I've been freelancing full-time for the past three years and a couple of recent conversations (both live and on-line) have made me try to understand why I've been successful this time, but wasn't in any of my previous four attempts.
Each attempt to freelance full-time coincided with a job loss. This time I knew the job was doomed about a year before it ended.
My wife and I spent a great deal of time discussing the possibility of my freelancing. How much income would I need to generate and how quickly? How long could we last if I had no income? How much might we save (gas, clothing, lunches out, etc.) if I worked at home full-time?
During that year before the job ended, I put extra effort into my part-time freelancing, attempting to build a backlog of sales that would generate income into the future. (Given that I write for many pay-on-publication markets, the mss. I was selling were providing income as much as a year after the move to full-time.)
The moment I knew my day job was gone, I contacted all of my former clients and asked them to keep me in mind if they heard of any opportunities. Because I had worked in prepress, many of my clients worked for publishing companies and advertising agencies, and most of them already knew I was a writer.
Within a week, one of my former clients offered me a steady editing gig and within five months another former client also offered me a steady editing gig. With a solid income foundation under me, I was able to increase the amount of writing I did and my sales increased rapidly. I've since added a third local client--for whom I create advertising, marketing, and public relations materials--and I now have editors offering assignments to me.
Of course, I still submit a great many mss. that get tossed in slush piles all across the country.
If there are any lessons I learned by comparing my recent success to my previous failures:
1. Plan ahead. Be ready when the day comes.
2. Be certain that everybody knows you're a writer and that you are available for writing opportunities. (Make sure they also know of any related skills you have, such as editing or photography. I have strong desktop publishing skills and those skills have helped me land assignments that other writers can't get.)
3. Be flexible. (I'm writing things now--like television and radio commercials--that I had never even considered writing a year ago.)
4. Don't forget why you're freelancing. Devote time to writing whatever it is that brought you to the table in the first place--whether it's poetry or romance novels or literary fiction--and don't let yourself be sidetracked. (I devote a fair percentage of my time to writing short fiction, and will continue to do so.)
I've probably learned other things during the past three years, but I think those are the most important.