Congratulations to Jennifer Grimes for Winning the December 2025 Barefoot Writing Challenge! (Your $100 prize is on its way!)
The challenge was to write an essay that answered this prompt:
What are the top two or three non-negotiable goals you want to achieve next year?
Jennifer shared a frank and vulnerable take on the roller coaster that is early freelancing. Enjoy her winning submission:
The writer’s life sounds like freedom. Glorious, wonderful… horrible freedom.
When we think of “freedom,” we think of finally having control: over our schedule, projects, fees, stories, even the words themselves. What could be better? Why is the jump so terrifying?
As it turns out, I am much like my indoor cat: When he finally escaped from the confines of the house into the boundless outdoors, he realized he had no idea what to do with his infinite possibilities and just — sat down. That’s me, sitting baffled in the grass. I left medicine where my every minute was spoken for, my patients were assigned, the treatment algorithms are evidence based and well established, and the track I was on, with its specific academic route and training requirements, was suddenly gone. I was relieved until I realized that instead of following a well-charted course, I was now off-roading. There is no one way to become a writer. There is no one “correct” path.
There are questions that multiply when you answer them. Do I need a lawyer to prep contracts? Errors and omissions insurance? An LLC? (What is an NAICS number?) I’m new, but I’m also a subject matter expert. Am I undercharging? Overcharging? How do I handle a sales call and sound professional, not like a wide-eyed, half-terrified introvert hoping I got it right while projecting ~*confidence*~?
I didn’t have all the answers. I didn’t even have half of the answers.
But the magic came when I realized that that’s normal, and that’s okay.
It takes a mental shift to rekindle a joy in learning and discovery, to let curiosity beat fear so you can pioneer your way. AWAI offers a lot of great resources that become much less intimidating to work through and utilize when you make that shift and give yourself permission to figure out the answers as you go.
I learned that lesson this year, but next year, I plan to fully embrace it — not just with my mind, but in my heart — as a guiding idea.
Second, I plan to integrate this celebration of mildly chaotic freedom with the way I am trained to work: to organize and chart my own path forward with contingencies but also with patience when parts of the plan require recalculation. (I also plan to embrace “recalculation” over “failure.”)
Third, I plan to get past the hurdle of the administrative learning to delight my first client. I know I’ll feel happier, more relaxed, and more convinced I’m on the right path when I have a little evidence to back it up and build on. Often, the impressive catastrophizing of how you can mess up with your first paid project is wildly out of proportion to the client’s perspective of the rough edges.
In sum, 2026 will be the year I finally embrace freedom. I wish everyone a happy and successful new year with self-kindness, curiosity, and growth driving all of us forward in our embrace of the writer’s life.
