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Meaning

to live in ease

To live comfortably without having to work hard.

Example

家賃収入だけで左団扇で暮らせる身分がうらやましい。

I envy people who can live in comfort on rental income alone.

Origin

From the image of someone leisurely fanning themselves with a round fan (uchiwa) held in the left, non-dominant hand. From this it came to mean living a relaxed, easy life. Hidari ōgi, with a folding fan, means the same. Hidari uchiwa appears in a sharebon from 1784.

Sources