How to Make it [Online and Off] in Good Times and Bad By Keith Regan

My first connection with the Internet came in 1993. Together with a fellow reporter, I devised a definition for the World Wide Web for inclusion in a newspaper story. Little did I know then what a major role the Web would play in my life.

Eight years later, I am a full-time freelance writer, thanks largely — though, importantly, not entirely — to the Internet. And while I had the good fortune of making the leap to freelancing during a strong economy, there are rules and guidelines that apply to taking the step any time.

It’s a tough life and I have the burn marks and roller coaster savings account balances to prove it. But by not relying on any one outlet or area of expertise for my income, I have managed to make a solid living and live the life I dreamed of while grinding out newspaper stories. While every case is different, these guidelines have helped me to build a $40,000 a year freelancing career in about five years.

1. Be trusting yet skeptical. Especially when I was starting out, I took a few chances. But I made sure there was a safety net and never extended myself too far with a single client. This approach helped me cut my losses last year when a dot com client abruptly filed for bankruptcy. While some of my fellow freelancers were out $5,000 or more, I have a bill for less than half that in the bankruptcy file. Send invoices as soon as they’ll be accepted and don’t be shy about asking for your money. Editors aren’t shy about asking for copy, after all.

2. Diversify. One of the oldest chestnuts of writing advice is to become a specialist. This is good advice, to a point. I say to become a specialist on not one but several topics. For instance, I write a monthly column for a tree care industry trade magazine and daily and weekly pieces on high technology and business. In the past several years, I have also specialized in educational writing and in writing about real estate. I did it mostly by throwing myself at subjects I knew little about and trusting my research skills and intelligence would get the job done. The same is true about balancing clients: My base includes a weekly business newspaper, a monthly trade magazine and a daily Web site. And don’t forget geography. For some reason, I take comfort in the fact that my writing has been bought by publications all over the U.S. and in Canada.

3. Pursue every opportunity, no matter how small it may seem. Often, great writing gigs turn up by accident. Have clips and resumes at hand and respond to every posting you see. I once applied for a part-time writing job that, it turned out, didn’t exist but had been posted in error on a job board. The editor who received my resume and clips liked what she saw, though, and before long I had a $1-a-word writing assignment — and then another and another. Having said that, let me say that I would never write for free.

4. Have faith and constantly recharge your batteries. Editors are tough characters, all the more so when times are difficult and when you never meet them face-to-face thanks to the Web. Find a support network, online or in the real world. I try to go to a writer’s conference at least once a year. If nothing else, it helps remind me that I’m doing exactly what I want to.

5. Focus on quality. Editors have difficult jobs, too. And they will forever love and reward the writers who make it a bit easier by doing the little things: Making deadline, getting facts correct and writing copy that needs little editing. When the work load is lighter, bear down even harder on each piece, making them sparkle. It won’t mean extra money right away, but this is no time to sacrifice quality.

Freelancing is a difficult, lonely business, especially when times are tough. Slower economic times mean extra digging for assignments. But having a plan can make it a little easier and a lot less scary.

Keith Regan is a freelance writer based in Massachusetts. His writing appears regularly on, where he is a news writer and columnist, in the Boston Business Journal and in TCI Magazine as well as other online and print publications.