A handwriting guide including an active and/or inactive writing guide is rendered by displaying a shaded outline object having a line for receiving electronic ink, displaying the active writing guide thereby indicating a location of a current active context, and expanding the active and/or inactive writing guide up to a maximum width of the outline object in response to receiving more electronic ink within a line. The active writing guide can comprise a bracket displayed on each corner of a writing area distinguished on a line and can correspond to an insertion point upon switching to text mode. A drawing guide that includes an active and/or inactive drawing guide is rendered by displaying a shaded drawing guide and the active drawing guide in response to detecting ink strokes within the drawing guide. The active drawing guide can comprise a bounding rectangle encompassing a drawing area that receives ink strokes.