Dasein is a lonely, individualized human who releases himself from both inauthentic being and immersion in mass crowd (Kierkegaard), horde (Nietzsche) and Das Man (Heidegger) with his own choices, and prepares many possibilities and situations against requirement, certainty, and necessity for himself too; the possibilities that separate him from happenings of life and move him towards transcendence. Boundary/crisis situations like pain, suffering, despair, failure, fright, journey, ageing, death, and so on are the best conditions for confronting the self and existential borders; fragile situations which by disintegrating fixed mindsets, established schemes, and packed experiences pave the way for taking a leap towards self-understanding. The present article explores the life-journey model of flying Shams considering existentialist philosophy key concepts (authentic self, individuality, choice, possibility, lived experience, movement, boundary situation, journey, and death). By analyzing quotations and manner of living of Shams, it explicates the ways by which Shams experiences and lives the journey as life, with a conscious choice, and in this inner experience and personal world (Sartre) breaks himself off from everydayness and mediocrity and moves continuously towards the transcendent and infinite with consciousness, self-knowledge, and subjectivity. Journey is the best option for Shams to remain anonymous, non-adherent to repetitive and public norms and forms, and to experience boundary situation. One of the most important boundary situations, which is more likely to encounter during a journey, is understanding the death presence as the most fundamental option of Dasein. In moving towards death, Shams experiences existential development, desires death, and also by observing the instability of possibilities and finite affairs of existence his faith to absolute truth becomes harder and firmer.