Free-hand interaction using a smartphone lacks natural spatial depth information due to the small 2D display's limited visual feedback. Through an autobiographical design process, three authors explored free-hand drawing over a total of 14 weeks. During this process, they expanded the design space from a single-display smartphone format to a dual-display smartphone-wearable format (Portalware). This new configuration extends the virtual content from a smartphone to a wearable display and enables multi-display free-hand interactions. The authors documented experiences where 1) the display extends the smartphone’s canvas perceptually, allowing the authors to work beyond the smartphone screen view; 2) the additional perspective mitigates the difficulties of depth perception and improves the usability of direct free-hand manipulation; 3) the wearable use cases depend on the nature of the drawing, such as: replicating physical objects, ``in-situ'' mixed reality pieces, and multi-planar drawings.