Start by breaking the head into its most primitive 3D forms, like spheres and cylinders, rather than focusing on features.
Leo blurred the back of the jawline into the shadow, letting the viewer’s mind finish the shape, while sharpening the bridge of the nose into a razor-thin highlight. The portrait stopped being a person and started being a feeling. It was distorted, yes, but it was more "real" than any photograph he’d ever taken. Start by breaking the head into its most