Chip on his shoulder means that someone is bitter and will not let go of offenses. This is reported as originating with the nineteenth century U.S. practise of spoiling for a fight by carrying a chip of wood on one’s shoulder, daring others to knock it off.

Burning the midnight oil refers to someone who has a late night. Originally this was by the light of an oil lamp or candle. More recently, the phrase is used figuratively, alluding back its use before electric lighting.

Chip on his shoulder=attitudinally, he’s looking for a fight

Burn the Midnight Oil=used in the context of studying, it’s someone who stays up late/all night working on something

means a person is spoiled and doesn’t have to work for the nice things they have

“Chip on his shoulder”

means a person is unnecessarily holding a grudge, or a person who feels they must prove themselves by acting aggressively

“Burn the midnight oil”

means to stay up all night working, studying, etc. basically, to work for a very long time on something

born into moner, oppratunities , ect…

You have a grudge……..Challenging people…being contrary

You’re gonna be up all night.