A Year of Growth, Gratitude, and Live Art: Looking Back on 2025!
As this year comes to a close, it feels like the right moment to pause, reflect, and say thank you!
2025 was filled with meaningful moments, beautiful celebrations, and countless connections that made this business what it is today. From painting live at weddings, to guest portraits at private events, to meeting new faces at markets and pop-ups, this year was a reminder of why live painting is such a special way to tell stories and bring people together.
Cayla setting up mini magnetic guest favors at a wedding.
A Growing Niche & A Lot of Heart
Over the past year, live painting has expanded beyond weddings. While weddings will always hold a special place, there was something incredibly exciting about expanding into live event painting for markets, private parties, and community events. Each setting brought something new and different… the energy, people, and stories waiting to be captured.
One of the most rewarding challenges has been creating meaningful artwork within a short timeframe. Whether it’s a couple celebrating their wedding day, a 15-minute guest portrait, or a beloved pet transformed into art, the goal is always the same: to capture something personal, joyful, and lasting. That challenge never gets old!
The live painting set up with three dog portraits, finished, and ready to go to their new homes.
Markets, Pop-Ups, & Community Connections
This year marked Cayla the Painter's first season at holiday markets, and it was a learning experience. From preparation to booth setup and inventory, there were many lessons learned and many moments of gratitude, too. Holiday markets were a significant part of this season’s growth and opened the door to new conversations, commissions, and connections.
Markets also offered something just as valuable as sales: community. Meeting people face-to-face, hearing their stories, and creating art in real time remain among the most fulfilling parts of this work.
There’s something special about building relationships locally in Milwaukee and beyond. From events throughout Wisconsin to pop-ups and collaborations in Chicago, and even applying for opportunities as far as Dallas, it’s been exciting to watch this work travel and grow.
Milwaukee truly feels like “Small-Waukee”. The wedding and events industry here is welcoming, interconnected, and incredibly supportive. Everyone knows everyone, and that sense of community makes each collaboration feel personal rather than transactional.
Cayla with two of the best wedding professionals, Caroline Cavalcante & Monique Cunningham at the WI Bride launch party.
Gratitude for Clients, Friends, and Family
None of this growth happens in isolation. Every wedding booked, every portrait painted, every market visited, and every recommendation shared is the result of trust and support from clients, fellow creatives, friends, and family.
This year brought the chance to work alongside so many talented vendors, planners, photographers, and small business owners, many of whom quickly became friends. It also came with constant encouragement from family and loved ones who show up, help out, and believe in this work wholeheartedly.
That support is felt every single day, and it matters more than words can say.
A fun portrait that Cayla made for a customer.
Looking Ahead to 2026
As 2026 approaches, there’s a lot to be excited about. With more time and intention being poured into the business, the focus moving forward is growth, exploration, and saying yes to new ideas.
Private parties, live event painting, expanded markets, weddings, and even future painting classes are all on the horizon. There’s a genuine excitement around discovering opportunities that haven’t even been imagined yet, and continuing to evolve creatively along the way.
If you’re dreaming up an event, hosting a private party, planning a wedding, or have an idea that involves live art, this is always an open invitation to reach out. Some of the best projects begin with a simple conversation.
A live pet portrait Cayla created.
Thank You!
Thank you to everyone who made 2025 what it was. To the couples who trusted live painting on their wedding day, to the guests who stopped by booths at markets, to the families, pet parents, planners, and collaborators, and to the friends and family cheering from the sidelines…this year was truly shaped by you.
Here’s to everything learned, everything created, and everything still to come. Cheers to 2026, and all the beauty waiting to be painted.
Cayla with a Bride and Groom in front of her painted ceremony panels.
