The shadow under the nose is what's killing the whole face
Working on a portrait of my neighbour's daughter, toned grey paper, and I've been circling the same problem for two evenings now. The face is fine. The eyes are actually good, which never happens, so of course I am afraid to touch anything near them.
The problem is the shadow under the nose. It's too hard. There's a clean dark shape with a crisp edge and it reads like a moustache, or like she's been in a fight. In life that shadow is soft and it wraps, and I know this, and yet I keep drawing it as a shape instead of a transition.
What I noticed tonight is that I do it because a soft edge feels like I haven't decided anything. Like I'm being vague and cowardly. So I press harder, and I make a decision, and the decision is wrong.
Tried going back in with a kneaded eraser and a fingertip and it went grey and muddy, so now the whole area is duller than the rest of the face and it pulls the eye straight to it. Which is the opposite of what a shadow should do.
If anyone has a trick for softening a pastel edge without lifting the paper tooth, I will take it gladly. Otherwise I'll be here tomorrow with the same nose.
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That last bit you wrote is the actual problem, not the nose. A crisp edge is easy to draw and easy to check, so the eye goes there and the hand obeys. The soft transition has no definite location, so there is nothing to verify, and that is why the hand avoids it.
Practical thing that worked for me: don't fix the edge, get rid of it for a while. Take a kneaded eraser and lift the whole shadow back to paper, then rebuild it as tone, not as a shape. Paper tone showing through the middle of it does half the work of the wrap. When you go back to the edges you will find only one of them wants to be sharp anyway.
And keep your hands off the eyes. They are good, they will survive a bad nose. A portrait with one nervous area and one solved area is still a portrait.
"nothing to verify" is going to sit with me all week, honestly. That's exactly it and I never had words for it, I just knew the soft part felt like standing in fog.
The kneaded eraser idea is scary because the face around it is working and I have this fear of smudging into the eyes, but you're right that a shadow is easier to rebuild than to rescue. And the bit about paper tone showing through the middle doing the work of the wrap, yes. I think I've been treating every dark area as "I must fill this with dark" instead of "I must leave some of it alone."
Going to try it tonight with a light hand. If it goes badly you will hear about it 🙂
The eraser advice is right and I'd add one thing: check the light before you rebuild. Most people drawing that shadow are working from a photo where the flash or the window flattened it. If the daughter will sit for ten minutes under a real single source, the wrap takes care of itself because you can see where the dark actually stops. Drawing soft edges from a photo is guessing. From life it's just looking.