The Freelancer’s Hustle

Choire Sicha’s new book chronicles the panicked, fax-filled, poverty-waged life that keeps writers coming back for more

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“Very Recent History” by Choire Sicha

The opening pages of Choire Sicha’s Very Recent History: An Entirely Factual Account of a Year (c. AD 2009) in a Large City, released Tuesday, paint an accurate portrait of New York as it stood in 2009. Sicha describes the disadvantages of fluorescent lighting in an office, the painfully expensive commodity that is public transport in New York and even the nuances of contemporary marriage.

It has the same time-capsule charm as a book many of us read and were fascinated by in elementary school, Motel of the Mysteries by David Macaulayin which the world was destroyed and future generations were left to wonder at what objects like a toilet might have been for us.

One of Sicha’s first mysteries preserved for future readers is the life of a freelance writer circa 2009. Sicha’s character, John, makes just over $13,000 a year. For anyone who has treated freelance writing as an entry-level job, this figure is probably as haunting as it is hilarious.

Sicha’s interpretation of freelance life is most revealing when he attempts to enlighten the reader on the way a freelancer pays taxes, mainly because Sicha has trouble articulating how exactly it all happens.

(MORE: Beware of Simple Solutions to the Tax Code)

Since a writer isn’t a temporary worker, even though technically freelance work is a temporary assignment, an employer isn’t responsible for a portion of Social Security, nor are taxes deducted from the final check. As a result, for a young writer who hasn’t yet learned that a summer job with a regular paycheck is taxed differently from freelance work, it can be particularly confusing to learn that $1,000 isn’t actually $1,000, but is really more like $750, even though until April it’s physically possible to spend the $250 on well drinks or a new iPod.

Failure to understand this means that at some point in the year, freelancers will have to scurry and write something else for slightly more than $250 in order to pay back the amount of money they thought was theirs to spend. A surplus, a writer learns, is actually a deficit.

There are a few subtle aspects of freelancing that Sicha forgets to mention. Sicha also does not cover the editorial shakedown, a practice that involves composing polite notes to editors because some editors seem rather forgetful when it comes time to pay. The only recourse is to send tactful e-mail reminders. A response comes quickly, sometimes in as little as two minutes: “I didn’t forget, I’ll put it through now!”

Seems friendly enough, but nothing is being put through, and there won’t be a paycheck anytime soon. It may take another three such e-mails to get the point across, which, the very act of writing can be panic-inducing, because while the editor is late in paying, a freelance writer never wants to step on an editor’s feet or become too much of a pest. After a long day, you start to feel like a mafia caporegime on collection day, only in this case you can’t kick the doors off some midtown accountant’s office and hold someone’s hand over a stovetop.

(MORE: How to Rack Up Debt and Ruin Your Life)

Sicha also neglected to point out that many publications ask writers to fax over a new contract and a new tax form for every story they submit. Indeed, many publications still do not accept digital signatures and don’t use the word fax as a general stand-in term for “sending over a document,” but actually require writers to locate and use a fax machine.

Sicha’s protagonist does engage in perhaps the most popular freelance tradition: convincing oneself that there is something subtle and even romantic about freelance work. “He didn’t have to be anywhere, he didn’t have to get up early and go into the office, any office, every day,” Sicha writes.

Freelancers like to think of themselves as they once were: mercenaries, weapons for hire, restless artists who (now thanks to Obamacare) are subject to the will of no other person. As a freelancer, it is not so much that one is afforded the opportunity to be anywhere one pleases, but rather, a freelancer belongs nowhere and must convince himself that it is a choice as opposed to a condition of being unemployable. This so-called freedom to be anywhere is nice in theory, but often it is this very lack of structure that prevents a freelancer from working, as opposed to sitting at home and watching Judge Judy.

The unspoken humor of this passage goes beyond the embittered tone and pseudo objectivity of the description; for anyone who has freelanced, the drawbacks are, at any particular moment, incredibly annoying but are still unable to obscure the advantages. The appeal of freelance work is that success or productivity in that particular field is often more rewarding than work done for a day job. Freelance work is a rare opportunity to work on becoming the writer one hopes to be, eventually. It is a hustle, and hardly a noble one, but one that is still difficult to knock. And things like “dental insurance” or “401(k)” are really only theories and social constructs anyway.

MORE: The End of the Full-Time Salaried Job