Richard Morgan has written the best article about freelancing I’ve ever read at The Awl.
Excerpt below, but make sure you read the entire bitter-sweet funny-sad melancholy-hilarious magnum opus.
Heroes be damned; a writer should not model themselves after an editor. That is probably the single best realization I have made as a freelancer.
Moss said the thing that all editors inevitably tell all writers—something along the lines of “I really admire your determination, because I tried freelancing and didn’t last six months.” Editors like to talk about how much they need freelancers and how much they envy our freedom and our work ethic and our Rolodex. Whenever a friend loses his staff job at a magazine or newspaper, his ensuing panic reminds me that they put all their eggs in one basket and that I am cushioned because I have my eggs spread across so many baskets (which is a different kind of panic). Freelancing has great rewards, but trajectory is not really one of them. You do not go from being a freelance writer to a freelance editor to a freelance deputy managing editor. Essentially, I’m doing the same thing I was doing in 2003. The market for my vaudevillian sales of wonder tonic can dry up at any moment. An editor leaves. A magazine folds. And poof! Gone.
For the record, I’ve been freelancing for nine years and I’ve liked nearly all the editors I’ve ever written for. Editors are a writer’s best friend!