Good Things Happen When You Paint!

Painting Plein Air ~ Inspiration: Artist Robert J. Simone shares his inspiring journey from late bloomer to award-winning painter, proving it’s never too late to follow your passion.

by Robert J. Simone, OPA, NOAPS, ASMA, OPS

I’d like to share a bit of my painting journey in hopes that it will both encourage and inspire others. This is especially for all the other late bloomers and boomers. Not that I’m some great artist – I’m just a kid in his 60s with some brushes and canvas who loves to paint.

I’ve had plenty of ups and downs, bumps and bruises, and numerous hiccups along the way. Regardless of circumstances, I kept painting because I believe that’s what I’m supposed to be doing, and surely some good would come of it.

My dad was a pretty good amateur watercolorist, and he was my early inspiration, so that’s where it all started. Like a lot of kids, I had the Jon Gnagy Art Kit and the 120-count Crayola Crayons Box Set (Sea Green is still my favorite!). I wore them out and spent many Ohio winter days wiling away the hours drawing, coloring, and painting. It seemed like a natural thing to do. I read dad’s drawing books and withdrew library books on Renaissance art. I wanted to be an artist in the worst way.

After high school, I went to a public university to study painting. That’s where things went awry. The curriculum lacked basics and structure. I became disillusioned, dropped out, and started bouncing around from job to job.

Fast forward 20 years, having benefitted from urban sprawl, I was the owner of a successful lawn maintenance company in Tampa, Florida. I bought a house, a truck, and a boat. Life was good, but I was not doing what I was supposed to be doing. I had done no drawing or painting since dropping out of college. I was beginning to feel a mysterious sense of dis-ease.

That’s about the time I got married. Soon, my wife Penny realized I was a frustrated artist. We went to museums, galleries, and art shows where I would critique all the paintings. Pretty arrogant, since I wasn’t painting myself. She knew what I needed and gave me the push to take weekly classes.

That got me started, but I outgrew the classes quickly. They weren’t serious enough. I wanted the basics and structure I sought years ago. That’s when I discovered PleinAir Magazine. A whole new realm of possibilities opened. Surely painting outdoors on location would be the best way to develop real painting chops. If I could do that, I could do anything!

I took workshops with artists like Scott L. Christensen, Stapleton Kearns, and others. My thirst for basic principles was quenched. I painted, studied, and entered local plein air competitions. I did well in some. Not so well in others. But I kept painting.

Eventually I got into national level plein air events and discovered that one of the best parts of those events was the camaraderie. There are so many talented artists out there, many of whom have become my de facto mentors. I painted alongside the best. I looked over their shoulders and asked questions.

Eventually, in 2024, one of my paintings received the Grand Prize at Plein Air Easton. I’ve received awards at other national shows and made Signature Member in some prestigious organizations. My paintings have landed in some surprising collections. I’ve taught many workshops throughout the eastern U.S., and I’ve now been blessed to mentor other artists.

What’s the point in telling you this? It’s that so many good things come with persistence! So, keep your brushes moving, master the basics, and – mark my words – good things will happen.

Connect with Robert J. Simone at robertjsimone.com.

Editor’s Note: Join us for the 6th Annual Plein Air Live online art conference, featuring Kathleen Hudson, Kevin Macpherson, Kami Mendlik, and many more! The event takes place November 6-8, 2025, with an Essential Techniques Day for painting plein air on November 5. Learn more at PleinAirLive.com.

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