Two lawyers in academia sit down in this dialogue to explore career selection and advancement. Robin Boyles Hennegan is Assistant Director of Special Projects at South Texas College of Law,  which has an advocacy program that has won more than twice the championships as any other law school in the United States. Her own career has included work with law offices of varying sizes and corporations. We review some of the lessons learned through her work and life experiences. The value of internships, relationship development, and time management are among the topics covered in this discussion.