Numerous studies have noted that depth psychology has been one of the most prevalent frameworks for the interpretation of Buddhism in the West. Similarly, many commentators have bemoaned the assimilation of Buddhist thought and practice into western psychological discourse. This paper argues, however, that such critiques often fail to adequately distinguish between reductive approaches that reduce Buddhist phenomena to psychological states, and dialogical enterprises that utilize psychology as a tool to extend, through dialogue, the aims of Buddhism. Through a focus on what I identify as "West Coast Vipassana," a distinctive current within the American Insight Community, I examine attempts to incorporate personal life into Buddhist practice. While there are numerous incidents of the reductive approach in the Buddhist-psychology interface, I interpret West Coast Vipassana as providing a more legitimate and dialogical or "skillful means" approach to Buddhist practice in a contemporary Western climate.