Failure is commonly conceived either as a provisional state or as the unwelcome endpoint of a process. In both scenarios, failure occurs when there is a discrepancy between an expectation and result, presupposing a well-defined comprehension of intentions and anticipated outcomes. This assumption is particularly challenged when conferred to creative projects, where expectations are not always as explicitly defined and undergo frequent changes. To understand how failure evolves, this chapter analyzes failure experiences of individuals working in creative projects in the arts and sciences and investigates how shifts in expectations occur with setbacks experienced. We develop three interconnected dimensions of expectation in creative projects: uniqueness, do-ability, and resonance. Together, these create a malleable evaluative space within which a creative project is deemed worthwhile doing. Our findings suggest that disappointed expectations are met by either prioritizing certain expectations over others, or by realigning expectations with new opportunites, and in so doing shape and change the relative importance or meaning of these expectations. We argue that these responses transform the evaluative space in a way that keeps the creative project going. An endpoint failure only occurs when those involved in a creative project run out of possibilities to alter the evaluative space of the project. Our study overcomes the binary conception of failure as being merely the opposite of success and demonstrate that success in creative projects is not always output orientated. It also involves creating and maintaining sustainable ways to continue.