Let’s take the diving board approach to this topic: Should you be a freelancer? If the answer is you have to be, fine. If you think you might want to, then answer a few questions that could determine whether you sink or swim. How will you handle paying all of your payroll taxes (traditional employees only pay half), health insurance and office expenses? Keep in mind that you won't get paid for organizing your work, marketing yourself and anything else you might do at a regular job that is not directly billable. You also won’t have an IT person to fix your computer, your spouse will ask you to run errands because your time is "flexible," your in-laws will wonder when you are going to get a "real" job.
Still thinking about it? Okay, here’s how it happened for me.
I have always had the temperament to be a freelancer. I like a wide field of topics, I’m not fond of office culture, I take deadlines seriously and I prefer the client-provider dynamic to the boss-employee. There’s more—I don’t get sick to my stomach when work dries up temporarily and I can live through a monsoon of assignments. These, I believe, are essential attributes to being a happy freelancer. The working in the pajamas bit—not a draw. Many freelancers I know get their own office, eventually.
I did not instantly jump into a career as a freelance journalist and I don’t know many who did. I started as a reporter at the Lake of the Ozarks, chasing down crime stories, writing human-interest pieces, snapping "grip-and-grins" at the local bank. I did not love the work, but it was perfect preparation. Then I edited two newspapers, one in Illinois and the other in Wisconsin. I learned how to copy edit, teach my staff the basics and plan a publication every morning that had to be out the door by noon. Then I became the Publications Editor at the Kansas City Public Library, where I learned to write promotional and development copy.
What came out of those experiences were three invaluable tools for a freelancer—contacts, work samples and experience. They are ordered by importance. My first freelance gig, which was at The Kansas City Star while I was still working full-time, came from two different contacts. My "clips," or published samples of writing from the Star, got me work from other publications. Finally, I landed a contract with America Online that sprung me into fulltime freelancing.
You have to sell yourself. You have to come up with good ideas that catch people’s attention. And it is much easier if you know someone who can help. One thing leads to another.
But nothing lasts forever. I have been freelancing for 10 years now and some clients stayed the same, most changed. Managing your clientele is essential to stay afloat. There are two kinds of mistakes worth mentioning here.
First mistake—some writers work hard to publish in a variety of publications, spending an abundant amount of time on pitches and query letters. The good sellers end up with a long list of publications, but very little steady work. They are not cultivating their relationships with clients and, perhaps, not delivering articles that are as good or better than what they promised.
Second mistake—some freelancers rely on just one or two clients for all of their work. (This was my mistake early.) I’m convinced that contractors of all sorts should spend some part of their time looking for new clients and, when overloaded, try to shrink the size of a specific client’s workload before dropping it all together. I’ve had one client for 10 years that I, at times, considered dropping. I could never bring myself to do it. Thank goodness, because during hard times that client kept the work coming.
This next advice may be obvious, but it’s worth saying anyway. No matter what creative work you do—writing, photography, graphic design, you name it—be good at it. If you are just getting started, get some honest feedback from professionals. Take a class that promises critique and listen to it. Sending out sub-par work is no way to start this career. I feel this is particularly true for would-be writers. I know it looks easy when you read it. I know your English teacher or your aunt or your neighbor told you to think about writing as a career. Trust them, but verify.
Be good at your work and be professional too. Don’t whine, don’t miss deadlines, don’t oversell what you can do, leave the daytime dramas to Susan Lucci. Nothing creates client loyalty like being a good person who works hard. That’s important, because this business is competitive.
One last piece of advice—be realistic. Don’t expect to start at Time Magazine or the New Yorker. Understand the media market—look for Web sites and publications that eagerly seek writers. Get some clips. On the other hand, beware of scams and bad deals from Internet content mills. If just anyone can write for a Web site, then do you seriously think there’s a future in it?
I am usually an upbeat person who likes to make people feel good about their hopes and dreams. As I was writing this essay, I knew it would not come across that way. So let me end on a positive note. Freelance writing is wonderful work and has democratic tendencies. What I mean by that is if you work hard, think like a craftsperson and sell, sell, sell, you could make a splash in this business.
Michael Humphrey has been a freelance journalist and writing teacher since 1999. He is a native of Arvada, Colo. and a graduate William Jewell College.
Working for Yourself: Law & Taxes for Independent Contractors, Freelancers & Consultants 
By Stephen Fishman
Careers in Writing: Freelancing and Creative Writing 
Institute for Career Research