Earlier this week, I did a foolish thing: I wrote an article without even trying to get paid for it. The piece in question–a 313-word listicle relating ten thoughts about Facebook on the day of its tenth birthday–only took a few minutes to write, and in the moment my Facebook page seemed like an apt spot for it.

Most of the time, however, I’m not in such a rush and I do want to make some kind of money for writing something longer than a few paragraphs. (For about a year, this blog generated no income, but since the spring of 2012 WordPress.com’s ads have been paying me an exceedingly low per-word rate.) But if I have an idea that’s not an obvious fit for one of my regular clients, where do I try to sell it?

For me, the answer is not always the obvious “whoever will pay the most money.” Assuming the options are all offering about the same range, other considerations come into play:

Audience: If I’m writing something that I hope will change people’s minds, then I’d rather a site be able to get my words before more people. If it’s more of a personal essay or some specialized topic that won’t get a large readership anyway, that’s not such a concern, and I’ll even write behind a paywall.

Old or new client? I don’t want to let my connections with editors go stale–when an editor knows you and your work well enough, you can pitch a story and get it assigned to you in a minute’s worth of Twitter direct messages. But if I’m not getting my byline to show up in different places, it feels like I’m not trying hard enough.

Contract: Most freelance contracts are written to reserve as much of the post-publication upside as possible for the client. Ones that instead let me keep copyright to my work and resell it later on (thanks, The Atlantic Cities and The Magazine) easily get my attention.

CMS: Being an outside contributor generally insulates me from whatever horrible content-management system a newsroom uses, but if a site uses a good CMS it gets a little extra credit. For example, it doesn’t hurt that Yahoo Tech uses Tumblr, and one big reason I want to write something for The Magazine’s venture on Medium is to spend some quality time in that CMS without writing for free.

Comments: Because I’m one of those weirdos who actually enjoys reading and responding to reader comments, I appreciate writing for sites that make it easy to do so–and have commenters who generally know what they’re talking about. (Yes, Yahoo Tech doesn’t have comments yet. A custom system that, per, David Pogue, will “attempt to eliminate awful anonymous drive-by potshots that add nothing meaningful to the discussion” is on the way; when it launches, you will see me on it.)

Ease of payment: I usually don’t think to ask about this until after I’ve filed, but if I don’t even have to invoice the client to get paid, that’s great. Having the payment deposited directly in my business account or sent via PayPal helps too, but my bank’s nearest branch is only a 10-minute walk away, and I could always use its app to scan in a check. Really, just don’t make me have to invoice twice and I’ll be happy enough.