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The adventures of a freelance writer doing his own taxes for the first time
BY CHRIS BERDIK

In the spirit of forthright disclosure that marks every tax season, I have something to confess. While I’ve always paid my share, this is the first year I filed my own income-tax returns. My prior freeloading resulted from a mix of laziness, obliging relatives, and, of course, laziness. But after obtaining the latest tax-preparation software, I determined that this year would be different. So, on a recent wintry weekend, armed with a thick file of invoices and receipts, I sat before my computer ready to assume the yoke of responsible citizenship.

The tax software was user-friendly enough. From the start, onscreen tax professionals, sporting solid red ties and modest strings of pearls, offered up bits of revenue wisdom. And as I filled out my name, address, and Social Security number, I felt the smooth pleasure of past-mastery.

But then the computer asked for my occupation. That’s where the trouble started.

It so happens that 2002 was also my first year subsisting entirely as a freelance writer and editor, which apparently isn’t a lifestyle the IRS encourages, or even really comprehends. Not that I blame them. Sometimes I don’t get it myself. For instance, my income came from about 10 different sources last year, and the largest chunk wasn’t from any newspaper or magazine. It was from a group of Iraqi dissidents who’d smuggled documents out of Iraq and paid me to copyedit the English translations.

And it wasn’t just my audit-inviting Iraqi connections. As the software moved along, its income and expense queries appeared like round holes before the square pegs of my financial existence. Very little of it made sense, and most of it seemed to be costing me money. Indeed, to the IRS, I wasn’t the creative, ink-stained chronicler that I sometimes fancied myself; I was a business, a " sole proprietor " who’d escaped a year of income withholding and was about to get slammed with one mother of a tax bill. Soon, I was mired in " Schedule C, " reporting the drips and drabs of my income with my eyes darting around my desk in search of " depreciating assets " and my hands scribbling frantic business-expense calculations for every notebook, ink cartridge, and mini-cassette tape I’d purchased.

It all seemed so pitiful. If only I’d had the sense to incorporate myself in the Bahamas, like Enron and the other corporate high rollers, I could have avoided this misery. But I was far from the tropics. It was freezing outside, and I owed a shitload to the government.

According to the onscreen tax professionals, I wasn’t even allowed a so-called home-office deduction, since the desk in my bedroom wasn’t exclusively a place of business: in my cramped quarters, the desk routinely doubles as a place to write personal e-mail, a lunch counter, a knickknack haven, and, on some weekends, a laundry basket.

Still, I read each question with the eagerness of a mutt at the pound eyeing a new visitor, hoping against hope that liberation might be at hand. Instead, I encountered only the growing sense that the tax code had been written with somebody else in mind. Was I storing any inventory? Did I have any capital-loss carryovers from previous years? What about seller-financed-mortgage interest? No ... no ... huh? Even the possibilities listed under " special situations " weren’t encouraging: did I earn any money while in jail? Had I died before filing this return?

I’m certainly not the only person who’s felt estranged by the tax code. Most likely, it’s not an uncommon sensation for single, childless, non-home-owning folks who don’t earn much and aren’t heavily invested in the stock market. And in many tax-related ways, I suspect I have things easy. Plus, in all seriousness, I salute those who have normal jobs, earn regular salaries, own homes, tend to 401(k)s, and fit more snugly into the IRS framework. They work damn hard, and they give our economy life. I even tip my hat to the massive corporations who strategize about market share, brand cultivation, and tax avoidance. Their TV commercials are so musical and catchy.

But something else was going on. As marginal as this filing process made me feel, something hinted at my deeper unity with every American taxpayer. I mean, I could get preachy and say I disliked supporting a government that invested more in missiles and prisons than in education and affordable housing, or that I disapproved of a tax cut that mainly benefited the über-wealthy. True, but that wouldn’t tell the whole story. The deeper truth was that, like so many of my fellow Americans, I was wrestling Uncle Sam for every stinkin’ nickel, and I was doing so with every fiber of my bleeding, liberal heart.

Long ago, a European finance minister claimed that the art of taxation was " plucking the goose to obtain the largest possible amount of feathers with the smallest possible amount of hissing. " Well, there I was, at my home-office-cum-lunch-counter-cum-laundry-basket, hissing away, just as millions of other Americans had hissed before and would hiss again. It was kind of a stirring notion, in a way, Walt Whitman–esque. On that bleak winter’s afternoon, I heard America hissing — the mechanic, the carpenter, the shoemaker, and me, the sole proprietor. And to think I’d ever considered incorporating myself in the Bahamas.

Chris Berdik, now headquartered offshore, can be reached at cberdik@hotmail.com

Issue Date: April 3 - 10, 2003
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