The author is on the borderline of two generations: digital natives and digital immigrants. Thus, this paper presents the autoethnographic perspective of these two worlds as experienced by her. The first one, as Umberto Eco said, is a Built-in Orderly Organized Knowledge world and is the analogue world of the book (BOOK). It is close to the author because of the fact of her educational experiences related to her childhood and youth. The other one is related to using the digital space or educational mobile applications, and is experienced by the author during didactic and research work at the University as well as during workshops she leads for school teachers of different educational stages. Combining these two worlds together gives food for thought and critical reflection on possibilities that are hidden in each of them as well as signalizing the potential risks they both pose.