Congratulations to Barbara J. Anderson for Winning the June 2020 Barefoot Writing Challenge! (Your $100 prize is on its way!)

The challenge was to write an essay that answered this prompt:

What continues to be your biggest, can’t-seem-to-kick-it challenge as you move forward with your paid writing goals?

Barbara shared a colorful confession about the single biggest thing holding her back from launching her copywriting career. Enjoy her winning submission:


Why haven’t I called anyone and asked them if they needed a copywriter? I’ve studied hard and done all the exercises. I’ve turned in the assignments. I feel like a professional writer. So why haven’t I taken the first step toward becoming a paid professional writer? Why not?

It’s not fear. I know I write better than I talk, but I’m not afraid to talk to professional people. I have a college degree, I’ve held good jobs, I’ve never been homeless… yet.

I guess it’s a matter of pride and preference. It’s humbling to ask someone to put me to work. I used to create my own work. Started a business advertised as Jill of All Trades and did every legal job I was offered. I cleaned guano out of attics and buried a dead dog in a snowbank till spring. I mowed lawns and weeded gardens, scrubbed smoke-stained walls and ceilings, and cleaned garages and basements. Hard work, but it paid the bills for myself and my three children.

Then for years I had nice homes and bad husbands. I moved on and worked in leather-chaired offices. The paychecks were big, but the joy they brought me was small. The kids were grown, so I picked up my keys, whistled for my dog, and drove west. I looked for places far away, and I found them.

Rode a mule to the bottom of the Grand Canyon, then river-rafted 185 miles down the Colorado between towering canyon walls. Never did see a pink rattlesnake. They exist, you know. They’ve gradually evolved from brown to a deep rosy pink, the color of the surrounding rock.

I hit three corners of the country — California, Washington, then Maine — and had no direction left to go but south. Got to Key West and ran out of land. I hopped a ferry to the Dry Tortugas National Park, a Civil War–era brick fort on a speck of island 70 miles out in the Gulf. Slept on the beach under a full moon. Got dizzy watching frigate birds soar in circles over my head in the morning. Pure heaven. And then I came home.

So now I have to get real. Wandering takes income, and I don’t have any. If I pick up the phone or write a few emails or place an ad in the church bulletin, I will end up working for someone. I love writing, so it won’t be painful work.

Can I be persuasive? Can I aim for a star and hit the moon? Set a goal and surpass it? I suppose so. I guess I have to try. Why not?

Let me pull up LinkedIn. I’ll check the job board… Here’s a nursing home wanting a senior copywriter. Where’s their number? Oh, here it is… “Hello? Yes, sir, I’m calling about the ad. I need to tell you, ‘I’m ready to write for you!’”