Freelancing as a Woman: Weighing the Prose and Cons


TO BE a freelance writer is not all cool, calm, and collecting checks. To succeed you need Drive (like Ryan Gosling), old-fashioned American Hustle (like Jennifer Lawrence), and connections– which means shaking hands and braving the possibility that your pitches will be rejected, and rejected often. In this sense, pitching editors is a lot like Hollywood castings, in both instances you are responsible for selling your self.  However unlike blindly pitching an editor, actors arrive at castings expected. They’re there because they’ve been vetted. When you arrive in someone’s inbox without an appointment, no matter how many times you do it, it always feels a bit like breaking and entering– no one asked you over, but there you are, papers in hand, begging for them to pay attention to you.

When they don’t, it stings, and it stings more for women than for men because from a young age we’ve been conditioned to think that “success” should come to us. “Seeking out” is a traditionally male characteristic– men were hunters, women were gatherers. And it beings young. “Don’t chase boys,” a mom chastises her daughter when a teacher reports home that “Sally was running around the playground planting wet ones on little laddies’ cheeks.”

“Let them chase you,” dad says. This carries over into teenage years. We wait for men to ask us on dates or for our numbers. We wait for them to call. We sit on our hands until they put a ring on our finger. And when they don’t we find ourselves asking why? What could I have done differently? What should I do better next time? Sometimes the answer is nothing, and sometimes it means you shouldn’t have made out with his best friend that one night.

We’ve been conditioned to be sought out and after, and freelancing is the antithesis of this conditioning. So when we get rejected the first couple hundred times it burns. Opening an email that conveys something like: It doesn’t sound quite right for our purposes, but best of luck placing it elsewhere, brings an inevitable sense of shame and embarrassment– the full body flush of “I’m not good enough,” as if the whole world is privy to your inbox. It’s like we’re being told it’s not you, it’s me, but here’s a pat on the ass as we slam the door in your face. (Also, “quite” is a bitchy word.)  But an editor is not an ex-boyfriend or a potential mate, they’re not your parent, and what they’re saying isn’t personal, even though it toes the line. They’re not employed to sugar-coat rejection for you.

Writer Scott Muska agrees, elaborating, “It spurs from the simple fact that society never really gave women the same opportunities as men. People were less likely to accept items women wrote, and when they were rejected, there were fewer places they could take the same idea and re-pitch it. I hope I live to see the day of real gender equality, but it’s not really there yet.”

Time and again we hear from women who deal with rejection terribly. They mull it over all day long, vacillating between the stages of grief:  denial (should I write the editor back and explain further, probably, yes), anger (how dare they tell me I don’t meet their criteria, how DARE they not respond to my second email), bargaining (maybe I can just send it somewhere else), depression (I’m a failure), acceptance (failure happens).

Don’t be too down on yourself. There is a set of alternative responses and stratagems that give you the confidence to move on to the next without feeling dejected.

Allow yourself the emotional budget for failure.

It will happen. You will get upset, especially when you’re pitching something near to your heart. You may pitch 100 times or 1,000 before someone says, this sounds interesting (only to say, it’s not quite for us ten emails in), but with each new pitch, you are working; you’re refining your work. Build confidence inside that failure by accepting it is part of the business.

If there’s no time stamp on the piece, wait a day, or at least a few hours before you pitch it again.

This may feel counter-intuitive at first because with the speed at which articles are posted we’re primed to believe that if we don’t get there first, someone else will. That’s possible sure, but if you send something out steeped in the anger of the first rejection, you’re going to take the second “no” even harder. Moreover, spending all day hitting the refresh button on your email is not advancing your cause– you’re only wasting precious time. Instead of anxiously waiting for a second response, and possible rejection, brainstorm ideas, work on something else, read a new site, taking note of how they do things, and add it to your pitch list. Which leads us to…

Instead of pitching every outlet the same story, optimize your potential for success by creating different tabs for different companies.

Whether you do this in an Excel spreadsheet or in a binder, create a tab for the top twenty sites you’d like to write for. Every time you have an idea, consider where it would best fit, and enter the idea or write it down in the corresponding tab. Pitches should be like cover letters– if they’re not tailored to the section, site, and editor, you’re much more likely to get a no.

Beyond that, while it is nice to swing for the fences and home runs are possible, most writers don’t get published in the New Yorker during their first at bat. The top twenty list should be tiered as to avoid tears.

If you’re going to pitch, do so with passion and without apology.

Women apologize for their answers before they begin. “This may be wrong, but,” “I just…,” “Can I ask you a question?” “It seems like…”

Remove these from your writing vocabulary. Men take risks, they decide on an idea and take that stance without apology. We receive so many submissions peppered with  phrases like “seems like,” and “appears to be.” But the reality is such phrases detract from the quality of your work (we’re guilty of this as well, but we’re working on it). If you don’t commit to the pitch, how do you expect an editor to? The more we work on removing these qualifiers of certainty from our word bank, the stronger our writing becomes.

The more confident you are in your words, the more confident you are in your pitching.

And the harder you work, the luckier you get. A man said that. But the same applies to women. So keep pitching. Get your heart broken. You’ll only be stronger for it.

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