Yesterday on twitter I offered to answer folks’ questions about freelance writing as an occupation. A handful of people took me up on it, so here are the questions and my best shot at answers.
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What is a reasonable annual earnings expectation for a freelance writer? Full time.

Really variable, I think is the answer here. I’ve been very lucky to make a decent living at it which is actually quite a bit more than I made at my full time writing job. That’s by dint of (a) being able to write very quickly, (b) working more or less all the time, and (c) doing a good deal of work for hire writing for educational publishers, business publishers, and the like. I’m also in my mid-40s and have been writing professionally for about 20 years now; that has a big effect on what kind of work for hire gigs you’re likely to be considered for.

I started out doing freelancing part time for several years, working at a full time job during the day, until I’d lined up enough clients that I felt like I could make a go of it. I’d definitely recommend that. Also, it’s a lot, lot, lot easier if you’re married to someone who’s got a full time job, both for health insurance (less of a problem with Obamacare, but still) and because *someone* needs to be making a steady paycheck if you don’t want to go completely crazy. With freelancing, some people will make less, some more, but the precarity is a constant. It’s really hard to know if people will or won’t have work for you. My main client, for whom I was editing like 20 books a year, just decided to have me write 0 books this year. I found something else…but that’s the sort of thing that really plays havoc with your blood pressure.
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How do you develop relationships with editors?

Relationships with editors are often about networking, like most things. I’m always looking for new venue, and trying to reach out to people who might have editorial contacts. It feels pushy, and I always feel nervous about it…but it’s part of the job.

I’ve had editors reach out to me a couple of times too, which is really nice. And I’ve cold contacted a couple of editors…which usually doesn’t work, but every so often. And then I’ve also had editors who I thought I was doing well with stop talking to me. Part of the reason you need to constantly be trying to find new places is that the old places stop working with you, for one reason or another. Someone goes out of business, some editor moves on and the new person isn’t into you. I counted up the number of places I’d written for at one point and it was over 50 I think.

How many of your pitches actually get accepted?

I try not to think about this one too much. I bet probably 70% of my pitches get rejected. However, I think 80% of my pitches eventually get published somewhere. That means I only rarely place a piece at the first venue I send it too. Most things by me you see in print were turned down by somebody at some point.

dHow does a freelancer compensate for the stigma of not being permanent?

This is not a stigma I’ve really come across that much? Most places that are interested in working with freelancers are interested in working with freelancers. People seeking freelancers aren’t going to turn you down because you have freelance experience.

It might(?) be different if after working for a freelancer for five years I went to try to get a permanent job somewhere. It’s true nobody’s come to me offering me a staff position…but on the other hand, I haven’t applied for any staff positions. Not sure what would happen if I did. Freelancing’s working okay at the moment though.
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What are the best ways to establish contacts with alt news publications? How sustainable is it to start off as a freelancer?

I think I answered these above….
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It seems like it would be hard to cold call people for research/quotes on pieces if you’re not affiliated with a media outlet. True?

I think it depends. You can definitely get bigger names if you’re writing for a bigger publication. But on the other hand many people are interested/excited about getting their ideas out there. It can help to have mutual acquaintances who can make introductions, too.

But the general rule is it never hurts to ask. If you’re writing a piece for a blog and there’s someone you want to talk to, write them an email/dm/whatever. If they’re too busy they won’t get back to you; but if you don’t ask, you’ll never know if they would have been interested.
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Do you permanently sign away the rights to your work? How common are “buyout” clauses?

It really depends on the publisher. A lot of the times yes, though there are exceptions (Slate’s relatively good about letting some rights revert, for example.)

I don’t even know what buyout clauses are!

For me, for the most part, this just is not that big a concern. I work on the expectation of one time sales. Every so often something is picked up by someone who pays me for it again, and that’s nice; every so often something is picked up by someone and I don’t get paid for it, which is a little irritating. But realistically, I’m not writing things where the copyright is going to be a moneymaker decades down the road or anything. You sign the contract and you shrug and you write the next piece.