I have a dear friend who’s trying to make the leap into freelance writing (she’s published a book and now wants to quit her day job.) I just emailed her some rambling thoughts on the subject, and thought they might be useful to some other folks as well.

If you have other questions about the writing biz and I have the time to answer them (bli neder! No promises! We’ll see about that time thing!), feel free to post ’em in the comments.

Some basic things to know about freelancing:

1) Network.

If you know someone who knows an editor at some paper, you start a pitch letter with, “so-and-so suggested that I get in touch” or whatever (get their permission first to namedrop, duh). Go to Media Bistro (www.mediabistro.com) events and similar gatherings (lots of orgs/groups organize Shmooze Nights here and there) and shmooze with editors, get their cards, pitch them stories afterwards. Don’t have anything to say to Forbes magazine readers? Think of something, ’cause you now have a connection at Forbes (or wherever). Take friends who might know editors or other freelancers out for coffee and ask them for help getting hooked up. Make friends with other freelancers–they’ll help you figure out taxes [save every receipt for EVERYTHING!!] and give you good gossip about who’s leaving what gig and what might be open and who might be a good person to pitch. Plus, sometimes your writer friends become editors. Keep the favor bank open–help people when you’re in the position to do so, because it’s the right and nice thing to do. Also, freelancing has a pretty short karmic boomerang–you’ll get back what you give out sooner than later.

Also join listservs, Livejournal forums, whatever, for working writers. It’s a great place to learn tips, get support, and ask questions as they come up.

Of course, networking isn’t a prerequisite. I’ve pitched plenty of places cold (ie just finding an appropriate editor’s name and email on the masthead of the publication–whether the pub is a print or web mag, you can usually find a masthead on their website–by the way, that appropriate editor is usually not the Editor-in-Chief of the Managing Editor. Look for someone who seems to be in charge of the stuff you want to write, like Book Review Editor or Arts and Culture or etc. Though the Managing Editor will work in a pinch–s/he can forward email to the appropriate person, if you’re really stumped re: who that person should be.) Pitching cold just requires sending a polite, professional email with some compelling pitches. As with any pitches (to friends of friends, to people with whom you have a relationship with, etc.), sometimes you hit, sometimes you miss. Sometimes you’ve given them the right idea at the right time and sometimes you’ll hear “no.” Don’t give up–persistence is really key to succeeding in this business. It’s not the only thing you need, but you definitely need it!

2) Pitch letter.

Here’s my silly letter that I banged out as a model for my friend. Understand that it was written in 30 seconds and that yours should be better:

Hi, Jane–

John Johnnyson suggested I get in touch (or if you’re pitching cold, just start the letter with the next line.) I have a few ideas for stories that I think might be a fabulous match for Forbes (or wherever).

Then you write a short graf (3ish sentences) with your story idea–what you’d write, why it’s timely if it is, that sort of thing. Identifying new trends or offering a fresh take on some current thing is always good. Is it a first-person essay? A reported piece (ie you go ask a few people questions and then you quote them)? An interview? Etc. Feel free to be funny, engaging, charming. A well-written and interesting pitch letter is a good sign for potential editors. Let them see some of your style come through, but be professional.

Read the kinds of articles you’d want to write and think about what the writer pitched and why. Start seeing everything as a potential story idea. New ad campaign get on your nerves? Does it tap into some larger issue? That’s a story. Etc. (I never wrote hard news; I can’t tell you anything about how to do that. I’ve always been all about the “cultural issues.”)

In a perfect world, your pitch email has 3-5 paragraphs with different ideas, because you never know which one might be interesting to the editor in question. I’ve totally had pitches with three fantastic ideas and tacked on a fourth just ’cause, hey, why not, and had editors hire me for the forth idea–you know, the one I thought was not so exciting.

