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As traditional definitions of retirement change, work status categories may be more difficult for certain subgroups of older adults to interpret. This study examines the relationship between select work status categories and respondent’s verbal descriptions of respondents’ their work status. A convergent parallel mixed methods design was used. The sample included 175 adults 50 years old and over from Toronto, Canada. Content analysis was performed to identify nine work status themes in the qualitative strand. Logistic regression models examined differences between categorical and verbal descriptions of work status. Thirty-two percent of the sample reported a work status category that did not correspond with his or her verbal description. Regression models illustrate that being female was associated with increased odds of selecting retired but failing to describe retirement; higher educational attainment was associated with increased odds of selecting working and subsequently discussing one’s own retirement or volunteering; and being an immigrant was associated with increased odds of selecting other and subsequently discussing one’s own retirement. These findings contribute to a growing body of research on contemporary transitions to retirement. Furthermore, they demonstrate potential differences between categorical and verbal descriptions of work status among older adults by demographic traits.