The Business of Freelancing

The Complete Writer
Section VIII: The Writing Life…
Sittin’ by the Dock of the Bay?

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The Business of Freelancing

Someone once asked Don Dedera, author of ten books and innumerable magazine and newspaper articles, how he accounted for his success as a freelance writer.

“I attribute it to two things,” Dedera replied. “A working typewriter and a working wife.”

Freelance writing is a tough, unremunerative affair, not one for the frail ego or the free spender. Average incomes range from $4,000 to upwards of $50,000 a year, depending on the survey. An annual take for a freelancer of $25,000 can be considered exceptional. If one’s ambition is to make a living as a writer or editor, one is really better off to get a job on a magazine or in a publishing house. Editors rarely develop much loyalty toward freelance contractors, and publishers try to extract as much work in return for as little pay and commitment as possible. Turnover in the publishing industry is breathtaking. So is the bankruptcy rate; when a magazine is in trouble, the first supplier it will short is the writer. If you have any ideas about freelancing to support yourself while you stay home with the kids after school, live in a Rocky Mountain retreat, and work whatever hours you please, think again.

Given these grim facts, one might sensibly ask why on earth anyone would take up such a dismal occupation.

Three good reasons:

  1. It’s a way to eke out a few pennies and work a small tax break between jobs. Like many “business consultants,” writers who call themselves freelancers often mean they’re unemployed. By freelancing, you can keep your hand in while you look for regular work.
  2. Because it lets newcomers display talents to many potential employers, freelancing can open the back door to jobs in journalism. After selling several stories to an acceptable magazine, you let the editors know you need a job. Then you wait and keep writing for them. Sooner or later, someone leaves and you have the inside track for the vacant position. This is the hard way to get hired, but for many a writer-turned-editor, it has worked.
  3. For all its agony, frustration, and penury, freelancing is just plain fun. It’s one of the few jobs in which you never do the same thing twice and you truly learn something new every day. You meet people you would never encounter otherwise, and you get to ask all sorts of nosy questions. You go places and see things that a desk-bound editor can only dream of while she reads your copy. Established writers decide what they will write about and decline projects that don’t interest them—a choice you don’t have on staff. And yes, you get to pick your hours: any eighteen hours of the day you like.

Building a professional image

Let’s assume, since office rentals are expensive, that you will work from your home. This alone tends to diminish your credibility.

If you are to sell magazine articles—or any other kind of writing—you must go about it in a businesslike way. Editors and other clients are not interested in dealing with amateurs. To persuade potential clients that you are a pro, you must act and appear professional. Among the strategies for accomplishing this:

  • Establish a web site and be sure it looks professional. Services such as and Blogger offer free server space; however, to engineer a professional-looking URL, one that doesn’t end in, for example), you’ll have to pay something, and you may have endure annoying conditions and ads placed on your site. GoDaddy and BlueHost are among the several web hosts that charge reasonable prices for server space and assert no sovereignty over your site.
  • Hire a professional web designer to establish and lay out your site, even if it’s based on a WordPress template. Once you have a good design and understand how to add to and take away from it, you can change content to keep your facts up to date. But unless you are a trained web designer, you should avoid a DIY job on this important tool.
  • Create a letterhead with matching envelopes and business cards. You can do this in Word and store the results on your computer, or, for not very much money, have quick printers at places like Kinko’s or OfficeMax do the job for you.
  • Establish a presence on LinkedIn, Facebook, and Twitter. Do not, ever, publish frivolous posts or images on these sites! Do not troll, and never engage trolls in arguments or pissing matches. Keep your image friendly but professional on all social media.
  • Join trade organizations. The best writer’s groups for these purposes, in my experience, are the Society for Technical Communication, the Society for Professional Journalists, and the American Society of Journalists and Authors. Business groups are even more useful for those who seek remunerative corporate accounts; joining the local Chamber of Commerce will bring you into contact with many potential clients.

