We caught up with the brilliant and insightful Jen Sterling a few weeks ago and have shared our conversation below.
Jen, thanks for joining us, excited to have you contributing your stories and insights. Can you talk to us about a project that’s meant a lot to you?
Funny enough, one of the most meaningful projects I have worked on is unfolding as I answer this. I have built an online community platform for all Maryland visual artists. I have been craving the connection and shared knowledge of my peers, and figured I wasn’t alone in this. Now we have a place where we can all share our experiences, help each other with our work, our businesses, and even just coordinate get-togethers to visit exhibits or co-create. We just soft-launched to a small group of artists and will be launching publicly in the next month or so.
Many artists went through formal schooling and thus built a network with fellow students and their instructors. I am a self-taught artist but I bring 30 years of business experience to the table, which many artists have never learned, or have been struggling through the hard way. This is not a revenue-generating project, but it is a soul-enriching one. By bringing our collective knowledge and experience to the community, we all help each other to be the best artists and art business people we can be. As President Kennedy once said, “A rising tide raises all boats.”


As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I enjoy creating paintings that are visually stimulating and emotionally evocative. I live for the wow moments… the sudden intake of breath when someone views one of my paintings in person. I want to inspire people to live life in full color.
I was born in Wisconsin and primarily grew up in Northern Virginia. A graduate of George Washington University, I hold a BA in Visual Communications with a minor in Psychology. I painted as a hobby while I was an entrepreneur in design and branding for 30 years and founded three creative agencies. Eventually, the design firm was not enough to feed my need to create. I sold my last company and now focus on my art full-time.
When I first started painting, it was purely for selfish reasons. I had emotions inside that I needed to let out. Colors that needed to be free. I have always been artistic and creative, but I was not formally trained in how to paint. So in the beginning, I felt that my work was very clunky and immature. Over time, I learned to react to what I was applying to the canvas with more refined layers and brushstrokes… to add depth and sophistication to my messages.
My work was awarded an International Grand Prize and has been shown in numerous galleries and festivals throughout the mid-Atlantic. My colorful acrylic abstracts adorn clothing, skateboards, private homes, and several commercial buildings.
Like many artists, I find a blank canvas to be paralyzing. I need to mess it up… get some marks and color on it as quickly as possible in order to make it feel approachable. Once that is out of the way, I am in the flow of mark and response. Each stroke or shape leads me to the next one on the path. I have had paintings where I knew before the first mark was made exactly what it would look like at the end. But more often than not, I am as surprised as anyone at the final result. It is almost like getting to your office and not remembering actually driving there. My brain goes into a flow state, and I follow the path the painting provides. Sounds crazy… but it works for me.
Inspiration comes from various points and at various times. I always carry my iPhone with me so that I can snap a photo or take some notes if something has sparked an idea. I hate the chance I may lose a single spark. I even keep paper and pen by the bed so that I don’t miss out on that idea that occurs when I am half asleep and my brain is free to play. Sometimes a spark leads to one piece, and other times it will lead to half a dozen paintings in a series. I never know until I am in the thick of it, and the spark tells me where I will be going this time.
One particular piece was inspired by the many colors and layers of a Tahitian black pearl. Something so small and simple…. yet it had such depth and variety in it. At other times, I may see a bird or a piece of litter on the sidewalk or packaging for a box of biscuits… I never know where the initial tiny seed may come from that will trigger my next piece. My job is to maintain an ever-fertile ground for that seed to take root.
I maintain a love of business and am an active mentor for emerging businesses and fellow artists. I live with my husband and multiple dogs in Annapolis, Maryland.


What’s a lesson you had to unlearn and what’s the backstory?
I spent 30 years working in design and branding. I ran three companies and helped numerous brands build their own. In all of those cases, the goal was to sell something. Build a product or a service, find the audience, and sell it.
My art is very different from that. I started painting because I had feelings and emotions that I needed to express. I was painting a feeling and chasing the reaction it would get from me or from my viewer. I wanted to inspire, to be a catalyst to the viewer. However, when I took my art full-time, I began looking at it more like a business. Don’t get me wrong… I need to see my art as a business. It’s smart to track expenses, communicate well, market my work, etc. But I also need to remain true to the seed of what I am creating.
At first, I had lost track of my reason for creating… my “why.” I began painting to sell. And with each new work completed in that mindset, my results were flatter and less emotional. There was no connection when people viewed the work. I had lost the spark of what made me want to create to begin with. I completed a massive purge of my inventory of work this past spring. I threw out hundreds of works or painted over them. And the new work that has emerged? It is so much better! It screams my style and my emotions. It feels true to who I am. And in the end, it will end up selling better because of that.


Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?
I have read a ton of books on business, entrepreneurship, and art, as well as listened to a crazy number of hours of podcasts and interviews. I am a sponge, soaking up resources, ideas, and lessons whenever I can. But, there are very few that are as simple in concept and yet as monumentally impactful on me as “Eat that Frog” by Brian Tracy.
I don’t remember when I first read it, but it was published in 2007. He provides quite a few tips or processes to help with procrastination, but the biggest one is easy (and gross). If you had to eat a big, slimy, nasty frog each day… would you put it off to the last minute and spend all day dreading it? NO. You eat it first, get it out of the way so that it doesn’t take up a huge amount of your mindshare and energy while you dread its approach. That way, you can get on to the rest of your to-do list.
I actually keep a plastic frog on my desk as a reminder, and even place it on top of the one big, nasty task I have to undertake the next day, so that it is the first thing I see and focus on the next morning.
Contact Info:
- Website: https://jensterling.com
- Instagram: https://instagram.com/jensterlingart
- Facebook: https://facebook.com/jensterlingart
- Linkedin: https://www.linkedin.com/in/jensterling/
- Other: The community for Maryland Artists: AOScollective.org


Image Credits
Photos of the artist by Mary Gardella.

