We recently connected with Jessie Keylon and have shared our conversation below.
Jessie, appreciate you joining us today. How do you think about vacations as a business owner? Do you take them and if so, how? If you don’t, why not?
My partner and I take 2 months off every year. Two full months! We drive all over the west, staying at homes of friends and family, and car camping by lakes and rivers in between. As we travel through the weeks, I go through different stages.
The first stage is relief; relief to finally be on the road after so many months of planning the trip, stocking up and getting projects done at the studio, and making sure everything will be in working order when we get back. Open road ahead and adventure awaits!
The second stage is a bit disorienting for me. It’s strange not to be making art for clients or creating prints from my art or working on specific projects. My only job at that point is driving, maybe weeding a friend’s garden, and floating in the middle of the lake on my paddle board.
Third stage is full engagement. I am one with the trees, I’m drinking my coffee in the mornings while watching the sun dance across the water, listening to the songs of the birds. I live in nature, I am a forest creature.
The fourth stage is a moment of clarity. New ideas for paintings, new songs are floating through my mind. Looking forward to getting back into the swing of it all, I remember how amazing it is to work for myself. I finally crack open the sketch book and the journal and enjoy the purity of being a creative force.
The fifth and final stage follows us on the final week or two on the way home. It’s full of a bit of stress and anxiety of how much work there is to be done when I get back, of the planned projects I had hoped to get done during the trip but didn’t. A bit of dread.
After 7 years of doing this, all while running my own art studio/shop business, I am convinced it works. It helps balance out the chaos of the other 10 months. When I get back from the trip, I have been recharged so I can hit the pavement running right into the busiest time of the year. The entire year is better because of the third and fourth stages. I think it is important to recharge, especially when in a creative field. Creative output needs to be refueled from time to time, and while smaller refueling trips and mini vacations are helpful and necessary, I now see how valuable an extended vacation can be, physically, mentally, and creatively.

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?
My first few art festivals were life changers for me. I was a meek puddle of social anxiety. But through my paintings, through these lines and colors, I started to find a language. I started to not balk when complemented. I started to respond with substance. I started to represent the art that represented me. My art became a way to navigate a world I had never (and still don’t fully) related to.
After years of markets and festivals and booths, I moved into a tiny studio/shop in the tiny western movie studio desert town of Pioneertown, CA. The shop is just big enough for one table and some shelves for my art supplies, and the rest is packed with paintings, prints and other little items printed with my artwork. I open the front doors to the public on weekends to meet and greet with the public while working on projects between conversations. It’s a strange little town, with local characters, tourists and travelers passing through. But it has been here where I have found my community. A group of artists, like me, who were once lost, floating through the city and found themselves one day blown to the desert on a gust of wind to live a quieter life of making art and enjoying the moment.
During the pandemic, my partner and I were struggling with the chaos of the outside world so we started a short animated film with my artwork. It is set to an acoustic song performance by Lukas Nelson and tells our tale of love. Seeing my artwork come to life was pure magic, and after three years of hard work and learning all about how to design and illustrate for film, our little film was finished and is now on YouTube living it’s own life, spreading love. We are proud to create something positive out of such a dismal period of time. We are now active on our second film, carrying on our new tradition of turning off the chaos of the outside world and focusing on a project of love to share with the world once finished.

We’d love to hear about how you keep in touch with clients.
Social media has changed the business model for independent artists. I try to keep posting some of my latest works for my small following, and find that it’s another handy form of a portfolio. If someone wants to commission a painting from me, they can check out my past feed to get an idea of the kinds of paintings I can do. I have many repeat customers and more collectors as time goes by, but I don’t buy into the idea of brand loyalty with art. With so many amazing artists making and selling and sharing their art, I am honored to be included in the mix, and can’t let myself see it as a competition amongst artists, even though I am told that it is. Art is expression and incredibly subjective. If one of my clients also likes to support other artists, it is a win-win. That said, I still update my website and social media with recent projects incase a client, repeat or new, is interested in what I’m doing.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
The Artist’s Way by Julia Cameron is a well known motivational resource for many artists striving to create more and expand their potential. In fact, the idea that it was so popular made me not want to read it for many years. If I was going to stand out as an artist, why would I read something everyone is reading? Once I actually did dive in, I understood that its a basic guidebook for getting into a daily practice of creativity, even if it was terrible creativity; in fact, ESPECIALLY if it was terrible creativity. While I have never been able to do my daily artist pages or have a perfect consistent daily practice, I tend to now practice more than I would have before because of the ideas in the book. I also am less critical of myself if I don’t happen to create 24 carat gold creativity every time. It’s okay. The “not so good” stuff has to be flushed out of me so that the flow continues and allows the “better” stuff to arrive.
Many many years ago I signed up to take an online course ran by artist Lisa Congdon. Taking a course by someone who has successfully transformed her art into a business and has tackled textile design, product design and marketing and licensing, collaborations with companies and other successful artists, helped put things into perspective. The first thing this artist said, with all of her experience and knowledge, was that I needed to own the fact that I was indeed an artist. At this point I had almost three decades of being good at art. Everyone always called me an artist, but I always balked at the label. Maybe it was too much responsibility to handle, maybe I just didn’t think I was good enough. But here was this artist telling me that yes, I too am an artist. I can call myself an artist. I can sell my work. It is possible. It is a viable career choice. There are no guarantees or paid time off or comfort of someone else holding financial responsibilities for failure or free coffee in the breakroom, but there is a flexibility to working for yourself and forging your own path, taking one step at a time. From what I learned from Lisa, I was able to start visualizing what a self-run art business would look like.
From there I took an online business course from the local community college and educated myself on the basics of running a simple business. No more was I just a freelance artist or someone doing an occasional art festival on the side. This was the new lifestyle. One that gave me flexibility to design my day, my own week, and my own year.
Contact Info:
- Website: https://jessiekeylon.com
- Instagram: @jessiekeylon
- Youtube: https://www.youtube.com/jessiekeylon


