This study presents a qualitative ethnographic exploration of professionally successful lifestyle migrants' self-perceptions of premigration etiologies of “modern distress,” and postmigration pathways of healing and outcomes in Guatemala. Reflexive accounts of perceived etiologies of distress include self-commodification, atomization, and disengagement from “true-selves” as stressors motivating relocation. Migrants depict postmigration healing practices as embedding popularized therapeutic narratives that amplify introspective self-dialog reproducing hypercapitalist and emotional capitalist “liquid-modern” unstable and disengaged selfhood. Constituting what we term a “pure relationship with the self,” lifestyle migrants describe a “modern trap” of “addictive” chronic healing, self-seeking, and unfulfillment while resultant self-deliberations continue to exhibit no less liquid and potentially adaptive life paths. Implications will be considered pertaining to self-dialogic therapeutic processes that reproduce distressed liquid selfhood and the potential of sites of self-relocation to amplify socially disengaged introspection. Yet reflexive self-dialog problematizes reductionist readings of structural subjectification, calling for further examination of the way distressed selfhood is a product of shifting social structures and zeitgeists but no less a self-crafted outcome of self-deliberation that critically evaluates emergent selves and alternative contexts of self-constitution.