"To lead, one must follow." Lao-Tzu's quote embodies the belief that many 1st-semester students at our institution hold regarding their approach to creativity. Whether working on an essay or an art project, many have a tendency to imitate a more skilled person's work as a way of learning, improving, and building confidence. Conversely, it is not uncommon for their instructors to push them to generate original ideas and think outside of the box. These conflicting approaches and other opposing cultural tendencies can lead to a host of challenges for both instructors and our student artists, especially students from Confucian heritage cultures. This article shares observations of these challenges and suggestions for addressing them.