Making Freelancing Work With Britany Robinson (One More Question)
Job updates and deadlines + pitching freelance articles, making freelancing work as a business, learning to embrace your weaknesses, and advice for future freelancers
Hello folks, happy Friday! Hope everyone has nice weekend plans. I’m heading back to my mum’s to help her dig out some pumpkins she’s grown. They’re huge, the size of a small table apparently. So large that she can’t lift them by herself. Bless her. I’ll include a picture of them next week. Pray for me I don’t put my back out.
Today we have another fascinating Q&A, this time with Britany Robinson! Britany has been a freelance journalist for more than a decade, and is the founder of One More Question, a newsletter dedicated to helping freelancers find work and opportunities.
Britany’s been on both sides of the table — as an in-house editor and full-time freelancer — so she has a ton of advice and wisdom to share. While Inside The Newsroom focuses more on finding folks full-time work, you never know when you might need extra work and extra cash. I found that out this year, and OMQ quickly became my go-to resource for all things freelance.
If you’re intrigued by the prospect of freelancing, or already freelance, check out Britany’s newsletter for free. Or sign up for the premium version for as little as $3.60 a month with 40% discount exclusively for Inside The Newsroom subscribers.
Be sure to also check out Monday’s job board update, as well as a bunch of full-time job deadlines approaching in the next few days below.
Until then, enjoy today’s newsletter and we’ll speak again on Monday! 👋
Britany 👇
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Introducing Britany Robinson 👋
Daniel: Hey Britany, thanks so much for doing this! You’re the author of the One More Question newsletter, which is dedicated to making it easier for freelance writers to enter the industry and find work. How and when did you start OMQ?
Britany Robinson: Thanks so much for having me, Daniel. I started One More Question when I was feeling a little panicked about the future of my career. But first, to backtrack…
In November 2019, I left my job as managing editor of a startup publication, to return to freelance writing. I felt a deep sense of urgency to write about climate change and the environment, and I knew freelancing would provide the freedom to explore those stories. Having freelanced for years prior to that in-house position, I hit the ground running on pitching and picking up assignments. But then the pandemic hit and everything dried up.
It was a scary, stressful time for all of us, for so many different reasons. But it was also clarifying. Even with budget cuts and publications folding left and right, I knew this was the work I wanted to be doing and I knew I’d figure out a way to make it work. So many writers were struggling to find work and questioning the sustainability of the industry, and I wanted to create something that honestly addressed the challenges, but also felt uplifting and supportive. So, fueled by panic and the conviction to stick with freelance writing, I did what so many writers have done in recent years: I started a Substack.
I launched OMQ with the intention of writing an essay about writing each week. That snowballed into a 2-3 times weekly newsletter, with one each week dedicated to writing opportunities (pitch calls plus info on fellowships, grants, and other useful writerly things) and the other being either a Q&A with another writer or editor or an essay about some aspect of the industry.
You’ve written for some big titles in your career — The New York Times, The BBC and CNN to name just a few. What made you want to start OMQ specifically to help other writers coming up behind you?
I think having written for some big publications and then still sometimes struggling to secure assignments is what inspired me to start helping other writers. There was a time when I would have assumed a byline in The New York Times meant you’d made it and every editor would be thrilled to work with you. But that’s not how it works at all.
So much of “making it work” as a freelancer is about establishing a strong foundation of work, which is so much harder than landing that one big-name byline. You have to build relationships with editors, find anchor clients, and identify what type of work can cover your bills without sapping your creative energy for the work you’re most excited to do (but maybe doesn’t pay as well).
I wanted to have candid conversations about the many different ways of making enough money and doing work that we enjoy. I’ve had a lot of experience figuring that out, which could be helpful to others. Interviewing other writers and editors on how they make it work has also been an exciting opportunity to share advice with writers that I can’t offer myself.
It’s been really cool to be able to help other writers (through pitch feedback, answering questions via email, and sharing my thoughts on writing in the newsletter) while learning from them, too.
You describe yourself as a “kinda shy” writer, but one who’s turning into a “one more question” kind of writer. What do you mean by that?
I’ve always been a little nervous and shy in big group settings. For example, I was just on a reporting trip with 15 other writers and so many of them would ask really smart, pointed questions of the people we were meeting. But I’m more comfortable hanging out in the back and listening, and then asking someone questions one-on-one later. There have been times I’ve felt insecure about that, like maybe I’m too timid to be really good at this. But the more I do this kind of work, the more confident I feel about my own set of skills.
I know I ask good questions. I’m just better at asking them outside of a group setting or press conference. I think we can all be much more productive and confident when we focus on what we’re good at rather than worrying about our weaknesses. That said, it’s helpful to feel uncomfortable and push yourself to be better. But it’s also okay to get the work done within your comfort zone. Our strengths are what give us our voice and style.
What else have you learned about yourself on your journey as a freelancer, starting your own newsletter business and helping the next generation of writers?
