Tom & Alissa

A bad rule for life, perhaps, but not for freelance writing.

This morning we were discussing various projects at IAM, and Christy asked me if I sometimes went on work overload because I was so excited when someone asks me to write for them that I have a hard time saying no, because as she said, it’s a common dilemma for relatively new writers.

And as I told her, yes, it’s a huge problem. Mostly because I never, on principle, say no to an editor.

Okay, so occasionally I do. But it’s always when I legitimately can’t write the piece (i.e., I have class that night and can’t go to the screening). I haven’t said no to an editor for anything I could do for two and a half years.

I do have the luxury these days of almost always writing for money, or of choosing to write for free because the opportunity is worth it (notably at ConversantLife). But I started out writing entirely for free, at Relevant. I spent two years editing the Career & Finance column there for free because I knew it was worth the opportunity to work with those editors.

And I’ve been very blessed; I’ve rarely had a pitch turned down (fairly astonishing, and I don’t expect it to keep up), and I fell into most of my regular gigs by accident, or providence, depending on how you look at it. Three years ago I wouldn’t have dreamed that I’d be writing for a living, but there you have it. Even here in my bill-paying day job at the University, my title is “writer/editor”.

I have had the grateful luxury of specializing, as well, which isn’t a given. I now write about culture, film, and books, instead of my old career & finance work or general interest pieces. If I were making a living as a freelancer, you can bet I’d be writing about everything, but I’m glad that’s not the case.

Back to our discussion this morning - I explained that the reason for my unequivocal acquiescence is that if you don’t say yes to an editor, they probably won’t call you back. Editors are phenomenally busy people who rely on a small set of reliable writers with a style they like. You say no, or you start turning things in late, and you end up getting knocked off the list. At a lot of publications - and, I suspect, several of the ones I regularly work for - there’s a million writers out there, some much better and more trained than me, who would be very happy to take my spot. And I’m just a freelancer.

The long and short of the matter is that until I hit my sweet spot, my inflection point, I can’t turn down an editor. When will I know I’ve hit that point? I’m not sure. I’m thinking it will be when someone calls me and gives me at least a part-time staff writer or contributing editor position, hopefully in culture or the arts. (Hello, New York Magazine? Are you listening?) And that probably won’t happen until I finish my master’s degree, which provides credibility, and have the option to leave the day job and work for myself.

I spend a lot of time dreaming of that day.