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. 

A Few Telling Signs That You’re a Freelance Writer

 

Last week I had the pleasure of spending a few days in Cancun with a handful of awesome writers (you can watch the story highlights here). We’re all freelancers, so once the margaritas start flowing (and boy did they flow…), naturally the conversation turned to all of the highs and lows of freelancing. Most of my friends IRL work regular 9-5 jobs in the public sector and while they think what I do is cool, they don’t always understand or relate to the behind the scenes stuff that goes into writing full time for a living. So, while these press trips  can be a bit logistically crazy (I was literally in Mexico for 3 days), I love that they give me a chance to connect with other awesome women writers and journalists who just get it.

Inspired by conversations I had in Mexico, here’s a few of things that most freelance writers will be able to relate to. I may just turn this into a regular series.

[Note: I realize some of these points are probably specific to sex and relationship writers/bloggers, so keep that in mind]

1. You don’t go to the dentist as much as you should.

A fellow writer friend posted a selfie that other day with the caption, “went to the dentist for the first time in 3 years! #freelancelife.” It was only once I saw her post that I remembered that I haven’t been to the dentist in far too long. I’m not talking about going to a cosmetic dentist, I mean a straight up cleaning and check-up. I have the best dental clinic — it’s in a gorgeous, easy to access area and my dentist is awesome — and yet, I always leave appointments way too long. Part of this is because of a hectic schedule. It’s also because I have to pay out of pocket for treatments (versus before when I worked at a corporate job and everything was covered by my benefits plan).

2. You have a precarious relationship with health care/insurance.

I’ve met a lot of freelance writers from the States that don’t have health insurance. The struggle is real. The only way I’m able to get away with not having insurance is because I live in Canada and the only thing I pay out of pocket for is dentistry and the occasional massage or chiropractic treatment.  Friends living in the States, I don’t know how you guys do it, but know that you’re not alone.

3. When you’ll actually get paid is even less reliable than your period.

While I have a general idea of when my anchor clients will pay me based on when I invoice them, I can’t always say that I’ll have the money by a specific date. Sometimes there are delays or a payment takes longer to clear through PayPal. It’s tricky and you always have to think ahead to make sure you have your expenses covered.

4. All of your zip drives and pens are branded.

In my case, most of my office supplies come from sex toy companies, sexy resorts and other places I’ve traveled.

Hi. I like sex and hotels and writing about both.

5. You’ve gotten hooked on an unlikely beverage or snack thanks to a press event.

There was a time in 2010 when it seemed like every PR event in Toronto was sponsored by Vitamin Water. The company even dropped off a free crate of it at my former retail job and a week later I found myself at an open bar fashion week party where all the drinks were infused with the beverage. A year later, it was Pop Chips, and after that, Starbucks Refresher energy drinks (which, I still sometimes get a hankering for — another fashion week addiction). Currently, I have a friend who is hooked on the Aperol Spritz. The last thing I became addicted to was ONE Coconut Water, which I’m not mad about because I’m pretty sure it won’t give me diabetes.

6. You re-use free items in creative ways.

While I don’t really enjoy silicone lubricant, Uberlube makes a great hair styling product. I’ve also heard it works wonders on creaky door hinges. Also, 90% of the candles in my home are actually aphrodisiac scented massage candles. I don’t have anyone to massage currently, but I am prepared for the next blackout or apocalypse!

Sex candles for the apocalypse.

7. Your work wardrobe looks less like this…

…..and a lot more like this.

 

If you see a photo of me on Instagram dressed up, that’s literally because it was a rare occasion when I actually wore real clothes and therefore, felt it needed documenting. While I do wear my “uniform” (jeans, a striped shirt & black leather jacket) to go to work at a coffee shop or co-working space, most of the time I’m in workout wear and wrapped in multiple long cardigans and/or a Slanket because my desk area is cold AF.

8. You frequently wonder if you should just pack it in and get a desk job.

This is something I think about at least a couple of times a month. I’ve gone through phases where I’ll apply to a bunch of 9-5 jobs, go to interviews and then something will happen — I’ll get offered a cool opportunity or I’ll secure a new client. When this happens, I interpret as the Universe telling me that I need to stay the course. While there’s definitely some downsides to freelancing, the freedom to create my own schedule is pretty amazing.

If you’re a freelancer, what would you add to this list?

My Bummer-Proof Guide to Getting The Most out of 2017

 

The world may be going to hell in a knock-off handbag, but I’m determined to make the most out of 2017 no matter what.

In December I participated in Molly Mahar’s Stratejoy Holiday Council for the 4th year in a row. I love the Holiday Council – it’s  a great way to wrap up the past year and plan for the one ahead. The course encourages everyone to pick a theme word for the year and five “ways of being” that embody your theme.

The theme I chose for 2017 is shift While there’s lots of things I love about my life, there’s certain pivots I want to make in both my personal and professional life for 2017. I want to expand my career, save money & finally move back into an apartment/home of my own.

To make my goals happen I’ve chosen these five ways of being in 2017:

BE PERSISTENT

Stop letting myself off the hook. Give fear the middle finger & persistently pursue my goals. Embrace positive forward progress over perfection.

