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Made these emotion illustrations for a client a while ago. They gave me the words (in Dutch, sorry) and I drew the faces. It was a nice exercise in drawing subtle emotional expressions. If sometimes what you have in your head just doesn’t want to appear on the page (like with facial expressions), it can be good to focus on just that one thing. Start by writing down various expressions. Don’t think about the body or the direction of the face, just draw a head (or even a circle), copy it and fill in the various expressions. Keep this digital document or sheet of paper paper at hand or even hang it on your wall. If ever you get stuck again, you can look at this ‘poster’ and remind yourself of how you drew a certain expression. It will help, I promise ;-)