Actual wuss here. By no means am I amazing at skateboarding, but decent enough to the point where I've gotten some free gear, etc. and also to the point where sometimes my friends and other people would be legitimately wondering why I was being such a little bitch not committing to the simplest things like a back 50 on a ledge (I'm terrible at ledges and rails only because I slammed pretty hard on certain tricks doing them at some point in my life) because given my relative confidence and aptitude in other aspects of skateboarding (flat, banks, minis) it seemed very incongruent.
The annoying part is sometimes I have a terrible day skating just because I feel so out of it and disconnected with my body, which might have something to do with the massive amount of drinking, cigarettes and drugs especially in my late teens and early 20s. I know I could easily do those tricks I've been bailing 2901302130 times if I just stopped being a wuss and committed. More often than not I get a little frustrated spending so much time filming a line that I know I could've done within a few tries. I have this habit of visualizing the absolute worst thing that could possibly happen trying something (like hitting a stone I can't see going down some stairs then scorpioning and breaking my spine in seven places, that kind of thing) which puts me in a pretty bad zone.
It was a lot worse for me when I felt like I had something to prove to other people. I just came back from almost a year of not being able to skate and have just been trying to keep it low, just chilling, and it's been a lot more fun. I'm in my mid 20s now and whatever dreams I've had of being an actually good skater with some future have been shoved into a corner in the deep recesses of my little mind and that's fine with me. I'm having a lot more fun now and I have to say when I'm in the zone and just messing around doing tricks for myself, sometimes I skate and feel a little better. Having fun = better skating, IMO.
Just work your way up. I did a whole bunch of flatground as a kid/teenager and got pretty decent with it and throwing down tricks at the local pyramid/hip has been mad fun. Street skating is still pretty hard for me but it's also pretty entertaining just going to random spots and seeing what I can work with.
I was filming a line the other day and it was just a pretty simple line with 'quick feet' and I was joking with my homie saying I had to channel my inner (younger) Tom Knox (who has crazy control and confidence on a board) and he told me I was more of a Max Palmer (obviously I'm not even CLOSE to his skill level, that guy is amazing!) but in that I wasn't super clean and calculated as hell like Tom but more of a winger like Max. That made me take a step back and evaluate just how much my idea of good skateboarding was influenced by the media or whatever. Like playing a game of SKATE we all naturally subscribe to the idea of Berrics rules, but I mean what's stopping us from playing in a way where, say, even if we bail and land primo and eat shit, then the other person has to bail the exact same way?
I guess what I'm trying to say is that there really aren't any rules to it other than the ones we give ourselves.
But I totally get the idea of wanting to be a great skater like the skaters you see all the time. Sometimes I wish I was that good too, like a homie would bust out a 5050 on a fat rail and I'm like, 'man I haven't 5050'd a flatbar in like 5 years!' but I am where I am and I can only work with what I got for now. That being said, I do try to consciously be better at skateboarding than I was the session before but I'm a lot more forgiving of myself when I have a crappy day out. Skateboarding remains a major part of my life but it's not the only thing I do anymore and I try to branch out and focus on other creative projects.
Skateboarding is awesome man, it is whatever you want it to be. Don't get sucked into an idea of what 'good' skateboarding is, whenever I see someone skating and they just look comfortable and natural cruising on their boards I already feel like they're a good skater. Doesn't matter much what tricks you can do, tricks are just that, tricks. Just my two cents, and anyone can get to that level where they can just have a great time cruising down the streets or ripping a mini with just basic but beautifully executed tricks, and whatever fancy thingamajigs you can learn are just a bonus.
Have fun with it yo!