Making a Living, Making a Life

In Caroline County, freelancing isn’t just a hustle — it’s a way of life and a path to a good living for many in unconventional careers.

For local creatives like Chris Dorr, Kayla Abbott, and Joanne Gelles, the gig economy isn’t just about flexible hours or extra cash. It’s a way to make space for their talents, connect with the community, and — often against the odds — build sustainable, fulfilling careers in a rural setting.

Chris Dorr: From Corporate to Creativity

Chris Dorr’s journey into freelance photography and video production began with a gut feeling — and a need for joy.

“I didn’t want to be that miserable guy walking around just making everyone else miserable,” Dorr said. “And I enjoyed doing what I was doing outside of work much more.”

That realization prompted him to leave his job in a prepress department and dive into gig work, turning a hobby into a career.

A longtime band drummer, his transition was seamless. His background in design gave him the skills to pick up photography and video quickly. What began with casually shooting videos for friends led to a referral for a corporate event. That single gig became years of ongoing work and a steady client base.

But it wasn’t all smooth.

“For a while, it was making sure people paid me,” he said. Financial instability, marketing, and self-management posed early challenges.

Dorr, who calls himself “terrible at marketing,” jokes that his best advice is to “be married to someone who’s good at numbers.”

Despite that, his work and reputation speak for themselves — and in a small town, that can be more effective than any ad campaign.

By focusing on storytelling over sales, Dorr brings emotional depth to his work.

“You have to create that connection... with the person you’re interviewing, the client, and the audience,” he said. “It’s not just about taking a great picture. It’s about connecting. Sometimes, you see people react emotionally to your work — that’s what makes it worth it.”

One of his key takeaways? The value of collaboration. Having trusted creative partners keeps projects fresh and fulfilling.

Today, he finds the most satisfaction in mission-driven work.

“It’s pretty satisfying when you’re doing work for a client who is doing good in the world,” he said. “And it’s up to you to help create that message.”

Kayla Abbott: Gigging with Purpose and Joy

For Kayla Abbott, gig work is a calling — a way to uplift others while staying true to her entrepreneurial drive.

“I love people in general,” she said. “I love to interact and make someone’s day — smile, laugh, just to bring a little extra joy.”

Her company, Kay Productions, grew naturally.

“It just happened,” she said. “You have gifts that you need to make room for, and you’re supposed to operate in your gifts so someone else can gain what they need from what you do.”

Abbott DJs events across the region — from skating rinks to church gatherings — often squeezing in DoorDash deliveries between gigs.

She recalls one long day: “I dashed all the way up until the event when I had to DJ at the Dover Delaware skating rink.”

That work ethic is part of who she is. “I started Door Dashing with other things to keep myself challenged, and to help with cash flow while my DJ business takes off,” she said. “That’s how you grow.”

Now, she’s known locally as the “Dashing Queen,” complete with a logo and merchandise — another facet of her growing brand.

For Abbott, gig work also has a human side.

“I've been a caregiver as well,” she said. “So, it really gets me — I just want to stay there, for example, when I go into nursing homes... Dashers might be the only humans some people see in a week.”

She sees Caroline County as full of potential.

“So many people don’t realize what we have,” she said. “We are really blessed. We have businesses here that many don’t know about.”

Her dream? A permanent creative space in the community.

“In the next five years, I’d love to have my own studio in Caroline County,” she said. “A space where people can be creative, record music, do video, play, and sing. A place to commune and to create.”

Her advice for new gig workers: Be honest about your discipline.

“Think about how disciplined you already are before you start,” she said. “It’s easy to get consistent — and just as easy to be inconsistent. Plan your work and work your plan.”

Joanne Gelles: Making Art, Making Connections

For Joanne Gelles, gig work began as a practical pivot and grew into a rich, creative lifestyle.

“I didn’t want to be stuck in an office all day,” she said. “I was struggling to find something that I really enjoyed doing.”

She began with antiques. Every Wednesday, she’d fill her minivan with auctioned items, refurbish them, and resell them.

“I loved it,” she said.

Her gigs soon evolved into writing, face painting, teaching, and promoting the arts. Writing business profiles for the Caroline Review is one of her favorite outlets.

“I like that my stories make the people I write about feel good about their business,” she said. “I’m fortunate to be able to use my writing talents to help put a little spotlight on them.”

Her roles span journalist, artist, and teacher. She says drawing caricatures at parties and events, and face painting gigs are especially joyful.

“Watching the joy on children’s faces as the paint transforms them is like watching magic,” she said. “I like to make people feel good, if I can.”

Her art classes are just as varied: mosaics, painting, tie-dye, paper-mâché.

“I host painting events throughout the year, including one this July 13 at Caroline’s Table in Denton,” she says. “We will paint a fruit and wine still life, and the chef will be choosing a winner for a free appetizer or dessert.”

Living in a rural area, she’s found, actually nurtures her creativity.

“When you’re in the country, there’s not as many distractions… so you have more time to do things like craft or art — you can explore that side of yourself,” she said.

A Community of Creators

In Caroline County, freelancing looks a bit different. There are no sprawling coworking spaces or cafés full of laptops. But the work is no less relevant for Dorr, Abbott, and Gelles.

Their stories reflect a broader shift, where passion, people, and place intersect. In a time when job titles can limit and office walls can confine, they’ve chosen a different path.

One built not just on what they do but also on why they do it.

For them, gig work isn’t a fallback. It’s a purposeful choice, even if the path isn’t always smooth. And in Caroline County, it’s clear: that choice transforms lives — one portrait, delivery, story, or brushstroke at a time.