Everything You Wanted To Know About Freelance Writing

freelance writing

In addition to being the News & Politics Editor at Literally, Darling, Bridey is a freelance writer. She’s a contributor at HelloGiggles, Trazee Travel, and WildSpice. She has work forthcoming in BUST, BITCH, as well as at PANK and LARB. She has also appeared at Huffington Post, xoJane, NO TOFU, and A Practical Wedding.

Taylor Prewitt is a freelance writer currently trying to figure out how to make it work in Austin, Texas. From her office at the nearest coffee shop, she contributes to AllDay.com and Gritstyle. In 2015, she hopes to pitch at least one piece a week (hopefully more!) and to publish at least one investigative longform piece by the end of the year.

How do you begin freelance writing when working a full time job?

 Bridey: I really lucked out because I got my full-time job after deciding to go freelance. As a result, I started substitute teaching, which allows tons of time to write and exactly zero pressure outside of work hours. That being said, it is a little up-in-the-air every day whether I’ll be free to write and if so, when during the day. To get around that, I try to give myself cushion time when promising finished work to editors, so that if one day I can’t get to the computer all morning it doesn’t throw off my routine. I also don’t spend too long working on pitches before I send them, so that I don’t get bogged down and lose time!

 Taylor: It’s definitely doable and probably practical to start freelancing while working full time. When I had a full-time job, I used free time like lunch breaks to send off quick pitches. At home, I would set aside an hour or two (or four if the assignment was long) to write and send more pitches. There’s no way around it—you’ll have to work after work, which isn’t necessarily the first thing you want to do when you get home.

 How you deal with insurance/retirement/financial insecurity?

 Bridey: This is something I’m just starting to get into. My job doesn’t offer benefits, so I’m already on my own for everything. Having an emergency fund with more than the usual 3 months is one way we’ve gone about making sure we’re financially sound. As for retirement, investing is kind of a must.

 Taylor: Financial insecurity is probably the biggest hurdle for me in this industry—more so than even rejection. It’s just something you have to swallow if you want to freelance and I’m still working on being ok with it. An emergency fund is a great idea as is an IRA.

 One word: Rejection.

 Bridey: I’m very non-confrontational and I take things very personally, so I was really worried about rejection. But strangely enough, it doesn’t bother me. It helps that a lot of places just ignore you if they don’t want your pitch, so you can live in denial that they ever even saw it. But even getting a negative response doesn’t ruffle my feathers, and it never really has. You just keep on keeping on, and plan to blow them out of the water with your next pitch!

Taylor: I also take things especially personally, but it helps to know that rejection happens to everyone, even to your favorite writers or journalists. It’s also not personal—publications are businesses and are acting in their business’ interests. Lastly, it’s important to remember that rejection of a pitch from a publication doesn’t mean that publication or its editors never want to hear from you again. Just keep pushing/pitching.

How can writers with little experience be taken seriously in such a competitive industry?

Bridey: I worried a lot about this starting out. In any other field you have other people who tell you if you are qualified, but when you start freelancing you really have to sell your skillset. Starting small and, in some fields, working for free to build up clips is one way many go about gaining credibility. If you are in a field where clips aren’t really a thing, like ghostwriting or tech, make sure you work out with the client how you can display the work for marketing. At the end of the day, exceeding expectations is going to be your biggest asset. Turn in well-edited work ahead of deadline, be open to edits, and be pleasant to work with. Editors remember that kind of stuff, and are more likely to offer future work or vouch for you as a reference.

 Taylor: Everyone has to start somewhere even if that means writing for a smaller publication just to gain experience and clips. I’m of the opinion that clips, quality work and unique pitches are more important than experience. In the beginning, spread your feelers far and wide, make necessary connections and write like crazy.

Where do you find good, reputable sites to pitch?

Bridey: There really isn’t a one-size-fits-all approach to where to pitch. It all depends on what you’re writing about, what your style is, what your background includes. But one thing I’ve learned is that it never hurts to try. Shoot out an email and see what happens!

Taylor: Great readers make great writers. Most of the places I pitch to are publications that I read. Being a frequent reader of several great sites means you understand which pitches those publications will love and which pitches are better suited elsewhere. I also like to keep up with some of my favorite journalists to see where they’re writing. Lastly, I keep a Google spreadsheet organized with my favorite publications and any editor contact info I have on file. That way, if I have an awesome pitch in mind, I can scroll through the document to find a perfect home for the idea.

