>>5872332Look for some videos discussing digital painting skin in regard to light & shadow on the face. Deconstruct the contours in a face to then reapply them in a stylized way.
There's a lot of skills at play here but none of them are out of your reach.
Using the brush direction/texture to imply the shape of his face and neck is a great method in addition to the shading. Painting courses will be your friend.