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What Makes a Freelance Writer a Winner? The Den Contest Results

Carol Tice

Freelance writer contest winner. Makealivingwriting.comI’ve learned something in the past week: My blog readers can really write.

More than 40 writers entered the essay contest to win a year free in Freelance Writers Den I hosted with Other Den Mother Linda Formichelli. And I’m here to say, judging this contest was hard.

Linda and I wondered if there was a way to create 40 different prizes…but that’s crazy talk.

We did add an Honorable Mention category so we could sneak in a few more winners, though.

I’d like to recognize the creativity and courage of each writer who entered. Some even acknowledged their pride in taking the risk of putting it out there.

Keep on doing that.

What separated the winners and made them stand out? A few things:


The winning writers had a clear sense of where they were in their career and how the Den could help them. Some writers’ goals didn’t fit well with what the Den offers — we don’t coach fiction writers, for instance.

The winners, as one entrant said, were the right fit. Linda and I could see where time in the Den could ignite their career and grow their earnings.


Each winner’s story gave us a chance to get to know them. They shared — without oversharing.They talked about hard times — layoffs and relocations — and how they’ve launched their writing careers despite everything.

One found a clever way to let us know she was in contest mode, for instance, “I have been in the perpetual state of contest entry known as ‘job seeking,'” she wrote.

Another wrote, “I’m a long ways from writing for content mills or leaving a bleeding kidney on the doorstep of an editor that ignored my query.”


Ultimately, any writing contest is about the craft. Winners told a compelling story about their lives and writing aspirations and made us want to read it through.

One told of her life as a home health nurse, and her escape plan. Another relates her struggles with ADD, but with humor and grace.


We were a little surprised to see quite a few entries pocked with grammar, spelling, and word-choice problems. In a writing contest, those details matter. Also, in your freelance writing assignments for about any kind of client you can name.

So…watch the small stuff.


All the resources we can provide won’t matter if you don’t have that flame inside to push yourself and carve out a career as a freelance writer. We saw that heartfelt desire to achieve in each winner’s entry.

“I am hungry for a better life as a writer and I’m willing to fight for any chance I might have to receive it,” one winner wrote.

“I want to shove myself violently out of my comfort zone,” another writer told us. OK, shove granted — so get ready to do it.

Here are the winners (you can check out the original post to see the details on all the prizes, including mentoring from me and Linda, the Audit of 4-Week Journalism School and our Freelance Writers Blast-Off Class, and the basic level of Linda’s Write for Magazines course). Congrats to all — and enjoy reading their entries.

1st Place Winners: Tom Bentley of The Write Word (check out the visual funny Tom did, too!) and Jennifer Hawkins of Slashing My Way into Freelance Writing.

1st Runner up: Kasie Whitener of Life on Clemson Road

2nd Runner up: Lynette of ADD Ranger Ramblings

3rd Runner up: Bree Normandin

Honorable mentions (win a copy of Make a Living Writing: The 21st Century Guide):

Glori Surban of The Not-So-Crazy Introvert, Rosella LaFevre of The Happy Millenial (her entry is in the comments to the contest kickoff post, though) and Megan Harris of MeganWrites.

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