Operating your business

Set aside time every day for writing. Treat the time precisely as though you were in an office. Use it only for work. Friends, relatives and neighbors, who generally regard work as a place, not an activity, will assume you are free to operate at their beck and call. Resist impositions on your work time, at all costs.

Set goals. Once you’ve staked out some time, you need to organize it by setting goals and arranging your time to meet them.

Assignments provide built-in goals. On your calendar, block out the time you’ll need for backgrounding, interviews, and writing. Plan to finish a first draft several days before the real deadline; then schedule a day to let the copy cool and a day or two for revising and polishing.

Remember to build delivery time into your schedule. If your editor or client accepts e-mail delivery, send the attachment a day ahead of the agreed-upon deadline, to account for Murphy’s Law. This will give you time to resend should your editor not receive your message. If you’re shipping hard copy, figure four working days to send first-class mail coast-to-coast.

Meanwhile, you should aim to send out a certain number of queries in any given period. A reasonable goal is to launch four good, solid proposals each month. When matters lapse, it can take about three months to land a new assignment. So the freelance writer must always stay in circulation. While you’re working on an assignment, search out new ideas, devise fresh angles, write up proposals, and keep them in the mail until they sell.

These, then, might be your short-term goals:

  • To meet your deadlines
  • To develop a certain number of ideas each month.
  • To keep several proposals circulating at all times

Long-term goals address what you want to accomplish over, say, a year—or a lifetime. These are issues you must articulate for yourself and perhaps change as you mature. Writers have various motives. The most common probably follow these lines:

  • To get published, anywhere, at any price
  • To make money
  • To break into national publications
  • To write a book
  • To get a full-time job in journalism
  • To quit worrying about money and produce high-quality writing on subjects that matter for people who care

Market yourself. A website, a blog, and a presence on one or more social media sites not only help to build a professional image, they let people know what you have done, what you can do, and what you want to do. Membership in professional groups and business organizations also helps build visibility in your community.

If you want to write magazine and newspaper stories on a freelance basis, you must to learn to pitch your ideas to editors through the use of the query letter: a formal proposal targeting a specific market. This is a skill unto itself: in one to two pages, you need to show an editor a) that you can write for her or his publication; b) that you understand the publication’s audience and purpose; and c) that you have an idea that fits. Probably the finest discussion of this skill appears in chapter 18 of Bruce Garrison’s Professional Feature Writing. Rather than reinvent the wheel, I refer you to his excellent work.

Most of the Writer’s Digest books on freelance writing include passages or chapters on query letter. Surprisingly little advice appears online, but Monica Shaw at Writer’s Residence provides a nice collection of successful examples.[1]

Successful freelancers sell all the time. When your blog hits the top 100 in its niche, when your book hits print, when you win a writing award, send out press releases to all the local and regional media. If you have a specialty, call radio talk shows and offer to speak on matters of current interest. Write short articles for local shoppers and business publications, and be sure your bio tells readers what you do and how to reach you.

Watch good sales agents in action. And read a few how-to manuals on sales technique. You can use much of what you learn in your own marketing efforts. The key is to stay in motion. Never stop hustling. Never allow yourself to become discouraged, never waste time with people who aren’t live prospects, and always make yourself keep trying to sell every day.

Keep good records. You must maintain records of all your transactions for tax purposes. Keep every receipt, every canceled check, and evidence of any financial exchange for at least five years. Large accordion-style folders are cheap and work nicely for this purpose.

Make records of any toll telephone calls. Some magazines will pay these expenses. You can write the rest off your taxes, but only if you can prove you incurred them for business.

For the same reasons, maintain careful records of your automobile mileage. What you can’t get a publisher to pay for, you can write off your taxes.

Keep a copy of every manuscript you submit, as well as contracts and correspondence with editors. Obviously, electronic data must be backed up regularly. It’s a good idea to have an external hard drive for this purpose. However, remember: all hard drives fail sooner or later. So, it’s useful to back everything up twice, once on an external hard drive and once on a flash drive. You may want to look into free or moderately priced server space on the Internet, such as DropBox or Carbonite. Some writers keep hard copy of all important papers, including manuscripts.

