We were lucky to catch up with Jessica Buckley recently and have shared our conversation below.
Jessica, thanks for joining us, excited to have you contributing your stories and insights. What’s been the most meaningful project you’ve worked on?
My husband’s job requires us to move. Like, a lot. I’m forever grateful for the opportunity to live in these new (mostly) amazing places and experience the world, but leaving behind our friends, family, and support network every two to three years presents some challenges. One of the biggest challenges is finding my people in a new place where I don’t know anyone at all. As I gradually started meeting other moms on my block, I realized I wasn’t alone in this struggle. We were finding it hard to not only make time for ourselves but to socialize with our peers while juggling the demands of parenthood. Sure, we all said “hi” in passing or chatted if we happened to bump into each other at the playground, but when the kids’ bedtime routine rolled around, we were in for the night. I realized that we were all in need of some adult socialization, but none of us needed the project of scheduling a babysitter, planning an outing, and then embarking on said outing. I started to brainstorm ways we could support each other without having this list of things to do to make it happen.
I thought, what if we all meet up after the kids are in bed, I teach a brief watercolor lesson, we do a paint project, and we get to socialize while being creative? At that point, I had only been painting with watercolors myself for about a year, so I wasn’t feeling particularly confident about teaching it to a group. But I took a chance and invited a few moms over for a watercolor night at my dining room table. What started as a risk (Do I know enough about watercolor to teach it? Will anyone even show up?) turned into a regular event. As I hosted more art nights, I worked out the kinks and every get-together went smoother than the last. I found that people will show up when the conditions are right. I provide all the supplies we need, from paint to brushes to my favorite cold-press cotton paper. I host most of my art nights at 8 p.m. when the kids are asleep or almost asleep so moms can pass the bedtime baton and slip out of their house. Dress code? Pajama casual. Hair wet from the shower? We do not care. Late because the baby is fussy and refuses to let mama pass the bedtime baton? We’ll catch you up when you can get here. Can’t make it for literally any reason under the sun (or moon)? No big deal, we’ll see you next time. No time to make a snack to contribute? Show up empty-handed, we’re normally too busy painting to eat the snacks anyway!
When I first started these watercolor nights, I didn’t realize the impact they would have on our lives. These art sessions felt more like group therapy sessions where we could talk openly about our struggles, our accomplishments, our ideas, our career aspirations. The initial group I started painting with became incredibly close. Unfortunately, many of those friends have moved away. But even though they aren’t at my table anymore, they are still painting. One of them discovered watercolor was her new way of coping with stress, purchased her own supplies, and started painting all the time in Arizona. One of them, who found the adult socialization life-saving while her husband was deployed and she solo-parented an infant and toddler, decided her watercolors were precious enough to include in her limited luggage space on the journey to her new home in Tennessee. And one of them missed our art nights so much she started hosting her own watercolor nights in North Carolina.
As I slowly meet new friends, I invite them over for watercolor nights. I share my knowledge and love of watercolor with them. It’s what brings us to the table for a sense of community and belonging. Once we’re at the table, there’s a supportive and uplifting vibe. What started out as just a way to get us together to socialize turned into so much more than that.


Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
My name is Jessica Buckley and I am the artist and owner of Carolina Chickadee Co. LLC. I am a one woman show: I create botanical watercolor paintings and sell prints, cards, and other items with my artwork on my website and at markets all over the island of Oahu. I also teach informative but casual watercolor classes in my home.
Years ago, I taught art for elementary and middle school students, but after leaving that job, I struggled to make time to create art on my own. Fast forward to marriage, baby number one, an international move, and then baby number two … I was definitely not making time for art. When my youngest son started attending a daycare program I found myself with 10 child-free hours a week. Not enough time for a traditional job, but I started thinking about what my career path might look like moving forward.
Around this time, my son’s day care hosted a holiday craft fair. I committed to it with a plan to make as many original magazine collage birds as possible. I had made these adorable bird collages on vintage sheet music as wedding gifts throughout the years, but this was the first time I had attempted to sell my artwork in a public setting. I got to work creating my magazine collages and then took a stab at watercolor, which I hadn’t attempted in 10+ years. I paid my $45 booth fee, set up with the artwork I had been creating during naps and bedtime, sat down, and waited for the crowds to gush over my amazing one-of-a-kind vintage collages. I sat down alright, but the crowds did not come, and I didn’t even make the $45 booth fee back that day.
Most people would have probably thought, “Alright, maybe craft fairs and markets aren’t for me.” But I didn’t look at that market as a loss. I viewed it as a learning experience. I talked with my booth neighbors, learned about other more popular craft fairs, and discovered that people seemed more interested in smaller, inexpensive items. A month later, I set up at another market that was far more successful than the first.
Six months later, we moved across the country and the Pacific Ocean to Hawaii. In Hawaii, my mind was blown by the amazing botanical inspiration for paintings. I spent the first year here painting the plants and flowers I walked by every day. I went to local markets to check out the outdoor market scene, but I didn’t feel ready to participate. Meanwhile, I learned how to turn my original watercolors into greeting cards and high-quality prints, which was a game changer. Now I could offer my artwork at a much more affordable price to customers. This was so important to me because I wanted my artwork to be attainable for everyone.
At the encouragement of a friend, I signed up for my first market in Hawaii. No vendor fee, right down the road from me, low risk. My friend offered to watch my kids so I could focus on the market and to my surprise it went really well! My vendor neighbors again told me about bigger markets to try and those fellow vendors are close friends to this day. That first market was a year and half ago: now I’m setting up at three markets a month all over the island. At every market I attend, I learn something new, like how to display my items to catch the customers’ eye, or what customers are looking for, or that my original canopy was water resistant and not waterPROOF … big difference!
Today I sell over 20 different prints of my watercolor paintings in various sizes and almost every print is available in a card version. I also sell coasters, ornaments, and stickers. Whether a customer is looking to add a piece of artwork to their wall, send a card, or buy a gift, they have many options and price points to choose from.
Aside from painting watercolors to sell at markets, I also coordinate and host watercolor nights with old friends, new friends, and strangers. I am so proud of how these watercolor nights have grown and helped build a sense of community. Starting in January, I plan to open up more of these watercolor nights with the option to attend with a group of friends or, if you haven’t found your people yet, come to a watercolor night that has an open seat and be a part of a welcoming and supportive environment.


We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
I grew up in a religious cult. I sat through hours and hours of sermons where it was preached that we should never be proud, always be humble, never draw positive attention to oneself, always serve, and always be submissive. So even though I’ve always been chatty, I have never felt confident, or even comfortable, talking about myself or my artwork. When people compliment my artwork, I have to resist the urge to say, “Thanks, but let me show you this one detail that isn’t exactly perfect!” I am so proud of everything I have accomplished with my business over the last few years, but I am still working on accepting compliments about my artwork and business. I am slowly gaining confidence and getting more comfortable when speaking about myself and my artwork.


What do you find most rewarding about being a creative?
The most rewarding aspect of being an artist is meeting customers in person at markets and learning which piece of art resonates with them and why. I also love chatting with customers who are early in their own watercolor journey and have questions. It truly brings me so much joy to pass on the knowledge I have to other people. I was so humbled and honored when I realized how meaningful my watercolor nights were to each group I hosted. I would never have imagined that numerous attendees would learn so much and love it so much that after one night of instruction and painting, it sparked a new hobby for them. I was feeling especially mama bird-like when I learned that one of my attendees who moved away and missed the camaraderie had started her own very successful watercolor nights.
Contact Info:
- Website: https://www.CarolinaChickadeeCo.com
- Instagram: https://instagram.com/carolinachickadeeco
- Facebook: https://www.facebook.com/p/Carolina-Chickadee-Co-61560902264055/


Image Credits
Madeline Delling
Nicole Goodsell

