This chapter demonstrates how overcoming the inside-outside dualism makes it possible not only to do justice to the dynamic and relational character of the self but also to recognize how technology increasingly inscribes its “grammar” in the structure of our mind and self. It shows how in the Extended Mind theorists’ account of the relation between the human organism and the world of external objects and artifacts, the inside-outside dualism is preserved, a dualism which they proclaim to have overcome. Therefore, the Extended Mind Thesis is not capable of sufficiently grasping how and in what sense external objects and technical artifacts can become part of our human cognition. Inspired by Charles S. Peirce’s philosophy of mind, it is argued that external objects, artifacts or processes are not inanimate and unintelligent matter utilized by a separately living, inner mental sphere that has set certain pre-established goals for itself; mind has rather an artifactual character. It is not extended by an inner biological cognitive core, but rather unfolds itself through objects and artifacts. Recognizing this artifactual dimension of mind enables a more critical analysis of contemporary claims that ascribe certain original and irreducible features to thinking.