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Here it is, the end of February. Snow on the ground. The dregs of Valentine’s Day swirling in the backwash of winter soon to end (at least if my pact with The prince of darkness holds out). If you had income last year, you’re dreading paying your taxes and are deep in the throes of tax preparation.

(If you had income last year, and aren’t planning to pay taxes, you’re busy obtaining a passport under an assumed name – Sven O’Donnell, cockroach gynecologist from Toledo – and painting your hair a different color with the kids’ water colors because buying hair dye would arouse suspicion.)

But tax evasion is a topic for another time – perhaps my upcoming Fraud Trilogy: Tax Evasion, Disposing of the Corpse and Fooling More Suckers with Monopoly Money Than Bitcoin.

Today, I’m here to help you actually defraud the government get away with it pay your taxes quickly and efficiently. If you’re hung up on also paying your taxes legally, well, there’s no time for wussies here.

Your tax preparer will tell you all the boring deductions everyone takes. Here are a few you might not have thought of.

That day you bought coffee at the gas station in Green Bay on the way to work? That’s a deduction for work supplies. How many times have you said you sang function at the office without caffeine? Even if you forget to get a seven-year-old doughnut out of the case, but don’t forget the receipt.

Get a receipt when you pay your gym membership. You’re WORKING out, right? “Work” is right there in the name of the thing you’re doing.

Make a bunch of Candy Crush in-app purchases last year? Deduct ’em! You might not have receipts, but just show the IRS auditor your wicked awesome score and I’m sure she’ll understand.


You know how socks mysteriously disappear from the dryer? They had to go somewhere, right? It’s safe to assume some other foot is benefitting from your argyle. Go ahead and claim the cost.

All those times you let another car get ahead of you on the road or let someone with fewer items go ahead of you in the checkout line. Those kind acts cost some of your precious time, time is money, friend. And money is tax deductions. It’s accounting 101, which is a number but not a deduction. See, math is fun!

Ever been in the drive-thru Starbucks one and play the “pay it forward” game? You never want to be the schmuck who doesn’t play, but inevitably the car paying your order gets away with just picking up the one venti blonde roast you ordered while the car behind youis a clown car with an order of 47 lattes and 18 brownies. That’s like feeding a small nation. And people get tax credits for that. So should you. Also, front row seats under the big top. And so much cotton candy you’ll puke.


Let’s step back for a moment and consider what we’re really doing when we pay “income tax”. As with all things economic, the best way to analyze this is through the game Monopoly. There’s a space on the Monopoly board called “Income Tax” and if you land on it, you have to pay either 10% of the value of your property and cash or a flat $200. How do you get income in Monopoly? Bankrupting your friends, of course. And screwing your friends is fun, right? Income tax is like calling your friend the morning after you drunkenly insulted him because his life choices are stupid. Which they are. But that’s a topic for another blog.

But if you follow the tax advice in this post, you can get away with paying less income tax. You’ll probably get audited and possibly prosecuted. But in taxes, as in life, it’s easier to ask forgiveness than permission.

Happy auditing!


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