Chelsea’s Guide To Freelancing
Table of Contents
About the author
How to get started
Pitching and following up
Tracking your work and invoices
Showcasing your work
Time management and stress
Want this guide as a pdf? Email me.
About the author
My name is Chelsea Cirruzzo and I’m a health care reporter in Washington, D.C. For the past two years, I’ve been freelancing on my off-time from work for both local and national news outlets, including DCist, Washington City Paper, The Lily, Washington Post, and others. I’m hoping this guide can serve not only as information for myself to keep track of my freelancing, but also as a guide for anyone interested in getting into freelance writing. I still have a lot to learn and there are so many more accomplished people than me (see resources) so these are just things that have worked for me. A lot of people who I admire a lot and look up to freelance full-time, so these tips may not resonate as much. I intend for this to be a living document that I can continuously update as I grow, learn more and get better.
You can follow me on Twitter or check out my website. Have questions, feedback, etc? Get in touch!
How to get started
When I left my first job from D.C. local media and began reporting full-time for a trade publication, I wanted to continue reporting on local news, too, as well as experiment with other types of writing.
I am in a unique position and I feel very lucky that I do work full-time at a reporting job I enjoy and also get to freelance on the side, which has been very helpful in paying down my student loan debt.
Anyway, when I left my first job, one of the first things I started doing was emailing editors at publications I wanted to write for and introducing myself. I often asked if they had pitching guidelines. Some even agreed to meet with me for coffee, so we could talk a bit about what they were looking for. This later helped me pitch them smart, informed stories. I always came into meetings with very specific questions and always left by asking: Who else should I talk to?
However, this isn’t always possible and editors are extremely busy, so please be respectful of their time and do your homework! Some publications have their pitching guidelines on their website, so before you ask for them, do some research.
Another thing you can do is start talking to other freelancers. Reach out politely and ask for a phone call, particularly if they’re someone you admire, but always have specific questions like:
* How did you get started in freelancing? Which publications do you write for?
* How do you write your pitches? Can you show me a pitch of yours?
Some people will say no or not respond. That is okay! Don’t take it personally. If cold-emailing people scares you, here are places to start:
* Digital women leaders
* Journalism mentors
One of the hardest things I’ve found about any type of writing is simply getting ideas, especially when you’re starting out. Once you start to develop a beat or an area and develop sources, stories may come to you (for example, I keep my email and my social media DMs open—both a blessing and curse on social media as a woman—for tips. An anonymous tip sent to me led to this story on D.C. libraries during COVID-19). But what do you do when you want to write but aren’t sure where to start? Here are some tips:
* Read a lot! Read things you like and things you hate. If you ever read something from a publication you want to write for and think, wow, this is great, but I wonder about this other thing...then you might have a story! Can you add to this coverage in any way? Do you think it could be better? How? Is there a particular aspect of the story you think should be fleshed out? Start thinking about it.
* Go to what’s happening. Wherever you live, there’s probably something going on: Events, protests, parties, performances, local government meetings, school board meetings, businesses opening and closing, etc. Go to them and just talk to people. I acknowledge that this advice is probably not helpful right now, but that doesn’t mean you can’t see if local governments or schools or organizations are having virtual events. See what people are talking about and what they care about. Get to know those major players at those events, spend time on Zoom calls. Not every event will yield a story, but it’s worth a try. Some of the best advice I’ve ever received is: You can be a reporter anywhere. Something happening where you are? Check it out.
* Listen and watch conversations on social media. Are lots of people talking about something? Is it making you think? For example, after watching some people discuss IUDs on social media in response to RBG’s death, I was reminded of a similar discussion post-2016 and wrote about it. I follow a lot of local business, organizations and people in my area on Twitter, Facebook, Instagram and even TikTok to see what’s going on.
* Think about how to connect with people off of social media, which may go back to going to events via Zoom or in-person. Not everyone has access to social media and lots of stories are happening in other ways. For example, I’ve written about homelessness in D.C. and I’ve made connections with organizations that are made up of people who formerly experienced homelessness or are advocates for people experiencing homelessness. These connections are incredibly valuable to me and help me speak with people who may not always have access to social media or the Internet. This is important to think about, too, if you largely use social media for source call-outs like I do (if I get better tips on this, I will share!)
* Always foster connections beyond immediate stories as well. Check in with sources for phone calls even when you don’t have a story idea. I like to ask people: what’s on your mind? Is there something you’ve read recently in your area of expertise that you liked? What’s missing out on coverage right now? That may give you story ideas.
* Spitball your silliest ideas off of your friends. The ideas that come to mind in the shower may seem like silly or dumb or unimportant ideas to you, but talk them through with friends or other freelancers. Workshop them. And then pitch them.
* And right now, ask yourself: How was the pandemic impacted [insert literally anything]? There are so many stories to write about this. For example, I wondered how the pandemic has impacted museums in my area and wrote about it. Think hyperlocal or think big, workshop it, and pitch it.
How to pitch
When I speak with people who want to get into freelancing, the biggest question I get is how to pitch, so I thought I’d break down the anatomy of the pitches I write. First things first: Make sure you’ve done your homework before you pitch. Check the publication you’re pitching to make sure you aren’t pitching something they’ve already written or something they wouldn’t normally write. Usually, I do this by Googling: [Name of publication]: [key words related to the story I want to write] and spending some time reading. Also, make sure you’re pitching the correct editor. Read their author page, check out their Twitter to see if they’ve said anything about the types of pitches they accept (I will search on Twitter: [@editor]: pitch to see if they’ve tweeted anything on pitching)
Sometimes publications have specific styles they want pitches in, but if not, here is the formula I use:
1. The subject line
1. The subject lines I normally use say: PITCH: [A brief headline-like sentence of what the story is]. Try to make it engaging, but beware of writing it too much like an advertisement because they may get shuffled out of an editor’s main inbox.
2. Examples of successful subject lines I’ve used:
1. PITCH: Museums can start reopening. What will be the same and what will be different?
2. PITCH: Confused about working from home? Listen to people with disabilities and chronic illness
3. PITCH: Here’s how coronavirus is impacting D.C.-based sex workers
2. The address and email
1. Address your email to an editor, not just a general inbox. Do your research and find the correct editor and write a polite address: Dear so-and-so, or hello so-and-so.
3. Give a brief introduction
1. Introduce yourself and let the editor know you have a pitch! You don’t need to make this too long.
1. Example: I hope you're well. My name is Chelsea Cirruzzo and I'm a [freelance reporter / health care reporter / etc]. I have a story idea I hope would be a good fit for [your publication]
4. The pitch itself
1. Right after your introduction, paste your subject line back into the body of the email in bold:
1. PITCH: TK TK TK
2. First, give a couple of brief lines on what the story is about. Make sure you’re pitching a story and not a topic. For example, don’t say you want to write about TikTok. Say you want to write about the top 10 TikTok accounts to follow in your area (Yes, I did this!)
1. Here’s an example from my story on disability and work from home I pitched in March to the Wellness section at the Washington Post which had started writing about work from home but I realized there was a big conversation on remote work that had long been happening within communities of people with disabilities and chronic illness.
1. Here’s what I wrote: As the U.S. workforce braces to work from home through the end of the month — or perhaps longer — due to COVID-19 many people are struggling with how to effectively work from home. But for people with chronic illnesses and disabilities, working from home is familiar.
2. There’s a few parts to this: I set up the situation (remote work during coronavirus) but then got directly into the exact story: People with disabilities have long been fighting for or using remote work policies.