Transitioning from CD player to Apple iPod was pretty great. All my iPods (earlier models, when the color options were white, then black and white) remain fully functional.

There was also a moment in time when Google Translate "broke the mold" for me. It was mid-2010s. I was traveling through Eastern Europe. Using Google Translate I could have real-time conversations with persons speaking another language, in a less common dialect of that language. Translate captured both the semantics and pragmatics of each conversational exchange. Couldn't believe it. I could also use my phone's camera to translate text on signs and menus in real-time. Granted, it ate my battery. It also closed the gap in human-human communication instantly.

When I used torrents for the first time - the client had these funky animated packets coming from seeders and leechers. I don’t know if that counts as a “moment” but my mind was blown.

These days my feeling is that the most memorable moments are still yet to come.

First time I pirated Windows XP.

Bought the disc for 5£ from an ambulant seller who'd sell also porn DVDs (but that's a story for another time)

The disc was in a soft plastic envelope, inside printed in B/W the XP logo and also loose inside the envelope the "serial" to insert when prompted and the instructions on how to install.

I did all the procedure according to the instruction provided and inserted the serial without much hope and sure enough it worked!

Visited the guy for a couple of years for pirated PC games, movies and porn DVDs....good times.