It’s wise to keep old copy, research notes, and interview tapes (or digital audio files) indefinitely. Often you can recycle this data, and occasionally some question comes up that can be answered by something you wrote five years before. Consider using inexpensive cardboard file boxes to store hard copy in a closet or garage. These boxes are also convenient for collecting sample magazines and hard-copy writer’s guidelines.

Keep the production line moving. Your business’s “production line” generates work for pay. Keep it moving steadily. If your client doesn’t give you a deadline, set one of your own. And always meet your deadlines, even if it means working all night to do so.

An odd phenomenon afflicts most writers. I call it “work-avoidance maneuvers.” One starts the day with delaying tactics to keep from sitting down to work: brew another pot of coffee, write a personal letter, water the plants. Because I’ve never met a writer who doesn’t do this routinely, I think it serves a psychological purpose. Some projects, for example, seem so huge you must back into them to keep from feeling overwhelmed.

You can indulge the work-avoidance impulse in constructive ways. Try reading the newspaper, studying a potential target magazine, or reviewing and polishing yesterday’s copy.

If your day’s schedule requires you to telephone people you don’t know—always a stressful task—start the morning with the toughest call. This makes the rest of the day feel like skateboarding along the beach.

When you have a hard time beginning a story, skip the lead and start at the nut paragraph or some later point in the piece. You can work out the lead later. If that trick doesn’t work, try writing a first-person narrative, like a letter to a friend or sympathetic editor, describing what you saw and heard as you interviewed people and did your legwork. If you still can’t get a handle on the piece, set it aside and work on some other assignment; the momentum of accomplishing a small project will carry through to the more difficult one.

Use telecommunications professionally. Consider the telephone a business instrument during business hours. Ring tones for your cell phone should be conservative and discreet; not cutesy, loud, or annoying. Voicemail messages must be professional-sounding and give callers the impression that they are calling an office. If you have a predilection for land lines and your family uses the phone heavily, consider installing a separate line in your office (do not tell the phone company that you will be using it for business, to avoid being charged at a higher rate). Better, get a VoIP service that will let you use your desk phones and also provides NoMoRobo, the only effective phone solicitation blocker.

When crafting a voicemail message, women may want to imply that several people work at the establishment; “none of us can come to the phone right now.” It is unwise to advertise that you are at an address alone or that no one is likely to be there for awhile.

Whenever you call people, they’re always “in a meeting.” This means you spend your day leaving word all over town—or all over the country. When someone returns your call, it is to your advantage to sound like a professional, not like a stay-at-home mom or dad with a laptop on the kitchen table waiting for the brownies to bake.

When I began freelancing, I once left word with a top executive at a Fortune 500 electronics firm. He called back, and I answered the phone with my customary housewifely “Hullo?”

A long, eloquent silence ensued. He clearly thought he had the wrong number or something eccentric was going on.

Business people do not want to talk with eccentrics. During business hours, answer the phone as though you were in an office—with your name or with your business’s name. Set up your voicemail to sound businesslike, too. This is an effective way to build credibility.

Accounting. In this area, you must hire expert help. It’s fine—even advisable—to keep your books in Quicken or at an online budgeting site like But while TurboTax works well for many folks’ personal tax returns, a business return is another matter. Have a tax professional, preferably a certified public accountant, prepare your tax return, at least the first time you fill one out as a self-employed writer. People who claim deductions for home offices make tax collectors itch. Because the tax laws are complex and capricious, you should never try to deal with the Internal Revenue Service yourself.

Deposit the money you earn from freelancing in a separate checking account, and pay your business expenses from that account. This much simplifies the task of keeping track of receipts and business expenses, and, by never mixing freelance income with other money, you can help a tax preparer see how much you earn and how much you spend on business costs. Using a separate telephone line only for business calls also simplifies your bookkeeping.

