He grew up in Delray Beach and graduated from Atlantic High School in 1980. He attended Sewanee: The University of the South, from which he received his Bachelor’s degree in 1985, and conducted his graduate studies in philosophy at the University of Miami, receiving his Ph.D. in 1991. He has been teaching at Florida Atlantic University since 1993 and served as Chair of the philosophy department from 2008 to 2010. Professor Headley publishes regularly in scholarly journals and anthologies and is a founding member of the Caribbean Philosophical Association. He teaches courses in a variety of areas, including ethical theory and political philosophy.