This episode covers chapters 22 through 25, marking a significant transition in Rebel’s life as she moves from her undergraduate years into the rigors of law school and the military. The hosts, joined by a special guest editor, dive into the opening of the mysterious box from Rebel's grandparents, which contains personal mementos and cryptic "going away" letters that hint at long-held family "demons" and secrets. The conversation explores the foreshadowing within these letters and the lack of financial relief for Rebel, who remains steadfast in her plan to use military service to fund her education. The discussion then follows Rebel to Boston in 1987, where she begins her studies at Harvard Law School. The hosts highlight the introduction of her stern but ultimately kind landlord, Miss Fallon, and describe Rebel as an "old soul" who prioritizes her academic excellence and long-distance running over social life. The episode concludes with a look at Rebel’s graduation as the editor of the Harvard Law Review and her immediate entry into Marine Corps boot camp at Parris Island. The hosts marvel at her continued excellence, specifically her newfound status as an elite sharpshooter, and discuss the chapter's final, intriguing line about the arrival of "another" good leader.