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The role of the analyst can be conceptualized in different ways, a topic that concerns both transference and countertransference, as well as different epistemological positions for the analyst. Deviations from the desired and usual role are one of several aspects of countertransference. This paper focuses on the analyst’s difficulties as they appear in a case study. What happens when the analyst’s insufficiencies come to light, similar to the cases discussed by Harold Searles (1979) in his article ‘The Patient as Therapist to His Analyst’? Are there two patients in the analysis? Is the analyst simultaneously analyst and patient? When are transgression and submission failures in the analytic work with strong emotions such as love and hate, and when is it inevitable, perhaps necessary? What happens when we allow ourselves to stay and examine our role when we have become the other patient in the analysis? The paper aims to create a basis for further discussion about countertransference, the role of the analyst, transgressions (of the usual way of working analytically), and submissions (of the assigned roles).