Bailey is a third-year evening student at the University of Denver, Sturm College of Law. Prior to law school, Bailey earned a Bachelor of Science in International Studies and competed on the college rodeo team at Tarleton State University. Bailey served as a judicial intern for the Honorable Richard L. Gabriel at the Colorado Supreme Court and the Honorable Christine M. Arguello at the United States District Court, District of Colorado. Bailey also worked as a medical malpractice law clerk at Leventhal Puga Braley, P.C. Bailey is a member of the Minoru Yasui Inn of Court, Colorado Women's Bar Association, Colorado Bar Association Young Lawyer Division, and a mentor through Law School Yes We Can.