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In workplace cultures and wider society, massive change and loss have become an increasingly menacing juggernaut when not followed by acknowledgment and acceptance of the loss and grieving for it. The triad of change-loss-grief looms ever larger in the face of recurrent and massive organizational change and globalization at the end of the twentieth and into the twenty-first centuries. What Alexander and Margarete Mitscherlich called ‘the inability to mourn’ often keeps organizations and entire societies ‘stuck’ in a repetition of the past and the inability to venture into a future that does not repeat it. Organizations, no less than entire cultures, can undergo efforts to revive the glorified past in the face of enormous loss. To illustrate this process, I present the example of an American Jewish synagogue that has long been in decline, yet whose leadership, religious and secular, have continued to struggle heroically to keep the past alive if not to revitalize it. I describe aspects of a consultation in which this process became conscious via countertransference, and how the synagogue leadership gradually began to acknowledge the enormous loss, grieve that loss, and begin to imagine a new future in which the congregation could let go of who and what they were in the service of who and what they could realistically become.