After learning about Frank Sinatra's life, the first author sensed the need to study him in depth. Sinatra played many roles during his lifetime, the most significant of these as an actor, singer, and producer. Sinatra was one of the greatest influential artists in the 20th century. The first author sought personal and professional growth and development by learning from his work and life and using his life-giving positive qualities in her life. The academic framework of this study was the method of Appreciative Inquiry. The 5 D cycle of Appreciative Inquiry was applied as the structural and scientific groundwork of the study. The first author identified 4 positive themes from traveling to places of interest and from conducting a workshop: Sinatra persevered to accomplish his dreams and passions despite his setbacks; Sinatra had a no-nonsense, confident, dedicated, and spontaneous approach toward his life and work; Sinatra was sensitive and dynamic toward the unremitting changes in the world and his life; and Sinatra believed in himself and kept his own personalized manner of doing things.