Philosophical inquiry promotes critical consideration of important values and beliefs, communication and argumentation skills, and self-reflection. Yet in the U.S., widespread familiarity and interest in it remains limited. Philosophy’s been consigned to universities, with academic Philosophers becoming de facto stewards for the entire history and practice of the European and Anglo-American thought tradition. Even within universities, philosophy tends to be derided and insular: many students don’t find it useful or worth exploring; if they do, they might find its presentation impenetrable or alienating. There is a growing body of literature expressing dissatisfaction within and about the discipline of Philosophy, but also a great body of work promoting strategies for amelioration and innovation. This dissertation expands on both. In the first half, I articulate what I take to be missed opportunities, misguided norms, and misplaced priorities within Philosophy. These manifest across pedagogy, research, and engagement with the world beyond the disciplinary institution. Philosophy should be inclusive and accessible, applied to real-world, relevant issues at the forefront of peoples’ minds—right now, it’s not. Throughout, I highlight strategies for meeting these challenges. In the second half, I present two projects of my own research, which both attend to several dimensions of the discipline’s shortcomings. The first is built around my collaboration on a deck of conversation cards about ethics and technology. The cards create a playful, low-stakes entry to philosophical inquiry, and when scaffolded into structured activities invite further opportunities for recreation and for student-led, empowering pedagogy. I present games, classroom activities, and a major course assignment to that end. The second project centers a claim common in disagreements about whether to support or participate in university teachers’ strikes: that teachers’ strikes harm students. I unpack this claim and explore considerations on both sides of the debate. I present my exploration in three modalities—an academic piece that’s accessible across disciplines, a public-facing op-ed, and one-page pamphlet to be distributed to teachers and students during a strike—to demonstrate how philosophical work might be presented to various audiences and for various purposes. The aim: philosophical work, done differently.