My Son Did His Taxes for the First Time. Rage Ensued.

Nothing focuses the mind quite so intently on the sheer stupidity of government as doing your taxes. What is taken from us is excessive, the intrusiveness is maddening, and the rules are byzantine, which is the distilled essence of most of our interactions with the state. So, it was with a certain degree of anticipation that I told my son that, after working hard at the supermarket in addition to his homeschooling and martial arts, he would have to file his first tax return. Much fun ensued.

Given the complexity of our returns, involving a trust, commercial real estate, and business entities, my wife and I pay an accountant to wrangle our taxes. But before Anthony heads down that path, we thought he should understand what it means to fill out his own return and hope for the best.

"The whole system is based on the premise that the government already knows how much you owe, but won't tell you. You have to guess," I told my son.

"What happens if you guess wrong?" he asked.

"Well, there's no actual right answer in terms of how much you're supposed to pay. If you can even reach them, IRS employees contradict each other all the time because nobody really understands the rules. But if you come up with something they don't like, they just might destroy your life."

"Oh, shit," he said.

At the IRS website, we clicked on the "File Your Taxes for Free" link which touted "a public-private partnership between the IRS and many tax preparation and filing software industry companies who provide their online tax preparation and filing for free." The first option was for "guided tax preparation" involving "simple questions" and letting "software do the work." That sounded like a great way to undergo an expensive and potentially perilous process without understanding what the hell is happening. We opted for "free fillable forms" instead, which walked Anthony through a 1040.

"What the fuck does that even mean?" my son asked multiple times as he worked his way through the usual questions about wages, capital gains, deductions, withholding and the like.

"Pull up the instructions," I told him, as if they offered much in the way of help.

He doggedly plowed through the dense verbiage. Because I'm not a complete monster, I helped him through the spots where he was stuck. When the 1040 itself was finished, he had to reenter all of the information from his W-2 because scanning has not yet come to the world of free fillable forms. Then, he submitted his return.

Two days later he received an email rejecting his tax return. For reasons unknown, rejections consist of gibberish such as "XML data has failed schema validation. cvc-complex-type.2.4.b." You copy the email into the IRS's Error Search Tool to get a (sort of) clear explanation that could have been included in the rejection to begin with. In Anthony's case, we narrowed it to a missing zip code for his employer on the W-2 form. I could have sworn he filled that in, but who knows? He entered the zip and resubmitted.

Two days later, he received another rejection. This time the Error Search Tool told him that he had checked "Yes" to "the Third-Party Designee area at the bottom of Form 1040" without including a required PIN. That was very helpful, except that he'd printed the forms before submitting and the box in question was definitely checked "No," so no PIN was required.

Fortunately, the public library had a rack of paper 1040 forms and booklets. Anthony copied the information to the old-school form, stuck it and his W-2 in an envelope with a stamp, and mailed it off.

"Let the IRS do it the hard way," I told him. "It's more work for them, which is all the more reason to send them paper forms."

Then it was on to state taxes. To give Arizona credit, it was actually possible to file a return through the means provided. All Anthony had to do was navigate past the Arizona Department of Revenue (AZDOR)'s prominent warning of "intermittent issues with AZTaxes.gov. Technical staff are actively working to resolve the matter as quickly as possible. We apologize for the inconvenience." Then he clicked on the box promising that he could "E-File My Taxes for Free" only to find the AZDOR, like the IRS, was trying to slough him off on a "fast, safe and free way to do your tax return online" through partnered services.

"Oh, hell no," we both said after the experience with federal taxes.

It took an internet search to find that the AZDOR had PDFs of its 140 (individual income tax) form in both it-does-the-math and simple printable formats on its website, along with instructions. We chose the calculating form. It was our own fault that we overlooked the instruction to use it only with stand-alone Acrobat software, since it locks up in web browsers. With just a little drama, Anthony got his return filled out and mailed to the Department of Revenue.

As expected, my son was less than enthusiastic about the experience, amidst much cursing and references to official incompetence. He could have bypassed a lot of the hassle by going with a tax preparer, or one of the answer-easy-questions services. That's certainly what the tax collectors prefer.

"Filing electronically with direct deposit and avoiding a paper tax return is more important than ever this year to avoid refund delays," the IRS urged in January. "If you need a tax refund quickly, do not file on paper – use software, a trusted tax professional or Free File on IRS.gov."

But that would also bypass the full experience of preparing a tax return and wondering over its arcane terminology and the judgment calls necessary for navigating the form's many entries. It reduces the pain of filing (though not of watching money disappear from your pay) while also diminishing comprehension of the process. There's a lot of value in having to stop and ask yourself, "What the fuck does that even mean?" as my son did many times while wandering through a minefield of rules.

With part-time income and refunds due, the stakes are low for Anthony. This is a good stage in life for him to experience filling out a 1040 form and a state return and to wonder if he got it right. When his income rises and there's more at risk, he'll be able to go to a professional tax preparer with a better understanding of just what he's sparing himself.

And when his accountants mumble curses under their breath, as mine frequently does, and complain of the arcane red tape and incompetence of tax collectors, my son will know exactly what they mean.