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Deb Simon

Born in Kingston, PA

Lives & works in Guilford, CT


When I was 24 years old I was, as they say, “in between jobs”. I had left my position as a staff therapist at a social work agency in Binghamton, NY. It was supposed to be my life long career. I knew I wanted to be a psychotherapist since the 10th grade. I burned through college in 3 ½ years, knowing exactly what I wanted to be. After 2 years, it was clear that this was not meant to be. The combination of youth (I started when I was 21), lack of training, and being way too empathetic to be able to take care of my client and (more importantly) myself, caused early burnout. Because I didn’t have a plan B, I was adrift.

I bounced about for a couple of years, lived on a kibbutz in Israel, then moved to Miami, doing odd jobs. My parents were worried about me and came down for a visit. At this point I had been sleeping on my grandmother’s couch for a couple of months. I had hit my personal bottom. My mother took me aside and said if I wanted to go to art school, she would pay for it. You need to know that my mother did not have control of the checkbook. For her to offer to pay for anything was momentous. I turned her down for 2 reasons:


1. I didn’t think I was good enough to be a professional artist.

2. It seemed so impractical. How would I be able make a career (translate, enough money) as a painter?


But I did have a strong drive to be creative. And one day it hit me like lightning. At 6:00 one morning, I sat bolt upright on the couch and said, “Furniture!”. It made so much sense to me. I would design furniture.


Practical art.


I thought learning to build furniture and cabinets would make me a better designer. I moved to Connecticut and apprenticed at Eastern Woodworks in West Haven. My hope was that I would only be hands on for a little while and transition into design. After I was fired (!), I moved on to help start Fair Haven Woodworks. It turned out I was a pretty good cabinet maker.  After a few years there, I started my own business. During the 8 years I owned The Woodshop, I made a lot of furniture, but very little money. It wasn't working. Closing out my business was one of the most painful things I ever had to do. Aside from feeling like a failure, I was back to “Now what?”. And, “what was I thinking?”. Now I’m 40, what do I do with a background in woodworking?


I worked for several years at a retail furniture store. Not particularly satisfying. By a miraculous turn of fate and incredibly good timing, I heard that the Yale British Art Center was looking for a cabinet maker. I applied, and much to my surprise, I got it. I built all of their displays, frames and some permanent furniture. It was creative, challenging, but very physically taxing. Everything I made was out of 1 ¼” rift white oak. Very heavy stuff. When I turned 50, I knew that I couldn’t do this for the rest of my working life. I transitioned into a desk job. Also, not satisfying.


Again, I felt the strong need to be creative. About 12 years ago, I tried my hand at watercolor. It turned out I was pretty good painter. I started out with seascapes and landscapes. But once I started to work in acrylic paint, and began painting animals, I found my passion. To attempt to capture an animal’s character, personality and intelligence on a canvas is both challenging and, well… satisfying!


If you, or someone you know would like a portrait of their fur baby, either here or across the rainbow bridge, please get in touch!


Deb Simon

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