5 Mistakes Struggling Freelance Writers Don’t Even Know They’re Making
Succeeding as a freelance writer is about more than pitching and meeting deadlines.
Freelance writing is challenging to break into and even harder to stay in. One of many reasons for this is that generally, freelancers aren’t taught how to succeed beyond developing their writing skills and learning how to pitch. These are essential first steps. But success in writing is dependent on so much more.
When your application or pitch is approved, your writing samples are a worthy ticket in the door, and you’re finally working with an editor — how do you impress them enough to get hired again? What makes a freelance writer someone editors want to work with? And how can you increase your chances of receiving future opportunities?
I’ve been an editor for over a decade, but I’ve been a freelance writer for even longer. I didn’t have anyone to guide me when I started pitching, applying for jobs, and working with editors. These tips are for freelancers struggling to get consistent work who may be excellent writers, but need to improve in other areas crucial to success in the field.
I once worked with a writer who avoided all these mistakes, and she is now my co-editor at one of the sites I freelance for. Writers I’ve edited in the past have gone on to work at The New York Times and The Washington Post; I taught them to avoid these missteps too, and it worked out nicely for them. You could be next.
You’re resistant to feedback
Many writers are unprepared for the criticism that trickles down from editors, and it shows.
There are two reasons I give feedback to writers, and neither of them has anything to do with wanting to make you feel bad or discouraging you from writing.
- Reason 1: You’re doing something wrong, and that’s okay and I’m not mad, but I need you to learn how to do it correctly so that it doesn’t take me twice as long to edit your work.
- Reason 2: I genuinely care about your writing career and I want to help you learn and grow if you’re willing to work with me. I can and would love to mentor you in areas where you can improve. But I can’t do that if you refuse.
And if your only responses to feedback involve arguing, refusing to fulfill edit requests, and taking everything personally, you’re not doing yourself any favors. You’re wasting everyone’s time, and honestly, you’re setting yourself up for failure not just with me but also with most of the places you’ll end up working in the future.
While it’s absolutely okay to ask questions, get clarification on feedback notes, and point out things you feel have been misinterpreted along the way, remember that not everything is life or death. Feedback helps you and it helps me. Learn to recognize when pushback is helpful (maybe something in the style guide is incorrect and I can fix it so others don’t make the same mistake) and when it isn’t (you’re just looking for a fight).
You don’t follow the rules
I’m fairly forgiving when it comes to style mistakes — to a point. As a freelance writer, you will likely be working with multiple clients who all use different style guides. Keeping them straight is even hard for editors sometimes. We understand the struggle and we’re going to do the best we can to help make things as easy as possible for you.
But repeated mistakes — especially when proper feedback is given to prevent repeated mistakes — are a problem. The general rule of working with an editor is that it is actually not your editor’s job to fix all your mistakes for you.
I know — but I hope this isn’t the first time you’re hearing this.
As a freelance writer, you need to get in the habit of reading style guides from beginning to end, making editing checklists (often these have already been created for you), using spelling and grammar checkers, and proofreading your own work — all before submitting things to your editor.
Most of the editors you will be working with as a freelancer are not copy editors. Copyediting is part of their job, but they also do about 14 other things simultaneously.
If you genuinely want to impress your editor, the best way to do that right out of the gate is to submit work ON DAY ONE that adheres to your publication’s style guide rules. And if you’re unsure about something or you want to check that you’re doing something the right way, an editor will never be upset that you reached out to them and asked.
In fact, freelance writers who ask for help make fewer mistakes and usually end up performing better in the long term. If your editor discourages you from asking for help, they’re doing it wrong, not you.
You under-communicate
Life happens. Deadlines sometimes don’t get met, things come up, and due dates come and go. It happens to the best of us. The clearer you are about your circumstances, the more understanding your editors will be.
I’ve never punished a writer for telling me their article will be a day late. I’m not a monster. Writers are human beings, not robots. (Don’t think too much about that sentence.)
