The expression 'chip on your shoulder' is rooted from ship yards workers in the 1600's. The phrase reflects shipwrights that allowed workers to take home 'chips' or pieces of wood they good use for their family.
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To have a chip on one's shoulder is to have a negative outlook on life, by thinking that the whole world is against you. A person who has a chip on their shoulder is holding some sort of a grudge against someone or something.
It is like being proud and having an attitude. You are just looking for trouble and want someone to challenge you so you can lay into them. Some people characteristically are hot-tempered and very easily become antagonistically angry -- then we say that they always carry a chip on their shoulder.
A person who has "a chip on his shoulder" is usually resentful but not necessarily angry because of something that happened or was imagined to have actually occurred in the past. Thus, a normally friendly, easygoing personality can suddenly turn sullen, sarcastic, abusive and antagonistic when a specific topic or point is mentioned in conversation. That's when we would use this idiomatic expression.
The mental image for this idiom is usually a man with an actual chip of wood on one shoulder, daring a conversation partner or perhaps anyone in a nearby crowd, to try to knock the chip off -- the signal or challenge to physically fight, in order to establish who is right, believing that "Might is Right".
The LITERAL meaning is that he has a chip or small piece of something balanced on his shoulder.
a chip
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Chip off the old block means someone closely resembles their parents or mentors in some way, usually by appearance, mannerisms or skills/hobbies.
The plural of chip is chips.
shoulder season