How writing for free can lead to paying writing work

I used Grammarly to grammar check this post, because despite my horror when I see discreet and discrete mixed up, I have my own grammar bugaboos.*

Let me start by saying that this is a complicated topic, and I don't have all the answers. There are many factors that go into deciding whether to write for free, how much to charge, what your minimum fees are, etc. What I want to do with this post is offer a few examples of how writing for free led me to paying writing jobs. That being said, I believe everyone should be paid for their work, and don't think you should aim to write for free. You should aim as high as you can, and equal pay for equal work isn't just about gender equality, but about knowing, owning and demanding your worth. That being said, if working unpaid can lead to bigger and better things that you might not have access to otherwise, it can be worthwhile, in my experience (and of course I'm only writing from my own very limited experience here).

My aim here isn't to debate the finer points of what writers should get paid; you can get fascinating insights into that at The Awl in "How Much Should A Writer Get Paid? A Conversation", and Noah Davis breaks down his freelancing assignment rates by the numbers.

Ann Friedman offers up some excellent reasons to write for free, based on her work experience. Of her pie charts for The Hairpin, she writes: "After I published a few and people seemed to like them, I made it a goal to find a publication to pay me for similar work. "

I also can't recommend enough Virginia Sole-Smith's writing about freelancing, especially "On Getting Paid (And Knowing Your Worth)" (her math on figuring out how valuable your time is was a whole new way of looking at the topic for me) and "Why Creative Word Fairies Need Business Plans, Too".

In my case, I'd written a few pieces for Nicole Cliffe when she was at The Hairpin, for free. Why? Well, I'd pitched my review of The Feminist Porn Book to a few sites that passed, and wanted it to be read, ideally by readers who'd be interested in the topic, plus I wanted it to be timely. I didn't want the work I'd put into the review to go to waste, and I wanted to join the conversation about the book. I also did an interview with former Westboro Baptist Church member Lauren Drain about her memoir, Banished, for similar reasons. When it was announced that Nicole was leaving The Hairpin to launch The Toast, I queried her, and so far have written "Sympathy for E.L. James" and "Hoarding Isn't Fashionable or Glamorous." Both pieces are paid. I couldn't have known that would happen at the time, but it was fortuitous.

I got invited to write for Medium.com in May, and was interested because I'd read about the site on Gawker, and was avidly reading all sorts of essays about a variety of topics. Most were tech-related, but there was also a great column by bakery owner Allison Robicelli, about everything from appearing on Chopped to her letter to a first-time father.

Even though I wasn't being paid, I agonized and agonized over what my first post should be; I even decided I'd try to go all out and push myself to write an essay a day. That so didn't happen, despite my handy chart of what I planned to write about. Maybe someday it will. But when James Gandolfini died, I hammered out my first post for them: "James Gandolfini Was My Celebrity Crush." I worked all morning on it, then hit publish, and went to lunch. I didn't get paid, but you know what? I felt great, for having written it. For not having thought about it for weeks or months until my ideas turned to mush in my head. Salon reprinted it. I didn't get paid for those, but it was okay, because I had contributed something I thought was important, and perhaps brought in new readers in the process. One thing I especially like about Medium, as a reader and writer, is that your profile is linked to your Twitter account (you must have a Twitter account to post on Medium), so it's very easy to start following writers you like. I've found some amazing writers that way. You can also view your statistics, and I'm trying to use this information to help me figure out what works and what doesn't in terms of drawing readers, which I plan to use when formulating pitches for other publications. For me, since much of the focus of the writing is tech-oriented, I have a feeling I'm reaching readers I wouldn't normally reach, which to my mind is always a good thing.

When I was asked to contribute to the Boinkology collection at Medium, I was honored, but I said I'd only do it if I was paid. This was different to me than the Gandolfini piece, because this is my area of expertise, the topic I write most about, and I'd probably be writing things I'd likely sell elsewhere if I didn't write about them for Medium. Based on the Gandolfini piece, someone who I don't think would've known my work previously, knew who I was and agreed. So far I've written "Wikipedia Thinks I’m a Lesbian — And This Bisexual Is Okay With That" and "I Don’t Want or Need an App to Measure My Sex Life" and "5 Ways to Use Technology to Write Erotica". One thing browsing Medium, including their monthly top posts(right now "Why I Quit CrossFit" was the most popular in July), has shown me, is the power of a headline. Think about your title standing alone on Twitter as a link. Then, it won't be your name or your writing or wittiness selling it, it'll be your title. That has helped me crystallize exactly what I'm trying to say, hopefully in a snappy way.

