In retrospect and over the past eighty years, it appears that the author has tracked a somewhat consistent pattern in his educational, employment and investment pursuits - all centered on the theme of decision sciences and engineering systems (DSES). Indeed, the author’s papers, lectures, speeches, and range of academic and work activities have likewise tracked such a DSES theme. Since an early age, the author came to realize that his interest in mathematics served to help him make consistent sense of his decisions about life and his various pursuits; he further understood that life itself is intertwined in a number of different engineered systems, connected with and in support of each other. Certainly, each person adopts a somewhat different personal journey in their DSES quest; this paper, of course, documents the author’s own unique journey.