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I got the image in my mind of a sun coming out of an umbrella.
It seemed like an interesting visual so I whipped up a sketch.
I often create a sketch in my sketchbook then take a pic of it. This pic gets transferred to Photoshop so I can easily move shapes around and fiddle with colors.
I threw a wash of blue into this sketch because blue (from the rainy skies) was the core color I'd be working with. I also knew I wanted the umbrella pink so it would contrast and pop out against the blue background.
I first did this sketch without a lot of thought to the location. After completing this I decided to create this in an Impressionistic painting style. And nothing says 'Impressionism' more than France. So it just seemed natural to set this story in Paris.
Then I started gathering reference. Images like these inspire my imagination and also let me base my concepts off reality.
Once the research phase was completed I started sketching a few variations of the scene and character.
As you can see, the location is very different than what I ended with. Instead of the storefront location you see below I went with more of a park like location (I specifically was thinking of the park next to the Eiffel Tower).
As soon as the sketch was locked down I started doing a color pass. You'll note that I was still playing around with the paintings caption. Here I'm making fun of public transit. Riding the bus is up there with getting a root canal.
Because I always like to play around with the character I toyed with giving her more of a 'bob' haircut (retro 60's) but this made her too 'dark'. Remember that this character personifies 'bright happiness' so she was changed back to blond.
After I locked down the character I took reference photos of the model (Jessica). Unfortunately I couldn't find the images on my computer. This was long before the days of my organized Apple Photo app.
I then sketched the image up in Photoshop to lock down the line work. Once this phase is done I divide the images into rectangles (that equal the size of an 8 1/2 x 11 piece of paper). I then have to create individual 8 1/2 x 11 images (note the white and pink rectangles that are individually numbered.) Each of these gets printed onto a sheet of paper and then transferred to carbon paper. I then place the carbon paper sheets and 8 1/2 x 11 printouts over the canvas and 'trace' over the lines so the carbon paper leaves guide lines on the canvas.
Once the canvas is ready I spend about 6 months painting. Because its oil the painting takes forever to dry, so I can't work too fast! It forces me to slow down and savor the process.
Often I'll take a picture of the work in progress oil painting to fine tune it. The key to a great image is contrast. Therefore it helps to only look at an image in black and white. If the viewer can easily tell what the image is about (the story its trying to tell) in black and white then the artist is on the right track!
Once all the planning and painting is done I'm left with a final image! Enjoy!