This paper asks: What is philosophy and what are some current challenges and future prospects for pursuing and teaching it? What role can and should students’ imagination, interests, and circumstances play in addressing these challenges and prospects? It argues, first, that there are at least six senses of the term “philosophy”: the personal, social, branch of inquiry, theory, school of thought, and wise sayings senses; second, that a variety of stimuli contribute to motivate philosophy in all of its senses. Third, (...) it argues that teaching philosophy involves not just teaching one or more philosophies historically held, nor just partially or totally defending one or another of these philosophies; but also engaging in the third sense of “philosophy” above listed: philosophy as a branch of inquiry. Finally, the paper argues that by relying on the interests of philosophy learners that match the stimuli motivating philosophy, philosophy teaching sensitizes philosophy learners to the grounds that make this investigation viable and promising, and motivates them to engage in it. (shrink)