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I've come across this interesting expression which doesn't seem to be listed in many Japanese to English dictionaries:

二足の草鞋を履く

From what I could gather, I believe it has a meaning of "being engaged in two trades" (?) But since this is the first time I've seen such an expression can someone explain its nuances?

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The origin of 二足のわらじを履く (literally "wearing two pairs of straw sandals") dates back to the Edo period (circa 17-19c). At first, this expression referred to gamblers who worked also as policemen who arrest gamblers. Originally, "wearing two pairs of sandals" was a metaphor for doing something impossible and/or paradoxical. This was not really a good word at first.

The meaning of this expression has been broadened since then, and people started to use this phrase to praise someone who works in two totally different fields by profession (e.g., a novelist-and-doctor, a lawyer-and-actress). Still, the key connotation of this idiom is "doing seemingly impossible/incompatible things". People today even use this phrase for merely having a small side business or working at two places as a part-time worker, but strictly speaking, such a usage is questionable.

Finally, 二足のわらじを履く does not always appear in its full form, just as the latter half of "when in Rome" is often unsaid. You can safely say 二足のわらじで働く, 二足のわらじの生活, and so on, even in casual conversations.

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Roughly speaking, 草鞋{わらじ} is a shoe made of straws.

I'll show you the nuance:
You say "to stand in someone's shoes" which is an idiom meaning "to see from another's point of view; to feel what another feels". If you stand in your own shoes, and at the same if you stand in someone's shoes, what happens? You can see from the point of both your view and someone's, right?

So, in Japan, if you wear two kinds of 草鞋 at the same time, you can be engaged in two trades.

I'll tell you why.

Literally 草履{ぞうり}を履{は}く means to put on zohri shoes, and 草履{ぞうり}を脱{ぬ}ぐ means to remove zohri shoes. From these literal meanings, 草履{ぞうり}を履{は}く means to start a trip, and 草履{ぞうり}を脱{ぬ}ぐ means to finish a trip.

And, 草履{ぞうり}を脱{ぬ}ぐ means metaphorically to retire from one's occupation.
From the metaphorical meaning of 草履{ぞうり}を脱{ぬ}ぐ, the metaphorical meaning of 草履{ぞうり}を履{は}く could be implied as to find one's occupation and start to engage oneself in it, though we don't use this metaphorical meaning usually.

From these metaphorical meanings, it is somewhat natural that to wear a pair of zohri shoes 一足{いっそく}の草鞋{わらじ}を履{は}く has a nuance of being engaged in a certain occupation or trade.
So, 二足{にそく}の草鞋{わらじ}を履{は}く has a meaning of being engaged in two different occupations or trades.

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