This is someone who worked on radar systems, cryptographic systems, computers, power electronics, control systems, and measurement systems in the military and civilian worlds from the 1960s to early 2000s. He built his own kit electronics for home audio and later a ZX-80 computer. He followed the whole PC revolution from the CP/M and DOS days to Windows 7. He participated in BBS systems in the 1980s and used the Internet since around 1991. He exposed his children and friends to science and tech.
He followed countless changes from minicomputers and teletypes, to PCs with CRTs and text CLIs, to window-based GUIs. Then, he started to struggle with the abstractions of these same GUIs as well as web sites. He struggles to identify the boundaries between different programs and content, like some novice user who never understood how it was all put together. Worse, he is aware of this struggle and of his losses. I can see that it frustrates him daily. Once in a while, I'd say it terrifies him.