One of my biggest weaknesses is that I tend to rush to a finish. A long time ago an instructor asked me if I was trying to finish an oil painting in one sitting. It's taken me a long time to learn that a painting or a drawing needs to be built on a strong foundation, that what I'm painting needs to be carefully examined or all the drawing errors that I glossed over in the start will reappear and weaken the final image. Most of the important work is done at the beginning of a painting.
I made the pencil drawing (above left) with the intention of painting over it in gouache. I took the time to carefully map out where the lights and darks were to be placed. I scanned the drawing so that I would not lose it, just in case I need to start over on the painting. With the drawing scanned I thought it would also make a good under drawing for a digital painting. I opened the file in Sketchbook Pro and painted the monochrome self portrait above.
The painting went very smoothly because I already mapped out and planned in my mind how I was going to paint the portrait. The time I took to make that careful drawing in the beginning carried me through the entire painting.
Bellow is a YouTube video I made showing and explaining how I made the digital portrait.