Can Freelance Writing Help Aspiring Novelists? Considerations, and Some Warnings

On December 1st, 2020, actor Elliot Page came out publicly as transgender. And on December 4, 2020, I became a published writer.

There’s a story here, of course, connecting the two. It begins with an excited Facebook post on my end about the Elliot Page news–practically a national holiday for the transmasculine community!– followed by a text from my good friend and fellow writer, Sara Shukla, asking if I might be interested in pitching a short piece about Elliot’s coming out to her editor at WBUR–Boston’s NPR News Station.

I’ll be honest– my initial reaction was “no, thank you.” Though I’ve wanted to be a published writer since I was a kid, my dream is novels, not articles. And besides, I’m not a trained journalist or someone particularly important. I’d always assumed that if I published any sort of personal essay or the like, it would be to accompany my novel’s eventual publication, or perhaps afterwards, when I had some credit to my name. Who would want to hear anything I had to say now? 

But like all great ideas, once it was planted, I couldn’t get it out of my head. My “no thanks” quickly became a “well, maybe” and then an “okay, so I drafted a short piece.” With some encouragement and coaching from Sara, I sent it off, figuring that at the worst WBUR would pass, and at best they’d take it and I’d get my fifteen minutes of attention from friends on Facebook and Twitter.

It was of course the best case scenario. Better even. Not only was the piece accepted, polished, and published within three days, but it wasn’t just my friends who saw it. Nor did its impact end with my fifteen minutes of (minor) fame. My article was seen by not one but two people who then reached out and asked me to write for their websites. Writer Unboxed was one of those opportunities. And I only received that opportunity because one writing friend encouraged me to take a leap I wasn’t sure I was qualified for, and another re-shared my work on Twitter and vouched for me as a writer.

I don’t tell you this story to brag, but because my experiences in the past few months have taught me a lot. I haven’t given up on my novel or that particular dream, far from it. If anything, freelance writing has shown me that the years pursuing writing have not been in vain. If you’re anything like me, years spent working on a novel, or multiple novels, or multiple drafts of multiple novels, can leave success and completion feeling elusive, at best. Freelance writing has been a way to hone my craft, make connections in the writing world, get my name in print, and even make a small amount of money. It’s an opportunity I didn’t realize was an option, and now I’d like to share some of what I’ve learned with you, including the whys, the hows, and a couple of warnings.

Potential perks of freelance writing for novelists-in-progress:

Complete the circuit. Writing a book is long and hard and sometimes feels like a dark slog through a cold forest in Siberia with a cast of characters who have no intention of listening to a word you say, and each time you think you’re about to find your way out you realize you’re back at the beginning like some sort of labyrinthine journey out of the underworld. And yes, I’m mixing metaphors and myths and it probably makes no sense, but neither does writing a novel at least half, if not 90% of the time. And I love it. I truly do. But every once in a while it is nice to have a win, and if that win is in the form of a piece of work that can be written and completed in hours to weeks rather than months and years? All the better. And if that piece of work is also accompanied by some social media likes and praise from friends? Well –I’M A SHALLOW PERSON WHO NEEDS AFFIRMATION, OKAY?

But seriously, writing articles and essays is a great way to feel a sense of completion, as well as to practice working under a deadline, bringing a project from beginning to end through revision to publication, and yeah, maybe getting a bit of positive attention along the way. 

Create new opportunities. I’ve been terrified before each opportunity I was extended, whether that be the initial suggestion from Sara that I pitch a piece to WBUR, the offer to write for Writer Unboxed, or the offer to write a first (and then a second) piece for Them. But each new opportunity has been so fulfilling and has helped me gain the confidence to take on the next piece. I’ve also learned that one opportunity often leads to another. Each step I’ve taken in this six-month journey has contributed to an opportunity I couldn’t have predicted just a few short months ago. And even when an opportunity might not lead directly to someone knocking on your door with the next one, it can give you the confidence to seek it out for yourself.

How to dip your toes into the freelancing water:

Research. Start to familiarize yourself with possible publication outlets. My first submission was through WBUR’s Cognoscenti, while another friend has published a piece at McSweeney’s. Read personal essays, humor pieces, think pieces, and then do a search to see if the websites take open submissions. Certain websites also have fast track consideration if a piece is considered “timely” — that is, relating to some newsworthy event or issue currently in the public’s attention. 

And in case you’re worried about what qualifies as timely, my friend Sara wrote a timely piece for McSweeney’s from the perspective of a ball pit reopening after Covid. Yes, really. And it’s absolutely hilarious–do check it out!

