How to Thrive as a Freelance Writer

I’ve been working as a freelance writer for the last five years, albeit not yet full time. What I’ve learned is that writing is, in the words of Lean In, not a ladder, but a jungle gym. There’s no direct path to where you want to be, no perfect job or internship that opens doors.

You make moves that may lead to something bigger, or not. Everything I’ve learned has been from doing and from making the mistakes, especially when it comes to invoicing and keeping track of payments. So I’ve compiled a list of tips for aspiring freelance writers, which applies to nearly every style of writing and to many fields.

Work For Free When Necessary

When I first started out, I thought that writing for free was something that only those who could benefit from “exposure” or the highly naive would do. The “Huffington Post” model was scoffed at and, honestly, still is. And if your goal is to make a name for yourself, HuffPo is the way to go.

But I’ve actually gotten paid work from unpaid work and there’s something to be said for “paying your dues.” The situation is more common than you think. Sometimes you take work that’s a step down but inevitably propels you forward in the long term. You have to prove to a publication that you have something to offer them, so if that means writing for free for a period of time, you can.

Here are the jobs I’ve gotten from free work:

• Her Packing List– I started with unpaid guest posts and Brooke liked what I wrote, so she offered me a regular gig writing posts and helping edit.
• AFAR– I started contributing to the community and was then asked to be an ambassador, which involved promoting the magazine and writing posts. From there, I became a freelancer, working on special projects like the Atlanta City Guide, a Westin Finds guide and a Chase guide.
• National Geographic Traveler– I wrote an unpaid guest post for their I Heart My City section. I was contacted almost a year later to write a paid feature, also about Atlanta.
• Skyword– The folks at this content management company saw my Contently profile and emailed me about writing for the Priceless Caribbean program. My work with that job led to more work with them on the Love This City site.
• US Airways, Shermans Travel, Travel Mindset and Matador Network– Friends have recommended me because of the unpaid blogging I’ve done for my own sites.

But with that said, don’t be a pushover. If a big name publication offers you only $20 for a 2,000 word post, I would pass unless you think you’ll get something out of it, namely links to your blog or name recognition. Don’t be afraid to speak up to get your fair pay. Exposure doesn’t pay the bills. Follow Who Pays Writers to see who’s looking for writers and what they pay.

Collaborate, Not Compete

You aren’t in competition with other writers, so don’t think of it that way. This isn’t an individual sporting event. We only get better from learning from other writers and editors. I love having a group of writer friends because they understand what I’m going through. They can also send work my way or give me a heads up to avoid a certain editor or to make sure I get timely payment.

I would also argue that thriving as a freelance writer is 50% who you know, if not more, and 50% hard work. Most of the work I’ve gotten is from referrals, which is great for me because it means I don’t have to pitch nearly as much and that my work ethic is noted by editors. When you’re at networking events or talking to colleagues, let them know that you’re looking for work and they’ll remember you when they see an opportunity you’d be a good fit for.

It also helps to set yourself apart as an expert in a specific field. For example, there are thousands of “travel writers” out there. So if someone is looking for a travel writer for a specific topic (let’s say Atlanta), they’d usually rather find someone who is an expert in that particular field than someone who writes general travel articles about every topic under the sun.

Set Goals

In my head, I have a “dream publications” list I’d like to see my byline on. They may not be realistic for me at this particular moment, but they’re on my radar for what I’d like to accomplish. Set regular goals for yourself at intervals and check up on yourself. For example, my goal for the next 18 months is to slowly get away from my additional jobs (tip #100: have backup jobs) and move solely into writing. My long term goal is to take a writing class to develop more long form stories that could one day become a book.

Pitch (and Fail) Hard

Set aside your feelings about rejection immediately, as it’s something you’ll need to get used to. Cold pitches are just a gamble in the field and they occasionally pay off. I’ve done 2 cold pitches this year to major publications and never got so much as an email in response. But you’ll never know if your idea is what they’re looking for unless you ask.

Also learn to recognize the voice of each publication you’re pitching to or writing for. For example, the pieces I’ve written for Matador are a bit more snarky, while the pieces for Mastercard are very descriptive and SEO friendly. Know which publications publish short form and long form so that you don’t send in an idea for the opposite.

Be Your Own Cheerleader

Don’t expect editors to tell you how great your work was or how lovely it was to work with you. It happens, sometimes, but you can’t thrive on gold stars, as you won’t be given them often. Be confident in your work and treat yourself when you’ve completed a big project. Also be able to speak up about your work when pitching, telling a potential editor what you’ve worked on in the past.

For more tips on being a freelancer, check out this video from Contently’s CEO. It may be long, but you can listen to it while you’re doing other things.

Any more tips for an aspiring freelance writer?

For more on being a freelance writer, read my guest post for MediaShower.