I hit a progression drought for a while and what’s helped me move past it has been a) skating by myself more b) going into a solo skate session with a specific trick at a specific spot in mind c) filming said trick in an attempt to motivate myself and produce something to create a sense of accomplishment.
I know I’m not going to psychotically throw myself at the same obstacle trying to learn something new for 45 mins straight in a skatepark full of strangers (or waste my friends’ time trying to film something new like that) so I really appreciate the no pressure, calm atmosphere of working on new tricks solo.
Exactly what I've been doing and why I've been doing it, minus my planning aspect is different, for from experience I've observed skateboarding and planning (tricks in particular) never quite works out exactly as intended and then at the end of the day you've just limited the scope of the session to yourself. I do have set ideas for set tricks (who doesn't always) but what I do pick for my days is just a general area of the city to skate, so for instance I'll psych myself on going to skate this or that particular neighborhood (with a general idea of what exactly is there, but specifically kept only so vague in the moment) and then I basically just see what happens. I've learned that there are days for, and not for, certain specific spots and tricks and there's little point in forcing that. Usually - as expected - the day never goes as planned, I end up going with the flow, usually getting a clip or two of the kind that just couldn't be premeditated (e.g.. when you run into an ephemeral spot), and sometimes one of the tricks I had been thinking about for a long time but naturally and as a bonus. It's pretty great too because then you sort of surprise yourself every day instead of making it either a win or a loss for no real reason or stakes.
I'm specifically with you on the meditative, introspective aspect. Can't stand the skatepark these days and been finding the exact solace my sessions there had crucially been missing in the solo skates.