In this episode of Stang Stories, host Hunter Caggiano '27 interviews Milton alum Diana Rakow '95, president and CEO of Hawaiian Airlines. Diana recounts her unconventional career path from chemistry at Harvard to public health and healthcare leadership, and ultimately to aviation at Alaska and Hawaiian Airlines. They discuss the influence of Milton’s people and arts on her leadership style, the challenges of leading large, community-rooted organizations, and Diana's practical advice for students exploring meaningful careers.