out of my mental harbor. And thus when I found myself staring mournfully at a mountain of crumply receipts, I chose to change the way I looked at them. I realized that each expense represented a mundane little moment from the past year — a fun business dinner, a book bought for “research,” and, whoa, an insanely expensive drunken cab ride home from Midtown. It was like reading a diary or maybe more like looking at a very poorly organized scrapbook. I found after a while that reflecting on all these little purchases got me thinking about the bigger moments and also made me feel like I’d actually done a lot of fun things in the span of those 12 months. (I know, I’m a regular Elizabeth Gilbert over here!) I will not go so far as to claim that this revelation has made me look forward to doing my taxes, but at least now I don’t dread the whole thing quite as much as I used to. — Cassie Murdoch

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