The analyst’s inveterate characterological weaknesses and deficits—say, being detached, distracted, over-aggressive, too literal, etc.—may elude identification, correction, or repair during the training years and beyond. Such “Achilles’ heels” in a clinician will taint at least some of the analytic relationships this clinician forms and compromise the outcome of the therapeutic work with those patients. The defenses the analyst may erect against recognizing their vulnerability amplify its disadvantageous effect. This article explores how we might more effectively register such Achilles’ heels in ourselves. Homing in on specific instances in the literature and my own practice, I trace the impact of our intrinsic deficiencies within the transference/countertransference matrix, and offer a perspective on how to address and mitigate their deleterious effects. My purpose is to help us, as analytic clinicians, relax our inherent anxieties about recognizing our frailties, so we can more creatively and effectively offset any negative influence these may have on our therapeutic functioning.