This position paper explores the significant ontological shift from analog to digital tools to support human creativity. Based on our research lab’s extensive experience with studying and designing creativity support tools, we build on creativity research and human-computer interaction (HCI) research to examine two dissimilar cases of creative design ideation ap- proaches. First, we discuss Inspiration Card Workshops as an example of a clearly-structured design ideation method, then sticky notes and white- boards as an example of a more open-ended design ideation setup. Over a fifteen-year period, we have conducted in-situ studies and developed pro- totypes for each of these design ideation approaches based on different tool ontologies. This enables us to contribute an overview of the most im- portant opportunities and barriers we have experienced and identified when deploying analog, digital, or hybrid tools to support creative design ideation among professional designers.