Image by Sam Woolley

Oh holy living fuck, Tax Day is Monday! Have you filed yet? Do you owe penalties? SHIT YOU’RE GOING TO FUCKING JAIL. You better run. I know a place in Mexico where you can lie low for a bit while the Feds go searching for you. It’ll buy you the time you need, and then you can jump a shipping freighter to South Africa. NO TIME TO PACK, FUCKWIPE. We gotta go!

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Okay, all right. We should calm down. I’m calm. Are you calm? Let’s be calm for a moment and think this through. Even if you are a responsible citizen who pays his or her taxes in a timely fashion, Tax Day can still conjure a remarkable amount of angst. It is the cop in your rearview. And the cruel truth is that taxes only grow more prominent in your psyche as life wears on. If you’re a swinging swingle who works just one full-time job, rents a place, and has no large assets of any kind, you should get down on your hands and knees and thank the Good Lord that you are young and carefree and only think of taxes as an annual nuisance of a form to complete. You can go back to drinking frozen margaritas at a bar with a large porch immediately.

Because there will come a time, my friend, when taxes become more complicated than that. Oh, do they ever become complicated. The byzantine nature of the American tax code has become accepted lore at this point. Even children know that taxes aren’t to be fucked with, and that the arrival of an IRS tax packet in the mail will turn you Republican on the spot. Once you find yourself with a house, or children, or freelance income, or a rental boat service that makes marginal profits, you become ensnared in the IRS’ silken web. You will never extract yourself.

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But here’s the scariest part … you won’t WANT to extract yourself. Every old man I’ve ever known has been obsessed with minimizing tax penalties. They are in THE GAME. They’ll leave money untouched and transfer it from place to place, ensuring the tax basis will be reduced to nothing so long as they don’t spend the cash until they are 316 years of age. Online tax forums are maxed out with grandpas swapping tips on how to save 10 bucks by applying for a commercial fishing license. When I talk to my dad on the phone, the conversation usually lasts 40 seconds UNLESS taxes are the subject, in which case the conversation runs longer than a fucking Judd Apatow movie. Americans may hate taxes, but they positively ADORE finding ways to skirt them. By 2018, the U.S. accounting industry will post annual revenues of $180 BILLION DOLLARS.

You cannot avoid any of this. If you want to make money, then you will have to pay taxes. And the more money you make, the more concerned you’ll be about keeping taxes down, wondering if you’re somehow missing out on thousands of dollars in savings by not reallocating your shit into a Cayman Islands 529 college fund under a fictional LLC (you probably are). And there’s always some fuckface who gets his taxes done right at the beginning of year and is walking around with some fat refund check, waving it in your face like a prick. I hate those people. I am at the age now where my outrage at rich fuckers hiding their money in offshore shell companies has been surpassed by my need to know how they pulled it off. WOW CAN I DO THAT?!

Alas, I cannot. And neither will you. But since we’re just two days away from the deadline, here are some last-minute reminders to keep you out of Poundtown. By no means are these reminders complete, or even accurate! I implore you to ask around for a decent tax professional, or listen to my fellow curmudgeons as they include their own tips down in the bowels of Kinja. Let’s get into the pain:

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1. Go through all your expenses. Even if you use an accountant, you will save more money if you have a detailed and accurate record of your spending throughout the year. Save all your bank and credit card statements and keep them in chronological order in a file. Sometimes I even enjoy trying to solve the mystery of some credit-card line item from way back in February. “Hey, $250 to Assticklers, Inc.? What was that? OH WAIT NOW I REMEMBER.”

2. Use Turbotax. Turbotax is expensive, obnoxious, and requires endless updates. And the people at Intuit are shitbags who want to CONSTANTLY upsell you on crap. No matter. If you do your own taxes, Turbotax is the best you’re gonna do. I hate that I need it.

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3. Don’t forget to pay your estimated quarterly taxes. If you’re a freelancer (and you are, because America no longer has any full-time jobs), you need to pay your taxes on a quarterly basis using 1040-ES vouchers. The IRS will actually calculate your estimated payments for you based on last year’s tax form. But if you’re starting from scratch, you need to account for all the untaxed money you made each quarter, and then do all the annoying calculations provided in the voucher packet. I hope you have a calculator handy. You also need to pay estimated taxes to your STATE as well, unless you live in a scam state like Florida. Once you’ve ponied up, you are free to sit back and fume as Obama hosts a State Dinner for the premier of Uruguay. I BETTER NOT BE PAYING FOR THAT CEVICHE.

4. If you work from home, do NOT overstate the size of your home office. You can knock money off your tax bill by using a home office, but the IRS will come and burrow deep into your rectum if you try to claim that the office takes up 50 percent of your house. They aren’t stupid. They’ll storm into your house, take measurements, and then discover your home “office” also doubles as the ping pong room. JAIL.

5. That said, try to write off all the shit you can. There’s a whole lot of shit that the IRS will let you partially deduct: mortgage payments, day care, cell phone bills, self-employed healthcare, car depreciation, that apartment you rented for your mistress under an alias, etc. Turbotax will ask you about all this and then ask you, “Do you REALLY use this for business only?” And then you will shit your pants for a moment, and then press ahead anyway.

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6. Unless something is really wrong with you, you’re probably not gonna be able to deduct medical expenses. Did you spend more than 10 percent of your income on medical expenses? Congratulations, you’ve met the deduction threshold. Also, you are dying.

7. The more money you stash away, the less taxes you will pay. FACT: You can open a SEP IRA account right now, this instant, and have it applied to the previous tax year. You can only do this before Tax Day. As long as you put any money into an individual retirement fund (pick an index fund if you’re a financial dolt like I am), that money becomes tax-exempt so long as you never take it out prior to retirement age.

8. Be sure you have accounted for ALL vital tax documents. Every W2. Every 1099 you receive (this is freelance income). Every 1099-DIV you get from an investment service. A lot of companies have gone paperless with tax documents now, so DO NOT FORGET a digital tax form if that’s all your company sends you. The IRS will notice if it’s missing. Somehow, despite having to wade through tens of millions of tax returns, the IRS notices EVERYTHING. They’ll never arrest anyone at Goldman Sachs for driving the economy into a ditch. But they’ll hunt you down for that under-the-table lemonade-stand revenue.

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9. Your ideal refund check is $0. If you get a big refund check, tax experts will tell you that you did a poor job by overpaying the government, allowing them to make money off the interest instead of you. Of course, that wildly overestimates your ability to manage your own money, but you understand the theory. You want to pay just the right amount of taxes during the year. Not too much and not too little. Got it? Good.

Now go finish those taxes and then get loaded. You’ve earned it.