Apple-Obsessed Author Fella

The Freelance Writer’s Guide To Stabbing Oneself In The Eye With A Highlighter, A.K.A., “Taxes”

It’s that time of the year again! When I go to a lady and I vomit forth a bushel of faded crumpled receipts and then we talk for a half-hour or hour about my “work,” and then a week later she writes up this very nice helpful packet detailing exactly how much money the Tax Imp is going to steal from me while I sleep… the way cats thieve breath from infants. Good times.

I’ve had a few people now say, “Chuck, you should do a post about freelancers and taxes. It would be helpful!” to which I ask, “How would a post in which I weep and gnash my teeth and headbutt the computer monitor help anybody?” But, apparently, it will, so here goes.

Let me put forth this most critical of caveats: I am not an expert. I write stories about vampires. I write blog posts about unicorns and Bourbon. I am not to be trusted with critical financial information. You want help on the tax code, you go see Dan O’Shea, who is both a) a really great writer and b) a guy whose brain has been shattered by the intricacies of the American tax system. Anything you read here should be taken with a grain of rice big enough to hollow out and use as a luxury cruise liner. Capiche?

Do Not Pass Go, Do Not Collect Your $200: Get An Accountant

The tax code is a labyrinth, and at its heart lurks a terrible minotaur that will hold you down, teabag you, poke you in the eyes with his horns, then eat your bowels for brunch.

In much the same way that you would not arrange a trip up into the Himalayas without getting yourself a bad-ass Sherpa, you should not attempt to handle the trip into Tax Hell yourself. Taxes are not merely complex. They are downright Byzantine, and this is doubly true for the freelancer.

You may say, “But what about software? Like Bobo’s Tax App or the Tax-Bot 12000?” My opinion is: get an accountant. A human accountant. Because we cannot trust robots with our financial future. Robots secretly hate us for our ability to have tickle fights and eat ice cream, and so they will betray you. Seriously, though, a human being will tell you things, respond to questions, and explain stuff that software cannot.

That being said, not every accountant is born equal. (And ohh, they are born, not made. Anybody who is willing to do this is the product of nature, not nurture — like the birth of a hero willing to slay dread beasts.) I had one accountant who was a real dog-fucker, that guy. Didn’t tell me shit. Didn’t interact with me. Didn’t get me squared away with critical information. The next accountant was the polar opposite. Informative, interactive, actually friendly. Mileage varies. Get recommendations. Test ’em out.

Also To Be Gotten: Booze, Booze, Boozy Booze

Listen, I’m not condoning the use of alcohol during the varying stages of tax prep and resolution, I’m just saying — *wink wink, mimes drinking from a big bottle of wine, whisky, or motor oil, then goes on to mime crying in the shower, shooting heroin in between toes, and praying to all the gods in all the heavens for a glimpse of forgiveness* Booze is your little tax buddy. Like that animated Paper Clip in Microsoft Office?

Except, y’know, less annoying.

Pay Your Shit Quarterly

Throughout the year, you must, you must, you must increase your bust pay your taxes quarterly. When I first started freelancing, nobody told me this. Not even that dickwad accountant I had. Turns out, yeah, you actually really need to. Otherwise, they penalize you. I always wondered, “Hey, why is it every year a big bare-chested dude in an executioner’s mask breaks down my door, steals my money, then pummels me in the kidneys with his giant hamhock hands? Did I order this over the Internet? Damn you, Amazon Prime!” But, no, no, it’s because I wasn’t paying quarterly.

If you don’t want to pay more than you already do, pay quarterly. An accountant can get you set up with estimated quarterly taxes. The accountant is a mighty wizard who can read the languages of madmen.

Sweet Deductions Born From Between An Angel’s Thighs

*chorus of singing Cherubim*

Provided you’re not spending more than you make and shooting up a signal flare for the IRS to see, you have at your luxury the ability to deduct lots of wonderful things as a freelance writer. Take a meeting in a coffee shop? Buy books for research? Blog hosting fees? Travel to cons? Lunch with other writers? Magazine subscriptions? Office supplies? Electronics? Porn? Okay, maybe not porn. But if a purchase is for your business, ta-da, deduction. I have a room in my house that is my office, and any resources that go toward maintaining this space (including oil, electricity, etc) are figured into the equation.

All this only works if you save your receipts.

Invest, too, in highlighters. And accordion folders. And small foreign children to put it all together (in fact, you can deduct what you pay them!).

It really is critical if you keep some kind of organization. Like, what I do is I shove receipts in various pockets, drawers, wallets, cubbyholes and orifices, and then when tax time comes, I run around like Mike the Headless Chicken gathering up all my lost and forgotten receipts. So. Yeah. … On second thought, maybe use a file drawer. (To be fair, I have a file drawer set up for this purpose thanks to my wife. But halfway through the year I sort of… usually forget about it? Ennhh. Oops.)

Are You Your Own Corporation?

Some freelancers will tell you that they performed the grim magical mechanics (re: paperwork) and have become their own corporation and that this helps them come tax time. This may be entirely accurate, and they can (and should!) sound off below on the value of doing so. I am not yet that guy, as my accountant has advised me that it wouldn’t be all that beneficial for me at this time. I am not yet Chuck Wendig Enterprises, Inc (Terribleminds Division). I do not have my own corporate cyberpunk army of dudes in suits and sunglasses with powerful ocular implants and laser fingers. But I will. You just watch! Pyoo! Pyoo!

What I’m Saying Is, Prepare To Pay Out The Crap Can

Everybody pays a lot of taxes, but freelancers also don’t put in for things like Social Security or, I dunno, paying for your state senator’s anal bleaching fees or whatever. So, freelancers kick in a little extra cream. It’s not actually more than other people pay, I don’t think, but it feels like it, and so we often emerge from tax season wondering exactly who bent us over a trashcan and took us at both ends with a corncob.

Sound Off

I know a number of freelancers — writers, artists, knights of the realm, hobo warriors — orbit in the space around this blog, so feel free to descend from the rheumy nebula and sound off on your tax strategies. Do you use software, or an accountant? Are you the mythical “S-Corp?” What do you deduct that others do not? What booze do you drink? Where are your pants? Have you found a way to deduct pantslessness?