This thesis focuses on addressing the gap between contemporary philosophy of technology and other stakeholders in the technological system such as designers, users, or management. The point of departure is two of contemporary mainstream theories - Critical Constructivism and Postphenomenology. After being presented through the seminal case of the Internet as a communication tool, critique of the two theories is presented. Thereafter, the contemporary discourse on the complementarity of the two theories is summarised and analysed. Lastly, the shortcomings in connecting the theoretical insights with stakeholders in the technological system are identified and suggestions are given towards their resolution. Specifically, Anarchist principles are imported as a possible theoretical basis for the next step in philosophy of technology. Furthermore, Science-Fiction prototyping is offered as an example of a methodology that could create common grounds for communication between different stakeholders. The thesis closes with a summary of the arguments that lead to the two suggestions made, as well as with identifying alternative routes that could be taken to address the overall question of brining philosophy of technology closer to wider acceptance.