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The taxman don't scare me...

"You got somethin' to say sucka? You wanna get audited?"

You probably already know this if you have any money at all and you're not so destitute that your idea of Web browsing is staring at gutter spiders in the street.

TurboTax is the greatest piece of software ever.

Because it organizes you and makes your taxes easy? Not really.

Because it's cheap? Yeah, but that's not why I love it.

TurboTax is like a friend who saw you pick your nose, but won't tell anybody about it. TurboTax makes it easy to cheat on your taxes, and even makes you fell good about it.

Now, let's just pause for a second. I am not saying you should cheat on your taxes. You should never cheat on your taxes. That's just wrong.

All I'm saying is that if tax fraud were an outright robbery, TurboTax would make a really good getaway car driver.

I do not cheat on my taxes. But (ahem) if I ever (cough) wanted to (spit), TurboTax would just make it that much easier. It's like an extremely friendly bouncer:


TurboTax Bouncer: You're 21, right?

19-year-old: Um, no, actually I'm not.

TurboTax Bouncer: Let me rephrase that: You're not too young to be in this club, right?

19-year-old: What? Oh! Yeah. I'm totally 21.

TurboTax Bouncer: That's what I thought.


It's not so much the stuff that TurboTax asks you; it's what it doesn't ask you. You're the king of Tax Avoidance Land if you have a bad memory or you're just dumb. Or if you pretend temporarily to be mentally impaired.


TurboTax: Have you done any work in which you received payment from a company in another country, like say, Canada?

Omar: What's a "Canada?"

TurboTax: Okay, I'll take that as a "No." Next question...


My parents have a lady named "Diane" who has done their taxes for as long as I remember. I don't think I've ever met "Diane" face to face. She's always been this faceless entity who does my parents' taxes and answers the odd question whenever a situation with my own taxes came up.


Mom: Remember when you were asking if you could deduct all those "Spankie" devices you bought because you wrote about them on your Web site?

Omar: Yeah?

Mom: Diane said no.

Omar: Damn.


"Diane" is exactly the faceless character that I imagined "Diane" from Twin Peaks to be. In fact, I shared a kinship with that show, imagining my parents forwarding their tax queries to "Diane" via microcassette recorder.

When I got to college, and strayed far enough from the homestead that Diane couldn't roll me into the family taxes, my parents suggested I go to H&R Block, the country's largest fly-by-night organization. You know how around March, you suddenly see H&R Block everywhere and then it disappears right after Easter? They're like the bad Halloween store in the mall that only opens around late September and is housed where the old musty video arcade used to be.

For about three years, I had H&R Block do my taxes, and with only one nice exception, the people who did my taxes were surly, borderline incompetent and they never had answers to any of my (albeit sometimes silly) questions.

It would go like this:


Omar: Okay, I write from home a lot and use my home computer for a lot of my freelance writing. Can't I deduct some of the computer upgrades I did this year? Oh, and I spent about $100 on printer toner. And can't I deduct part of my rent since I use my home office for business purposes?

H&R Blockhead: Well, you can, but you shouldn't.

Omar: What do you mean?

H&R Blockhead: It's not worth it.

Omar: Not worth it? I spent like almost $700 upgrading my computer. I thought writers got all kinds of tax breaks for office supplies and trips and stuff as long as they use it in something published for money. And I thought the room where I write could be deduced. I pay rent out the ass. Isn't there a line in the 1040 for "Out the Ass Rent?"

H&R Blockhead: (long silence)

Omar: Well?

H&R Blockhead: Yes, technically. But you'd have to keep a log of each time you used your computer or office supplies for business purposes.

Omar: A log? You mean like keep part of a tree under my desk?

H&R Blockhead: (even longer silence) You'd have to keep a detailed log showing each time you used your computer and for how long you used it.

Omar: That's the most ridiculous thing I've ever heard. Who actually does that?

H&R Blockhead: Nobody.

Omar: So this tax rule is useless.

H&R Blockhead: Yes.

Omar: Shit. How much do I owe you?

H&R Blockhead: More than your refund is worth.


More tax terror ==>


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