My post-punk tax guy has absolutely killer taste in music: Elvis Costello, Talking Heads, the Cure. (Mercifully, for the sake of pointed kitsch, no George Harrison-sung Beatles.) And each year around this time, when I make my melancholy trip to his walk-up, my pathetic little binder of important papers tucked under my arm, I am treated to a well-curated track list as my stomach drops for two hours straight. Doing taxes is a nightmare for most of us, but for the media freelancer, it's a particularly funereal pageant.

"The money feels good, and your life you like it well," Paul Simonon sings as I sit there, shuffling and reshuffling my 1099s. Simonon wasn't singing about the plight of the modern slave to the Content Industrial Complex, but the line resonates anyway. In truth, the money does feel good, and I do like my life well enough. I'm by no means well-off, especially judging by Boston-area standards, but after 15 years of doing this, I've managed to eke out a living wage.

Stocksy

The pay structure for people in my position, or designers, artists, producers, and so on, varies wildly, but almost universally it works like this: You take on an assignment, you turn in an invoice, and you wait way too long to get paid. (Esquire does a much better job of this than most others I've worked for, for what it's worth, although there was a close call leading up to this tax day.) This is the key distinction: You don't have any taxes taken out of the payment. That can be a boon for those of us living check-to-check. If the article or photo commissioned by a publication pays $500 or $1,000, you get a full $500 or $1,000.

A prudent freelancer will dutifully squirrel away a portion of each check to clear the tab with Uncle Donny and the boys down at the IRS, and he will chip away at the bill with quarterly payments (I do an adequate job of this). But without any stable concept of how much money you make per week—some weeks it may be $5,000, others $0—there's no telling how much you're going to owe in taxes. Sitting here, watching my accountant toggle between his computer and his calculator, at turns chastising and cajoling me for my irresponsibility and foresight, is like waiting for the grand reveal at the climax of a game show—just one where you find out how many thousands of dollars you're on the hook for.

Without any stable concept of how much money you make per week, there's no telling how much you're going to owe in taxes.

This sense of slow, creeping malaise isn't unique to me, of course. The freelance economy in the U.S. is now at 55 million, or 35 percent of the total workforce, according to a survey last fall from Upwork and the Freelancers Union. Among those freelancers surveyed, a significant percentage point to the freedom that comes from being your own boss, as well as having location and scheduling flexibility. Seventy-nine percent said freelancing is more satisfying than working a traditional job. The definition of freelancer is also broad, encompassing part-timers, gig economy workers, moonlighters, and what you might think of as a "traditional" freelancer like myself.

Every year my tax guy runs through a series of questions like a doctor translating symptoms into a workable diagnosis. Have I joined any professional organizations? Do I pay any dues? Have I employed anyone else this year? No. No. No. He's trying to help me help myself. Have I considered an IRA account? If I start one now, I can get a tax credit for it, he tells me. My dude, I have barely enough money in my bank account as we speak to cover the balance of my likely tax bill. That, plus a slew of outstanding payments from a number of publications I'm hoping will arrive in time to help me save the family farm. I am not exactly thinking about my dotage at the moment. I'd be lost without him, though. A poll last week from the Pew Research Center found that 72 percent of Americans are bothered some or a lot by the complexity of the system. Like most Americans, I have no idea what I'm doing when it comes to filing.

There's a cliche online these days, where when someone says they "have the receipts," they mean they can expose someone's faults. I can't help but think about it as we go through all the possible write-offs for the year. It's like taking a tour of all the poor choices I've made, quarter by quarter. Did I purchase any large office equipment or make improvements on my home or automobile? Uh, no, but I do have 20 pages of receipts for airport pizza and GoGo in-air wifi, if that helps my case any.

The questions he's asking are helpful though, because, in truth, there is a certain amount of leeway freelancers like myself are provided when it comes to reckoning the tab. Writing about music, restaurants, and travel means I'm afforded write-offs for things that might otherwise seem like entertainment. Sounds fun, right? Yes, but no one tells you that when you get to write about fun things, it makes everything you ever enjoyed in your prior life feel like work. There's nothing that screams joyful, unburdened libertinism like keeping all your receipts at the rock show.

There's nothing that screams joyful, unburdened libertinism like keeping all your receipts at the rock show.

At some point, Patti Smith's "Free Money" comes on tax guy's playlist. It's still in my head as I leave, shell-shocked at what I owe. It's fine, I tell myself. This is the price one pays for a functioning society. I'm fortunate to be able to do my part. And surprisingly, a slight majority of Americans, 54 percent, seem to agree that they, too, pay about the right amount in taxes. It might take a couple of checks, but it's not going to ruin me. I'll just make sure to start being more frugal this year.

As I walk outside, I get a car to take me the mile and a half back to Harvard Square. It's an extravagance, but maybe I can write it off next year.

An earlier version of this post listed Joe Strummer instead of Paul Simonon. This has been corrected. We regret the error.

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