How to suck and how to succeed in a freelance writing business

I’ve been a freelance writer for fourteen years now, typically supporting my income with part-time roles in communications and publishing. When I dusted off my CV last year to go in search for another part-time writing gig, I still felt the balance of freelancing and an inhouse copywriting role suited me. Eventually I got the knack of writing cover letters (hint: not everyone enjoys a pun) and I started getting interviews. But while I was a great match for the roles, no one was picking me. And weirdly, I felt relieved. Which made me think:


What the hell is wrong with me?
Meanwhile, I began to think about ramping up my freelance writing business to fulltime. The thought terrified me but, in between the heart palpitations, I felt excited for the first time in a long time.

A little confession though. Five years ago I launched into fulltime freelancing and failed miserably. Here’s why.


How I’ve sucked in my freelance writing business
I was idealistic. I didn’t think of myself as a business – I thought of myself as a “writer”. At the time, I was only writing semi-regularly for one news outlet, but figured I’d just pitch to lots of different media platforms (surely others would see my genius) and the commissions would flow in. They didn’t. In fact, I was rejected so many times I felt like the fish that John West rejects.


Here’s the other thing. I didn’t consider other income streams such as copywriting until I was desperate, and my rainy-day money had hit drought status. In addition, I didn’t market my business properly because I thought that having a website was enough. In retrospect, I was completely unprepared to run a freelance writing business. Six months later, I limped back to a part-time role which, at the time, really saved my arse.


This time round, I’m doing things differently – I’m planning, marketing, learning, listening, sharing and networking. Rinse and repeat.


Despite my failures, I don’t think I would have lasted fourteen years as a freelancer in any capacity if I didn’t do the following.


How I’ve succeeded in my freelance writing business
Freelance writer, Lindy Alexander, is a huge advocate for building relationships with editors and clients.


“If you’ve got one-off gigs, then your income and your livelihood is much more fragile than if you have recurring income.” Lindy Alexander, The Freelancer’s Year


Prior to reading Lindy’s blog, I hadn’t thought of freelance writing in terms of relationships. And yet, unbeknown to me, I’d been doing exactly that. I have two long terms clients that provide the bulk of my freelance work, one for whom I write weekly content. I also have an editor who I’ve been working with on and off for six years, and even when her inbox is overflowing with emails she still takes the time to respond to and commission my pitches.


So what’s the trick to fostering long-term relationships with editors and clients?


I’ve thought a lot about this and it’s actually not dissimilar to other relationships. I think the trick is being reliable, trustworthy and respectful. File your work on brief and deadline (and to a word count if applicable). People are busy, so don’t make them chase you for outstanding items. Take feedback on board and make the requisite changes (as long as the requests are not outside of the brief). Be responsive to emails. I don’t believe you have to be on 24/7 so, if you can’t respond within a few hours, try to respond within the same day. On the off chance you can’t deliver, just be honest about it. I’ve found that people are usually pretty understanding if you just let them know.


While I initially failed to diversify my freelance income streams, I discovered content marketing. I now have five years experience writing weekly blogs, eDMS, white papers, case studies and website copy. Just recently I added guest blogging and award applications to my cache of expertise. I never thought I would say this, but I love writing marketing content. For the right client and industry, it’s a real buzz.


The other thing I’ll touch on here is money. While I need to generate more work and money to hit my new freelance goals, I do not work for peanuts (though this could be subjective). And that’s because I’ve already made that mistake. In the beginning of my freelancing career, I “won” a job on a freelance job site by dropping my rate. I also didn’t anticipate that the job would take me so long. In the end, I was paid $15 an hour and I had to pay for images on top of that (because I didn’t read the contract properly!) I felt completely duped and dispirited. Fortunately, I told a seasoned freelancer about my experience and she retorted, “Karla, get the hell out of that cattle yard. You’re worth more than that.” Still, it’s disappointing to see so many writers out there today creating 1,200 word blogs for $50 for profitable businesses. And don’t even get me started on “exposure bucks”. A blog for another time.


So how about you? How have you sucked or succeeded in your freelance writing business?

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