The 5 stages of freelance tax grief

Apr 3, 2015

Some of you may find taxes painless, because you are well-organized and responsible about the entire process.

This post is for the rest of us.

Stage 1: Denial

It’ll be easy, right? You kept pretty good track of your receipts this year, right? Um, okay, so most of them are curled in a slowly-disintegrating ball of paper at the bottom of your closet, getting regularly dripped on by your rain boots. And you haven’t gotten 1099s from three separate clients and you’re pretty sure that one contractor actually ended up fleeing the country and maybe you should have been saving more than the change rattling around in your retro He-Man coin bank (not deductible, by the way).

But… deep breaths.

Hey, how bad will it REALLY be if you just sorta forgot about taxes this year?

Okay, very bad. Okay, yes, that is how they took Capone down. But you aren’t making people sleep with da fishes or whacking stool pigeons, or whatever! You’re harmless! You’re just a wittle defencewess fweewancer twying to scwatch out a wiving! Surely the Government doesn’t need YOUR information!

… dammit.

Stage 2: Anger

WHY? WHY do you do this to yourself every year, subject yourself to all of this disorganization and subsequent angst? There are people who meticulously itemize every expense, who keep their business and personal finances pristine, who probably work out five times a week and floss three times a day and never get asked by Netflix if “they’re still watching” after six hours and eat only organic raw locally-sourced avocadoes and their hair never gets frizzy and they never feel inadequate doing the Saturday New York Times crossword puzzle and WHY can’t you be more like THEM?

You know what? You should not even pay taxes, because you should not even earn money. Money is evil. You are going to move to a cave in the woods and eat only honey that the bees will give you WILLINGLY and then everybody will be sorry.

You’ll be like Thoreau. Thoreau of the Bees.


Stage 3: Bargaining

If you can count half of your lunches out as expenses and not get audited, you will become such a good person. Like… Angelina Jolie PR-item good. You’ll adopt a half-blind hedgehog and nurse it back to health. You’ll happily donate half of your free time to helping your mother with her computer (she spilled coffee on it again; also, what is a Snapchat, and why?). You will cease wasting energy scrolling through your high school enemy’s online photo albums and making witty but fundamentally unfair observations. You will stop glaring at people on the subway even when they block the doorway like dazed cattle headed to the stockyard. You will meditate. You will crochet. You will radiate love and goodwill towards all humankind. You will hear birds sing! And smell flowers! And you will appreciate life…

… if, please oh please God, you just do not get audited this year, even though you definitely deserve to because you’ll misplace a zero somewhere because your math is haphazard at best because you NEVER STUDIED IN CALCULUS, DID YOU? DID YOU?!!!


Stage 4: Depression

So you’re now on your second glass of cheap wine and seventh high-fructose-laden cookie, curled up in a nest of cryptically-labeled receipts (what does “January meeting thing” even mean?) and papers containing messy calculations. Buck up, kiddo! Things aren’t so bad. You can do this!

… why are these receipts all wet? Oh, right. The tears.

Stage 5: Acceptance

Give in. Call an accountant. Scrape together your sad little lists and chicken-scratched math, and sit white-knuckled across from her as she does your taxes a) legally b) well.

Write a melodramatic blog post about freelancer tax prep. What a wild ride, huh? But, phew, at least now your taxes are done forever and you’ll never have to do them agai-------



Begin collecting 2015 Ball o’ Receipts.

Kate Hamill lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.