Is it cringey? Sure. But it's not like I expected a John Searle soliloquy.
To me, the problem is not in faux-introspective voice-over. Even some of the b-roll was cool. I completely agree with trying something new, because if everyone pleased our expectations - we'd be having the same part over and over again. With slight variations in pantaloon looseness and facial hair density.
It's just the lenghth. Skating is undeniable, but if trimmed to, say, even a bit above 6 minutes, it could have been THE SHIT.
Will replay it still, though.