The author explores the friendly presence of serendipity in a life that took him from the Chicago area to Mexico to East Africa to Japan and eventually to the American Southwest, a lifetime that also turned into an intercultural career. Serendipity has been explained as: “a fortunate discovery made by one who is focused and alert, searching for one thing and comes upon something even better” (Strogatz, 2015, pp. 103–104). There’s no map to the serendipitous, except the one you retrace after you’ve traveled that unpredictable road, though my daughter, Christina, tells me that a Jyotish astrological birth chart would show that it all was foretold. In this song as I travel my life’s road, there’s a refrain: “Little could I imagine…” That’s when we sense the serendipity.