Of the several processes that purportedly contribute to psychological flexibility, that of enhancing self-as-context, or transcendent perspective taking, has been the least investigated. To address this omission, we conducted two analogue studies with college student participants examining the relative impact of a brief exercise for enhancing the contextual self on pain tolerance (n = 22) by comparing it to control-based (n = 22) and attention-placebo (n = 22) protocols. In Study 1, the self-as-context intervention was a generic one that we modified only slightly from the "observer exercise" presented in Hayes, Strosahl, and Wilson (1999, pp. 193-195). Significant, but equivalent, increases in pain tolerance as assessed by the cold pressor were obtained for the three protocols, with the largest effect size noted for the control-based condition. In Study 2, we compared a self-as-context protocol (N = 22) that was contextualized to the experience of pain to data from Study 1. The contextualized intervention significantly increased pain tolerance compared to the generic self-as-context and attention-placebo conditions of Study 1. The increase was statistically equivalent to that obtained for the control-based condition of Study 1, but represented a greater effect size, suggesting that the relative impact of a generic self-as-context exercise is increased when contextualized to a specific psychological challenge. We discuss the implications of these findings for future research investigating the impact of interventions targeting self-as-context within both analogue and clinical research.