The premise of this dissertation is that Buddhism must inculturate to meet the context of contemporary North America. Given the widespread interest in the application of Buddhist-derived ideas and practices in a host of secular settings, the capacity for teachers to engage with new ideas and disciplines will be crucial to the tradition's continued relevance. Because there is a high demand for and interest in Buddhist-derived programming in secular spaces, the number of individuals and organizations striving to meet this demand is mushrooming. This trend, coupled with a dearth of professional training programs and accreditation processes means that not only are there an eclectic array of approaches being used to teach meditation, but there is also minimal discourse engaging the crucial question of what constitutes effective pedagogy or adequate training processes for teachers. Chapter 1 establishes the need for the inculturation of Buddhism. This imperative for adaptation raises fundamental questions regarding how to best evaluate the authenticity of changes to traditional teaching methods. In Chapters 2 and 3, the Buddhist doctrine of skillful means is explored with an eye toward distilling guiding principles for analyzing this process of adaptation of teachings to meet a variety of cultural and personal perspectives. Drawing from Mahayana and pre-Mahayana sutras, traditions of commentary, and contemporary hermeneutics, a set of priorities based on the perspective of the Buddhist tradition is proposed. In Chapter 4, it is established that finding points of relevance to particular cultural concerns such as physical and mental health issues has been a vital component of existing efforts toward secularized meditation programs to date. This chapter concludes by drawing out of such present practices additional guiding principles to advance the process of pedagogical inculturation. Despite the widespread interest in applying meditation to a variety of settings, the pedagogy and philosophy of education behind the various approaches remains largely under-theorized. To fill this need, Chapter 5 establishes a set of guiding principles for pedagogical adaptation, drawing from the tradition's own self-understanding as well as from the insights of Western education as discussed in the prior 4 chapters. Finally, Chapter 6 offers an example of inculturated pedagogy at work.