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How to Become a Freelance Writer

I’m excited to write this post today because it’s long overdue. I regularly get emails from people who are looking for advice on how to break into freelance writing. While I’m happy to help other writers, I’m sometimes hesitant to give advice for two reasons. 

1. I started writing for magazines and websites in 2010. 

A lot has changed. My freelance career is the direct result of the blogging boom of the mid-to-late aughts. I also lived in Toronto, a major media centre and was able to do a lot of in-person networking. So, I fully recognize that my experiences aren’t necessarily relevant to 2020. 

2. A decade in, I’m still trying to figure this shit out.

I’m not an expert in pitching magazines. Instead, I’ve managed to get most of my writing jobs through people I know either directly or indirectly. If you’re looking for a magic recipe to get into The New Yorker or guarantee a cover story with the Atlantic, I’m not your girl (I’m pretty sure this isn’t a thing but if you manage to crack the code let me know). 

The short and super transparent story of how I started freelance writing for magazines and websites. 

I started this blog in 2009 as a portfolio with the end goal of writing for magazines (it happened!) and eventually penning a memoir (still working on it!). I wrote voraciously and within a year, I’d developed a readership. In 2010, I connected with a friend of a friend who was the beauty editor of Elle Canada. I wanted to learn more about writing for magazines. Familiar with my blog, she offered me my first gig writing for 29Secrets. This led to me writing pieces for Elle Canada. I also had a friend who worked as an editor at Slice and Food Network Canada, who assigned me some writing work. I did all this while still working at my former day job. 

In 2013, another acquaintance that I’d met at Toronto media events recommended me as a relationship expert for a video event with the Toronto Sun. I loved the experience and clicked with the editor. She didn’t have any writing work for me at the time, but a couple months later she reached out and offered me the Toronto Sun Sex Files column, which I’ve been writing ever since. Writing for the Sun has allowed me to build up a body of work which I’ve been able to leverage into other opportunities. 

I make it sound easy, but it wasn’t. There were a lot of late nights and bleary eyed mornings at my day job, alongside the usual blood, sweat and tears that come with side-hustling your way into a career. With that said, I also networked my ass off and was very, very lucky that I already knew a few people in the media. 

[I also think it’s important to acknowledge my privilege here. I’m a white, straight passing woman. Because of this, I was able to access certain media spaces with relative ease. I know this isn’t the case for everyone.] 

I can only share what I know based on my own experiences, which in some ways are atypical.

So without further ado, here are a few things that will may help you launch a freelance writing career. 

1. Start writing the stories and creating the content you want to see. 

One of the smartest things I did when I first started out was use my blog to showcase my skills as a writer. While blogs don’t have the same cachet that they did back in the late aughts, you can still use your online presence to create a portfolio and show the world what you’re capable of. 

Create a personal website or blog and regularly post things you’ve written. Publish on Medium. Don’t wait for permission. Whether you want to write about the local food scene, beauty products or your personal obsession with iguanas — just start writing and creating content about the stuff that interests you. This is a great way to sell a potential client or editor on your writing chops even if you don’t have any bylines yet. 

A great example of this is one of my favourite writers, Kate Kaput of Greatest Escapist. She has channeled her love of Cleveland, Ohio into an engaging & ultra long-running blog, personal essays and articles for local and national outlets. 

2. Take a pitching class. 

Not sure how to pitch publications? Looking to improve your pitching skills? I feel you. One thing that really helped was taking a version of Pitch Like a Honey Badger with Julie Schwietert Collazo. Not only did I learn the ins and outs of pitching, but it gave me a much needed confidence boost (the cost of the course paid for itself once I landed my first assignment). It also provided really great insight into the industry and how editors actually work. 

If you have budgetary restrictions, there’s a lot of free info online like this piece on freelance writing pitches that worked

There’s also a handful of writers online that regularly share pitching and freelance advice on Instagram. I love to follow travel writer and beauty editor, Kristin Corpuz for this reason. She’s another creative that’s used her platform in a really lovely way to showcase her skills as a writer and content creator. If you sign up for her newsletter, she sends you a quick guide to pitching. 

3. Use the resources available to you. 

While going to in-person networking events isn’t realistic during a pandemic, there are still many ways you can connect with fellow writers and editors online. Start by follow writers and editors you like on Twitter to get an idea of the kinds of stories people are looking for. They’ll often share bylines and calls for pitches. 

There are also a host of Freelance Writer Binder groups on Facebook. I don’t know what their current joining criteria is but Binders Full of Global Freelance Writers is the one I frequent the most. It’s where you can connect with other writers, ask for advice about stories and see editor’s calls for pitches. 

4. Ask yourself why you want to write.

If you’re reading this, I’m guessing that you have a desire to tell your stories in a big way and get paid for it — and that’s totally valid. Just be aware that if you’re looking to make money quickly, freelance writing isn’t necessarily where it’s at. Yes, you can make money doing editorial work but outlets typically don’t pay as soon as you turn in your assignment. While there are exceptions, on average don’t expect to receive payment for an article for at least 4-6 weeks. Which brings me to my next point..

5. Don’t limit yourself to publications and editorial work. 

Only ⅓ of my income comes from editorial work (writing articles for other media outlets). The majority of my monthly revenue comes from “behind the scenes” writing (copyediting, ghost-blogging, copywriting, curating and managing social media feeds) for a small roster of regular clients. While it’s less glory than a bunch of splashy bylines, doing this kind of work ensures that my bills get paid on time. The editorial work I do get is a fun bonus. This is true for most of the successful freelancers I know. 

If you’re looking to make money writing I’d suggest looking beyond magazine writing. Can you help a local business or brand revamp their blog or social media? Do you have a friend that needs editing help? Are there other ways you can get paid to write? Reach out to your contacts and put yourself out there! This is where having an online platform that showcases your skills really comes into play. 

6. Don’t be gross about “networking.”

It’s alarming how many times I’ve had aspiring writers reach out to me and straight up ask for my rolodex of editor contacts and clients. Do not do this. This isn’t how you network. Freelance writing is a precarious, unpredictable line of work that’s all about relationships. Most writers have spent years cultivating relationships with editors. No one wants to hand over their contacts and potentially jeopardize these relationships and their paycheque. So, don’t do this. Ever. It’s gross. 

Instead, do the work. Start writing. Set up your portfolio. Ask writers and editors thoughtful questions and be mindful of their time. If someone declines your offer to “pick their brain” don’t take it personally. As freelancers and/or editors they’re probably (like me) juggling a bunch of different projects and deadlines that are all time sensitive, while also trying to maintain a semblance of a personal life

(With that being said, if you’re friendly & respectful I will always try and help in whatever capacity I can — even if I can’t meet up in person or virtually.) 

Is there anything I missed? What else are you curious about? 

Drop a comment or feel free to send me a private message on Twitter, Instagram or via email. I’d love to hear from you. 


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