This chapter illustrates why the conception of self-formation as boundless self-enhancement is for yet another reason untenable: in our attempts to form ourselves – through education or technologically – we come across “something within” that resists complete appropriation, something “uncanny” that we cannot simply mold as we please. This view is developed through an examination of the “uncanny valley.” After reviewing various explanations for this phenomenon, the uncanny feeling toward humanoids is interpreted not as a response to a lack of humanness, but rather as a response to the inability to fathom and appropriate what makes the viewer of the robot different from the robot, that is, what makes the viewer human. The more technologies become intrusive, the more this inability is intensified, making the technological uncanny a permanent dimension of selfhood. This notion of the “uncanny within” is elaborated with the help of especially Lacan’s notion of the “extimate” self, which is complemented with Nancy’s view of the self as being “closed open.” From the developed framework, technology cannot be simply externalized and conceived as an outside factor that can determine or liberate us, nor as something that can destroy or strengthen us. Again, it is proposed that the notion of “sublimation” might prove itself fruitful in this respect.