The nature of design and development work requires self-directed proactive and persistent efforts from both the design team and other stakeholders. However, the question of how to enhance development motivation can be a daunting one to answer, as the literature is dispersed, partial answers being presented in multiple fields of research. This paper specifically examines the role that experimentation, a typical and widely supported approach to design, can play in awakening and sustaining development motivation. The paper reviews literature from several streams of research and discusses findings from a recent attempt to realize support for these mechanisms within a university setting, at the Aalto University Design Factory platform.