When "having your work cut out for you" first evolved into a more causal usage, to do so meant being well-prepared to complete whatever was in front of you with the appropriate tools and amount of time to do so, like a dressmaker sitting before their mindfully crafted pieces of cloth.
As time went by, the general meaning of the phrase shifted. Whereas it first meant that you were at an advantage, the 1800s introduced a new interpretation: the task at hand was an overbearing and strenuous one (via The Grammarist). Essentially, it started to mean the opposite of what it originally implied, and it's more or less the idiom's modern denotation as we hear it used casually in our everyday lives.
Though it sometimes goes unnoticed, there's often a deeper meaning and longer history to the words we employ. When it comes to unpacking what they really mean, we certainly have our work cut out for us.
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