Ordained a Baptist minister in 1991, Watkins served as youth minister at the First Missionary Baptist Church of Hueytown in Bessemer, Alabama. He attended the United States Naval Academy from 1994 to 1997, where he was elected class president and earned the rank of battalion commander. In 1997, he resigned after allegations of homosexual activity. He finished his degree at the Embry-Riddle Aeronautical University in Florida, and has worked as a business analyst, math teacher, and health educator focusing on gay youth and communities of color. In 2000, the South Florida Conference of the AME Church denied his application for ordination as an A.M.E. itinerent deacon (the lowest level of itinerent minister). He founded the Ministry of Reconciliation, which is an inclusive and affirming education and worship experience primarily for Black Gay, Lesbian, Bisexual, Transgender, Questioning persons, Persons Living With AIDS (PLWAs), and their family members. In 2005, Watkins
published a book about his life experiences titled "Living Out Loud."