How do you pitch a freelance story to a site or a magazine? Here is some quick advice for those who may be new to pitching.

1. Write the pitch in an email. Do not attach a file. An attachment makes it harder for the editor. Editors are busy people and get a lot of email. Also, editors hate email. I don’t think it’s possible to overestimate how much they hate it. I mean, we all hate it, but editors definitely hate it. My point is that in my mental model of the editorial mind, email is bad, but email with attachments is worse. I can’t say I have verified this theory in real-life conversations with editors but I do live “as if” it were true.
2. 500 words max. 250 or 300 is preferable.
3. Three short paragraphs will do it. First paragraph: Hi, I’m so and so, and I have an idea I think would work well for you. Second paragraph: Here is the idea, briefly, and here is why I am the appropriate person to write it. Third paragraph: I’m happy to tell you more if the idea intrigues you. A bit more about me: [links to clips, or in the absence of clips, a tiny bio]. (After I posted this, I asked for editors to weigh in on Twitter, and a few made this important point: these three paragraphs should convey that you’ve read the publication you’re pitching and that you know what sorts of stories they need. The pitch has to be tailored to them. Editors don’t like it if they sense that the idea is generic and could be pitched anywhere. As an editor from Slate put it, the pitch should “include a real sense that you understand how the piece would fit into MY magazine and not some other magazine.”)
4. When I was first starting out, people told me that it might take editors a week or two to decide on my pitch, so I should wait for a while to hear back. I don’t think this is right or true or good. If the industry really worked like this it would make everyone crazy. My impression (again, from my mental model of the editorial mind, perhaps hilariously incorrect, but always evolving) is that editors decide within minutes or even seconds whether they are going to assign your piece. Any additional time that elapses between the moment they read your pitch and the moment they reply is due to other factors (workload, conflict avoidance, dread of having to write yet another freaking email, etc.) If the story is going to happen, if you have triggered any sort of excitement or curiosity, you’ll hear back from the editor almost immediately. So this is maybe the most important thing I can tell you: If you don’t get a response within a day or two, move on. Pitch someone else, or pitch a different idea. Don’t mope, don’t take it personally, don’t waste time. (O.K., so several editors with excellent reputations told me on Twitter that following up once is fine, because they sometimes miss the first email due to busyness or email load — see rule #1 — so I am maybe being too harsh on this point. I still think the principle of moving on quickly is a good one.)
5. The world of publishing/media/whatever can be arbitrary and frustrating but at base it is a creative business that needs new voices and good writing. It cannot exist without these things. It must have them. So there is room built into it, by definition. And the vast majority of editors I’ve met are bright earnest people with good hearts. Stay optimistic.
6. You can do it.