Oodles and oodles of wisdom here! Happy to read you started with bringing Zen master Alan Watts to mind, who always said, sit or stand but above all don't wobble! I have always felt skaters have a special lesson to learn that karmically connects them: man can't fly, but he must not wallow either. We don't need to (yes, there's always the aeroplane...). From a light-darkness perspective, you don't want to let Lucifer rule (prideful delusion) - nor Ahriman (with set ways and re-production v originality). You want to represent the middle way, with ideals instead of wings and good deeds instead of dead ends (too much goal setting). But that's where fear does come into save the day for us: it's not a delusion, but something to face and even embrace and watch melt away. Or like you do, to ride on it and respect it as a bail-out card from time to time to. The trick is not to get paralysed by it!
Enjoyed the ride with you!