Here's where it gets a little woo-woo: you never know who is going to read your work, and where that might lead. Ann Friedman says she plays a long game. As someone who is both trying to sell freelance articles and promote my anthologies and, hopefully, someday, my own authored books, I know that there may be readers who've never heard of my erotica, or never thought about reading erotica, but might think, Hmmm....Baby Got Back. That's funny. Maybe I'll check that out. That's why I have stories posted for free on my website and Goodreads. I got paid to write them, but am now giving them away, in the name of building up a readership. And I think that figuring out what your end goals are is important. I don't have that aspect totally down pat, but I know that I have books coming out well into 2014, so I try to keep up with what's happening in the fields I write about, but also broaden my reach to readers who may never browse the erotica section but might want to check something out based on reading either my nonfiction or fiction. You never know who might see a post and, whether that day or down the road, recommend you or your books to someone else. That's the part that you can't control, and may never even know whether or how someone came to notice you, but for me, it's worth taking the chance. My royalty checks are what pay my rent (with a bump from freelancing), so if I write something for free but enough people see it and buy a few books, that helps.

Right now I'm working to get my career in alignment, so the things I want to write about are also the things I get paid for. I spend a lot of time pitching, and sometimes that feels like "wasted" time, in the sense that I tend to agonize over it and do a ton of research and most often it doesn't yield an assignment. Those pitches aren't paid, but the hope is that by honing my pitches, reading the publications I want to write for diligently, broadening my scope and keeping pitching, it will pay off. I'm not looking for more opportunities to write for free, but rather, more opportunities to expand my reach and try to make freelancing a sustainable career option for me. I almost didn't write this post because I feared that saying I sometimes write for free would give me less bargaining power when I do pitch publications I want to write for. But again, you need to know your own rock-bottom needs and criteria for writing for free or for pay.

A tangential but semi-related topic is that sometimes, for me, it's been worth it to pay money to get a byline. Not buying the byline, but spending money to attend an event or purchase a product so that I could write about it. I paid $129.12 (according to my PayPal record) to attend the E.L. James luncheon by Divalysscious Moms that helped me break into the New York Observer. Not only did attending this event give me insights I wouldn't have had otherwise into the Fifty Shades fandom phenomenon, but also this led directly to me covering a Koch protest in the Hamptons for them. I will also share something that is a huge no-no that I did, a mistake I hope you will never make: I never turned in my receipts to get reimbursed. I saved them, and meant to send them, and then...didn't. Oops. I've done that multiple times, and I have no excuse, but that's a surefire route to making your expenditures not worth it. Keep track of everything, and if your publication is reimbursing you, turn in your receipts right away. Even if they're not, save them for when you do your taxes. I'm attending another event soon that I paid for, in the hopes of covering it for a venue I haven't written for yet, and if that gambit succeeds, it will have been worth it (and if not, it will be an interesting life experience).

Ultimately, I agree with Slate's Matthew Yglesias (see also: his first post on writing for free):

The fact remains that if you have things to say that you think are worthwhile and nobody is offering to pay you to say them, you ought to say them anyway for free. If enough people agree with you that those things are worthwhile, it just may lead to something.

I write for free when the pros outweigh the cons, or I've simply run out of time or patience pitching a piece and would rather get it up, anywhere, than have it live on my computer with only me reading it. Or sometimes, I want a piece to fit in well with like-minded pieces. I weigh the venue and the effort involved and how important it is to me to give the piece a home, and what the possible gains might be. I've written plenty of pieces that never went anywhere because I couldn't sell them, and as I move into my third year of freelancing, I'm doing my best to make sure that doesn't happen, or else take it as a sign, to pitch better and smarter (which is why I very well may retake Anne Trubek's excellent How to Pitch and Submit class, which I highly recommend).

' Lately, I've been riddled with fear, anxiety, writer's block, self-hatred...I could go on, but the point is, I have barely been able to write lately, whether I'm being paid or not. I'm working on conquering those fears, which circle like vultures, zooming in on my weakest spots. In the meantime, any writing is useful to me, because it shows me I can do it, which is another piece of the puzzle, because first i have to believe in myself and prove myself, before I can expect anyone else to. Publishing the pieces I've linked to above for free shows me not every piece has to be perfect (according to me) to be valid, to be done, to be able to turn it in and move on to the next one, and the next, and the next.

* To wrap this all up and comply with the FTC, this post is sponsored by Grammarly, but I was planning to write it anyway.