How do you build up income while freelancing?

Bridey: I’ve been able to build up a steady income stream by starting small and pitching big. Get a few clients with monthly work, and build from there. A lot of people talk about the value of really needing to make a living off of writing when it comes to building your career, but I find the opposite. Having a steady source of income outside of writing has given me a lot of freedom to build my career in the way I want to, because I can put off a payday in order to place a piece somewhere larger and ultimately better paying.

Taylor: I’m with Bridey here. Though I’m currently full-time freelancing and receive all of my income from writing, I started with a full-time job where I was able to save up enough money to make the leap. Now that I have, I look for steady work and monthly paychecks, with personal projects and pitches on the side.

How do you deal with writer’s block? OR do you feel that freeze when it’s time to come up with new ideas? Some days I’m like, “OH GOD I AM TAPPED OUT AT 28 HAAAALLLLPPPPP!”

Bridey: Well, I’m only 26 so I can’t relate to this existential crisis you describe. JUST KIDDING IT’S MY LIFE. I deal with it by letting the day go. I make sure I’m always working well ahead of deadline, so that if I do get super run down in the dirt for whatever reason, I can spend a day on the couch feeling sorry for myself. Invariably, the next day I either have a great idea, re-read a piece that I wrote and has potential, or get an encouraging email from an editor that puts me back on track. Sometimes you just gotta ride the wave.

Taylor: This is such a great question. Writing day in and day out can really put a strain on creative sentence structure or even new ideas, especially when you’re not always writing what you’d like to be. I’ve found that taking breaks really turns the tide. Whether it’s taking an hour to catch up on article reading or heading to the gym to just forget about writing altogether, taking a step back really helps me face a blank page with fresh eyes.

Handling/reporting taxes, do you have a set amount of money you need to make each day/week in order to afford and if so how do you organize that?

Bridey: I was not great about this last year, because until the final quarter I wasn’t bringing in a whole lot. But starting on January 1, I’ve been tracking all my income, including what’s been invoiced and what’s been paid. I put all my writing income into savings right now, because it’s not my primary source of income. In a spreadsheet, I track pre-tax income and also what my estimated taxes will be on it, so that I have a sense of what will actually be my “take-home” pay. Later this year, when I go full-time freelance, I’ll “pay myself” from the “take-home” pay so that I always have the tax amount ready to send in.

Taylor: This will be my first year filing “grown-up” taxes so this is something that I’m still navigating. I also only started freelancing in August of last year so my taxes will be a confusing mess this year. I’m not going to do it alone though. I’ll be seeking professional help from an accountant. Like Bridey, I also keep track of what goes in and out so that I have an idea of how much I owe.

Do you find having to pitch for money makes you write better?

 Bridey: The only free gigs I take now are with sites that I respect a great deal, so I wouldn’t say my writing changes much between assignments. My pitches don’t really change much either. If anything, I think pitching for money has made me pitch more, because my income is directly related to the assignments I land. But that’s really the only difference.

 Taylor: My pitches haven’t really changed except for maybe the frequency. Since I have a pretty steady paying gig, I’m really about pitching the publication now and am less concerned with how much they pay.

Does the popularity of the listicle and the importance of viral posts make you feel like your creativity is hindered because you have to pitch what will get picked up, which is what will go viral?

Bridey: Honestly, not really. I do write lists sometimes, and will be doing more of them in the near future, but I don’t write them on topics I don’t find interesting. I did a list not long ago of female leaders in the ancient world, for example. I don’t think the listicle format has to result in pieces that belong in a dumpster. I think it can be a quick take on really awesome, obscure subjects that might be really daunting as a more traditional post. And since a lot of what I write is kind of niche (like Iran, for example) I’m willing to embrace the format and bring my own voice to it.

Taylor: I’m lucky in that I enjoy writing about pop culture and popular topics. I definitely consider how a pitch will do or how popular it will be when I send it a publication’s way, but I think that’s an asset. If I have a pitch that’s timely or a “hot take” (God forbid), I make sure editors see it that way also. I don’t mind listicles creativity-wise—it’s sometimes fun to break the normal article format.

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