A portable, retractable writing surface device provides a writing surface that may be extended from a housing and held sufficiently flat by the device to facilitate marking on the writing surface with a writing implement, such as a dry-erase marker, chalk, grease crayon, pencil, pen, permanent marker or the like. The device maintains sufficient rigidity in the extended writing surface, such that the device may be used without an additional support surface, such as a clip board or table. The writing surface may be retracted back into the housing to protect the writing surface and to reduce the size of the device for storage or transport, such as within a pocket or briefcase. Retracting the writing surface may include rolling the writing surface onto a spool, accordion folding the writing surface or otherwise reconfiguring the writing surface to make it fit into a compact space (collectively referred to herein as "compressing" the writing surface). One or more resilient members may be used to make the extended writing surface flat when the writing surface is extended from the housing. The writing surface may include a flexible computer display screen.