This chapter illustrates the career challenges faced by Lesbian, Gay, Bisexual, and Transgender (LGBT) community with a case study of a 45-year-old gay male whose employment was recently terminated. The LGBT community has made tremendous legal, social, and political progress over the last two decades; yet, LGBT persons still encounter barriers and obstacles in ways that can be very different than their heterosexual counterparts. Sexual orientation continues to be a workplace issue because no federal laws protect LGBT individuals from employment discrimination. A model for effective practice, Career Counseling With Under Served Populations (CCUSP), was developed by Dr. Mark Pope and was originally based on his earlier research in career development with LGBT individuals. The chapter provides a summary of the 13 key components that provide culturally appropriate career services. Using these keys as guidelines, appropriate holistic career counseling is a likely outcome.