Let's say you've done enough research on a certain publication to get the sense that your writing style and skill level is a good fit. Then let's say that you pitch an editor and get rejected. You'll obviously want to keep trying because you've done the research and set the goal of getting into that publication, so would you keep pitching different ideas to the same editor and hope that your persistence pays off? Or would you try a different editor and hope that maybe you'll have better luck with someone else? The media outlet that I'm targeting is general enough to publish a range of different voices, and it's possible that my youth or feminine perspective just didn't strike a chord with a fortysomething male editor. Or am I just fooling myself?
All very good questions. The short answer is that persistence sometimes does pay off, and sometimes it doesn't. But that doesn't really help you now, does it? :)
To begin with, I'd never suggest that you ditch an editor based on one rejection. One rejection is nothing! In fact, if you hit a home run on your first pitch, you'd be the rare exception, not the rule. So by all means, keep trying. How long you should try really depends on the responses that you're receiving from this editor. If, as you mentioned, you suspect that your tone and voice might not mesh with the editor you've selected to pitch, then yeah, try someone else. If, however, you're getting relatively positive feedback from the editor, i.e, "we just ran something similar," or "this isn't quite right, but feel free to pitch me again," then keep plugging away. I've mentioned this before on the blog, but I was once approached by an editor at Glamour. She asked me to send in ideas, so I did. And I did. And I did. For FOUR YEARS. Nothing took. But she eventually left Glamour and when she landed at a new magazine, she promptly assigned me three pieces. So if you have good ideas, and you're meshing with the editor, by all means, keep at it! Just because she's not assigning something to you immediately doesn't mean that she's not taking note of your writing and researching skills.
At the same time, I've also thrown in the towel on editors who were unresponsive or who clearly weren't interested in what I was selling. And yes, you can certainly try someone else...it's not as if you're black-balled from a magazine simply because of one editor. So regardless, you can keep at it.
One thing to keep in mind, which again, I've mentioned before but I think it's worth noting. You mentioned in your email that you're still getting your freelancing sea legs. If you don't have a slew of feature-length clips, you might have better luck breaking into these national mags in the FOB section. Editors take less risk when they assign a 200 word piece to a new-to-them writer, so they're more likely to give you the green light. They also need more FOBs each month than features, so you up your odds of landing one.
So...have you guys ever had luck many pitches later? Or ditched one editor only to find success with a different one?