This study examines how Singapore workers are redefining the balance between careers, aspirations, and personal lives, and the implications for underemployment. It aims to uncover the different types of underemployment and identify profiles of workers who are most at risk of being involuntarily underemployed. While time-related underemployment is useful, it is not reflective of the holistic underemployment situation in Singapore. As such, NTUC’s study also explored other indicators of underemployment, like skills-related and education field-related underemployment, to offer a broader and more holistic perspective. Findings reveal Singapore’s patterns in relation to OECD averages and underscore the need for lifelong skill development, flexible work options, and targeted support across career stages.