This chapter investigates how perceptions of person–environment misfit influence job choice decisions, proposing that misfit may deter applicants more strongly than fit attracts them. The authors fuse the attraction–selection–attrition model with prospect theory to explain why individuals and organisations place disproportionate weight on potential losses associated with misfit. Within this framework, they distinguish between anticipated and experienced misfit and elaborate on supplementary (value-based) and complementary (demands–abilities and needs–supplies) forms of misfit. The argument advances that individuals often rely on heuristics and biased evaluations when screening job opportunities, focusing primarily on cues that suggest misfit rather than on those that indicate fit. The chapter also explores contextual and career-stage factors that shape reference points in job evaluation, demonstrating how jobseekers’ and selectors’ decisions are bounded by cognitive, motivational, and environmental constraints. In doing so, the authors offer both theoretical and practical insights: conceptually, they establish a behavioural foundation for understanding misfit aversion; practically, they recommend integrating misfit assessments into recruitment and training processes to improve job choice outcomes. By combining behavioural economics and fit theory, the chapter reframes misfit as a critical determinant of employment decisions rather than merely the inverse of fit.