This article examines the role that the "element of surprise" plays in the implementation of the art curriculum at the Higher Education level. My critical analysis and evaluation of the subject matter are based on the outcomes of three case studies, organised and realised in the South African politico-economic and socio-cultural framework. Consequently, the research develops in the context of three most significant streams of policies in Education: "socio-cultural inclusion policy," "multiliteracies in education" and "the needs of the Fourth Industrial Revolution" for "soft skills." The aim of the study is twofold: to demonstrate an appropriate climate of interaction among students and educators in Visual Arts and Design discipline, and to propose different teaching strategies for the enhancement of skilful planning, accurate decision taking, as well as analysing and synthesising creative ideas under unfamiliar and challenging circumstances.