In this pictorial, we consider how the negotiation of creative boundaries with a co-creative AI system can create moments for personal creative reflection. We ground this in our experiences with Froggi-Draw, a single-initiative co-doodling system that gives users power to decide when and how much an AI "collaborator" (Froggi) contributes to their drawing. From a 1-week pilot study where (n=8) novice and experienced artists doodled daily with the system, we report on ways participants navigated creative risk and uncertainty, and how their usage and perceptions of Froggi shifted over time. In moments of disruption, participants described the system as encroaching on their creative territory. We consider how the design of a supportive, co-creative AI "collaborator" might look like the design of a supportive power dynamic---and finding ways to offer users control to find, reflect upon, and flexibly negotiate the boundaries of that dynamic.

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