The tax laws in the United States represent a wildly successful attempt to create a set of rules so complex and confusing that nobody truly understands them; sort of like the hand-to-hand combat rules in Dungeons and Dragons. Tax lawyers can spend endless happy (and billable) hours arguing about whether or not Olympic swimmer Michael Phelps can legitimately deduct the cost of an Armani suit as a business expense. (The answer is “yes,” but only if he actually wears it in the pool while competing.)

If you are unskilled at law, you might assume that the tax codes are the way they are because they’ve just sort of grown up like ivy in an untended garden or mold on cheese left too long in the bottom drawer of the refrigerator. If you think that, you’re not giving the government enough credit. Sure, at first, the tax laws grew complicated because nobody was paying attention, but once it realized what had happened, the government sensed a golden opportunity. (By which I mean they sensed an opportunity to seize your gold.)

Think about it. If the tax laws were straightforward — Mr. Cummings, please send us eighteen percent of your income or we’ll be forced to release a pack of rabid tax weasels near your home — you’d most likely pay exactly what you owe. (As an added bonus, you’d finally understand why your Fourth Grade Teacher Mrs. MacGruder was so hung up on teaching you to calculate percentages.) Unfortunately, the tax laws are convoluted — Mr. Cummings, please use table QQ to calculate your tax debt based on your adjusted gross income cross-referenced with the number of deductions you claimed in line three-point-one-four of form 1040BSG divided by your SAT score (from your first attempt, not your third) and multiplied by the inverse of the number of letters in your mother’s maiden name — so there’s no possible way you can get it right. No matter how hard you try or how many experts you hire to help you complete your taxes, you’ll make some tiny error that the IRS will use to create a genuine Federal case and you’ll end up owing thousands of dollars.

As an added benefit, all U.S. taxes are now calculated using imaginary numbers. In theory, there is some relationship between the amount of money you earn, the number of deductions you claim, and the amount which is withheld from your paycheck. The actual mathematics of this are a closely guarded secret known only to a select few IRS mathematicians and the the minions in your local Human Resources department. When you get your check, all you can do is stare at the numbers dumbfounded the way a caveman might stare at a calculus test. You could argue that they were wrong, but how would you know?

Once a year your employer is required to come clean and send you a simple document which tells you how much money you made and how much was sent to the IRS on your behalf. These numbers arrive on something called a W-2 form. Just to keep all of the various forms separate and confusing, the IRS has assigned them random numbers like 1040, 1040A, 1040EZ, 1099, 1098, 1098T, and ID10T. I suspect that the earlier forms (140, 140A, and 140EZ) were too understandable and had to be subjected to powerful mutagenic lawyer-rays until they were so complex that even the most powerful computers could not possibly understand them.
What chance, then, does the average home PC have against the awesome power of IRS forms?
Yet, year after year, thousands of us by the latest version of our tax software of choice; Tax Cut, Tax Act, Turbo Tax, Tax ME, Tax XP, Tax Vista, and the famous Mac tax program Tax Leopard. That is, if we can figure out how to install it. Remember, a lot of tax payers — I’m looking at you, Boomer generation — are reaching the age that doctors describe as “getting up there” and aren’t exactly Bill Gates’ class computer geniuses. They frequently require the assistance of their children or grandchildren to get the software installed and running.

Once the software starts, the real trouble begins.

In the ideal world, the dialogue between human and computer would be simple and easy-to-follow like an Advil commercial or an episode of Hannah Montanna.

Computer: Did you make any money this year?

Me: Yes.

Computer: Do you have any of it left?

Me: A little.

Computer: Good. Put that in an envelope and send it to the government.

Instead, possessed by the insanely complicated IRS forms and calculations, the computer’s monitor spins around and a deep voice asks disturbing questions like, “Enter the amount found on line 12a of your first W-2” or “Enter the total amount of dividends earned from stock purchased this year (do not report negative numbers)”. Once you’ve finished that, the program asks nosy questions like how many children you have, whether you rent or own, how much you donated to charity, your favorite color, whether you prefer Wilma or Betty, what you would do for a Klondike bar and how many licks it takes to get to the center of a Tootsie-Pop.

Eventually the program spits out a number and you willingly pay just to make the questions stop. Once again, the clever government ruse of making this too complex for human understanding has succeeded and you leave the transaction a little poorer, but happy to be getting out alive.