Eek! Don’t Be Afraid of These 13 Freelance Writing Challenges

by | Oct 9, 2018

Just in case the abundance of pumpkin-shaped decor in every storefront didn’t tell you, Halloween is on its way.

But for writers, the scariest situations have nothing to do with masked monsters or creepy, remote cabins. (Actually, a lot of us would probably like to spend some time out in the woods.)

So we put together this list of some common freelance writing challenges — and our best tips on how to crush them. Whether you’re a beginner yet to publish a single blog post or a full-time freelance vet, here are 13 writing-related conundrums you don’t have to be afraid of.

1. You want to become a freelance writer, but you don’t know where to start

There’s nothing more disheartening than compulsively putting words down…only to have them languish in your notebook or hard drive. (Though honestly, that’s how most of us got started.)

Although writing for yourself can be cathartic, writing for an audience is next-level fulfilling. And, bonus: it can get you paid.

While there’s no tried and true path to gainful freelance glory, there are some steps you can take to increase your chances of getting those words of yours in front of some eyeballs — and turning them into cold, hard cash in the bargain.

Here’s our step-by-step guide to becoming a freelance writer, and a foolproof way to make your first $100.

2. You can’t find work — or at least, work you’re paid for

Whether you’re looking for a full-time writing job or you’re a freelancer trying to fill out your client roster, finding paid writing work can be notoriously tricky.

(Most writers are probably familiar with a very particular type of hobgoblin: the client who asks you to work for free, thinking you’ll do it “for the exposure.”)

Luckily, we’ve got tons of resources to help you find paying gigs. Here are a few posts to start with:

3. You’ve got clients… but they won’t pay up!

With pretty much every other job, you can expect to be paid for your efforts — usually on a fairly regular basis.

Not so, unfortunately, with freelance writing, the career where it’s apparently totally acceptable for a client to pay you literally months after you’ve performed your service.

There are some effective ways to confront these belated boogeymen, however. Here are seven tips for handling a freelance client who won’t pay up by author and blogger Ali Luke.

4. You’ve got a hard drive full of essays and stories, but don’t know where to send them

Everyone talks about writer’s block, but the opposite problem can be just as daunting: having way too many good ideas, and no idea where to put them.

Whether you write fiction or nonfiction, though, there are plenty of magazines clamoring for your work. Here are 19 websites and magazines that want to publish your personal essays, and 23 that want your short fiction.

5. You know where your latest piece should live, but you have no idea who or how to pitch it

So you’ve got a story that’s just perfect for Salon. Or Harper’s. Or… wherever.


But how exactly does one go about giving Salon (or Harper’s, or wherever) that intel?

As difficult and time-consuming as writing the piece itself can be, figuring out how to pitch it — and to whom — is just as important. And it’s complicated enough that it’s definitely its own separate art form.

So if you’ve yet to pick up your pitching paintbrush, check out this post by veteran freelancer Susan Shain, who’s got all the details on getting your great idea into the right hands.

Think Freddy Krueger is scary? Try freelance clients who never pay on time.

6. You have a killer project in mind, but you just can’t make time for it

Name me a writer — nay, a human being — for whom this scary scenario isn’t a reality.

Finding the time to follow our passions is difficult, to be sure, but it’s also worth it. And if you’ve got a great story simmering on the back burner, a writer’s residency could be exactly what you need to get it down on paper.

If you’re unfamiliar with the idea of a writer’s residency, it might sound too good to be true. Basically, an artsy organization puts a roof over your head — and sometimes even feeds you — for a while, specifically so you can take the time you need to work on your creative project.

Specific expectations about community involvement and monetary contribution vary by program, but most of them are low-cost and many are actually free.

As in, yes, you could get free room and board — and most importantly, time — to do absolutely nothing but writing. Here are 27 such programs to check out.

7. You’ve got a great blog idea, but zero technical know-how

A blog is an amazing way to boost your online presence as a writer, and it can even be a viable business unto itself.

But even if you have the most amazing blog idea in the world, it’s not going to do squat for you until you turn it into a real, live website.

If you don’t know WordPress from Word and think a hosting package has something to do with dinner parties, you’re in for a learning curve… but with this step-by-step guide on how to start a blog of your own, it’ll be shallower rather than steeper.

(Psst: we also have tips for choosing a domain name, if you’re stumped for ideas.)

If you want to see whether a specific domain is available, try this domain checker:

8. You’re doing okay as a freelancer, but the money could definitely be better

Hey, let’s face it. There’s a stereotype about English majors working in coffee shops for a reason.

But there are plenty of writers who earn a living doing their craft. In fact, some of them earn a darn good one.

If you’re just scraping by on your freelance income, or if you’re looking to turn your side-hustle full time, check out these six tips. They’ll help you earn more for the work you’re already doing — and find some higher-paying clients to boot. You could also try pitching these outlets, which pay $500 or more.

We’re not saying you should rush out and put those Louboutins on credit… but you might be able to upgrade to two-ply toilet paper. (Kidding. Kind of.)

9. You went full-time freelance, and now you don’t even own a pair of non-yoga pants

This might not sound scary on its surface, but trust us: After a few months of working from home, you’re going to miss wearing real clothes. (And, you know, eating meals at actual meal times.)

And your wardrobe isn’t all you have to worry about. If you don’t maintain some sort of structure, you may find yourself answering work emails at midnight…or procrastinating until just hours before your deadline.

But don’t despair! All you need to do to combat this particular beast is to set some non-negotiable rules about your daily routine. Here are a few ideas from freelance writer and novelist Nicole Dieker to serve as a guide.

10. You’ve got an assignment…but you honestly know nothing about the topic

As a writer, you’re not expected to be an expert in everything you cover. But you are expected to know how to do the research to cover it well.

If your go-to research move is simply to Google… well, honestly, that’s part of it. But there’s a lot more to it, too.

Here are some insider research techniques to help you do (and ace) your writing homework.

11. You want to write a book, but you have no idea where to start

Even non-writers often put “writing a book” on their bucket lists.

But even if you’ve got an amazing idea, getting started can be insanely overwhelming. I mean, we’re talking about a book, here. It’s hard enough just to write a blog post!

But as our crowded shelves can attest, books do indeed get written — lots of them, in fact. And if you put your mind to it, you can write one, too. Here’s how to get started. (And if you’re extra brave, here’s how to do the whole darn thing in just three weeks.)

12. Your editor returns your manuscript, and it’s a sea of red

If you’re like most writers, your words are your babies, so it can be downright painful to see your manuscript covered over with so-called “corrections.”

But even if your editor has a heavy hand, you can get through the editing process without having a panic attack — we promise. Try these seven stress-free ways to handle notes from your book editor. (And remember: she’s only trying to help. Honest!)

13. You wrote a book (congrats!)…but no one’s actually buying it

Writing a book involves jumping so, so many hurdles. Just coming up with a viable idea can take a lifetime, and then there’s the actual writing (and rewriting, and rewriting again). And then you have to find a willing publisher.

How scary would it be to come through all of that… only to have a finished product that’s just sitting in your basement, collecting dust in cardboard boxes?

Unfortunately, that fate is a reality for a huge number of authors. But with a little bit of marketing know-how, you can get those books out of the boxes into the hands of new readers.

Here are some email marketing tips to get your list on board to purchase, as well as nine common marketing mistakes to avoid. If you’re extra tech-savvy and comfortable with the internet, you can also learn how to use social media to your advantage.

And if all that techno-schmoozing isn’t your bag, no worries. One great way to sell books is to actually get off the computer and go meet your readers in real life.

See? All those inky nightmares aren’t so scary after all.

Happy Halloween, writers!

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