For me, it's a matter of switching things up. Right now, I'm in a street phase... curb shit for some reason. This weekend I'm going to skate some concrete transition (hopefully with Hate on his way home to the Fort), and a few weeks ago I skated some wood park stuff. If you don't have the parks, just go to spots that require you to do something different (like a bank versus a set of stairs).
What I mean to say is that you can progress tons if you branch out. I think all types of skating compliment each other, so if you have some really diverse spots, make each session focused on that thing, then put your attention elsewhere. Progress organically.
A great strategy for overall progression and well-roundedness. But what about pushing forward with whatever you happen to be working onthat day? Breaking barriers? Climing out of a rut, and up the ladder?
While weight and strength play some role, everything else—pop size, flick ability, rotation accuracy, light-footedness—is mental.
I think getting better is nothing more than setting the bar higher and working with determination. As an example in my case, there's this small indoor park with a roll-in opposite an up-gap (aka Euro). When I started going there in February I had winter rust so severe it took me ten tries just to ollie up the thing. Getting an ollie that was straight and landed quickly took another ten or tries. There's only about three feet of flat before you hit the roll-in so you have to throw down after a single powerful lunge in order to get enough speed for a good blast up the ramp opposite. Anyway, it took me all night—more than 50 tries—to ollie into the ramp. I kept kicking it away for fear of a slipout or something, but once I did it I realized how easy I was, and that I was allowing my fears and expectations hinder me.
My second time at the park, after many tries I finally kickflipped up. I knew this was within my ability so I worked on getting it more consistently before I sought a new milestone—a personal NBD. I wondered if I could switch ollie up but told myself I probably couldn't. I'd never switch ollied an up-gap at a park, or up anything higher than a curb for that matter. After thinking about it during my next couple of visits I decided to try the Euro anyway.
The hardest part was committing to the first switch roll-in. Took a few minutes to work myself up to it. Of course with that first try I had nowhere near sufficient speed to blast up the Euro, so I kept trying to hit the roll-in faster until I was throwing down before rolling down the same way as I do regular-footed. When I finally made a crooked-ass switch ollie up and rolled it away I couldn't believe it. I worked on it all night to try to straighten it out. After two more visits I blasted up straight second try and was switch ollieing up this Euro more consistently than I could kickflip it. By night's end it got to be so easy I thought to try a switch 180°. A few weeks ago, I never thought I could do this. Eventually I did a sketchy one with a late-ass harsh pivot. The next time I showed up I did it perfectly, rolling out with speed.
Easy tricks, sure, but keep in mind that the switch 180° was well beyond my expectations of just weeks ago. It makes me wonder how much further I can bring it. Yes I suck but not long ago I had switch flips more consistent than kickflips—could I actually switch flip this up-gap? That would definitely not suck, and a few weeks ago I would have considered that trick impossible to land in my lifetime. Today it seems no more distant than the switch ollie was a couple weeks ago.
This again reminds me of what I read in an Andrew Reynolds interview years ago—"Anybody can do any trick. We all have the same legs and skateboards." While quick progression is common in younger skaters, it's almost unheard-of at my age. I suppose my point is that the more we expect from ourselves, the more we're able to deliver, and that improving in skateboarding is more a process of building neural pathways than jumping power (not to say that the latter doesn't help).