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I understand that it means to acquire a new skill, but what does it refer to? It makes me cringe every time I read it!

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OP is mistaken about the exact meaning of the expression. It's not about acquiring "new" skills, but about how you got started on the skills you already have. Here's a definition from dictionary.com

cut one's teeth on: to do at the beginning of one's education, career, etc., or in one's youth: The hunter boasted of having cut his teeth on tigers.

It's a metaphoric reference to when a baby's teeth first appear. They grow (cut) through through the gums - often painfully, which also gives us the figurative usage teething troubles.

Once the baby has "cut its teeth", it's properly equipped for the all-important "real-world" task of chewing solid food (metaphorically, for tackling more complex problems in professional life, etc.).


As that dictionary example suggests, the expression is often used boastfully/facetiously (in reality the hunter probably started with much less challenging prey, such as grubs, mice, and rabbits).

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Exactly. And children are given semi-hard things to chew on, to alleviate the pain and help the process along. –  StoneyB May 27 '13 at 16:33
    
@ StoneyB: It's only through ELU that I've come to appreciate how often idiomatic usages are mis-heard or mis-repeated. So it's no surprise to me now to see how many instances of "cut his cloth on" should clearly have been teeth, not cloth. I guess that's how language develops over decades and centuries. –  FumbleFingers May 27 '13 at 16:41
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