Difficulty is an under‐appreciated but powerful motivational force. As outlined by identity‐based motivation (IBM) theory, a social cognition theory of self, self‐regulation, and goal pursuit, people prefer to act (action‐readiness) and understand their experiences (procedural‐readiness) in ways that fit who they are (identity‐congruence). IBM also predicts that experienced identity congruence is context‐sensitive—though experienced as stable anchors, people's identities are dynamically constructed in context. Contexts shape which identities come to mind, what these on‐the‐mind identities imply for action, and what people infer when thinking about a task, goal, or life feels hard. People can draw two inferences (termed difficulty‐as‐importance and difficulty‐as‐impossibility) when a task or goal feels hard to think about and a third (termed difficulty‐as‐improvement) when their life feels hard to think about. IBM predicts, and studies support, a bidirectional relationship among these three components (action‐readiness, procedural‐readiness, and dynamic construction). Situations shape the identities that are on the mind and feel relevant (dynamic construction) and the inferences people draw from difficulty (procedural readiness). On‐the‐mind and context‐relevant identities shape inferences from difficulty. Inferences from difficulty affect identity and action—when applying a difficulty‐as‐importance lens, people feel more certain of attaining their self‐relevant goals. They perform better and find engaging a “me” thing to do—“no pain, no gain”. When applying a difficulty‐as‐impossibility lens, people find engaging a waste of their time and unlikely to yield self‐benefits unless an easy means to goal attainment exists—“cut your losses”. They focus on their virtuous character traits and prefer effortful means to attain self‐relevant goals when applying a difficulty‐as‐improvement lens—“the high road”. Difficulty can be a green light of importance signaling you to get going, a detour sign of impossibility signaling you to shift to something else, or angel wings pointing you to the effortful route.