Man I'm almost 43 and still struggling with being too hard on myself. I find myself getting flustered and frustrated as I watch the time it takes me to warm up increase, my pop decrease, my fear of certain tricks increase, my confidence decrease and my coordination in general suffer. I'm still holding the line pretty strong but I can feel it irreversibly slipping.
Man, did you ever nail it with those words.
DEAD ON.
I never cruised, carved, skated transition, or did any tricks that don't require pop.
Switching to a more laid back, lower impact type of skating is going to be a hard pill to swallow and I'll need to, like, reprogram my brain to accept a dopamine hit from forms of skateboarding I've never been that into or involved with...
When I was younger, like you, I never touched transition. I was a pure street skater. A life-long skater friend of mine had always liked transition. About five years ago, he started getting me to try ramps/bowls more. I was horrible because I had never spent much / any time learning to skate transition in the early years. I eventually learned some real basic tricks, and once you do that, it's like learning to ollie...suddenly the potential is blown wide open. Once that happened, I became obsessed with transition skating (mostly mini ramps), because is was a whole totally untapped area of skating that, in some sense, really was "new" to me. Hopefully something like that will happen to you, because it was a real game changer for me. Sure, I'll never be a great transition skater, but there is still so much I can learn, and I'm having stupid fun with it. And full disclosure, I wear knee pads on ramps 4' tall and over...initially it really helped with the learning process, now it really helps with the mental process (and has certainly saved my ass a few times, too).