Then tell them who you are in a couple of sentences. If you went to a fancy university and you’re *recently* graduated, mention that. If you wrote for the school paper, or some xeroxed ‘zine, or whatever, mention that. If you have job experience relevant to the task at hand (ie you work at a record store and you want to write music reviews, you work at a feminist nonprofit and you want to write a gender-related story, etc.) Don’t mention the feminist nonprofit if you want to write music reviews, the editor doesn’t care b/c it’s not relevant. Obviously, if you’ve written for other pubs, or been featured in any way (my friend was on NPR), mention that.

Ideally, you should attach some “clips”, aka samples of published writing. It’s OK if they were from the school newspaper or the xeroxed ‘zine. If you don’t have anything published, start small–write for free a few times until you have some clips built up. My first paying gig paid me $10 for a story. I wrote for that newspaper for six months until I had enough clips to pitch to a place that paid $100 for a story. And from there, I could go to places that paid something a little closer to market rate (which really varies, depending on the publication and the type of story.) I still write for way cheap when it’s for friends (one mag in particular) or the kind of thing that might be a good career move, or when I feel passionate enough about the story to be willing to do so. What choices you make will depend on a lot of things, including whether you’re writing to pay your bills or writing to build a writing career (these things are not always mutually exclusive, but they also may sometimes lead to very different choices.) Anthologies and such–contributing a chapter to a book–don’t generally pay the rent. There are a lot of reasons to write for books, but the vast sums of money you’ll be making off of your work is generally not one of them.

If you have clips, include 2-3 at the bottom of the email. URLs are best, but attached files are usually OK as well. I think! I always used URLs.

3) If the editor is interested, s/he’ll give you a word-count and a deadline, and let you know how much $$. Freelancers just starting out (and often more seasoned ones) don’t bargain–they take the job if it feels like a fair amount of money for their time, and politely decline if not. Sometimes editors have a contract for you, sometimes not. It’s not a bad plan to be careful about getting a contract (feel free to ask for one), especially if it’s a new relationship–that’s simple self-protection. I know writers who are militant about getting contracts every single time, and others who kind of go by their gut, only ask for one if they feel there’s any cause for concern, even in new relationships. It’s not unheard of to do things on a handshake, but it’s good business to get things in writing–particularly in this age of “things being archived online forever and ever and ever.” The terms of contracts, and the kind of rights the pub might want from you, are a bit different now than they were even 10 or 12 years ago. Know what you’re signing, and make sure you’re OK with the terms. Places like the National Writer’s Union can help give you guidance/guidelines, if you want ’em. Know that sometimes putting down your foot about rights and permissions might mean walking away from an opportunity, and that sometimes you might decide that you want the opportunity enough to give away more rights than you would otherwise. It’s your call, always, but be aware of what you’re choosing, and make it a conscious choice.

If for some reason the pub doesn’t run the piece after you’ve handed it in (this might happen for a variety of reasons, not always relevant to the quality of the work–sometimes it’s about timing, or something changing on the editorial side, or something changing in the news, etc.), they should pay you a “kill fee” of 25%-30% of what they were going to pay you upon publication. You still retain full rights to the piece and should by all means try to sell it elsewhere–send an email to an editor in more or less the same format as above, but the paragraph describes an already-written piece, and asks if the editor is interested in seeing it, and you don’t probably need clips.

If they ask you to write something “on spec,” that means that they want to see the completed story before they decide to buy it. You can decide it’s not worth your time to invest with no guaranteed contract, or you can figure if you don’t sell it to the one place, you can sell it somewhere else. I’ve done this before, for sure. It’s probably worth your while if you’re just starting out, or if it’s a pub that could really help your career. Sometimes the risk is worth it and it’s stupid to walk away. Of course, it is a risk and you can decide not to take it. Up to you.

OK, some cursory thoughts. Other things you’d like to know about the writing biz? Feel free to ask in comments, and if I can, I’ll talk about it.

Here’s some basic freelance info:

http://freelancewrite.about.com/

For agent/book industry stuff, though, you should go here:
http://www.misssnark.blogspot.com/
http://www.annasredpen.net/demystifyingpublishing.html