"Keep your day job" is probably one of the most common pieces of advice handed out to aspiring writers. Even writers who sell enough in a year or two to consider the possibility as more than just a remote fantasy are told to be patient. They're told to wait until you have X number of dollars in the bank from their writing, and a backlist of books that can keep them going in a lean year.
In general, it's a piece of advice I would give people as well. However, from my own experience, I know that sometimes the best piece of advice to give someone isn't "Keep your day job" but "Quit your day job."
As regular readers of this blog know, in the summer of 2004 I quit my day job to spend a year writing a novel. The novel I finished still hasn't sold to a publisher yet, but that's not really the important part in the grand scheme of things. The important part was that quitting my day job gave me spiritual fulfillment worth far more than the salary I had been earning. It gave me a chance to focus on one project and to learn through the novel-writing process of writing a novel just what I needed to do.
So, based on my own personal experience, I'd be willing to recommend quitting one's day job as a viable alternative. However, it's not a blanket piece of advice. Because if you do quit your day job to write, you really do need some sort of safety net so that you can eat for the year. In my case, I was very fortunate. Nomi was willing to see my year through, so we were able to manage for that time on her salary and her company's health insurance plan. (Never give up health insurance if at all possible.) If I had been on my own, and wanted to give up my day job to write, it wouldn't have been nearly as easy.
But...sometimes a work situation can become so detrimental to your writing that you really have no choice. Sometimes you have to take drastic measures if you want to write. And in the end, only you can judge for yourself the best course of action.
(As a final note, I should add that Masello's essay actually goes into other advice to the prospective freelance; for example, in a few brief paragraphs, he points out the type of writing that tends to sell more. If you're really looking to support yourself as a freelance writer, his advice is worth looking into.)
Copyright © Michael Burstein