When it comes to phrases about chips and/or shoulders, chip on your shoulder falls somewhere between chip off the old block—which is often used as a compliment—and cold shoulder, which is decidedly negative.
While having a chip on your shoulder can motivate you to better yourself, learn from your past, or achieve some high-reaching goal, it’s not exactly a positive quality. As Merriam-Webster defines it, the expression implies “an angry or unpleasant attitude or way of behaving caused by a belief that one has been treated unfairly in the past.” If you have a chip on your shoulder, you have something to prove, and you’re probably giving people the impression that you’d welcome an opportunity to prove it. Your demeanor may even seem a little belligerent.
These connotations line up pretty perfectly with the history of the phrase. As Pascal Tréguer writes for his word histories blog, chip on your shoulder had a literal meaning when it arose in the U.S. and Canada during the early 19th century (or earlier). If you put a wood chip on your shoulder, you were daring someone to come knock it off—and whoever did was essentially agreeing to a fight. Maybe you were even trying to provoke a specific person who had wronged you, or maybe you were just itching for hand-to-hand combat.
The earliest known reference to the tradition is from a letter written by James Kirke Paulding back in 1816. “ … a man rode furiously by on horseback, and swore ‘he’d be d—d if he could not lick any man who dared to crook his elbow at him,’” Paulding wrote. “This, it seems, is equivalent to throwing the glove in days of yore, or to the boyish custom of knocking a chip off the shoulder.” The way Paulding mentions the practice makes it clear that his audience would’ve already been familiar with it, so it’s possible that it had already been around for some time.
Although there’s no strict age or gender criteria for picking a fight via wood chip (that we know of), it does seem to have mainly been adopted by boys. “When two churlish boys were determined to fight, a chip would be placed on the shoulder of one, and the other demanded to knock it off at his peril,” read a Long Island Telegraph article in 1830.
It didn’t take long for people to use the phrase metaphorically, as one writer for Portland’s Weekly Oregonian did in March 1855. “Leland, in his last issue, struts out with a chip on his shoulder, and dares Bush to knock it off,” they wrote. As Grammarphobia explains, the conflict was between two newspaper editors: Alonzo Leland of The Democratic Standard and Asahel Bush of the Oregon Statesman. Whether Bush did knock it off is a story for another time.
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