We all probably know colleagues who have lost their jobs in the past year. In January alone, NBC News, Time magazine, Business Insider and The Los Angeles Times announced major layoffs.
Many journalists who are no longer staffers are turning to freelancing, perhaps for the first time. With that in mind, I spoke with Anna Medaris, who held staff positions for nearly 15 years, most recently at Business Insider, where she was a health correspondent. She took a buyout in June 2023 during a strike that was partly over proposed layoffs.
In this interview, Medaris discusses her approach to launching her freelancing career and offers tips to other journalists who may be thinking of making the same transition.
Questions and responses have been edited for clarity and brevity.
What were your initial thoughts as a new freelancer?
The biggest concern, of course, was health insurance. And I really had no idea of what my income could look like. I had done a little bit of freelancing on the side years ago when I was working for trade publications, but I had certainly never done it full time. And I’m married to an independent producer/director, so neither one of us had a predictable salary, and that was a little bit scary. But that was overpowered by excitement. It seemed like a good time to try something new.
What were some of the first steps you took?
It was mostly making connections. I had a lot of coffee dates. I went to a lot of happy hours. I had a lot of phone calls with old editors, old colleagues and friends that are freelancers. Most of those didn’t go anywhere in terms of bringing me money, but it was fulfilling to reestablish those connections, and by July, I had a few assignments.
What was your networking strategy?
I made a spreadsheet that I called freelance contacts, with different tabs: one for editors, another for freelancers, one for PRs, and another for mentors and people who aren’t necessarily in media but who might want to see where my career is going and might have an idea for me. In just one sitting, I had about 30 names of editors alone.
How did you secure clients?
One of my most regular and lucrative clients has been the American Psychological Association. I worked there from 2012-2014 for their monthly magazine, and one of my old editors is still there. I reached out to her on LinkedIn, and we got on the phone, and she started to send me assignments right away. That was really lucky but also a lesson: don’t burn bridges. I write a lot for Everyday Health, and that was through an old friend who connected me with her editor. I’m also a writing coach at the New York Writing Room, and the founder of that organization has sent some clients my way. And then at the Christmas party for The Newswomen’s Club of New York, I met somebody who had recently been laid off from Vox. She connected me with the health editor there and I landed my first pitch. So networking at parties works!
And you announced your career change on social media?
Yes, on Twitter, on LinkedIn, on Instagram. It was one of the first things I did. I wrote about why I had made the move from full-time to freelance work and a little bit about what I was excited about, not with any intention of getting jobs necessarily, but I thought I should tell my followers what’s up. I immediately had a DM from a New York Times editor asking me to pitch her when I was ready. I also posted this on Facebook, and an acquaintance that I knew 10-plus years ago from the National Press Club introduced me to his editor, and they were one of my first regular clients.
Why do you think you got such positive responses?
Rather than framing my posts as a cry for help, I explained what I’m doing and why I’m excited. I also included a quote from an editor praising my writing style. But mostly, I’m lucky to be a naturally social person with a lot of what psychologists call “loose ties,” and those people thought fondly of me and my work and genuinely wanted to help.
What else did you do to help motivate you as a new freelancer?
I started listening to a lot of podcasts about freelance writing. That got me fired up and opened my mind to all the different potential ways I could use my skills.
Are you pursuing other sources of revenue?
I’m still figuring that out. I’m exploring doing college essay coaching because I worked in admissions-related roles throughout college. It’s an old passion of mine worth revisiting. I’m also hoping to do more pitching workshops. I usually do two a year through the Writing Room, but I’m thinking about how to scale that up.
You’ve gotten many assignments. Are you also pitching?
In the first five months, I was only getting assignments, and I’ve been really appreciative of that. But I got to a point where I started to turn them down because I didn’t have any time to pitch my own ideas. I’ve now gotten three accepted, and I’ve probably pitched about 15. For example, APA was assigning me a lot of features. And now I’m saying, ‘Do you want my ideas?’ They do!
It sounds like you enjoy pitching.
Story idea generation has always been a huge part of why I like this career. I have a running document of all my ideas. And I have a different document that has pitches in need of homes, and I keep track of where I pitched, and then after a couple of weeks, I’ll try a different place or I’ll follow up. A lot of people don’t like pitching because it’s mentally and emotionally draining, often for little reward, and I might burn out of it. But for now I’m enjoying the honeymoon phase.
What are some of the downsides of freelancing?
Once you turn your assignment in, you don’t really know necessarily when the edits are going to come back, and once they do, how quickly they’re going to need to be turned around. Editor A doesn’t care that you’re on deadline for editor B. It’s definitely different from being on staff, where you’re working with one editor who knows what’s on your plate and can help you prioritize.
What are your goals for freelancing for the next year?
I’d love to have one or two clients where I know I’m getting X number of assignments from them each month.
Do you miss the office?
I definitely get my energy from being around people, even if I’m not talking to them. I’ve joined a coworking community in Manhattan, made basically for and by women. It’s a beautiful space, and there are lots of motivated people working there. I’ve committed to going on Monday, Wednesday and Friday. It’s been really nice to have some structure.