I keep constantly adding new music to my playlist. Most of the time I also listen music from the top of my "latest" playlist so over time the songs keep changing and are always the most recent additions.
This not only keeps my music fresh but also creates a convenient timeline (or soundtrack) of my life. I can go further back the list and immediately connect certain songs to a particular time of my life. Of course this doesn't require going through a chronological list of music. But it helps keeping things in order.
It works even better the other way around. When I'm trying to remember and find some particular song I can just think of the time I used to listen it. Then it's easy to scroll down the playlist until other songs around that time start coming up.
And if I don't remember the time something happened I can always search up a song from thst time and check the added timestamp from that song to at least give the lower boundary for the dates of that event.