Today we’d like to introduce you to Gaillynn Giles.
Hi Gaillynn, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I graduated from Moore College of Art & Design and started my career in a silkscreen shop, doing graphic arts and illustration while learning every part of the production process. It was solid experience, but not very fulfilling, so I shifted into teaching art classes for West Chester Parks & Recreation — and found real respite in those Saturday art classes. Working with children brought me a sense of joy and purpose I hadn’t felt before.
One day, the Parks & Rec Director told me she needed another face painter for the Turk’s Head Music Festival. I laughed and said, “I don’t paint on people,” and she shot back, “You paint on every other damn thing — why not?” I protested that I didn’t even know what kind of paint was used, and she said she’d get the supplies. That moment kicked off what became a long‑running side hustle.
Over the years, I worked with children in all kinds of roles — substitute teacher, day care supervisor, summer camp art director — while face painting remained a steady thread through it all. And what kept me coming back was the instant gratification and shared joy that face painting creates. There’s nothing like that mirror moment when someone sees their transformation for the first time. Their reaction is my favorite part, and it becomes entertainment for them and everyone watching. I’ve had so many wonderful experiences spreading joy with a paintbrush. It’s magical.
As the business grew, I expanded into maternity belly painting, which is such a beautiful and intimate way to celebrate pregnancy. I also added water‑resistant face paint for pool parties, water play, and those hot, humid summer days when regular paint just won’t hold up. And for guests who want something longer‑lasting, we offer glitter tattoos and henna designs that stay on for 7–10 days.
When I lost my job during the pandemic, I decided it was time to take the leap and turn face painting into my full‑time business. And that’s how Paintings on People became what it is today.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It hasn’t been a smooth road. Like many small businesses, I had to rebuild my income after the pandemic and learn how to run every part of the business myself — marketing, scheduling, pricing, boundaries, and all the behind‑the‑scenes work people never see. I decided I needed to have an official logo and website so, I saved up to hire a local artist to design my website.
Working with the general public can be both rewarding and challenging. Every event is different; every personality is different and learning how to navigate expectations while still protecting my time and energy has been a real growth process.
Another important challenge has been finding the right network of face painters and entertainers. Building a circle of people who understand the industry — who can offer feedback, share advice, and help navigate tricky situations — took time. But once I found that community, it was incredibly uplifting. Having peers who “get it” has made a huge difference.
Even with the bumps, the work itself keeps me going. The joy, the mirror moment, the reactions, the magic — that’s what makes every struggle worth it.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
Community involvement has been part of my story from the very beginning. I actually got my start in 2005 volunteering for the B. Reed Henderson High School Post Prom Party in West Chester, using my artistic skills to help decorate for the after‑party. It was a meaningful cause and a fun, creative challenge. Later, I continued that work at Downingtown High School, serving as Decorating Co‑Chair and painting murals for their Post Prom. Those experiences shaped my connection to the community and helped build the foundation of what eventually became my business.
Paintings On People still gives back today. Each year, we partner with local nonprofits that benefit children, offering several discounted events to support programs that make a positive impact. I’m also very proud of our experience working with special populations. Creating a welcoming, joyful, and inclusive environment for individuals of all abilities is extremely important to me, and diversity and inclusion are values I carry into every event.
What sets us apart is our commitment to continuing education. I invest in workshops, conferences, and online courses every year to stay current with best practices, update techniques, and learn about new products. The face painting industry evolves, and I believe in evolving with it — always improving so I can offer the safest, most creative, and most inclusive experience possible.
Networking and finding a mentor can have such a positive impact on one’s life and career. Any advice?
Networking in this field has been a mix of resourcefulness and trial‑and‑error. For general small‑business guidance, SCORE and the Small Business Association have been incredibly helpful — they’re free, accessible, and full of mentors who genuinely want to see you succeed.
For face painting specifically, a lot of my networking came from jam sessions. Getting together with other artists, sharing techniques, and learning from each other created a supportive community. But honestly, the best way to know if someone truly aligns with your values is to work with them. You learn a lot by seeing how someone handles real‑time situations — the public, the pressure, and the unexpected moments that happen at events.
I’ve learned that I work best around people who have a sense of humor, patience, and kindness. Those qualities matter when you’re dealing with the general public. If someone is impatient, unkind, or carries themselves like a diva, it shows during a gig — and that’s not energy I want to be associated with. Finding people who share your values makes the work smoother, more enjoyable, and ultimately more professional.
Pricing:
- contact us for your quote
Contact Info:
- Website: https://paintingsonpeople.com
- Instagram: https://www.instagram.com/paintingsonpeople/
- Facebook: https://www.facebook.com/paintingsonpeople/
