Just throwing out an idea: I recently stumbled upon an old-school website where someone is uploading a photo of their day (almost) every single day since 1998.
Came across screen captures of the original Everquest (SO COOL) and other games, photos of anime/cosplay events, city shots, family, friends, etc. Really fun for them, and fun for people who like me who still enjoy surfing the web.
edit: Screencap of an Everquest screencap for funsies: https://imgur.com/a/HUqc6p5
Everquest looked sooooo good back then. Man! No more Meridian 59!
Why did you have to destroy my memories? :)
It's like looking at the first DivX encoded movie that was soooooo good vs. VideoCD/LaserDisc. And then you look at it today and it's so damn blocky and also in that tiny resolution. Ugh!
When my mom was still alive and relatively new to a smartphone (at age 80) I decided to send her some sort of relevant picture every day via Whatsapp, to get her used to communicating that way. Sometimes it was a real stretch to come up with something. But yes, this forces you to evaluate your life from that viewpoint "surely something was interesting today? Let's keep a picture of it". Even if it's just what I'm having for lunch that day.
But she's gone now and so is that habit.