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ONE - CONCEPT AND SKETCHES
To highlight the comical nature of the scene I chose to contrast a fairly detailed rendering of the lute with a more exaggerated and loose handling of the donkey himself. The text for this picture reads:

  The donkey... went to a celebrated musician and said, “teach me your art, that I may play the lute as well as you do.”

  “Ah...”, answered the musician, “that would come very hard to you. Your fingers are not quite suited to it, and are far too big.  I am afraid the strings would not last.” 

  But no excuses were of any use.  The donkey was determined to play the lute.  And since he was persevering and industrious, he at last learnt to do it as well as the master himself.

I started with a really rough and simple sketch, about 4" x 5", to establish the basic composition. I then scanned the sketch into Photoshop for final adjustments. On a whim I tried flipping the head and felt the picture worked a lot better (see contrapposto).

The lute was the dominant instrument of the Renaissance, so I chose to incorporate Renaissance architectural elements, costuming, weaponry (the rapier) and of course tablature (a musical notation system) into the picture as well.

To wrap up the sketching stage I reduced the opacity of the scanned layer and did a quick draw over on a multiply layer in Painter (IX), using a custom brush that mimics my pencil work:

Lastly I did a quick overlay to establish how the shadows would fall, and to approximate the associated light source. I tried several different positions for the light, making sure the strong cast shadow didn't compete too much with the main figure.

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TWO - ROUGH COLORS
I first toned the canvas with an orangey color in Painter, under the sketch multiply layer, using a buildup brush. This breaks up that awful whiteness, and gets me seeing into the space. It also sets the stage for the color scheme.

I then laid in some solid areas of color over the orange tone and under the sketch layer, in Photoshop. 

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THREE - ROUGH PAINT
I collapsed the layers and quickly painted in all the main elements with a grainy bristle brush, working at about 25% zoom level so the entire picture fits on screen. The pencil work and the toned canvas are absorbed by the brushwork, but the shadow cast on the wall is kept on a separate layer so I can fine tune it later.

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FOUR - MODELING AND DETAIL
I continued modeling the forms, adding detail, and closing in on the final color and lighting scheme. I don't work the whole picture to the same level of detail here, but just enough of it to establish the scene. Working too much of the picture at this point wastes time because that just means more elements I'll have to readjust later as I continue homing in on the final scheme. But working too little of the picture means there won't be enough information to establish the scene strongly enough.

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FIVE - FINAL COMPOSITION, LIGHT AND COLOR
I felt the image wasn't integrating well with the white page, so I refined the composition. The music stand breaks deeply into the white area, but retains a lot of white space in and around itself, while the folio on the floor and the candle bring some white into the main image. I lightened up the wall quite a bit to further integrate the image with the page, and reduced the saturation in a few areas to establish the final color and lighting scheme.

I plotted the wall shadow using a reduced size image for the perspective:

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SIX - PAINTING
I used only three (custom) Painter brushes for this picture, shown below in order from course to fine.  With each of these I vary only the size as I paint (using the bracket keys "[" and "]" for quick changes on the fly). With the Grainy Round brush I do, however, also vary the graininess for certain applications.

Because I strongly established the scene in step five, painting in the details of the music and stand, rapier, candle, costume, etc. goes very, very quickly, with few side tracks or reworks.

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SEVEN - DETAILS
I paint as much as I can zoomed out, but eventually need to zoom in for the detail work. The lute has a lot of strings (15) each casting its own shadow. To paint these I used the grainy round brush, set to paint straight lines. I laid down a dark instance of each string, then a light instance on top of that, slightly above and to the left, giving the illusion of form to the strings. 

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EIGHT - TOUCH UP AND TEXTURES
I darkened up the shadow areas quite a bit here, and worked into the wall texture to break up the edge of the main cast shadow. I also finally got around to painting that darn candle.

I added the shirt bits to bring more whites into the main picture (see note on step five), and also to break up a few of the dark areas of the main image.

I made one more pass at the pegs because I wanted them to have a fair amount of detail without looking too slick compared to the rest of the picture. They're heart-shaped because the donkey eventually uses his musical abilities to woo his future bride.