The practice of Illustration has seen significant change in the last 30 years in response to affordable technology and digital communications. This period of rapid change has been accompanied by political and economic uncertainty. This climate of upheaval provides an opportunity for reflection on contemporary Illustration practice. A similar environment at the beginning of the 20th Century saw movements such as Constructivism and the Bauhaus emerge, with significant impact on design for the remainder of that century. I propose that discussions on the future direction of illustration may be informed by mapping practitioners on the boundaries of Illustration practice as well as the wider field of Communication Design. In my paper I have included a review of practitioners I believe to be significant in relating the diversity of contemporary illustration practice, who have adapted their practice effectively to change, and represent possible models for future illustration practice. I have also included work from recent graduates on the Masters in Communication Design at The Glasgow School of Art to relate their perspectives of illustration practice. I believe this will facilitate discussion on the possible future directions of illustration practice, informing the future teaching of illustration, and how we, as educators, equip our graduates for a climate of rapid change.