It’s almost Halloween, which has me thinking about scary stuff. What could be scarier than trying to convince an underpaid, overworked editor you’ve never met to take you on as a freelance writer? And actually pay you real money?
I know we have some freelance writers who follow Write Despite. This post is for you. If you’ve been freelancing for any length of time, you probably don’t need to read this. You’re living it. Still, it wouldn’t hurt to take a look.
If you’re new to the freelance trenches, click the link below. Forewarned is … as they say.
I’ve been both a staffer and a freelancer for numerous publications. I’m happy to share what little I know if you want to drop me a line.
http://absolutewrite.com/category/the-business-of-writing/
— Karen
Write Despite 
Freelancing’s not an easy gig, but the freedom is great–if you can swing it financially. But, yeah, thick skin required.
When you’re breaking in, don’t query the New York Times Magazine. Start small: local papers and magazines, university publications. They pay’s not great, but they’re a great way to build your confidence, get edited and build up your clips. No assignment is too small when you’re learning…
I freelanced for more than a decade before finally deciding I needed a more steady income. The #1 thing from this article that challenged me? Definitely “Outreach.” I’m a shy person–it’s why I write instead of speak. So tooting my own horn and begging people for work was tough. My best clients were past employers. Reach out to them first. They know your work and, if you left on good terms, shouldn’t hesitate to outsource to you if they need some writing/editing work done. Good luck!