I've been skating a lot since graduating this past Spring, and unfortunately I'm not nearly as good as I used to be (in comparison my increase in guitar practice has had great gains). There's a sort of 20% of the tricks that I'm missing. My coworker Nate always says that the last 20% is usually the hardest part of any task.
Honestly, it's fear. There's a sort of commitment required when you set up a trick and then there's a weightless moment where there's no going back and then you come back and snap the trick into the landing. I'm copping out and doing things like instinctively putting a foot on the ground in that moment. It's safe. It's lame. It ruins the trick.
That moment of insecurity is what doing tricks on a skateboard (or more realistically for me, a snowboard, my preferred sport), is all about. The reason people enjoy progression is because that feeling is like a drug. It's the rush of flying through the air or sliding across a 40 foot piece of metal or spinning across the top of a box and just enjoying the experience of doing it right. It's why fear is what what ruins tricks, the fear that makes you fight that moment instead of committing.
Progression is natural in board sports because people just want to extend that moment: another rotation, a longer rail, a bigger jump. Competitiveness with other riders is only a small part of it.
In snowboarding there's fewer opportunities to bail without falling and feeling some pain, I think it's a blessing in disguise. The thing that's terrifying about programming, is it's just the opposite. There isn't always an easy route from A to B, but you can hack one together. Programming is open ended.
Sometimes you have to rely on a piece of paper and some matrix algebra to get you to the other side.
Sometimes hooking up a debugger won't be an option.
Sometimes you'll be up all night trying to figure out why the AI is jittering as it moves.
I think that it's one reason why there's this gap between general software engineering and game development that a lot of people have trouble crossing. Especially when there's so much demand in the world for software engineers that only have to solve straightforward problems.
Don't put your foot on the ground. Do it right.