Making the switch from full-time employment to freelancing is a daunting move. Making the switch during a global pandemic? Presumably kinda terrifying. For many, that move was a necessity. US newsrooms lost 16,160 jobs in 2020, and publications folded left and right. But for Paige Lyman, the switch was a much-anticipated choice. And in following her freelancing journey on Twitter, it seems to be going really well! Paige recently celebrated her one-year freelance-iversary. So I was excited to chat with Paige about those first 12 months of pitching, writing, and making it work.
First, I gotta tell you—it really is such an honor to learn more about the writers who agree to do these Q&As. It’s definitely my favorite part of running this newsletter. Paige was one of the early subscribers to One More Question, and it’s been so cool to get to know her and her work as she navigated Year One of Freelancing.
While it’s great to hear from editors at top publications and big names you might recognize, I think it’s really valuable to share the insight from writers who you will and should recognize, too. They haven’t forgotten how hard it is to build up your clips—pitching and pitching and waiting and pitching. Hearing from people who are doing the damn thing, I think, is especially helpful.
(So if you’re interested in doing a Q&A, hit reply to this email and let me know what you’d like to chat about!)
Now let’s get to it. Writers, meet Paige!
“It was a little scary at the beginning, but once I finally just did it? Completely worth it.”
Britany: What prompted you to go full-time freelance a year ago?
Paige: The move to go freelance full-time was prompted by a few reasons. I'd been freelancing since 2014 on the side, while I went through university and moved into working some typical 9-5's as a copywriter and social media manager. I knew that working a typical 9-5 (though I'll be honest, it was more like 8-6 sometimes) was not really my thing. I'd previously gotten to experience remote work in a sense when I was in middle/high school through attending virtual school. The kind of flexibility and freedom that came from that experience over 5 years definitely stuck with me, even years after.
So when my at-the-time 9-5 job made the switch to remote work due to quarantine in March 2020, I had already been thinking about moving into freelancing full-time for several months. I wasn't happy where I was and I knew that something needed to change. Freelancing full-time was something I'd been wanting to do for years, but I kept putting it off because it didn't feel right. But COVID-19 and some very long discussions with my older brother who's always been a huge support for me kind of gave me the time and outside perspective to finally say to myself now is the time.
Did you prepare for the shift by pitching and/or finding jobs in advance?
I did prepare for the shift by pitching and looking for clients in advance! I'm primarily a content writer and journalist, so in the lead up to going freelance full time I really stepped up in how I was looking for clients. And I do think my pitching also increased a wild amount around that time as well! I think way back into 2019 I had made a pointed effort to start pitching more (that was a lot of late nights), but especially around the time I was making the transition I was pitching a ton!
What would you have done differently if you went through that transition again?
Oh gosh. I think the first thing I might have done differently would actually be to do it sooner. It was certainly a big deal and it was a little scary at the beginning, but once I finally just did it? Completely worth it. And there's definitely been moments this first year where I've thought "Ok, this is just a lull in work" that have made me anxious, but I think that's just typical of freelancing. There's going to be slower months every once in a while.
And secondly, I wouldn't have gotten so in my head about the decision. Like I mentioned, it was a long time coming and making the move into freelancing full-time was something I always knew I wanted to do. But in the lead up to the full transition, I very much was overthinking just about everything!
How has freelancing been different than what you expected?
It's honestly not too different from what I was expecting. I went in knowing it would be similar to the part-time freelancing I'd already been doing, but just much more and with plenty to learn as I went. I think the biggest thing I was semi-expecting but was more difficult than I originally thought was unlearning the idea that I have to be working almost every hour of my day.
Has there been a turning point when you thought, hey this might actually work? Tell us about that...
I think coming up on the end of my first six months was a turning point. I originally set myself a goal at the end of those six months: I wanted to be making equal to if not a little more than what I was at my last job. I went with that time frame because I knew that it would take some time to build up my freelancing and I wanted to set a monetary goal that seemed realistic to me. It wasn't just going to happen overnight. So coming up on the end of those six months, I was able to look at the work I was doing and my finances and really see that I had met that goal. And that was so awesome!
Has there been a point when you wanted to quit? What did that look like and what kept you going?
There hasn't been a point where I wanted to quit! I could chalk that up to me being stubborn, but I think it's just not something that ever crossed my mind.
What role has social media played in your work as a freelancer?
Social media has been kind of super important! It's been a great way to find calls for pitches and possible freelance gigs as well as chatting with possible clients. But it's also been amazing in how I've gotten to meet other freelance writers, too. Twitter has definitely been the biggest platform for getting to know other writers and that's been so awesome, especially during the pandemic. I've really found the freelance community to be pretty great, and I've made some lovely friends over the last year.
What does your pitch routine look like now? How often are you pitching, and generally speaking, what's your success rate like with cold pitches?
My pitch routine is pretty simple. I'm subscribed to a lot of great newsletters that pull together open calls (like Sonia Weiser's Opportunities of the Week and this one) and I check Twitter pretty often as well! I usually check for open calls that are relevant to my niche, and if I have a story in mind or a pitch that I've been trying to place, I'll work out if I want to pitch or not. If I'm not familiar with the publication I'm looking at, I make sure to take time to check out what kind of work they've been publishing recently and I look to see if anything similar to what pitch I have in mind has been published too.
As far as cold pitches, I'd say I've had a pretty equal amount of cold pitches picked up and pitches that were rejected/I never heard back on! I do know that my pitching method has improved sooo much since I went full-time though. One thing that I do try to do though is pitch editors again, even if my first pitch didn't land. If they have an open call again and I have something I think would work, there's no harm in pitching something new.
What has been the most important lesson you've learned this past year?
I think one of the most important things I've learned is that advocating for yourself is such an important thing. As a freelancer especially, I don't have someone else I can turn to that is going to speak up for me. I have to be the one that takes the initiative to speak for myself, whether that's in relation to clients, negotiating contracts, pitching, or even just in everyday life. It can be nerve wracking for sure, but it's definitely one of the most important things I've learned at a whole new level this past year.
What are you still struggling with as a freelancer?
Definitely trying to unlearn the idea of constantly needing to be busy. I'm in my mid-twenties, so the idea of constantly needing to work and be busy to prove you're a productive person is something I was basically raised with. It's definitely been a struggle to try and ignore that specific feeling now that I'm working less hours. It's kind of ironic that once I finally moved to freelancing, which allowed me to have a much better and healthier schedule for myself, that I still get hit with that productivity bug. I'm definitely getting better at managing it now, but it can be hard!
What has been the most satisfying story to write this year and why?
I've gotten to work on so many amazing stories in the past year, but I definitely think the most satisfying one was the New York Times piece I did last summer. Writing for the New York Times was kind of a "Wow, is this actually happening?" moment, but the story that I got to write was also something that was extremely important to me as both a person who has interacted with the community for over a decade and as a journalist. I covered independent artists that typically would be tabling at pop culture conventions and how the cancellation of conventions due to COVID-19 was impacting them. This was something I'd been following since quarantine started and finally getting to cover it in such a wide reading publication was just amazing!
What do you hope to achieve in year two of freelancing?
I'm really hoping to cover more stories in the culture and media space as far as journalism goes and continue working with my content clients on a long-term basis! Overall I just want to continue to build on the foundation that I've been working on for this past year and see where it can take me!
That’s all for today, Friends! A big thank you to Paige for doing this Q&A. If you’re a paid subscriber, I’ll be back in your inbox next week.
Stay inspired and hydrated,
Britany