This design is based on what I learned in Krishna Sadasivam's Creating Crazy Characters class at Lean Into Art.
More practice to come, this time I tried to do all the steps in Sketchbook Pro which led to some improvisation on the silhouette step. The characters silhouette step is a way to establish a character pose and outline that "reads clearly" showing key aspects of the character's inner and outer life in addition to their physicality.
Krishna uses the lasso tool on this step in Photoshop to great effect. The Sketchbook Pro lasso doesn't have the same feel or instant fill flexibility so in this attempt I blocked it all in by scribbling fills with the pen brush (pressure sensitive set to a brush width of about 10 pixels) to complete the character silhouette.