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Achieving expertise requires people to sustain strong motivation and autonomy, and its outcome could be desirable personal growth and mastery in one’s life. This study examined the relationship between psychological well-being and expertise as career achievement for 1,355 participants from the Midlife Development in a survey conducted in the United States. Using latent profile analysis, three-class profiles of psychological well-being were identified according to levels of well-being. Effects of expertise on the class membership were tested using multinomial regression analysis. The results showed that expert skills and decision authority were significant factors for differentiating the low and high well-being profiles. The results imply that acquisition of expertise can be a relevant factor affecting eudaimonic happiness.