The labour of creativity often manifests as persevering through moments of ambiguity, where the outcome of a process is tenuous.Creative practitioners intentionally manage this process, for example by developing strategies to break out of creative ruts. Some strategies get distilled into simpler, more memorable “rules of thumb”, such as sleep on it. These heuristics can inform the design of Creativity Support Tools (CSTs). We believe CSTs should address both practical and emotional challenges faced by practitioners.Through interviews with expert practitioners in diverse domains including performance, craft, engineering, and design, we identify strategies that support idea generation, personal motivation, and inspiration. We synthesize five themes, including:Strategic Forgettingand Omission,Mode Switching, andAesthetics and Motivation. We then present a set of heuristics to shape the design of new technologies to scaffold newcomers and benefit wider communities of practice. Finally, we present envisioned CSTs that embody these heuristics.