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.

Join my freelance writer community. Makealivingwriting.com


  1. Sugel

    Can I just take the webinar? I’m sure I won’t win the contest. I’ve read many of the comments here which I can relate to and have gone through. I took other full time jobs for years and wrote on the side or as one person mentioned, sat in my cubicle thinking about writing. Out of all the fears and issues that held me back, in retrospect it was my lack of belief in myself and my abilities as a writer and marketer that were the strongest. One of the turning points for me was to writer on a topic that I knew about. I tried topics that I either went to school for or had done as a serious hobby. That worked better, so I kept pushing in that direction and answered every online writing and magazine opportunity I could find. Some went out of business, others got sold, another had his business deflate with the economy. Now I’m at a good point in my writing career where I have a main consulting gig that pays well and am picking up a few smaller gigs to supplement it and provide some variety. I could use help organizing and managing my writing projects and need help marketing my business. But I’m on the way and I’m grateful to be doing what I love to do.

    • Carol Tice

      Hi Sugel — this contest wasn’t to win a single Webinar, but access to Freelance Writers Den, my writer’s community, which has many different Webinars available to members to view whenever you want – more than 60 hours of them so far, and more coming weekly!

      Currently, the Den is closed, but you can sign up on the waiting list (or check back to see when we reopen) from the home page: http://freelancewritersden.com.

  2. Lena

    Congrats to all the winners! That must have been such a great experience!

  3. Elizabeth Towns

    Congratulations to the winners!

Related Posts

You CAN Write a Query Letter That Gets a “Yes”: 5 Resources

Freelance writer getting a gig after learning to write a query letter.

Love them or hate them, queries are one of the most important marketing tools for any freelancer who wants to write for magazines. And the skills you learn from writing a good query letter also help business writers and copywriters pitch their potential clients.

If you’ve been sending queries off into space and never getting a reply, you may think it’s impossible to break into new magazines. But it’s not true! Editors are always looking for new talent.

To help you learn to write a query letter that will get you the gig, we’ve pulled together a collection of five of our best posts on pitching:

Can’t Write? Try These 9 Ideas for Writing Motivation

It’s the bane of every freelance writer’s life: You know you need to sit yourself down and get some writing done, but nothing happens. The writing motivation just isn’t there. Sometimes, you can't even make yourself sit down with the computer -- even if you...