The relationship between mindfulness and well-being has received considerable empirical and theoretical attention in the scientific literature recently, with researchers hypothesizing a number of ways in which the two interact. However, a closer examination of the literature indicates that the two primary conceptualizations of well-being, psychological well-being (PWB) and subjective well-being (SWB), are theoretically distinct, yet regularly conflated and rarely examined in tandem. As such, the purpose of this study was to explore the associations between dispositional mindfulness, SWB, and PWB, with respect to contemplative practice, using canonical correlation analysis to examine data derived from an online sample of 361 respondents (106 contemplative practitioners and 245 non-practitioners). Results indicate that contemplative practitioners typically report significantly higher levels of mindfulness, as well as psychological and SWB. Furthermore, dispositional mindfulness is associated with both PWB and SWB, but more closely associated with PWB, irrespective of contemplative practice experience. Finally, mindfulness and well-being appear to be similarly related regardless of contemplative practice, although our findings suggest that contemplative practitioners and non-practitioners may conceptualize SWB differently. Contemplative practitioners appear to group PWB and SWB together in a unified well-being construct, while non-practitioners appear to conceptualize SWB as distinct from PWB.