As a result of globalisation, automation and digitalisation, workers including those who are highly skilled, are facing worsening employment vulnerability and workforce disengagement. In this paper, we examine the career decision readiness of the unemployed and discouraged based on a nationally representative sample of 1621 highly skilled workers in Singapore. In addition to items measuring demographic, education, work, health and family characteristics, participants were administered measures of career decision state, vocational identity, and career self-management. The findings show that for highly skilled workers in the country, career decision-making readiness (in terms of career decision state and vocational identity) is related to career self-management, age, marital status, health, occupation, industry, and continuing education. Implications for practice and future research are also presented.