psychological studies and sketches

I am interested in working toward the goal of making these sketches more than an attempt at a likeness. I want to look at this person and try to show what is really there.

An experience that I am thinking of here is one that has happened more than once while visiting at the nursing home. I have found myself in conversation with someone who now looks quite differently from the person that they actually are or have been. Once I am engaged in the conversation, of course, I "see" the older person before me in a completely different light. The wheelchair and the oxygen tubes disappear and I only see the gallant war hero, a perky volunteer, or ultra-competent office manager who now sits in that spot.

I am not satisfied with my approach here, the drawing is not alive. My dear patient subject who sat for me was wearing her "Sunday best", her hair was just "done", and she gave me her nicest face. I did not feel like I got to the"truth" of her yet. There are many layers of faces that everyone wears, (oh, I feel a T.S.Eliot quote coming on.)
"There will be time, there will be time
To prepare a face to meet the faces that you meet;"
T.S.Eliot: The Love Song of J.Alfred Prufrock