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Starting with the English translations of Freud’s 1937 nuanced concept of ending analysis, the author touches on the history of subsequent ego psychologists’ more exact notions of termination. Merton Gill’s radical shift in perspective away from that attempt, shows how more modern, post-1990 theoretical developments have evolved toward more subjective, intersubjective, and ranging judgments about what may be practical (Freud’s own final 1937 word). Resuming ego development as a goal, for example, and the role of analyst as new object (Loewald 1960 for example), is linked to a creative process of a patient’s increased subjective well-being—one feature of ending that cannot be precisely measured. There are two clinical examples of terminations: (1) The author’s experience of hearing Hanna Segal tell impressively about a case and its ending, circa 1970; (2) a longitudinal account of a four-part analytic involvement, from a patient’s teenage to middle years, that demonstrates different kinds of endings over a patient’s life. The last analysis, with a new analyst, after the original analyst’s death, was supervised by the author. Summed up, the termination phase is a deep study of the complexity of human existence for both analyst and analysand. This appreciation, including its limitations, helps many analysands fruitfully continue their life journey.