Solitude, the Quaker leader William Penn wrote in Some Fruits of Solitude (1693), is “[a] School few care to learn in, tho’ none Instructs us better.” No doubt Penn would have preferred not to learn in that school; a politically connected confidant and supporter of King James II, Penn found himself suspected of treason, and arrested several times, in the aftermath of the 1688 Revolution. Finally, in early 1691, he went into hiding. Despite its inauspicious origins, Penn viewed his solitude as a valuable interruption to his public career, enabling him to “step a little aside, out of the noisy Crowd and Incumbering Hurry of the World, and calmly take a Prospect of things.” In this chapter, I explore the ways in which Some Fruits of Solitude—a Preface and 466 numbered aphorisms and maxims on a range of topics—navigates between public disgrace and private self-reflection, implicitly using the former to accomplish the latter. Penn’s reflections, I argue, represent far more than simply the consequences of his public disgrace. His act of writing constituted a source of solace in his enforced solitude, in which it is possible to discover his own lifelong perspectives on loneliness and companionship as well as his continuing aspirations for a return to public life.