Making the Leap from a "Real Job" to Freelancing
by Kathy Sena

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As a full-time freelancer, I'm often asked "How did you make the transition from your 'day job' to this? "My answer? Slowly and carefully. In my case, I spent several years making the move from "technical writer with a journalism degree" to full-time freelance writer, editor and columnist. Here are a few tips for making the leap from employee to business owner (while continuing to pay the mortgage):

Target your market. Even in the early stages of planning your freelance career, it pays to start thinking about what type of clients you'll want to work with. (For example, I decided initially that I wanted to split my time evenly between magazine writing and writing for corporate clients. I've since moved to writing almost exclusively for magazines, newspapers and Web sites.) Making a list of those potential clients will lead you to the next step.

Start moonlighting. Keep your job, but start spending your off hours going after small, part-time assignments with your targeted markets. By day, for instance, I wrote technical documents for an aerospace company. By night, I queried magazines and started researching the corporate clients on my list.

Build that portfolio. When it comes to selling your services to potential clients, you know you can do the job. Chances are, you've been doing a great job for your employer for years. Unfortunately, when you're in business for yourself, most potential clients want to know that someone else has already taken a chance on you -- with great results. So start collecting those clips and samples.

I lived a schizophrenic life for quite a while -- writing about radar systems all day and writing articles for Weight Watchers Magazine and Cosmopolitan in my "spare" time. But by the time I began full-time freelancing, I had collected clips from 15 different magazines; samples from my aerospace job; and samples from several vastly different corporate clients (a bed and breakfast, a computer distributor, and a pharmaceutical company). If you're just starting out, volunteer to write a newsletter for a non-profit group. Or create a brochure for a friend's business. While you won't see an immediate return on your volunteer efforts, the clips and samples will pay off down the road.

Invest in yourself. Spend some money on professional-looking business cards and letterhead. Take a class in small business accounting or newsletter design. Upgrade your computer equipment, if necessary. After all, one of the reasons to slowly make the leap into freelancing is so you can help finance your new venture with your current salary.

Become visible. Become a regular contributor to an on-line writers' group. You'll learn a lot from other members, and your regular contributions to the forum will go a long way toward establishing your name.

Get out of the house. Don't get too chummy with your modem. You'll want to attend professional meetings to learn what other freelancers are doing and to spread the word about what you have to offer. Writers' conferences can also provide great contacts and a big motivational boost.

Consider switching to a part-time job. At a certain point, you should have a sizable collection of clips and a good feel for the types of businesses in your community that could benefit from your services. It's time to think about making your move. Starting out with a part-time job (in addition to signing on your first few clients) can add to your feeling of security and to your bottom line during those lean, early months. When I left my aerospace job, I negotiated a four-day-a-week writing job with a computer products distributor. On Mondays (and nights... and weekends...) I edited a monthly health supplement for the Los Angeles Times -- my first official "client."

Make the leap! Finally, the day will come when you decide to become a full-time freelancer. It won't be painless, but if you've followed your plan all along, you can make it a fairly smooth transition. For instance, when I decided to officially start my full-time business, I presented a written proposal to my boss at the computer-products-distribution company, showing her the advantages of being a client of Sena Communications. For the next several years, that company was one of my largest clients. Remember, just because you're leaving a company's employment doesn't mean they don't still need your services. The difference is, now you're invoicing them and choosing your own lunch hour.

Starting your own freelance business is exciting. It's also a potential nightmare if you leave the security of your day job too soon. But armed with a step-by-step plan, you can launch your business, keep your clients happy, and maybe have a little money left over for a bottle of champagne after you've paid the mortgage.

After all, you've earned the right to celebrate!

Find Out More...

Balancing Act: Ten Reasons to Keep Your Day Job, by Denene Brox

To Plunge or Not to Plunge? Becoming a Full-Time Freelancer, by Moira Allen

Fifty Tips on Taking the Plunge, by Moira Allen

Ready to Quit Your Day Job? by Hasmita Chander

To Job or Not to Job: A Writer's Question, by Antonio Graceffo

Copyright © 2007 Kathy Sena
This article may not be reprinted without the author's written permission.

Kathy Sena's writing has appeared in Newsweek, Woman's Day, USA Today and many other publications. Visit her blog at


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