From Pitch to Paid: How a Freelance Writer Makes a Living

February 2014 stats:
Total earnings: $1,911.76
Completed pieces (all types): 87
Essays published: 0 (although one of my essay pitches was purchased for future publication)
Novellas being revised: 1

February’s earnings were lower than usual because I spent one week on JoCo Cruise Crazy, a six-night Western Caribbean cruise with singer-songwriter Jonathan Coulton. When you’re on a floating nerd boat in the Caribbean, you can’t write articles or earn money.

However, it’s looking like I’ll catch up on the lost earnings in March. I got two new clients in February (bringing my total client relationships up to eight), one of which pays several times more than the “content industry standard” of 3 cents a word. I also had a lot of good news in my inbox re: people wanting me to take on additional projects, which is great because the perpetual fear of the freelancer is that nobody will want to hire you for any projects.

Being a freelancer is like having to apply for your job all over again every single day.

With that in mind, here’s everything I know about pitching.

When I use the word “pitching,” I specifically mean “pitching essays to online magazines and sites like The Billfold.” I don’t mean “getting hired by listicle/copy/content clients,” which is a completely different process. (Getting content clients is like applying for a job: you fill out the online application, take the grammar test, submit a writing sample, and wait to hear if you’re in. Then, once you’re in, you use your growing body of work and networking skills to get to the next level of clients, the ones that don’t necessarily advertise job openings online.)

My goal is to send out one solid pitch a week, although I don’t always hit that goal. The hardest part right now is finding new sites to pitch; you have to really spend some time with a site before you understand its voice and its audience, and that work often gets bumped off the daily to-do list.

My pitches have about a 50 percent success rate. This is a useful data point because it is also creatively freeing. Once you get to the point where you feel like “this will probably be accepted” vs. “oh good gravy nobody’s going to like me,” you can take chances. You start to think that your ideas and instincts are good, because the previous ones have worked out so far.

(Also: yes, I know that 50 percent doesn’t actually mean “this will probably be accepted.” But it feels like it does.)

When I pitch, I keep the cover email as short as possible and I always attach the completed essay. Here’s why: If I send a pitch without an essay, the editor is going to have to sit there and guess, based on a three-sentence email, whether or not my writing is any good. If I send the essay along with the pitch, my work can speak for itself.

Yes, that means that I have to write the entire piece before I start pitching it. Yes, this process takes a long time. And yes, nearly all editors refuse to accept simultaneous submissions, meaning that I have to wait three to four weeks for a pitch to be rejected before I can send it to another site. (In internet time, that feels like three to four years. You will have pitches die because they stop being relevant between the time you pitch them and the time they are rejected.)

I have one piece out right now, a longform essay on Lev Grossman’s Magicians trilogy, that has been rejected four separate times. I started pitching it at the beginning of the year because I knew I had to get it placed by this August, when the last book in Grossman’s trilogy comes out. It will take that long. It seems like it won’t, because the internet is so instantaneous and because sites like The Billfold and The Toast publish a dozen new pieces a day, but you need to expect a four-month lag time between when you first write an essay and when it finally gets posted.

(Right now, for the record: I have eight essays that have been purchased but not yet published. Two of them were written in September 2013.)

And now payment, aka “why becoming a professional essayist is so incredibly hard and/or impossible.”

You’re either going to get paid at the point of acceptance (YAY!) or at some point after the essay gets posted (still yay, but less enthusiastic). Since some sites work on 60-day billing cycles, it is not only possible, but likely that you’ll write a piece, pitch it, get the pitch accepted, and not see payment for six months.

For all that the professional writing community is all “don’t fill in your income with content jobs, it won’t help you advance your career as a Serious Writer,” I have no idea how you do this type of work without including content and listicle jobs. The math just doesn’t make sense. I have a 50 percent pitch success rate and it still doesn’t make sense.

If you want to get started pitching articles and essays, here is my advice: Pick a site on which you already spend a lot of time reading and commenting, because you already have a good feel for the community and the site’s audience. Write the essay first. Write it for you, but write it for them, too — the real people you’ve come to know just by hanging around the website so much.

Craft a very short cover email. Neither over-explain nor apologize for your work. Then pitch, and see what happens.

Next month, I will tell you all about my expenses. (Teaser trailer: I live in a studio apartment with no kitchen, and hand-wash my dishes in a bucket in the bathroom.) What’s my monthly overhead cost? Do I have debt? A savings account? Regular health care? A retirement account? A coworking space? Answers to all of these things AND MORE are coming soon!

Previously:Listicles, Copy, Content, and Essays: How a Freelance Writer Makes a Living

Nicole Dieker is a freelance writer and ghostwriter, and is the only member of the band Hello, The Future!

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