In this article, the psychic and existential impact that fixation has on an individual's life is addressed. A person may drift through years that are dictated by the circuitous path of a fixation and its vicissitude of the repetition compulsion. When such “wasted” time is viewed through the revelations gained later in psychotherapy, insight becomes a double-edged sword. The regret of not having used one's life opportunely is superimposed on the analyses of transference and infantile conflicts, thus prolonging treatment. The phenomena of loss and incomplete mourning are used to illustrate the path taken from fixation through psychic drifting to regret. The therapeutic necessity of working through such regret is emphasized.