The potential for personal growth in cross-cultural travel has been posited by numerous psychologists, however, a "gaping hole" in empirical research has left these hypotheses unexplored (Montuori & Fahim, 2004). Meanwhile, rapidly increasing numbers of people are choosing to leave their careers to pursue a personal dream of extensive foreign travel (Travelex, 2009). The aim of this study was to explore the motivations, psychological experiences and outcomes from travel in this growing "career-break" demographic. Ten men and women who had exited their careers to pursue extensive culturally engaging travel participated in an individual semi-structured interview which was analyzed using constructivist grounded theory (Charmaz, 2006). Three main themes emerged: an existential yearning to travel, "jumping off the ledge" (courage) and discovering authenticity. Personal growth occurred via adversity within the travel experience itself, but also at the pre-travel stage of departure, where leaving security and venturing uncertainty was experienced with "milestone" significance and for some, as a seismic event akin to trauma. Future research should explore the potential for a new type of intrinsically-emerging trauma in posttraumatic growth (PTG;Calhoun & Tedeschi, 2006) and the potential for anxiety as a positive construct in authentic becoming and growth.