I hate when I need to solder jack positive(red color cabel) in angle and not straight.
Hard to get right. Smaller cabel breaks easily and thicker cabel bends badly.
I almost made working piezo pickup for my classical guitar. When I was installing the closed jack in guitar the soldered red cable broked because it was on angel.
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You're not holding your mouth right. Squint one eye and stick out your tongue a little bit -- and you should be able to solder it just fine.
Seems like the basis of the "Soldering Blues" to me.