This article describes ‘chronic relative underperformance’ (CRU), – a special example of person-environment misfit –, investigates literature on giftedness, underachievement, underemployment, workplace boredom and bore-out, and connects these to clinical psychological views on mentalization, in order to develop thoughts that are useful in the understanding of why some employees fail to thrive, even though that they are performing seemingly well enough as regards to the targets of the employer, with the intention to offer a frame of reference that can lead to further understanding of this condition. Relative underperformance is an issue that is hardly described within the literature. Recognising CRU in the workforce and taking steps to counter its effects, may lead to a more efficient and elegant way to reach organisational, and personal, goals.