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Psychiatry typically has trouble deciding whether transsexualism is a perversion or a psychosis. Labelling these phenomena as pathological is a delicate matter. Not only do transsexuals reject this label, but in many cases the rather normal behavior or astonishing achievements of such subjects discredits medical stigmatization. However, what should one make of the subjective reconstruction that takes place in the process of transsexualization? Based on Donald/Deirdre McCloskey’s autobiographical narrative, Crossing, this paper suggests that we ought to view the manifold dimensions of the case as a whole (including the theoretical reflections by this economist) in order to understand how transsexualization can sometimes be, as Lacan might say, a “crafty solution.”