Today, my wife and I went to Stowe (Vermont) and checked out a number of their galleries. For galleries that fit my style, my work would not be the best in the gallery, but it wouldn't be the worst, either. This may not be a bad stepping stone to other galleries outside of Vermont.
Before approaching the gallery, though, I need to do several things: 1) Greatly increase my inventory. At this time, I do not have near enough work to show in galleries, craft shows, and around local restaurants/stores/exhibitions. That will be the highest priority for this year. 2) Define what I like to paint and the style. At this time, my favorite paintings are the landscapes with the abstract shapes. I will need to provide more of this type of painting. 3) Check out more galleries to see where I would fit best and the type of traffic the gallery has. The point of getting into a gallery is to sell the painting. If the gallery is not on the beaten path or if there are not a lot of patrons, then the chances of selling a painting at that location is minimal.
Once I can get several local galleries (in Vermont) interested in my works and start building up a recognizable name for myself, I can then expand to other galleries that are outside of the state.
The gallery would only be one avenue of sales. Craft Shows/Art Fairs, the internet, and personal sales would make up other venues. In addition, may look into exploring character creations in oils to try to move into the licensing market (although, this may not be as feasible as I think that it is).
For the time being, I think that, in a year or two, my confidence and skill will be high enough that I can start approaching the galleries.
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