One of the challenges of effective goal pursuit is being able to flexibly adapt to changing situations and demands. The current studies investigate whether individuals exhibit effective metamotivation—successful management of one’s motivational states—in creating fit between an optimal motivational orientation and specific task demands (e.g., inducing a promotion focus, as opposed to prevention focus, in preparation for an eager brainstorming task). Using regulatory focus theory as a framework, 5 studies provide evidence that although North American individuals exhibit some metamotivational awareness of task-motivation fit in the realm of regulatory focus, they may also have competing beliefs that promotion motivation is generally better, regardless of task type. Given this tension, having metamotivational awareness of task-motivation fit did not always lead to successful behavioral enactment (Studies 3–5). We discuss connections to metacognition and implications for the role of flexibility in self-regulation.