How do you tell which freelance writing postings are legit, and which aren’t? What kind of important probing questions to ask potential clients to make sure that your gig is a) not a scam and b) well-defined with clear boundaries.

First, allow me to be honest here: I’ve never been much of a full-time freelancer. I’m not quite suited for it, really. Freelancing is lonely, isolating work. It’s hard to know when to call it a day, because you can always work more. It pushes me to a weird kind of crazy, where I’m always convinced I’m not working hard enough, and ultimately end up working myself to the bone. Or, you hit a dry month and stay up all night wondering if you’ll ever be able to pay your rent again.

So, while I’ve freelanced for years, I’m not the greatest advice-giver on how to be a freelance writer. I suck at pitching stories to publications. Most of my freelance work comes from my network of colleagues … folks I met through past gigs, people I’ve rubbed elbows with at industry conferences, etc, etc. That’s part of how I ensure the clients are trustworthy: I meet them socially or at another job before we’re talking business, so I have experience with them. That’s one way to go about it, and another hard thing about freelancing: you have to be marketing your skills and whoring yourself non-stop.

This is why I’ve always opted towards contract or part-time corporate work. Don’t let the bohemian exterior fool you. I am a stability junkie through-and-through, and not knowing where my next paycheck is coming from is a bit of a challenge for me. I can totally support myself, but not without FREAKING THE FUCK OUT the entire time. It’s not especially functional. I can pimp myself enough to pick up some moonlighting gigs here and there, but I don’t like the pressure of having to work that shit all the time to pay the bills.

Moral of the story here: I don’t exactly have a good answer about scammy writing jobs, because most of mine come from people I know through my extended network or through agencies. Of course web research is a good way to investigate any company you’re looking at dealing with, but that’s a “duh.”

As for the boundaries issue with gigs, that’s a great question and definitely an important issue. When I’m working on web writing projects I always make it very clear how many pages/hours I’ve got in me to give, and once we start getting close to that, I give the clients a heads-up that we’re nearing my pre-agreed limit. Sometimes this is a bargaining tool (ie “We can work on this page for another rewrite, but that means I won’t have time to do that page at all, because I’ll be out of time.”), and sometimes it can be an opportunity to extend the scope of the project. As with all kinds of relationships, communication is key.

I’ve now written a small novel about how I don’t know much about the topic and yet offering some half-assed advice anyway. Helpful! In all honesty, I think you’ll get more informative answers from Michelle Goodman, a friend of mine who actually IS a professional freelance writer (unlike me, who’s sort of a hybrid), and who literally wrote the book on getting out of day jobs. She rocks at answering questions on this subject. I don’t.