We recently connected with Debra Howard and have shared our conversation below.
Debra, looking forward to hearing all of your stories today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
I graduated from Ringling School of Art in 1977 with a BFA, majoring in Commercial Art. This was before computers, when everything was done by hand. I worked as an illustrator and designer and was happy with my career. In 1992, the computer arrived, I reluctantly embraced the new technology and became proficient, but I was unhappy sitting in front of a computer screen for hours everyday. I thought, if I could switch over to advertising, handle the accounts and hire designers to do the computer work, maybe that would work better for me. So, I leased office space, cold called endlessly and hired freelance computer designers. That worked for awhile, but I missed creating with my hands. Something was missing.
One day, in 1996, I was preparing for a client meeting. We had designed a catalog for foot products for a firm in Atlanta, I was reviewing the job, when I realized that my designer had made a huge format error. I was the only one left for the day, I was going to have to correct it before my meeting the next day!
I picked my 7 year old daughter, from her after school program, ordered in pizza and started working on the catalog. I finished up well after midnight. My daughter was sleeping in the conference room and I had just finished reformatting the catalog. A catalog about foot products! I realized my life had gone off track. I was 40 years old, single, raising my adopted daughter from Romania and producing a catalog for foot bunions!
As a teenager, I dreamed of sailing around the world as an artist. I had part of the dream…. My daughter and I lived on my 44′ sailboat, “Ling Ling”, but we were stuck at the dock and I was hardly an artist. I wasn’t getting any younger, it was time for a drastic change.
I closed my advertising agency, loaded up my sailboat, made arrangements with my daughters school to home school her using their curriculum and pushed off with her and an old dog named Koa.
I started painting small oil paintings on gessoed boards, of landscapes of the places we were sailing to. Eventuality, I ran out of money and had to varnish boats. I’m also a licensed Captain, so I worked doing boat deliveries. Eventually, (it took years), my work caught on, I improved as a painter, and now I work full time as an oil painter.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I was born in Arlington, Virginia, but spent my childhood in Miami Florida. I moved there in 1959, when it was just a seasonal village. Miami was a wonderful place to grow up, surrounded by turquoise water, beaches, the Everglades and exotic animals. I had a sailboat before I learned to drive. I’m drawn to the pure and clear colors of my early life, they still dominate my work.
When I started painting, I sold mostly through galleries. At that time, it was practically the only way to sell your paintings. In 2010, the plein air movement arrived. Early Plein Air events used to be a way for organizers to draw people into dying downtowns, but now, the events are mostly in beautiful and wealthy communities. As the movement caught on, the prize money increased and the big events, became juried. Hundreds of artists apply to an event and they will choose 30-50 artists.
I sold my sailboat in 2016, bought a truck and a small RV trailer and began to travel the country, participating in these events. My travels are dictated by which events I’m accepted into. There are no guarantee of sales or prize money… to do this you need to be fearless.
I find galleries along the way and I sell online. I have an e-store where I sell, small, unframed oil paintings for a reasonable price, but the bulk of my income comes from the Plein Air competitions.
I paint, in what I call, “Debra World”. My work is representative, but with a twist, expressive, free and usually with a story or subtext.
I use a limited palette and rely heavy on color theory to achieve the results that I see in my mind.
Off season, I return to my home on the Eastern Shore of Maryland and work on large studio paintings.


Is there something you think non-creatives will struggle to understand about your journey as a creative? Maybe you can provide some insight – you never know who might benefit from the enlightenment.
To be a Creative, is a calling. If you’re called, nothing else will satisfy you. All of the artists that graduated from with me, have given up and found jobs that offer security. To be an artist requires courage, focus and tenacity. You can’t give up. There’s no substitute for time at the easel. I think 40% is talent, 60% is work. Endless work, endless mistakes, endless failures… and then you round that corner and you’re there. When I first started painting, I produced what I thought at the time, was “gallery ready” work. I made an appointment with a popular gallery in Charleston, SC. The gallery owner, looked at my work carefully and said, “Come back after you’ve painted 100 paintings.” That gave me a glimpse as to how I couldn’t rely on just talent, I had to do the work. I’m at 1000s of paintings now.


For you, what’s the most rewarding aspect of being a creative?
I never tire or quit marveling, that someone has purchased one of my paintings. That someone has forked over hard earned money to include my vision of the world, into their home. Painting is personal, when someone purchases my painting, they’re inviting me into their lives, into their home. It’s a great honor and thrilling.
The second reward is immortality. If I manage a long life, we’re taking about 80-90 years, but my paintings will live on for maybe hundreds of years! I’m very careful to prepare my panels so that they will last that long, so it’s possible and it pleases me to think they will.

Contact Info:
- Website: https://www.debrahoward-artist.com
- Instagram: https://www.instagram.com/artist_debra__howard/
- Facebook: https://www.facebook.com/ArtistDebraHoward/
- E-store: https://www.dailypaintworks.com/artists/debra-howard-13005
Image Credits
All photos were taken by me.