BE BAD-ASS

Wear more red lipstick. Tell brave stories. Show confidence. Remind myself regularly that I’ve ‘totally got this.’

BE FRUGAL

Both in time and money. Use the library & public transit more. Spend mindfully. Save for a rainy day. Use what I’ve got at my disposal instead of giving in to instant gratification.

BE CONNECTED

Use social media to connect instead of distract. Do activities that get me out of my comfort zone and allow me to connect with my community, both online & in person. Write about things that will be helpful to other people.

BE LIMITLESS

Go big. Do the thing. Shift forward into fulfilling my goals. Know that there’s no cap on what I can do.

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Speaking of bad-ass, if you haven’t checked out my friend Casey Palmer‘s blog you should. Not only is Casey a top-notch Dad & all around human, I’m continually impressed with how much he does while juggling a career/fatherhood/marriage & blogging. Case and point: every year he posts a list of 100 things he wants to accomplish in the 12 months ahead.

As a naturally anxious person, just the idea of a 100 item to-do list is enough to give me heart palpitations, so I decided to be uber realistic and make a list of 12 things I’d like to do in 2017. One for every month.

1. Wear the lipstick and earrings.

When you work from home it’s so easy to fall into a fashion rut. But I’ve noticed that my friend Kate (who also works at home) is always posting photos where she looks super cute in fun jewelry & gorgeous lipstick. I have fun jewelry and lots of lipstick…I could do this too! So, my intention is to actually make it happen: wear my nice clothes, accessories and a bold lip even though I mostly just work out of coffee shops.

2. Get to Wardrobe Zero.

What exactly is wardrobe zero? Good question. For most of my adult life I’ve always had a large rubbermaid bin of clothes that are either off season (i.e. sweaters, bikinis) or need to be sold or donated. This bin sits in storage and takes up space. While I like the idea of creating a capsule wardrobe, it’s not realistic for me. Instead, I’d like to get to the point where everything I own fits in one smallish closet – in other words, a closet without waste aka “wardrobe zero.” If I can see everything I have in one place, I’m hoping this will discourage me from accumulating items I don’t need. I have one more bag full of items to consign in May and then I’ll officially be at wardrobe zero. Wahoo!

3. Get to Beauty Zero.

I did this about 5 years ago and it was so rewarding. Basically this just means using through all the products I have (including samples!) so I can get a better handle on what I actually use and like, so I can get away from buying products that I just end up abandoning in favour of more new products. Who needs 8 different kinds of shampoo in my shower? Not me.

4. Get to Bookshelf Zero.

I have a bad habit of stockpiling books. In an effort to embrace frugality this year I’m working towards bookshelf zero. This means reading everything in my to-read pile before buying more books. If I’m feeling particularly motivated, I might even start to tackle the 30+ books on my e-reader! If I manage to stick to this goal I’m treating myself to a hard copy of Roxane Gay’s Difficult Women.

5. Learn to cook something new every month.

[2/12 COMPLETE] Every year I say I’m going to cook more and every year this goal falls to the wayside. I decided to be super realistic this year. If I can learn one new dish per month, I’ll be happy. So far I’ve taught myself to make KimChi fried rice and Cajun Dirty Rice. Yes, things are still pretty rice-y around here, but it’s a start.

6. Take pole dance classes.

[IN PROGRESS!] I’ve wanted to take pole classes forever – because, who doesn’t want to spin and hang upside down while Rihanna plays in the background? I took an intro class in January and fell in love. It’s now been about six weeks of classes and I have the inner thigh bruises to prove it.

7. Take ballet classes again.

 This is next on the docket after I finish up the next round of pole classes.

8. Get my drivers license.

Jeebus, it’s time. I keep saying this, but let 2017 be the year I finally cross this off my list.

9. Publish at least 3-5 articles in American outlets.

After taking the Pitch Like a Honey Badger course, I finally found the courage to pitch some of my dream publications. If you’re a freelance writer and want to expand into new markets I highly recommend this course!

10. My own apartment.

 This is one of my top goals for the year (along with some big professional ones.) Real estate prices are insane here and rents are on the rise, but I’m hoping that with the help of this Pinterest board that I obsessively update, I can manifest the hell out of this goal and find the perfect place.

11. Get my Barre certification.

[MAY 2017] Over the past few years I’ve become addicted to barre fitness to the point where I’ve toyed with the idea of getting my certification to teach. There’s a course happening in May. Depending on my work schedule, I’d really like to take it. This is kind of a stretch goal: if it happens, it happens but if it doesn’t, I’m not going to beat myself up about it.

12. Get crafty.

This is another stretch goal, but I’d really like to follow through on turning Joe’s handsome mug into some large scale art prints like I mentioned in this post. I’d also like to create an album(s) of my favourite Instagrams from my two California trips. It wasn’t until I saw this post on A Beautiful Mess that I remembered how much I miss having actual photo albums to look through. Phones are great, but it would be nice to have hard copies of all of these photos.

What do you have on deck for 2017? Share one of your goals for this year in the comments!

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