The 4 Main Reasons Why You’re Failing as a Freelance Writer

Kelly Dawson
4 min readApr 24, 2023
a pedestrian-only street next to the beach, with houses on one side and sand on the other. it’s a blue-sky day.

If there’s one question that strangers often ask me online, it’s this: “How did you become a successful freelance writer?” I began freelancing more than a decade ago, as a supplement to many office jobs and then as a full-time commitment once I had worked as an editor for a while. Like many people in the media industry, my career as a writer hasn’t been a straight path. But freelancing made it possible for me to climb a ladder of my own making. Seeing as the wider economy has been equally unpredictable, I can understand why more people than ever are interested in freelance writing either as a side gig or a fledgling business.

Freelance writing is challenging, especially when you’re just getting started. If you feel like you’re failing at it, the issues you may be having likely point to four main culprits. Read on to learn what they may be, as well as ways to solve them.

You’re asking for ideas, not giving them.

As an editor, I’ve gotten emails from new writers that often go like this: “Hi! I’m so-and-so. I want to write for you. I’m open for assignments!” That’s it. They don’t share what they like about the specific publication, don’t clue me into the relevant work they’ve done in the past, and don’t list any pitches that might pique my interest. They just say hello and peace out, which makes the email very easy to delete.

If you are a well-established writer, then it’s much more accepted across the industry to list your previous accolades and ask if a publication is currently accepting pitches. But once an editor replies, even the most established freelancers send over pitches! Read the publication you’re interested in contributing to, and cultivate ideas based on the verticals that best suit your expertise. An editor is much more likely to respond to first-time writers if they’ve shown a little effort.

You’re emailing the wrong person.

There’s a lot of excitement that comes with striking out on your own and choosing to be a freelance writer. You set your own hours! You can hone drafts from wherever you choose! You’re probably, unwittingly, emailing the wrong person! Given all of the high hopes you have about where this career might take you, you…

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Kelly Dawson

i write, i edit, then i write again. | kellymdawson.com | instagram: @kellydawsonwrites