Digital culture has penetrated most aspects of our lives. Yet it has also dragged us into paradoxical situations and profound uncertainty. This, in turn, requires digital learning process that is capable of fostering mature individuals characterized by specific creativity; the kind of creativity rooted in prudence, deep insight into life as well as broad and integrated personal vision of the world. This research aims to see the extent to which digital learning process is conducive to the fostering of this type of creativity. This is an exploratory research with qualitative approach, conducted by means of questionnaires, in-depth interview and focus group discussion. Gen-Y and Z students from 13 Universities in West Java, Indonesia, were chosen for observation and interview, continued with focus group discussion in two courses which are Critical Reading and Cultural Entrepreneurship classes. The result shows that the practice of online learning so far contains some inherent constraints to meet the need. Some basic constraints pertain to the condition of the students themselves. Despite the flaws, however, online learning process also has some good potentials in fostering the required creativity, provided it incorporates 'engagement experience' and some strategies to 'go beyond data' in accordance with the students' suggestions themselves.