Pentiment

Starting in Act 1, you can find Paul at the Mill just outside of town, past the Church & Druckers location. He is the son of the Miller. Speak with him and he will explain that he loves to draw, but his dad yells at him for it. Depending on your character's build, your specific dialogue options will be different; however, you'll always be able to choose some option that encourages the boy to continue drawing. Do so and the achievement will pop at the end of the conversation!

In Act1:
From where you enter the forest area you can see a windmill in the distance, go there and talk to the Kid thats standing next to the dog.
Basically encourage him to through dialogue choice to keep drawing against his fathers will.