I’ve learned how much I value community. Writing can be an incredibly isolating profession if you aren’t intentional about reaching out to people and building community. I think when most of us get started, there’s a tendency to be competitive, rather than collaborative with other writers. But there really is enough work to go around, and we all have an easier and more enjoyable time doing it when we support each other.
Long hours, poor pay and mistreatment are just a few of the reasons why more and more journalists are turning to freelancing as an alternative to working in-house. What are some of the realities one should expect if they make the jump?
Freelancing is great in some respects. It gives you a lot of freedom in how you structure your day, what types of assignments you take on, and whether or not to put on pants when you write. But if you’re constantly stressed over finding that next assignment or a new client, then that freedom dissolves into anxiety and feeling like you have to keep hustling for hours longer than you might at a full-time job.
Honestly, sometimes a regular paycheck sounds like a huge relief. But when your work comes together in a way that feels sustainable, then it’s really hard to give up the freedom of working for yourself. I have months when I love it and months when I hate it, and unfortunately, a lot of that is tied to how much money I’m bringing in.
Figuring out the business side of freelancing is really key to making it work. It’s taken me years, but I’m finally figuring that end of things out. And when the business feels stable, I’d argue that the freedom of working for yourself, the variety of working for multiple publications, and the exciting challenge of piecing together different kinds of work makes freelancing a lot of fun.
Reading OMQ each week fuels me with optimism from the number of opportunities out there. In what ways has it become easier and in what ways is it harder to freelance?
You’re right, there are a lot of opportunities out there these days. You just have to break through the crowd to reach the editor and have a really good idea for them when you do. So it’s easier in that there’s a huge variety of ways to work as a writer. There are so many online publications producing daily stories, and just about every brand or business is in need of content to keep eyeballs on their page.
So there are a lot of words to be written, but there are also a lot of people willing to write them. And unfortunately, a lot of people are willing to do it for very little pay, because they’ve been told they have to do that as new writers. The challenge these days is finding publications and clients that pay fairly for your time and skills.
How do you go about pitching articles to editors? What are some things freelancers should consider when approaching new editors?
There are a million articles out there showing you how to pitch. But there isn’t some big secret on how to land assignments, and if every editor wrote a guide on how to pitch, each one would be different. What they all definitely want is a good, unexpected story idea that fits their publication. And those can be hard to find. So get to know the publication and spend time with the topic you have in mind before pitching. Do some pre-reporting interviews to find a compelling character.
I also suggest working out some headlines for your story. It can seem like a silly thing to worry about when you haven’t written the story yet, but capturing the heart of the story through a headline and a dek (or subhead) is a great way to show the editor you know exactly what this story is about and why people will want to read it.
Time literally is money when you’re a freelancer. How do you make sure you complete everything you need to for OMQ, while also finding time to pitch articles, while also having time to yourself?
That’s definitely something I struggle with. One thing that’s been helpful is optimizing the times I work most efficiently. I’m answering these questions at 6:30am because writing comes easiest for me first thing in the morning. If I have a big deadline I’m working towards, I’m usually up at 6am. Then I don’t have to feel bad about not working between noon and 2, which is when I like to go for a run or take my dog to the park.
Scheduling everything, even work time on various projects that aren’t time sensitive that day, has also been really helpful. So I’ll block off two hours on Tuesday morning to work on One More Question, then a break, then a few hours for research on an article. That way, I stay on top of the things that are less time sensitive but still need to get done.
And most importantly, I find enough time by working for publications and clients that pay me a fair wage. You can free up a lot of time when you charge more.
Aside from OMQ, what are some other resources journalists thinking about making the switch should check out?
I’m obsessed with the Longform Podcast. I love hearing deep dives on how writers pursued certain stories, and their journeys to becoming the successful writers they are today.
Also, find writing groups where you live or find people who you click with online. The thing that’s been most helpful on my journey is a group of women I’ve been meeting with online for years. We hop on a Google hangout once a month and talk about what we’re working on and the challenges we’re facing, and we help each other work through those challenges. They’ve all become good friends and I don’t think I’d still be freelancing if it wasn’t for their support.
So find ways to connect with other freelancers on that level. Find freelance writer friends who will refer you for jobs that aren’t right for them and vice versa. That kind of network is by far the most valuable resource you can have.
And lastly, is there anything else ITN subscribers should know about freelancing?
You’re going to have to make decisions every day about what type of work to prioritize, how to go about finding that work, and how you’re going to get it done to pay your bills. As a freelancer, you are a business, and every business decision rests on your shoulders, which can be completely overwhelming.
It helps to keep referring to the work that inspired you to go freelance. What makes you want to be a writer? What makes you excited to get up in the morning? You’ll have to do other things and they won’t all be fun. Sometimes you might even hate the work you love. But when you’re faced with difficult decisions about your career, prioritize making space for the type of writing you really care about. I truly believe the rest falls into place when we prioritize the work we love.
And always negotiate for a higher rate. Always.
Thanks for reading Britany’s story, I hope picked up a few things. If you did, subscribe to her awesome newsletter One More Question.