I'm gen Z, and even though my knowledge about current meme topics have lowered noticeably, but I'm finding myself happy, since I still get a lot of infos from a VRChat discord server I'm active in, and an another one where my old and still uni friends posts some random shits about whatever dramas.
I feel your pain of feeling left out. I think as with most cases, being in the middle might be the best approach.
I'm venturing into Transport Fever 2 as a total newbie and I definitely fucked up my first attempt make a profitable line on medium mode, by overspending with a train line in 1850 already. Imma try only some bus routes now as a start.