I’m a firm believer in the value of specializing in a freelance writing business. I’ve also espoused in this space about the benefits of being a team player when it comes to the publications and editors you work with, and how worthwhile it is to cultivate contributing writer gigs.

So if you specialize, and you regularly work for a handful of publications, do you tell the publications that you work for about each other?

On one hand, it’s kind of like being on a date with a guy one night and telling him about the great time you had with someone else the night before. “Oh Trade Magazine Editor Tim, I just finished the most awesome piece for Newspaper Editor Bob and he loved it.”

On the other hand, it can pay for your editors to know more about the writing you do for other publications.

A couple of events drove this home to me recently:

First, a trade magazine I write for on a regular basis is putting some additional tech coverage in their print issues in 2009. Since the editor there knows I’m a long-time tech writer and cover IT for a national business Website, she asked me to pitch stories for the expanded section – and subsequently bought two of my ideas.

Another example: I keep in touch with an editor of another business magazine on a regular basis – even when she doesn’t have stories to assign – and I always share about projects I’m working on and publications I’m writing for. Her magazine’s publisher is considering launching a new title in 2009. Knowing that the new title’s subject falls into one of my specialties, she contacted me about writing some stories for the premier issue – which they’ll use to sell ads against – maybe even the cover.

Finally, I recently heard about a soon-to-launch news Website. The site’s main focus isn’t what I normally write about, but it overlaps with areas I cover. So I sent a letter to the editor in chief introducing myself and including clips of half a dozen stories I’d done over the last couple years on topics in this overlap area. A week later I heard back – they’re interested and want to see pitches.

Moral of the story: it pays to blab. If you don’t know an editor well, or don’t have a good working relationship with someone, it’s understandable not to want to openly discuss the other work you do. And frankly, some editors could care less. But if you’ve worked with an editor or publication for a while there’s no reason to hold back. And in the case of a new-to-you publication, showing what else you’ve done may be the only way to gain their confidence.

There is a caveat – if you’re going to tell editors about your other work, make sure you show them the love when it comes to the work you do for them. Be reliable, get things in on time, bring your A game. Let them know that although you may work for others, when you’re on their dime, they’re your No. 1.

Want a quick way to an editor’s heart? Write your own headlines.

Make it a practice to send a headline – and a deck too if a publication uses them – with every story you submit. Whether an editor actually uses your headline is beside the point. Writing headlines is good practice. And it shows that:

• You know your story well enough to summarize it quite succinctly.
• You can write short as well as you can write long.
• You care enough about your story to apply all the finishes touches.
• You care enough about your editor to want to make their life easier by doing some of their work for them.

What’s the worst that can happen? The headline ends up on the virtual cutting room floor. What’s the best? Your editor remembers you as that thoughtful freelancer who always includes headlines with their copy – and gives you more work because of it. Or your headline ends up in print. Given the chance, wouldn’t you rather have your story called by the name you gave it than by someone else’s?

Headline writing is an art. The best are like the best kind of diet food: meaty yet lively – and sometimes downright spicy – but without a trace of fat. Cut out articles like “a” and “the.” Use active verbs. Use puns or other word play when suitable. Avoid cliches. Ditto phrases that could be read more than one way – like the headlines that end up on the back page of the Columbia Journalism Review.

Newspaper copy editors are masters of the art of headline writing. Here’s an article about how newspaper copy editors write headlines from Gannett Corp.’s weekly Newswatch column. The story’s really old but the lessons still apply. Magazine and other freelance non-fiction writers can also learn a thing or two from advertising copywriters, who specialize in snappy catchphrases. Here’s a good article called How to Write Headlines That Work in Copyblogger.

Another reason to focus on headlines: your blog. If you’re one of the legion of freelance writers with a blog, it behooves you to write good headlines so your blog posts get maximum exposure. There’s a special art to writing blog headlines. Learn more here and here.