To deduct the costs of running a home office, you must prove you are truly in business—not playing at a hobby. You have to be earning money, and you must make a profit three years out of five.

The Internal Revenue Service requires self-employed workers to establish a permanent, separate place within the home to use exclusively as an office. The space must be demarcated from the rest of the dwelling with room dividers or portable walls; to be safe, however, you should reserve a separate room for this purpose. You must use the space on a regular basis, not on and off, and it must be your principal place of business. If you have an office somewhere else, you can’t deduct a home office used for the same business.

Once you establish yourself as a for-profit enterprise, you may deduct “ordinary and necessary expenses.” These include rent, utilities, supplies, research costs, travel, subscriptions to professional magazines, membership in trade groups, certain conventions and meetings, communications and postage costs, and the like. Depreciate expensive assets, such as a computer, over several years; IRS rules govern the period over which you must spread the deduction of depreciable items. You are permitted to take a one-time deduction for such equipment, but the deduction may not exceed the income you earned in the year of the purchase.

The possibility of a tax audit is the best of all possible reasons to establish a well organized filing system, electronically and in hard copy. Copies of query letters, proposals, contracts, statements, receipts, and manuscripts will serve as evidence that you are trying to make a profit. If you are audited, you will have to produce all your receipts and expense records for the years in which you are challenged. Keep careful, accurate records and store them for at least five years. Among these records, you should include your appointment calendars.

Literary agents

Magazine writers do not need agents, and few agents will try to market magazine articles, because there’s not enough money in it.

Agents are useful in marketing certain kinds of books. Most writers find agents by word of mouth, through recommendations from other writers. Agencies list themselves in Writer’s Market and Literary Marketplace. To choose one blind, pick out several names and start telephoning.

If you should seek an agent, bear this in mind: legitimate literary agents do not charge reading fees. Avoid those who offer to think about marketing your work for a price.

Literary agents offer your work to prospective buyers and negotiate contracts and fees favorable to you. They retain 10 percent of the take as a commission and pass the other 90 percent along to you. Their services are worth this premium because agents usually can obtain higher rates than a writer can negotiate alone. If an agent agrees to represent you, he or she may provide advice and editorial guidance as a service—for free. Most effective agents live in or near New York City, because they depend on person-to-person contact with book editors and publishers, whose offices are concentrated on the East Coast.

Other jobs for freelance writers

If you have the hustle, business has the money. Some people make a good living writing for businesses. They write annual reports; edit in-house newsletters; write press releases, reference and credit reports, company manuals, company histories, brochures, proposals—you name it.

Get this work by word of mouth, advertising, and chutzpah. One method is to print up a professionally polished brochure describing your manifold skills and take it door-to-door, introducing yourself and offering your services. Another is by advertising in business and trade journals. If you have any gift at translating technical language into plain English, advertise yourself in county and state medical, legal, dental, and veterinary journals.

Put out the word to your editors that you’re interested in working for businesses. Magazines often receive calls from people seeking writers for brochures, newsletters, or press releases.

You can also take your brochure to printers, typesetters, graphic artists, and fast-print franchise outlets. These entrepreneurs often have customers who need writers.

Public relations agencies are another source of freelance jobs. When business is good, agencies may have more work than staff members can handle, and they will hire freelancers to write press releases. Writers with magazine credits may be asked to hack out self-interested trade journal articles for clients, at much higher rates than the magazine would pay. Agency fees to freelancers range from $20 to $120 an hour.

Associations and nonprofit organizations also need writers. They may not pay as well as businesses, although some do. They especially need people to write or edit newsletters.

You can write book reviews. You can write blog entries for pay. You can write resumés for job seekers. You can ghost-write memoirs. You can write genealogies. You can do outsourced public information for government agencies. You can handle public relations for schools and libraries.

Everybody needs a writer. All you have to do is see the need and fill it.