Not long after Mum died I noticed that she'd written on the base of a Robin (the bird) figurine "My Ruby wedding present to Jim 8/8/2004" At the time I thought it was typically Mum writing such notes on things. When we started going through her keepsakes in her "muniment chest" (that Dad made for her) we noticed many things had little labels pinned to them, for example her wedding dress a pair of trousers that Mum and Dad had bought for me on holiday in Scotland when I was about the same age as my son is now.
It was only a few months later when I was thinking of what would happen to all my possessions when I die and how some of them mean more to me than others that I really understood what my Mum was thinking. She was trying to communicate to us why all these apparently random things were important to her (we knew they were important or they wouldn't have been in the muniment chest or in pride of place on a shelf). She never actually said or wrote anywhere "Please don't throw this away" but I think it was implicit.
I wonder if, at the end of my days, I'll be labelling my things (digital and physical) and hoping that my children are as sentimental as I am.