I’ve been a professional writer since 2005 and a full-time writer since 2007. I moonlighted for a couple of years before transitioning to a full-time freelancing journalist, a “calling” I continue to this day.
Since then, these are some of the most frequently asked questions I get from aspiring writers or otherwise curious email inquires:
How do you become a self-employed writer?
My advice: write everyday and ask 50 people if they will publish your best work. If they all say no, ask 50 more and so on. This never fails but most writers will never do this and therefore go unpublished and unpaid. Usually I don’t even have to ask 50, but in two exceptional cases, I asked over 100 before someone said yes: My first story for Wired Magazine about college footballcomputers and my first travel column for Paste Magazine. Both were huge wins for my career and would have never happened had I quite after asking just 50. The harder you work, the luckier you get. (See also: How to succeed: Don’t quit until everyone in the room tells you “no”)
Is it actually possible to make a decent income at home and support a family by being self employed writer?
Yes. I’ve worked from home for the last 15 years, make a good income, and have six mouths to feed (wife and five children). In my experience, successful self employment requires persistence, low overhead (i.e. low maintenance lifestyle), extra emergency savings, and a willingness to sell your craft in addition to the craft itself. Self employment isn’t for everyone, but it can be done and is remarkably rewarding.