This particular lady has an unfortunately-shaped face but I love her features and the shading is reasonably successful. I know many art journalists feel a great deal of nerves when it comes to painting faces but as the ancient adage goes...practice makes perfect.
Now that I'm comfortable drawing faces in pencil and marker, I practice rendering different emotional states, head positions, skin tones, ages, and sizes. In addition, I am practicing adding bodies to those heads. This is an essential skill if I want to build my illustration abilities.
However, I'm still learning when it comes to painting faces, so I tend to keep the features in a neutral, perhaps passionless, expression. I'm just trying to cement in my head the placement and proportion of the all the parts as well as working out my particular face painting style. For now, I am a beginner and I need to start, naturally, at the beginning.
Once I feel competent at this, I'll branch away from the ubiquitous neutral face and start to produce characters that express emotion. Since my characters are stand-ins for things I'm feeling and experiencing, it is important to me that I be able to paint something other than a pretty girl staring off into space. (BTW, this is something I've written about before and you can find those old posts on the blank face trend here and here.)