A co-worker who's run into a financial rut is looking for a freelancing job on the side (writing, editing, etc.). Anybody know of any Web sites that offer freelance postings?

As far as writing goes ....

In my experience, you don't look for ready-made freelance work. You study your market, match what interests you to the publications that seem friendly to it, and then introduce yourself by dropping an enterprise piece on spec in their laps — something tailor-made for their readers. I've done this several dozen times and it's rarely failed. Not only did I sell the spec piece, but I impressed them enough to develop the kind of relationship which kept them coming back to me.

You have to be willing to take the risk of doing several hours of work that may not necessarily be paid back. Freelance work is not for the complacent, for people looking for ready-made handouts. You don't knock timidlyon doors and hope for a call back. You kick in some doors and make yourself impossible to ignore — because a) you know your craft; b) you know your market; c) your know your targeted publications' readerships; d) you have a professional track record; and e) you deliver on time and at the agreed-upon length.

Well-established alternative weeklies are a good place to start, in my experience. I did several pieces for weeklies in the New Times chain, and was paid very well.

As far as editing goes, I also made a sideline out of desking for short-staffed non-competing dailies. It involved some travel and a willingness to give up my weekends, but once I was trained on the in-house system, I was usually able to get steady work — and get it on my terms. Many papers are desperate for quality part-timers. Yes, even in this layoff-crazed economy. Maybe even more so.

Example: A few years ago, I regularly moonlit for the copy desk of a small daily about 80 miles away. They were desperate for help, particularly on weekends, so I was able to get them pay mileage and about $3 an hour over their going staff rate. If it was really short notice, they'd put me up in a motel. Because I was handy with a camera, I often added to that by taking back roads on the way there and shooting standalone scenics. If they published, that was an extra $30 a pop. There are all sorts of tricks for maximizing your financial mileage in such arrangements.

How do you get those jobs? Simple e-mail copy desk chiefs and managing editors all over. Work every friend and acquaintance you have. After a while, I developed a word-of-mouth reputation and often got jobs based on recommendations from the aforementioned daily. Convince them that you're sharp enough that you only need a day or two of training before being turned loose, and they'll love you forever. If anything, they'll want you far more often than you'll actually be available.

I'm glad to be where I am now, and don't miss the financial desperation that put me in the place where I needed to hunt down freelance work. But it was fun, too. You get to feeling like a hired gunslinger — "Have Red Pen, Will Travel." You ride in, save the day, and head off into the sunset feeling satisfied.

Wabberjocky pretty much hits the nail on the head. I have some regular strings that pay the bills but the quality of life comes from freelancing.
One thing to be prepared for is rejection. Your pitches will get turned down much more often than they turn in to work. This can be very debilitating psychologically. However, the longer you develop a working relationship with an outlet, the more work from you they will be interested in-- I now have a string that I have been doing for some 14 years and they almost never turn down a pitch, partly because they have learned to trust my news judgement and partly because I know exactly what to (and what not to) pitch.
Also, too many ME's agree with the "100% local 100% of the time" philosophy, so if you can get a story with a local angle its chances of paying for dinner or groceries will increase dramatically.
Good luck.

Anyone verify that the Writer's Market guide is a waste of money? I tried to use it to pitch magazine work a couple of times to no avail. Could well have been just me, though.

I wouldn't go quite that far, but I would say that the formal query process is a waste. Like I said, I just study the publication, study the market, prepare a story, drop in their laps as an introduction and see what happens. More often than not, good things result.

The magazines at which I make assignments and work with writers consider either pitches or finished pieces.

I'd just as soon as get an unsolicited story in the mail or by e-mail as deal with freelancers I don't know on the phone.

Few of the finished pieces run without major reworking by the writer, but if they impress us and the writer is willing to do the work, then we assign it.

A danger of submitting a full story is that an unscrupulous publication might steal the idea and give it to a staff writer. I don't know how common that is, but I've heard of it happening. One writer submitted an idea for a story that we had already assigned to someone else. Months later he called to wonder if he'd been ripped off.

Something to keep in mind with some magazines: Many articles are planned and assigned months or even years before they get into print. When you consider taking an assignment find out whether you'll be paid upon submitting it or not until it's published.

Take a look at http://www.staffwriters.com, which is run by a Newsday alumnus. They match journalists with employers, usually for short-term projects.

Ahh. I tried getting a start on freelancing when I was flat broke and couldn't afford to invest any time and money upfront. I may give that a try sometime now that I have more resources and experience.

One place to get tips about how to pitch to magazines is Mediabistro's How to Pitch series--they talk to editors at various magazines to learn the things that Wabberjocky mentioned: how to tailor the piece to the publication. You have to be a member to read these, but if you opt out of the "free" magazine subscriptions, the cost of membership is only about $30 a year.

I never had much luck with Mediabistro's freelancer marketplace, though.