Wisdom is often recognized as a great resource in resolving complex problems, including challenges in one’s career. However, current conversations on handling ambiguity in career development are disconnected from the wisdom literature, and a psychometrically sound measure of career wisdom is lacking. This article presents two studies that aimed to develop such a tool and evaluate its psychometric performance. Study 1 utilized a sample of workers (n = 349) from the United States to create and explore the factor structure of a measure called the Career Wisdom Scale. In Study 2, a sample of U.S. workers (n = 387) was tracked over 8 months to validate the Career Wisdom Scale by assessing its structural, convergent, predictive, and incremental validities. The results supported the psychometric soundness of the newly developed Career Wisdom Scale. Structurally, the results revealed a three-factor structure of career wisdom, which encompasses embracing ignorance, embracing intuition, and embracing vulnerability. Furthermore, the results indicated that career wisdom predicted various outcomes, including career satisfaction, life satisfaction, organizational career growth, psychological well-being, career adaptability, and work–life balance over and beyond personality traits and career decision anxiety. In conclusion, the present studies offer a valuable measure of career wisdom for both future research and practical application. Additionally, it underscores the importance of career wisdom in effectively managing career challenges that may lack clear solutions.