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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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up vote 21 down vote accepted

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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