<p>In this study, we sought to understand highly skilled Caribbean immigrants’ career transitional experiences and how this impacted their mental health. To do this, we utilized a transcendental phenomenological approach to answer two research questions: “What are the lived experiences of highly skilled Caribbean immigrants, specifically as it relates to career transition?” and “How do highly skilled Caribbean immigrants experience mental health counseling?” Data were collected from 10 participants using a semi-structured interview guide followed by coding and thematic analysis. Emerging themes relating to participants’ career transition included the need for recertification, the complicated process and expense associated with evaluating and transferring their credentials, and the length and expense around licensing and recertification. This resulted in many starting over in new careers while others addressed underemployment and loss of status. In discussing the impact on their mental health and their use of mental health services, themes of underutilization of services as a result of structural stigma relating to cost and lack of insurance and cultural stigma around mental, relying on faith and spirituality, friends and family, as well as reliance on their internal strength, are discussed. The researchers offer some implications for clinical practice and share recommendations for working with this cultural group.</p>