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My 3 biggest freelancing mistakes (so far)

By June 14, 2024 No Comments

Over the past few years I’ve been incredibly fortunate to be published in some great newspapers, magazines and websites. But that definitely doesn’t mean I haven’t made mistakes. I have. And some have been real clangers, let me tell you.

But the good thing is that I’ve learnt from my mistakes. I’m going to share three of the mistakes I think back to and wince, so that maybe you can avoid that sinking feeling when you read an editor’s feedback.

My 3 biggest freelancing mistakes (so far)

Mistake 1. Settling for mediocre case studies

A few years ago I had a big break into a magazine I loved. I was thrilled. After writing a couple of pieces that I pitched, the editor approached me and asked me if I was interested in writing another piece for her. This was beyond my wildest dreams. An editor of a magazine I loved was coming to me and asking me to write for her.  Of course I agreed.

The article was about multigenerational families living under one roof. 

I hadn’t realised how tricky it would be to find compelling case studies (the editor, of course, didn’t just want happy families in the feature – she wanted vibrancy, conflict and compelling, nuanced relationships). Finally I found two families who agreed to be interviewed and photographed. The trouble was, as lovely as they were, their stories about living with three or four generations under one roof weren’t fascinating. But they were good enough.

Or so I thought.

So did I pursue other case studies?


Big mistake. 

I wasn’t dogged about finding the perfect case studies and the piece suffered. The editor came back to me with: “There’s no colour in this piece. It falls flat.” As hard as I worked on it to improve it, I could never make it work with those case studies, because they weren’t the right ones. Despite hours of extra work, that piece never saw the light of day.

Those kinds of feature articles are interesting to read because the people featured are lively and have great stories to tell. My advice? If you haven’t found case studies that will make your piece sing, keep looking. 

Mistake 2. Not knowing (or understanding) who I was working for

There’s an old adage in freelance writing about needing to know the publication you are writing for inside out and it’s absolutely true. But it’s also true that you need to know a bit about the company/business/organisation/publication you are writing for and what they are hoping to achieve by having you write articles for them.

I recently started writing for a great website that helps with recruitment, talent management and talent retention for small businesses. I pitched a well researched idea (complete with stats) about the ways that outsourcing can help small businesses.

Spot my mistake? 

I received a lovely reply from the editor saying she couldn’t commission my idea because it was at odds with the company’s purpose – that is, to providing engaging articles about all manner of things to do with small business and ultimately to guide them back to the services they offer. An article on outsourcing would be utterly counter-productive to why they had content on their site. Good idea, but wrong publication. 

I wrote back rather sheepishly and admitted that I hadn’t thought that one through very well. The editor was very gracious and sent me a copy of their charter and has since commissioned me. 

Mistake 3. Pitching at the wrong time

Sometimes I’ve been so focused on getting a ‘yes’ to a pitch that I don’t think about the bigger picture. Recently I pitched an editor of an education website an idea about the pros and cons of mid-year intake for online courses.

It was a good idea, the editor said, except for the fact that I sent the pitch in August.

Mid-year intake in Australia is, well, in the middle of the calendar year, and if I had given it the thought it deserved I would have realised I should have pitched the idea in March or April, with the view the piece would go live in time for people considering applying for mid-year intakes. 

So there you have it. Three of the mistakes that have really helped me hone my skills as a freelance writer. I’m sure I’ll be learning a lot more this year as I go full time freelancing.

What about you? What have been some of your biggest learnings from your freelance career so far?





No Comments

  • Well… sending a terrible pitch to begin with!
    It took me a long time to figure out the pitches I was sending out when I first started freelancing were simply terrible. I was lucky to get one bite only on the basis that it was a well timed pitch, but I’ve not had any further commissions that year because my pitches lacked focus and depth!

    I know better now 🙂

    • Lindy Alexander says:

      Oh yes, pitching is such an art, isn’t it?! I think you identified it perfectly when you talked about the importance of focus and depth, and timeliness too. Quite the balancing act!

  • Collette says:

    I’m actually embarrassed to even admit this, but I quoted a source without researching how reliable it was. It ‘appeared’ reliable, but when the editor asked me for more details, it turned out that this ‘expert’ I was quoting had actually self-published the book I was quoting from, and had formed the ‘society of….’ whatever it was, himself. I was horrified that I’d made such a rookie mistake! I ended up ringing the editor to try and build some bridges and she had some stern words with me, which I, of course, just had to cop on the chin. But I felt like a total amateur! Thankfully that editor has commissioned me since then, but it took me a long time to pitch to her again because I was so embarrassed.

    • Lindy Alexander says:

      Oh Collette, I feel your pain! Thank you for sharing. I think it’s really easy to accept people at face value and put trust in how they present themselves, especially when you are starting out.

      Do you know what I love? I love that you rang the editor. That takes serious courage and I’m sure she appreciated your honesty and frankness.

      I always try to remind myself that mistakes are learning opportunities, but sometimes they make me cringe, even years later!

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