You can only sort of ever keep up.
The main issue preventing you an Old, from finding more about people who are Young, is that the Young don't exactly love the old filling up their spaces, trying to remain hip.
This is exemplified by the slow death of social networks as they grow in popularity. A new social network pops up, its quickly populated by the youth. Slowly, as it becomes more popular, Olds start creeping in, until there are so many Olds that the youth want to go somewhere else because they no longer have privacy.
When Mom and Uncle Jim are in the conversation, everything is suddenly less cool.
Happened to MySpace first, and it's happening to Facebook right now. It's basically ghost towns of people who will be dead soon.
We are limited because the youth will always want their own private spaces where they can truly be themselves without their weird expectations of the older generations. If you're older with zero expecations for the youth, congratulations: you're unusual, so don't hold it against the youth that they assume you're just another boring old person who is going to judge them for something. Most adults are out here judging them, so give them a break on assumptions they might make about you.
I used to keep up with music through YouTube channels, but even the ones I used to follow are aging up and soon enough those people I was listening to are Old now too, and they're doing the same thing as me, trying to keep up with what's hip and good.
I understand the desire to do so. New music is often so good, and I really get sick of people who act like the music they grew up with is the best in history. It's not, and it never will be. Music is always growing and making music is more accessible than ever, which means its really exploding and evolving. There's never been a better time to love music.
However, as Olds, we're just going to miss a lot of what's cool with the kids simply because we're Olds. So much is just going to naturally be hidden from us.