Your editor doesn’t need to know your whole life story, but we do need to be able to do our jobs. Our deadlines depend on your deadlines. If things come up, we would rather know when we can expect your work so that we can do ours. If you tell us, we can help you. If you don’t, we’re more likely to reassign your work and/or move on to other contractors.
There is a right and wrong way to over-communicate, however. Relevant, consistent communication does not mean overstepping boundaries with your supervisor or editor (it happens, and I’ve let people go because of it).
- Respect your editor’s office hours (if they have them) and/or their time. Wait patiently for responses to messages and understand that you are likely one of dozens of writers working under your supervisor. Chances are, you’re not the priority. If it’s not urgent, your editor will get back to you as soon as they are able.
- Don’t be rude. “Hey, why didn’t my article go up yet” is a paraphrase of a direct message I got from a writer earlier this year. I’ll let you decipher why I (and my bosses) didn’t appreciate this message or the ones that followed. You’re a professional. Act like it.
- Keep your communications short and purposeful. As much as your editor wants to get to know you (we really do!), we don’t typically have the time to read 5-paragraph emails, lengthy Slack messages, or 20 notifications in a span of 3 minutes every time you reach out. It’s not personal — we’re just very busy, as we assume you are. We want to chat, but there’s a time and a place for it.
You set unrealistic expectations
I say this as a chronic over-committer: Eagerness and enthusiasm are great in theory, but taking on too much work and then backing up the entire editorial workflow when you get overwhelmed will not impress your editors. Not even a little bit.
Yes, I’ve done this. I’ve learned from it, and I don’t want you to live as I lived. Editors love to see you active and willing to take on work — it’s good for everyone, really. But many writers overestimate the amount of work they can handle, and it always ends badly for them.
When you join a new team, take things slow. Diving in headfirst is much more reckless than it is impressive. Get to know your team, get a feel for the workflow, and figure out how this work is going to work for you. An article or post you thought might take you an hour might instead take you three. This could be the case for just one or for all of your assignments. If you take on three assignments all due by the end of the day and they each take three hours to complete, you’re not going to have a good day and neither is your editor.
There is no way to know how much you can handle until you familiarize yourself with the layout. Time and project management are crucial skills for successful freelancers, and if you don’t start mastering them now, you’re going to burn out before your first paycheck.
You don’t get to know your editors/clients
Every editor you will ever work with is busier than you think they are. While I do recommend keeping communications short and purposeful, there is always room for personalization. And this form of networking could make or break your career.
You never know when you’re going to need a letter of recommendation, a job lead after a layoff, or even just some friendly advice. I still keep in touch with many of the writers I used to work with, and all of them followed the advice I’ve laid out above. It wasn’t just about their work — they also behaved professionally and were genuinely pleasant to be around.
In the writing world, whether you’re a journalist, author, or land on some other branch of the industry, who you know often ends up being the biggest asset to success. Making connections matters. Contrary to popular belief, writers on islands do not win prizes (or bring home paychecks, or start businesses, or whatever your end goal as a writer might be).
This is another reason you should over-communicate within reason. Don’t slam doors the second someone tells you to stop writing in first person (it was probably in the style guide). Editors remember the names of people who make an effort to connect, and that connection doesn’t necessarily end just because you stop working together.
Be friendly. Show interest in your editor as a person without crossing their boundaries. Be respectful, but don’t be afraid to engage in “small talk” when appropriate. This is a valuable skill to have too, but I’ll write about that some other time. Not every editor is interested in that, but again, that’s their mistake, not yours.
While avoiding these mistakes alone won’t guarantee success, you’ll notice a huge difference in the way you interact with editors and the opportunities those editors offer you.
Many freelancers focus on important aspects of success without taking any of these things into account, and they struggle because of it. Never forget that your editor is your ally. Many of us have been where you are, and we are here to help you. But you have to put in the work, and that doesn’t just mean pitching winning headlines, turning things in on time, and being active in the team chat. All these things are great, but they aren’t enough.
This is a tough business for all of us. Everyone is struggling. But there are small things you can do to get yourself to a point where you’re struggling less. Start here, and if this is really what you want, don’t give up.
