The gig economy is a vicious, soul-consuming way to try to make a living, and there’s a special kind of struggle being a freelance writer. Through my own years of freelance work, I’ve been through my share of frustrating experiences. So, whether you’re a beginner or a veteran, here are 19 situations every freelance writer has probably been in…

1. Having oodles of ideas but not sure where to submit them

Three cartoon characters stand around a table and one says: "So many possibilities!"
[Description: Three cartoon characters stand around a table and one says: “So many possibilities!”.] Via GIPHY.
It’s a special kind of nightmare to have half a dozen ideas, maybe even a few drafts, but have nowhere to send them. Sometimes you might find yourself questioning whether your ideas are any good since they didn’t immediately fit somewhere.

2. The pro forma rejection e-mail

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“Thank you for your interest but we’ve decided to go in a different direction at this time.” You’re not exactly sure which would be worse, this email that lacks any soul or recognition for your work and time or not hearing from them at all?

3. Not hearing back about a pitch

A cartoon character waits dejectedly by the phone.
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I take it back, not hearing from wherever you’ve submitted your work to is way worse. There’s a period leading up to and immediately after sending a pitch where you can’t help but feel excited. You think it’s good, it’s certainly as good as other stuff you’ve gotten published… And then you wait for what seems like an eternity and realize they’re just never going to respond to you. You might even catch yourself refreshing your e-mail inbox hoping for news.

4. Getting your pitch accepted

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OMFG, they accepted my pitch?! I gotta tell my friends, I gotta tell my parents, I gotta tell everyone! It doesn’t matter if it’s the first or hundredth pitch accepted, there’s still a little jig the heart does when you see that your pitch was accepted.

5. The rush to outline everything

A man in a hoodie is typing excitedly.
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There’s that excitement of starting a new piece of writing where all possibilities are on the table. Nothing is going to hold you back from making this the best piece of writing you’ve ever put down.

6. Chasing down sources for the piece

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Whether it’s a person who has experience with the subject you’re writing about, an expert who might have professional insight, or you’re trying to hire a consultant on a topic so you can get up to speed. Sometimes finding the right people is harder than it would seem and you have to dig deep to find the right people.

7. Settling down to write with your favorite drink

A dark-haired man sips some tea.
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Whether it’s water, coffee, tea, soda, or something fancier, there’s something about setting down your drink at your desk that helps you settle in. Taking a drink gives you an excuse to rest your eyes, if only for a moment. This little ritual definitely helps get into the zone.

8. Having to go to the bathroom right in the middle of a sentence

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You’re writing up a storm and suddenly nature tells you to take a quick break. You’re right in the thick of it but you have to go now. Rush to take care of business and then try to settle in hoping you haven’t lost inspiration. Sometimes these little distractions can really take you out of it, other times it just means diving back in with fresh-smelling hands.

9. Pounding out the finishing touches with the deadline looming overhead

A cartoon man is speedily typing away.
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You’ve put in the time, the energy, and the emotions. You’ve reworked that one paragraph that didn’t read right when you read it to yourself. You’re pretty sure you’ve got a good piece there, but even if there were problems you couldn’t care. You’ve just got to turn it in and get it out there.

10. The wait for an editor to ask for revisions

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That time between submitting your work and getting editor feedback can be agonizing. How bad is it? You start thinking, “I’m going to have to rewrite this stupid thing, aren’t I?” Maybe if you’re really on the ball you don’t have time to think about it because you’re already working on your next piece or project and you’ll worry about revisions when they get back to you.

11. The back and forth on what needs to go and what should stay

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You know that in the end whatever feedback the editor gives you will make your piece better, but that doesn’t stop you from feeling a slight sting when those revision requests come back. With some editors it may feel like a battle, others it’s like being shown a whole different perspective on your piece. The editing process can be night and day for a freelance writer depending on who’s editing.

12. Getting paid

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Nothing feels quite as good as getting paid. Unfortunately, if you’re a freelance writer it means that you’ve probably already got a handful of bills that money is planned for. The money was basically spent before it ever hit your bank account. Weep for the money that was, is, but will never be.

13. Being your own social media manager

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As a freelance writer, if you want people to read your stuff then you have to promote it yourself. That means getting on all the social media: tweeting, gramming, posting, pinning, and every other imaginable thing. It’s never as simple as coming up with something quippy. It’s getting the right hashtags, tagging the right people, and knowing when to post so as to optimize your chances of being seen by the most people.

14. Getting sick and trying to pretend you’re not because you don’t have (good) health insurance

A man fans himself erratically as he visibly sweats.
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Getting healthcare coverage as a freelancer is difficult. In the US, you either have insurance through your spouse or you bought it yourself, but the latter is incredibly expensive even when shopping around on the government’s healthcare marketplace. Drink some tea, take a nap, cry in a corner… you don’t have the time or the money to be sick.

15. Getting a pitch accepted only to discover they don’t pay

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Big name companies do this all the time. They try to act as though the prestige of letting you write for them is enough.

16. Being low-balled for your work

A woman clenches her hands in frustration.
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Nothing stings quite like being paid $0.03/word or something absurdly small like that. This is especially prevalent among new writers, you get the worst of this and it’s all justified because you’re inexperienced. As if inexperience meant your bills were any smaller or food any cheaper. Sometimes companies think it’s ok to pay in you in experience or exposure, but I’ve never had a landlord accept exposure as a form of payment for the rent.

17. Writing something devoid of life but, hey, it pays well

A man says: "I am dead inside."
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Once in a while, you come across something that actually pays well, but it’s either a very boring assignment or something that you couldn’t care less about. The worst of these is when you feel like you’re writing something marginally in contradiction to your own values, but you need the money so you write with one hand and plug your nose with the other.

18. Watch as all the freelancing gigs dry up during economic downturns

A woman pensively rips up a piece of paper.
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When the economy takes a dip, online media companies clamp down on their spending and rely on their staff writers to provide the entirety of their content. This has been a trend years in making. Staff writers aren’t safe either since many media giants won’t hesitate to layoff employees if they think it’ll help their bottom line.

19. Do it all over again

A woman says: "Here we go."
[Description: A woman says: “Here we go.”] Via GIPHY.
Unlike traditional 9-5ers, there’s no punching out or no-work weekends. All you can do is keep working and hope that at the end of the month all your bills get paid and nothing awful happens in the meantime. It’s not all bad though, because now you can go back to some of those ideas you had before and maybe bring one of those to life. Some days it really can be a slog.Being a freelance writer is not for the faint of heart. Despite how it might sound to those who work in more conventional workplace settings, freelancing doesn’t mean one can just lounge around in their pajamas all day. Work is work wherever it may happen. Worse still is that freelancers have very little in the way of protection that other workers might have. Fortunately, there are a few labor organizing efforts underway, including a freelancers union.Get The Tempest in your inbox. Read more exclusives like this in our weekly newsletter!

  • Jamie Saoirse O'Duibhir

    Jamie Saoirse O'Duibhir is an ordained minister and contributor for the ENnie award-nominated project Uncaged Anthology with a BA in Social Science from Shimer College. Jamie does everything while listening to some variety of metal, folk, or Disney Showtunes.