"Someday I hope you make a video about your thought process when looking for subjects to paint. You tend to choose very mundane but familiar scenes. What makes something special? Composition? Lighting? Mood? I’d love to get a peek into your thought process."
This is a rich topic, and I'm glad you asked. You're right: I do often choose mundane scenes from a radius of about 15 miles of where I live, especially now in pandemic times. For me, the problem with "artistic" subjects like fishing boats or farm scenes with red barns is that I feel it's hard to create an original interpretation that hasn't been seen a million times before.
I'm more emotionally connected to ordinary scenes from my own quotidian experience, such as parking lots, gas stations, and grocery stores. For some reason I haven't seen such scenes painted very often by other artists. I get really excited by the prospect of interpreting something that I have never seen painted before, especially when that subject stirs emotions in me.
When I get to a location I often use a viewfinder to try to limit the view to something I can fit in a pictorial rectangle. Sometimes I do a quick thumbnail of the effect I want to capture before getting started.
Typically I'll have a rough idea in mind in advance of what I want to accomplish. Sometimes that idea is a color effect or a lighting idea, and the subject is almost secondary. If I'm mainly interested in lighting—such as a rim-lighting effect—I'll wait for a day and a time of day when that lighting effect is happening and try to find an angle where I can paint it. That same motif may be completely uninspiring at another time of day.
If it's a very complex subject, my first consideration before I start is how I can simplify it. Can I vignette it, or delete part of it, or reduce the colors, or use line. If there's an element that will be changing or moving, I think about capturing that element first so that I'm not caught short. Parked cars don't stay parked, and dairy cows don't stay grazing in the same spot.
I try to verbalize what's my goal for a given painting because I find it helps to keep that singular goal in mind as I get deeper into it. On a sunny day it's important to commit to the sun and shadows at one specific point in time, and try not to chase alluring effects that may emerge as the sun travels west.
There are a number of practical considerations that limit the available options, such as:
1. Do I have a chair or an easel? Do I need to find a bench?
2. How much will the light change in the time I have available?
3. Is it safe to stand or sit there? Is there a risk of a "gamestopper" event?
4. Women tell me that they need to think about whether it's too lonely or isolated.
5. Is there room for an easel? Will I be blocking pedestrian traffic? Or attracting onlookers?
6. Are there other artists with me on the painting trip? What do they want to paint?
All these things get factored together in choosing a subject.
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