We were lucky to catch up with Jonathon Romain recently and have shared our conversation below.
Hi Jonathon, thanks for joining us today. Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?
I started selling my paintings for whatever I could get. As I built an audience the prices increased along with my base. I have had art galleries, done art shows at museums, other galleries, fairs and client’s homes. This approach has worked very well for my, but I don’t if others would find it attractive because it required a tremendous amount of dedication, hard work and commitment. But I would not change if for anything in the world.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
My journey as an artist is as unique as the brushstrokes on my canvases. I discovered my passion for painting in an unexpected place—prison. Arrested during my junior year of college for selling drugs, I fought my case throughout my senior year. Two weeks before graduation, I was convicted, allowed to graduate, and then sentenced to 15 years, ultimately serving half under Illinois law.
Art had always fascinated me, but I hesitated to pursue it seriously, often comparing my amateur attempts to the works of accomplished professionals. However, incarceration gave me the uninterrupted time and focus I needed to hone my skills. Encouraged by fellow inmate and talented painter Charles Pruitt, I picked up a paintbrush and found that my skills developed rapidly under his informal mentorship.
Confidence grew alongside my talent, and I began trading portraits for cartons of cigarettes. Upon my release, I transitioned to a more conventional currency, setting up a small storefront that operated as both my studio and gallery. It was difficult initially, with little advertising or name recognition, but persistence paid off. I took my art to other galleries and participated in art fairs, gradually building a reputation.
After years of struggle, things began to align. My gallery, having moved locations between Peoria, Oak Park, and Chicago, IL, started generating income. While my prices never skyrocketed, they rose steadily, reflecting demand—from cartons of cigarettes to projects worth up to $30,000.
Reflecting on my path, I wouldn’t change a thing, for every challenge taught me invaluable lessons. Today, alongside my wife, we co-founded a community art center in a renovated 50,000 square foot school, offering afterschool programs, summer camps, and culturally enriching activities. Our nonprofit operates on a multimillion-dollar budget with a dedicated team of 15 full-time and over 50 part-time staff members. Though my route was scenic and unconventional, it led me to a fulfilling life dedicated to art and community.
We’d love to hear a story of resilience from your journey.
I had built a really good life for myself through my art and began moving too fast and over leveraged myself. I had a house and two apartment buildings with family members living in a large portion of the real estate which meant I was carrying the load and then the financial crisis hit in 2008! All of my available credit disappeared, I wasn’t selling as much as I was accustomed to and one of my properties caught fire and I lost a ton of art.
That was one of the most challenging moments of my professional career. I lost my home, one of my apartment buildings and my car. My credit went from outstanding to outrageous! I found myself not being able to sleep balled up in knots at night. I realized I was making myself sick with worrying and that’s when I let go and knew that certain things were out of my control. I stopped worrying about my credit didn’t care about the property and started all over again.
Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
I’ve always been a big reader of self-help books. Some of my favorite books are Think and grow rich by Napolean HIll, It was on fire when I lay down on it by Robert Folghum, The Innovators mindset by George Couros, The Purpose driven life by Rick Warren, Smart money moves for African Americans by Kelvin Boston, and the 24 hour MBA by Alexander Hiam just to name a few.
Contact Info:
- Website: https://www.artbyromain.com
- Instagram: jromainart
- Facebook: romainart
- Youtube: @romainart1