Find your angle. So you’ve done your research, found some potential outlets you might want to submit to, and now you’ve got to come up with a piece. If you don’t already have an idea in mind, have no fear, I’ve got suggestions. Perhaps you don’t think you’ve got a connection, an angle, or a story to tell. You’re wrong.

Start by taking stock of yourself, beginning with identity and profession. Identity can encompass everything from your racial or ethnic identity; sexual orientation or gender; disability status; to your identity as a parent during Covid, the child of an aging parent navigating a complex health care system, husband of an emergency room doctor, or even a ride-or-die fan of the summer Olympics. Think broadly and don’t limit yourself. 

Professional experience is another great lens through which you can offer your perspective to the world (or the small subset of Twitter that happens to check out a link to your piece). As we continue to deal with or start to move on from this past year and a half, the perspectives of teachers and other education professionals, gig economy workers, restaurant employees, unemployed artists, and overburdened psychologists, doctors, and nurses has never been more relevant. 

If none of those angles lead to inspiration, then perhaps it’s an experience you’ve had that you can share–a solo hike through the Portuguese countryside, a romantic meet-cute worthy of Modern Love, or your account of spending 24-hours in a Waffle House after coming in last place in your fantasy football league (yes, really). Or maybe your angle is humor — an old piece on The Toast about the pitch meeting for Wishbone is still one of my favorites. I do a dramatic reading with a friend at least once a year. 

Utilize your resources. I don’t just mean hit up any connections you have at a particular publication (although if you have them, you really should do that — for better or worse, connections are part of the game). If you have other writing friends, consider asking them to do a pass on your piece before you submit. Asking a friend to read a full draft of a book, or a partial draft, or many, many, many drafts of a book (thank you to all the friends who’ve done this for me!) can be daunting. No one wants to burden their friends with such a big request. But short pieces? 750 – 1500 words? That’s a much more manageable ask and, in my experience, can be the difference between a piece with promise and a piece that commands attention. And if you don’t have friends who can do a pass on your work, that doesn’t mean you’re out of luck. Maybe all you need is a friend who can tell you they believe in you, and give you the confidence to hit submit on that email submission. Or a friend who will retweet whatever piece you eventually get published. After all, you never know where it can lead. Take it from me.

And finally, some warnings: 

Don’t get (too) distracted from the bigger goal. Just as I’ve finished telling you how great freelance writing can be, I’m here to tell you not to be too lured in by the siren call of quick publication. I’ve been working on my current novel since 2018, and another novel before that, and a series of partially completed stories dating all the way back to the time I was a kid. Objectively I know I’ve come a long way, and I’m proud of where I’m at, but day to day? I often drag my feet on revisions and wonder why I haven’t gotten an agent yet. Freelancing these past few months has felt good and each time I see my name in print I get a jolt of satisfaction. But it’s also easy to allow myself to continue pushing off the hard work of revising my novel and querying agents in favor of one-off pieces. So if you’re anything like me, be sure you’re taking on other assignments in aid of your writing career, not as a way to avoid going back to your novel-in-progress!

Choose thoughtfully. There are so many different places to be published, and while I do believe that one opportunity often leads to another, there is always the potential to be taken advantage of when you are providing labor at will. The opportunities I’ve had in these past few months have been varied– everything from a personal reflection on Elliot Page’s coming out, to giving writing advice, to creating a guide to know if you are transmasculine, to an upcoming piece that involved interviewing an actor. As varied as the assignments have been, the pay has been even more so, ranging from nothing, to a small $50 stipend, to a few hundred dollars for a piece. But each opportunity I’ve said yes to, I’ve said yes to for a reason– because I cared about the assignment, because I wanted to contribute to an incredible writing community, because I wanted to advance my writing skills or connections, or because yes, I wanted to make a bit of money on the side. 

If we were just looking at the financial side of things, it could feel like I was being taken advantage of. But there is a huge difference between working for a community you care about, or a small publisher with less means, and a large corporation with the ability to fairly compensate for your labor. Money is far from the only reason to do the things we do, and as long as I am getting value in some meaningful way from an assignment, I will continue to do some work for free. But what I refuse to do is invalidate my worth. I’ve seen countless examples of large corporations or organizations asking (often marginalized) people to perform labor for free, or at a significantly undervalued rate. So be cautious as you step into the freelancing world, and don’t be afraid to do your research and say no when it’s necessary.

I know I’m hardly an expert in the freelancing world, but I’ve learned a lot already and anticipate that I will only continue to learn more in the future. It’s been an exciting time in my writing career, and I look forward to seeing what the next opportunity holds. 

For those of you who have done freelance writing before (and undoubtedly have much more experience than me!), what advice would you give to someone looking into it for the first time? And for those who have never done it before, what questions do you still have?