This chapter describes a kind of proto-Progressivism in the Kentucky childhood of Sophonisba Breckenridge, the daughter of Confederate veteran, former Democratic congressman, distinguished lawyer, and Lexington Herald newspaper editor W.C.P. Breckinridge who would later try to reform the lives of children in Chicago and ultimately become one of the most renowned reformers of the Progressive Era. It examines Breckinridge's prolonged quest to reconcile destiny and duty and how it complicated her coming of age and delayed her professional career, but also led her to find her calling as a progressive reformer. It also considers how Breckinridge's introduction to the suffrage movement and to institutionalized sexism inspired a lifelong commitment to women's rights, and how her pacifism shaped her adult understanding of her father's military service.