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10 Reasons the Freelance Life is a Good Life

Writer’s block. A bad economy. Dwindling markets. Freelancing can be frustrating—but there’s still plenty of motivation to write on. Here's why. by Art Spikol

No writer likes a blank screen.

I am sitting here with one—but comfortably, thanks to La Colombe, a coffeehouse where I often write, conveniently located just 3,700 miles west of Paris. While it pours here in Philadelphia, and the working class rushes by in a profusion of umbrellas, I wait for inspiration.

I have always believed that almost any activity is better than inactivity, so I’m having a latte. At times like this, when the words are slow in coming, I remember why writing is often called a lonely, isolating business. But such descriptions are less about the writing than about the writer.

It’s easy to forget that there are big advantages to the independent freelance writing life, no matter how bad times may be. There are many truly great reasons for being a freelancer, regardless of what you write—marketing copy, magazine pieces or even books on contract.

When it’s tough to stay at the keyboard, take a moment away from the rain to savor 10 of the best.

Most of what you need is already in your head: a reasonable command of the language, a knack for stringing words together, a love for sharing what you know and a curiosity about what you don’t. Few actual materials are required: a computer, camera and phone, all of which you probably have, plus a few incidentals that are available for less than the cost of dinner at a mediocre restaurant. Your writing business is one of the least expensive companies you can own—no warehouse, no sales office and, most important, no bureaucrats (unless you happen to be one).

When someone doesn’t want to hire you, it’s like someone not wanting to marry you: Any reason is good enough. But most editors don’t need to see you in person, so you won’t lose the assignment because you’re too old or too fat. By way of full disclosure, nobody currently working at WD has met me; my persona is less Brad Pitt and more Wizard of Oz, the unseen guy behind the curtain, though my getting-assignments ploy avoids terms such as unemployed or between jobs or trying to re-enter the work force now that the kids are gone (I never seek sympathy with a hard-luck story). And while I have too much respect for language to use euphemisms—e.g., my dog Sugar was euthanized, not put to sleep—I don’t mind calling myself an editorial consultant, author, world traveler, jogger or anything else that contains a hint of reality. Nor should you.

Outside of one or two formal occasions, I haven’t worn a tie in more than 30 years. And I remember a cartoon that showed a sign hanging above the door of a publishing company: “Through this portal pass the worst-dressed people in the world.” So as not to spoil your own standing, you might invest in some nice T-shirts and jeans (a hole in the knee will add credibility) for those rare occasions when an editor will want to take a chance on reducing property values by inviting you over. Don’t forget to wear your best running shoes.

Or you don’t. A blessing, but also a curse, since you may be inclined to squander your time. It’s easy to justify a walk in the park—there might be a story there. If there isn’t, that’s a story, too. It’s all in the packaging (remember the small-town paper’s headline “Mayor Dies,” which sold a lot of copies; the next day, when things were slower, the headline read “Mayor Dead for Second Day”).

If you’re going to freelance, what you need more than anything is discipline, because if you waste your time, there’s nobody else to blame. I worked on a novel from 6–8 a.m. every morning for a year while holding down a full-time job. I slept less, but I survived. And I sold it.

Many employers know there’s almost nothing worse than employees (seriously), and as a freelancer—you don’t need any! I had employees once, and I found myself performing daily functions as psychiatrist, clergyman, narc, lawyer and marriage counselor. Whereas you—you are in the enviable position of being the CEO of a small business. No meetings, no mission statements, no people failing to show up because of a few flurries of snow, no unions, no hiring, no firing. And you can work naked without asking some middle manager for permission.

When I got my first job (a clerk/typist), my boss was into psychoanalysis; if I was late to work because of a flat tire, he’d say I’d subconsciously wanted it to happen. If I called the stuff on my desk “stuff,” he’d say I had no respect for its importance. That’s when I began lusting for a business of my own. It took several years for me to get it, but after that boss, I had a good run of employers who let me grow and move on and up. Having a job, in fact, is an excellent base from which to initiate your entrepreneurship; it’s easier to build a base of clients while you’ve got a steady paycheck you can rely on until you get off the ground.

Remember, though, that self-employment also has its drawbacks: You may think you’re working alone in your study, but you do still have bosses—the markets that buy your work. It will be your work, though, and your business and your accounts receivable. Which brings us to the fact that you have …

Freelance writers select their own employers. They query the outlets for which they want to write. (More often than not, all you’re looking for is a home for something you already have.) Ad copywriters are an exception—they have to suffer the indignity of pleasing the agency’s clients, but that’s why they probably make more money than you. The other side of that is that you, the independent writer, have the greater opportunity to strike it rich—a screenplay, a bestseller. Don’t be intimidated by the fame of others; they were all anonymous once and soon enough will be so again. And don’t think of it as climbing the ladder of success—it takes too long. You’re a writer, and writers can advance in quantum leaps, any of which can change a life. When a door opens, take the elevator.

Today, a great piece of writing can be executed in a closet, on a park bench or riding the subway. You can write about malpractice from your gurney in the intensive care unit. Words can fit anywhere that will accommodate a laptop. I have an office, but I work best where I feel more connected—so here I am in a noisy, chaotic coffee-
house. If you feel that writing is isolating, work on your blockbuster in a nice little place like this one, with its tax-deductible lattes and biscotti. Which brings me to …

You can deduct subscriptions, dining expenses, office items, an iPhone, cars, insurance, research trips and plenty more, depending on what you write and how much you earn. Naturally, there are catches—for instance, you’ll have to be able to prove your deductions are business expenses rather than personal ones. And if it’s business, the IRS will expect you to make a profit. But if and when you do, the write-offs make it all worth it.

In most fields, it takes time to become an expert. But publish an article on a specific subject, and readers will assume that you really know something.

I was once asked to do a magazine piece about Keogh retirement plans. I had absolutely no interest in the subject. After the story was published, many readers thought I was an expert on the plans simply because I knew how to interview financial consultants. I could’ve spent my life speaking to men’s clubs. A close call.

If you should ever be unfortunate enough to get a full-time job, try to console yourself with the salary, vacation and benefits—just don’t forget that when it comes to your writing, you’re still the boss. It’s a wonderful life, freelancing, whether it’s your only job, or one you do on the side. And the good and bad news is, it’s up to you to protect it.

Learn how to develop article ideas magazine editors will find irresistible by considering:
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